starksia atlantica , the smooth-eye blenny , is a species of labrisomid blenny native to the western central atlantic ocean and the caribbean sea where it inhabits coral reefs at depths of around 8 metres ( 26 ft ) .

starksia atlantica

distribution of species in the starksia atlantica , starksia lepicoelia , and starksia sluiteri complexes . only locations for genetically analyzed specimens plotted . additional locations for some species discussed in text .
distribution of species in the starksia atlantica , starksia lepicoelia , and starksia sluiteri complexes . only locations for genetically analyzed specimens plotted . additional locations for some species discussed in text .
trunk pigment in the images and preserved specimen is similar to that of starksia atlantica from the bahamas and starksia springeri from curacao ( i . e . , mottled vs . barred as in starksia sangreyae ) , but the saba specimens lack the horseshoe - shaped blotch of pigment on the cheek characteristic of starksia atlantica and the distinctive dark and pale markings on the cheek of starksia springeri . the blotches of trunk pigment in the saba bank specimens are neither conspicuously block - like nor clearly organized in horizontal tiers as they are in starksia atlantica . specimens from saba bank presumably represent another new species within starksia atlantica , but additional specimens are needed for comparative purposes and description .
range kimura two - parameter distance summary for the starksia atlantica , starksia lepicoelia , and starksia sluiteri species complexes based on cytochrome c oxidase l ( col ) sequences of individuals represented in the neighbor - joining tree in figure 1 . within - complex ranges are shown in bold .
starksia langi is easily distinguished from starksia greenfieldi and starksia sluiteri based on pigmentation of the trunk , head ( females ) , and first dorsal fin ( males ) . the trunk pigment of starksia langi comprises both larger and more prominent markings than that of starksia greenfieldi and starksia sluiteri , and only in starksia langi are the markings in the second row vertically elongate ( generally round in the other species and sometimes considerably more diffuse in starksia greenfieldi ) . starksia greenfieldi lacks dark markings on the head in both sexes , and starksia sluiteri lacks them in females ; starksia langi males have a prominent dark blotch on the cheek , and females have numerous small , discrete , dark spots . males of starksia langi lack a dark blotch on the anterior portion of the dorsal fin , whereas this blotch is present in starksia greenfieldi and starksia sluiteri .
starksia atlantica , greenfield and johnson ( 1981 ) , fieldiana zoology 8 : fig . 3a–b ( black and white drawings of male and female specimens from belize )
seven new species within western atlantic starksia atlantica , s . lepicoelia , and s . sluiteri ( teleostei , labrisomidae ) , with comments on congruence of dna barcodes and species
seven new species within western atlantic starksia atlantica , s . lepicoelia , and s . sluiteri ( teleostei , labrisomidae ) , with comments on congruence of dna barcodes and species
seven new species within western atlantic starksia atlantica , s . lepicoelia , and s . sluiteri ( teleostei , labrisomidae ) , with comments on congruence of dna barcodes and species .
seven new species within western atlantic starksia atlantica , s . lepicoelia , and s . sluiteri ( teleostei , labrisomidae ) , with comments on congruence . . . - pubmed - ncbi
article : seven new species within western atlantic starksia atlantica , s . lepicoelia , and s . sluiteri ( teleostei , labrisomidae ) , with comments on congruence of dna barcodes and species
modal differences in some counts also help separate other species : starksia lepicoelia modally has 28 total dorsal - fin elements , 33 vertebrae , and 78 total dorsal elements + anal soft rays + vertebrae ( vs . 32 , 27 , and 75 , respectively , in starksia williamsi and starksia weigti ) . starksia williamsi modally has xix dorsal - fin spines , whereas starksia lepicoelia and starksia weigti modally have xx .
details - seven new species within western atlantic starksia atlantica , s . lepicoelia , and s . sluiteri ( teleostei , labrisomidae ) , with comments on congruence of dna barcodes and species - biodiversity heritage library
starksia lepicoelia and starksia starcki are the only previously described western atlantic starksia with the combination of an orbital cirrus , two externally obvious pelvic - fin rays , and a scaled belly ( williams and mounts 2003 ) . starksia starcki is easily distinguished from the species of the starksia lepicoelia complex by the presence of eight or nine irregular dark bars on the body and usually 19 segmented anal - fin rays .
descriptions of six new caribbean fish species in the genus starksia ( labrisomidae ) .
starksia sluiteri ( metzelaar ) is most easily distinguished from starksia langi by having the second row of trunk blotches almost perfectly round ( vs . vertically elongate ) , in lacking conspicuous dark spots on the head ( females ) , and in having a dark marking on the anterior portion of the dorsal fin ( males ) . from starksia greenfieldi , starksia sluiteri differs in lacking pale round spots on the head . although starksia sluiteri and starksia langi have very similar chromatophore patterns , starksia sluiteri appears to have more orange pigment on the second dorsal , caudal , and anal fins .
the purpose of this paper is to describe the systematic results of our recent genetic and morphological investigations of western atlantic starksia , work that was prompted by our discovery of incongruences between preliminary genetic data and the current species classification . we describe seven new species within starksia atlantica , starksia lepicoelia , and starksia sluiteri and provide keys to the species of each of those species complexes . we provide photographs of living and preserved pigment patterns to help in future identifications of the included species and in distinguishing them from western atlantic starksia species likely to be discovered in the future . finally , we discuss geographical distributions of starksia species and comment on congruence between dna barcoding data and morphologically recognizable species .
all material that we examined is from belize . the range of the species also apparently includes honduras , as greenfield and johnson ( 1981 ) noted that a specimen of starksia atlantica from honduras has regular vertical bars of pigment on the body .
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starksia atlantica
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in life , starksia weigti is easily distinguished from starksia lepicoelia , starksia williamsi , and starksia robertsoni by the conspicuous pale round spots on the lips . in preservative , starksia lepicoelia males are distinctive in having at least some very dark spots , streaks , or bars on the lips and lower jaw , and starksia robertsoni males have at least one ( up to three ) dark spots or bars on the ventral portion of the lower jaw ( but not on the lips ) . although the differences are subtle , preserved males of starksia williamsi typically can be separated from preserved males of starksia weigti in having the lips uniformly covered with melanophores except for the pale anterior tips . in starksia weigti males , lip pigment is variable , but there are usually one or two thin , faint , poorly formed bars of pigment following the pale anterior portions of the lips ; posteriorly , the lips may be uniformly covered with melanophores as in starksia williamsi or be quite pale .
starksia y - lineata , a new clinid fish from grand cayman island , british west indies .
neighbor - joining tree derived from cytochrome c oxidase i sequences showing genetically distinct lineages of western atlantic starksia .
neighbor - joining tree derived from cytochrome c oxidase i sequences showing genetically distinct lineages of western atlantic starksia .
starksia greenfieldi can be distinguished from starksia langi and starksia sluiteri by the white ( or pale ) , mostly round spots ( absence of melanophores against a darker background ) on at least portions of cheek , opercle , and gular region . this pattern is present in both sexes but is often much more prominent in males . williams and mounts ( 2003 ) noted that starksia sella , another species of starksia known only from tobago , has small pale spots on the head , but that species lacks dark blotches along the trunk , lacks a dark blotch in the anterior dorsal fin of males , and may be larger ( williams and mounts specimens of starksia sella are 13 . 7–27 . 7 mm sl , our specimens of starksia greenfieldi are 11 . 0–23 . 0 mm sl ) .
because we do not know how much more investigation is required to obtain a reasonably complete picture of starksia biodiversity and biogeography , the words of winston churchill included as an epigraph in this paper seem particularly appropriate . the study of starksia must continue .
starksia sluiteri williams and mounts 2003 , aqua 6 ( 4 ) : fig . 9 ( male and female specimens from tobago )
for starksia , future investigation must include more taxonomic and geographic coverage . increased sampling will assuredly result in the recognition of new species and likely of new species complexes . the faunal breaks that separate members of the species complexes are unknown . in starksia atlantica and starksia lepicoelia , our specimens from bahamas and turks and caicos represent the same species , and in starksia sluiteri , specimens from belize , honduras , and panama appear to be the same . specimens in close proximity geographically thus tend to cluster into recognizable species . as better coverage is attained , it will be interesting to see if the same geographical boundaries characterize more than one of the species complexes or if the boundaries are different for each . likewise it will be interesting to compare geographic boundaries of starksia species with faunal breaks in other reef fishes such as elacatinus . future phylogenetic studies in which relationships among species and species complexes of starksia and other groups are hypothesized should help shed light on patterns of speciation in small reef fishes of the western atlantic .
comparisons among species of the starksia atlantica complex . left to right for each row - - starksia atlantica : amnh 241247 ; usnm 399621 , bah 8176 , 15 . 0 mm sl ; usnm 386971 , 19 . 0 mm sl ; usnm 386242 , 17 . 0 mm sl . starksia sangreyae : ( note : top and bottom images in first two columns represent starksia sangreyae a and starksia sangreyae b genetic sublineages , respectively . ) males – usnm 398936 ( top ) , paratype , blz 8028 , 17 . 0 mm sl and usnm 398937 ( bottom ) , paratype , blz 8029 , 17 mm sl ; females – usnm 398934 ( top ) , paratype , blz 5161 , 17 . 0 mm sl and usnm 398940 ( bottom ) , paratype , blz 8353 , 16 . 0 mm sl ; preserved – usnm 276147 , paratype , 15 . 5 mm sl ; usnm 321073 , paratype , 18 . 0 mm sl . starksia springeri : usnm 399658 , paratype , cur 8148 , 15 . 0 mm sl ; usnm 398945 , holotype , cur 08 - 10 , 19 . 0 mm sl ; starksia sp . ( saba ) : saba - 06 - 01 , 15 . 0 mm sl ( no voucher ) . photographs by carole baldwin , cristina castillo , donald griswold , julie mounts , ross robertson , james van tassell , and jeffrey williams .
comparisons among species of the starksia atlantica complex . left to right for each row - - starksia atlantica : amnh 241247 ; usnm 399621 , bah 8176 , 15 . 0 mm sl ; usnm 386971 , 19 . 0 mm sl ; usnm 386242 , 17 . 0 mm sl . starksia sangreyae : ( note : top and bottom images in first two columns represent starksia sangreyae a and starksia sangreyae b genetic sublineages , respectively . ) males – usnm 398936 ( top ) , paratype , blz 8028 , 17 . 0 mm sl and usnm 398937 ( bottom ) , paratype , blz 8029 , 17 mm sl ; females – usnm 398934 ( top ) , paratype , blz 5161 , 17 . 0 mm sl and usnm 398940 ( bottom ) , paratype , blz 8353 , 16 . 0 mm sl ; preserved – usnm 276147 , paratype , 15 . 5 mm sl ; usnm 321073 , paratype , 18 . 0 mm sl . starksia springeri : usnm 399658 , paratype , cur 8148 , 15 . 0 mm sl ; usnm 398945 , holotype , cur 08 - 10 , 19 . 0 mm sl ; starksia sp . ( saba ) : saba - 06 - 01 , 15 . 0 mm sl ( no voucher ) . photographs by carole baldwin , cristina castillo , donald griswold , julie mounts , ross robertson , james van tassell , and jeffrey williams .
comparisons among species of the starksia sluiteri complex and starksia fasciata . starksia greenfieldi , left to right : usnm 398921 , paratype , tob 9275 , 17 . 0 mm sl ; usnm 398922 , paratype , tob 9282 , 19 . 0 mm sl ; usnm , 320832 , holotype , 19 . 0 mm sl ; usnm 320829 , paratype , 22 . 0 mm sl . starksia langi : usnm 398931 , blz 8266 , 18 . 0 mm sl ; usnm 398928 , blz 8062 , 17 . 0 mm sl ; usnm 349080 , paratype , 18 . 0 mm sl ; usnm 398927 , holotype , 17 . 0 mm sl . starksia sluiteri : usnm 399626 , cur8271 , 16 . 5 mm sl ; usnm 399624 , cur8226 , 18 . 5 mm sl ; usnm 195750 , 16 . 9 mm sl . starksia fasciata : usnm 399681 , tci 9204 , 14 . 0 mm sl ; usnm 399683 , tci 9349 , 18 . 0 mm sl . juveniles / small adults : starksia greenfieldi , usnm 398925 , tob 9213 ; starksia langi , usnm 398930 , paratype , blz 8216 ; starksia sluiteri , usnm 399625 , cur 8227 . photographs by carole baldwin , cristina castillo , donald griswold , and jeffrey williams .
comparisons among species of the starksia sluiteri complex and starksia fasciata . starksia greenfieldi , left to right : usnm 398921 , paratype , tob 9275 , 17 . 0 mm sl ; usnm 398922 , paratype , tob 9282 , 19 . 0 mm sl ; usnm , 320832 , holotype , 19 . 0 mm sl ; usnm 320829 , paratype , 22 . 0 mm sl . starksia langi : usnm 398931 , blz 8266 , 18 . 0 mm sl ; usnm 398928 , blz 8062 , 17 . 0 mm sl ; usnm 349080 , paratype , 18 . 0 mm sl ; usnm 398927 , holotype , 17 . 0 mm sl . starksia sluiteri : usnm 399626 , cur8271 , 16 . 5 mm sl ; usnm 399624 , cur8226 , 18 . 5 mm sl ; usnm 195750 , 16 . 9 mm sl . starksia fasciata : usnm 399681 , tci 9204 , 14 . 0 mm sl ; usnm 399683 , tci 9349 , 18 . 0 mm sl . juveniles / small adults : starksia greenfieldi , usnm 398925 , tob 9213 ; starksia langi , usnm 398930 , paratype , blz 8216 ; starksia sluiteri , usnm 399625 , cur 8227 . photographs by carole baldwin , cristina castillo , donald griswold , and jeffrey williams .
baldwin , carole c . , cristina i . castillo , lee a . weigt & benjamin c . victor . 2011 . seven new species within western atlantic starksia atlantica , s . lepicoelia , and s . sluiteri ( teleostei , labrisomidae ) , with comments on congruence of dna barcodes and species . zookeys 79 : 21–72 . , available online at urltoken [ details ]
s . atlantica occurs in the bahamas . s . springeri is found in the netherlands antilles and s . sangreyae is the species in the bay of honduras . other deeply - divergent dna lineages have been identified elsewhere in the caribbean .
average ( and range ) kimura two - parameter distance summary for the starksia atlantica species complex based on cytochrome c oxidase l ( col ) sequences of individuals represented in the neighbor - joining tree in figure 1 . intraspecific averages are shown in bold . n / a = no average ( one specimen ) . bar – barbados , sab – saba bank , pan – panama .
a review of the western atlantic starksia ocellata - complex ( pisces : clinidae ) with the description of two new species and proposal of superspecies status .
diagnostic features in preserved a starksia atlantica , usnm 386242 , 17 . 0 mm sl , male—note irregular horseshoe - shaped blotch of pigment on cheek and wavy margins of pale gap on pectoral - fin base ; and b starksia springeri , usnm 398945 , holotype , 19 . 0 mm sl , female—note pale regions at anteroventral and posterior margins of dark cheek blotch , thin dark anteroventral - to - posterodorsal streak of pigment along distal edge of preopercle , and relatively straight margins of pale gap on pectoral - fin base . photographs by cristina castillo and donald griswold .
diagnostic features in preserved a starksia atlantica , usnm 386242 , 17 . 0 mm sl , male—note irregular horseshoe - shaped blotch of pigment on cheek and wavy margins of pale gap on pectoral - fin base ; and b starksia springeri , usnm 398945 , holotype , 19 . 0 mm sl , female—note pale regions at anteroventral and posterior margins of dark cheek blotch , thin dark anteroventral - to - posterodorsal streak of pigment along distal edge of preopercle , and relatively straight margins of pale gap on pectoral - fin base . photographs by cristina castillo and donald griswold .
ty - jour ti - seven new species within western atlantic starksia atlantica , s . lepicoelia , and s . sluiteri ( teleostei , labrisomidae ) , with comments on congruence of dna barcodes and species t2 - zookeys vl - 79 ur - urltoken pb - pensoft publishers py - 2011 sp - 21 ep - 72 do - 10 . 3897 / zookeys . 79 . 1045 au - baldwin , carole au - castillo , cristina au - weigt , lee au - victor , benjamin kw - biogeography kw - dna barcoding kw - new species kw - species complex kw - starksia er -
the species name is in honor of david w . greenfield , in recognition of his work on blennioid fishes , particularly his work on the starksia ocellata complex .
a comparisons of head pigment of preserved males and females among species of the starksia lepicoelia complex . starksia lepicoelia : a usnm 399921 , bah 9103 , 26 . 0 mm sl , male b usnm 399617 , bah 8079 , 19 . 0 mm sl , female ; starksia weigti : c usnm 399648 , blz 5010 , holotype , 20 . 5 mm sl , male d usnm 399651 , blz 8024 , paratype , 19 . 0 mm sl , female ; starksia williamsi : e usnm 387675 , holotype , 21 . 0 mm sl , male f usnm 387869 , paratype , 19 . 5 mm sl , female ; starksia robertsoni : g usnm 399913 , paratype , 18 . 0 mm sl , male h amnh 249667 , holotype , 22 . 0 mm sl , female . photographs by carole baldwin , cristina castillo , and donald griswold .
a comparisons of head pigment of preserved males and females among species of the starksia lepicoelia complex . starksia lepicoelia : a usnm 399921 , bah 9103 , 26 . 0 mm sl , male b usnm 399617 , bah 8079 , 19 . 0 mm sl , female ; starksia weigti : c usnm 399648 , blz 5010 , holotype , 20 . 5 mm sl , male d usnm 399651 , blz 8024 , paratype , 19 . 0 mm sl , female ; starksia williamsi : e usnm 387675 , holotype , 21 . 0 mm sl , male f usnm 387869 , paratype , 19 . 5 mm sl , female ; starksia robertsoni : g usnm 399913 , paratype , 18 . 0 mm sl , male h amnh 249667 , holotype , 22 . 0 mm sl , female . photographs by carole baldwin , cristina castillo , and donald griswold .
@ article { bhlpart99078 , title = { seven new species within western atlantic starksia atlantica , s . lepicoelia , and s . sluiteri ( teleostei , labrisomidae ) , with comments on congruence of dna barcodes and species } , journal = { zookeys } , volume = { 79 } , url = urltoken publisher = { pensoft publishers 2011 } , author = { baldwin , carole and castillo , cristina and weigt , lee and victor , benjamin } , year = { 2011 } , pages = { 21 - 72 } , keywords = { biogeography | dna barcoding | new species | species complex | starksia | } , }
a color pattern of starksia springeri , usnm 399658 , cur 8148 , paratype , 15 . 0 mm sl , male ( ? ) b diagnostic pigment pattern on cheek and pectoral - fin base in preserved starksia springeri , usnm 398945 , holotype , 19 . 0 mm sl , female . photographs by carole baldwin , cristina castillo , and donald griswold .
a color pattern of starksia springeri , usnm 399658 , cur 8148 , paratype , 15 . 0 mm sl , male ( ? ) b diagnostic pigment pattern on cheek and pectoral - fin base in preserved starksia springeri , usnm 398945 , holotype , 19 . 0 mm sl , female . photographs by carole baldwin , cristina castillo , and donald griswold .
most information is from bohlke and springer ' s 1961 monograph
a review of the atlantic species of the clinid fish genus starksia
, greenfield ' s
. . starksia ocellata - complex . .
( 1979 ) , greenfield & johnson ' s 1985 large survey paper on
the blennioid fishes of belize and honduras . . .
, jeff williams ' 2003 review
descriptions of six new caribbean fish species in the genus starksia ( labrisomidae )
by williams and mounts ( note that there are many post - publication corrections by jeff ) , and our recent 2011 review paper .
böhlke and springer ( 1961 ) noted that counts of dorsal - and anal - fin elements in specimens of starksia sluiteri they examined from off colombia and venezuela ( xix dorsal spines and 15–16 anal rays ) differ from those given by metzelaar ( xx and 17 ) . based on pigment , their colombian and venezuelan specimens appear to be starksia sluiteri . our specimens from curacao , as well as böhlke and springer’s two venezuelan specimens ( usnm 195750 ) , have xix dorsal spines and 15–16 anal rays . there is thus a discrepancy between counts in our material and those reported by metzelaar for the holotype . we examined a photograph of the holotype , and there appear to be xx dorsal - fin spines as noted by mezelaar ; xx is likely a non - modal count for starksia sluiteri . we note that there is more variation in dorsal - and anal - fin counts in some starksia species than suggested by metzelaar’s description ; for example , starksia greenfieldi has xviii–xx dorsal spines , 7–9 dorsal rays , and 14–16 anal rays .
metzelaar ( 1919 ) described brannerella sluiteri from two specimens from bonaire , netherland antilles . longley ( 1934 ) synonymized brannerella with starksia jordan and evermann ( type species labrisomus cremnobates gilbert , from the eastern pacific ) . böhlke and springer ( 1961 ) concurred with longley’s synonymy , noting that brannerella is distinctive in a single character , and generic recognition of one - character differences would require the erection of several new genera within caribbean starksia .
note : some starksia species can barely overlap the lower range of fin - ray counts for those few malacoctenus species that can have 8 or 9 dorsal - fin soft rays and 14 or fewer pectoral - fin rays .
male and female color patterns of starksia williamsi : a usnm 387869 , 19 . 5 mm sl , male , paratype b usnm 387767 , 20 . 2 mm sl , female , paratype . photographs by jeffrey williams .
male and female color patterns of starksia williamsi : a usnm 387869 , 19 . 5 mm sl , male , paratype b usnm 387767 , 20 . 2 mm sl , female , paratype . photographs by jeffrey williams .
a species of starksia distinguished by the following combination of characters : no orbital cirrus , regular vertical brown bars on trunk separated by narrow white interspaces , and a well defined horseshoe - shaped blotch of dark pigment on cheek .
paraclinus larvae superficially look much like starksia larvae , but can be distinguished by their distinctive all or all - but - one spinous dorsal fin . they also have no preopercular spines and more melanophores , including the deep nuchal and deep pelvic and often the cheek and otic melanophores , as well as a regular anal row with more than 18 total pvm . the starksia species that share deep nuchal ( rarely ) and pelvic melanophores can be distinguished from paraclinus by having diagnostic irregular large or deep anal - row melanophores and shorter anal rows ) . starksia typically have 5 or 6 procurrent caudal - fin rays , one or two more than paraclinus larvae , and one to several fewer than the malacoctenus and labrisomus .
there are no taxognomonic characters uniquely identifying all starksia larvae , but the absence of a set of common markings is typical of most starksia larvae . typically , the only anterior larval melanophore is at the isthmus . notably , most larvae are missing the cranial , deep nuchal , cheek , internal otic , and pelvic melanophores ( there are exceptions for all but the cheek melanophore among the s . atlantica and s . ocellata complexes ) . on all species , the anal row spares one or more of the last rays and usually there are no ventral caudal - peduncle melanophores ( at most one on some individuals of some species ) . the absence of some of the usually consistent melanophores on a labrisomid larva should prompt a closer examination . chaenopsidae larvae share the light marking patterns but have more total pvm ( 19 or more ) and more dorsal and anal - fin soft rays .
comparative material . starksia atlantica . bahamas : usnm 386971 , 1 specimen ( not a dna voucher ) ; usnm 386580 , 1 ( not a dna voucher ) ; usnm 386242 , 6 ( not dna vouchers ) ; usnm 399619 , 3 ( not dna vouchers ) ; usnm 399620 , bah 8175 ; usnm 399621 , bah 8176 ; usnm 399622 , bah 8177 . turks and caicos islands : usnm 399643 , tci 9044 ; usnm 399644 , tci 9106 ; usnm 399645 , tci 9107 ; usnm 399647 , tci 9205 . navassa island : usnm 360422 , 3 ; usnm 360194 , 2 ; usnm 359543 , 2 ; usnm 360210 , 3 .
comparisons among species of the starksia lepicoelia complex . left to right : starksia lepicoelia ( bah ) : usnm 399928 , bah 10050 , 25 . 0 mm sl ; usnm 399617 , bah 8079 , 19 . 0 mm sl ; usnm 399921 , bah 9103 , 26 . 0 mm sl ; usnm 386972 , 14 . 0 mm sl ; starksia lepicoelia ( tci ) : usnm 399638 , tci 9291 , 23 . 5 mm sl ; usnm 399641 , tci 9294 , 25 . 5 mm sl ; usnm 399642 , 23 . 0 mm sl ; usnm 399641 , tci 9294 , 25 . 5 mm sl ; starksia weigti : blz 6120 , 24 . 0 mm sl ( no voucher ) ; usnm 399650 , blz 5193 , 24 . 0 mm sl ; usnm 399648 , blz 5010 , holotype , 20 . 5 mm sl ; usnm 274922 , paratype , 20 . 0 m sl ; starksia williamsi : usnm 387767 , 19 . 8 mm sl ; usnm 387767 , 20 . 2 mm sl ; usnm 387675 , holotype , 21 . 0 mm sl ; usnm 387869 , paratype , 19 . 5 mm sl ; starksia robertsoni : amnh 249642 , paratype , 21 . 5 mm sl ; usnm 399909 , pan 1419 , paratype , 21 . 0 mm sl ; amnh 249667 , holotype , 22 . 0 mm sl . photographs by carole baldwin , cristina castillo , donald griswold , ross robertson , james van tassell , and jeffrey williams .
comparisons among species of the starksia lepicoelia complex . left to right : starksia lepicoelia ( bah ) : usnm 399928 , bah 10050 , 25 . 0 mm sl ; usnm 399617 , bah 8079 , 19 . 0 mm sl ; usnm 399921 , bah 9103 , 26 . 0 mm sl ; usnm 386972 , 14 . 0 mm sl ; starksia lepicoelia ( tci ) : usnm 399638 , tci 9291 , 23 . 5 mm sl ; usnm 399641 , tci 9294 , 25 . 5 mm sl ; usnm 399642 , 23 . 0 mm sl ; usnm 399641 , tci 9294 , 25 . 5 mm sl ; starksia weigti : blz 6120 , 24 . 0 mm sl ( no voucher ) ; usnm 399650 , blz 5193 , 24 . 0 mm sl ; usnm 399648 , blz 5010 , holotype , 20 . 5 mm sl ; usnm 274922 , paratype , 20 . 0 m sl ; starksia williamsi : usnm 387767 , 19 . 8 mm sl ; usnm 387767 , 20 . 2 mm sl ; usnm 387675 , holotype , 21 . 0 mm sl ; usnm 387869 , paratype , 19 . 5 mm sl ; starksia robertsoni : amnh 249642 , paratype , 21 . 5 mm sl ; usnm 399909 , pan 1419 , paratype , 21 . 0 mm sl ; amnh 249667 , holotype , 22 . 0 mm sl . photographs by carole baldwin , cristina castillo , donald griswold , ross robertson , james van tassell , and jeffrey williams .
museum specimens examined from the lesser antilles ( dominica ) and puerto rico appear to be starksia sluiteri based on trunk pigment ( round vs . elongate blotches in the second row of markings ) and no conspicuous round pale spots on the cheek . the pigment is somewhat faded in those specimens , however , and more material , including tissue samples for genetic analysis , is needed . two female specimens from navassa ( usnm 361059 ) are not starksia sluiteri , as the markings in the second row of trunk blotches are elongate , not round . however , those markings are rectangular in the navassa specimens , and the markings in the upper row are square—much more so than in our material of starksia langi from the western caribbean . the larger of the two females has some dark spots on the head as in starksia langi . more material is needed . other museum material examined ( e . g . , the uf specimens from antigua and mexico ) are too faded to identify to species .
named in honor of victor g . springer , senior scientist emeritus , smithsonian national museum of natural history , for his contributions to the systematics of blennioid fishes , including starksia , and for advice and friendship he has bestowed upon the first author .
average ( and range ) kimura two - parameter distance summary for the starksia sluiteri species complex based on cytochrome c oxidase l ( col ) sequences of individuals represented in the neighbor - joining tree in figure 1 . intraspecific averages are shown in bold .
an additional character quickly separating paraclinus larvae from the far more abundant larvae of malacoctenus and labrisomus is the absence of cranial melanophores . paraclinus larvae also have no obvious preopercular spines , while many immature malacoctenus and labrisomus ( and starksia ) larvae have preopercular spines at the size of overlap with paraclinus larvae . a useful character , even on poorly preserved larvae , is the number of procurrent caudal - fin rays : paraclinus larvae have only 3 or 4 vs . 6 to 10 in malacoctenus and labrisomus ( and 5 to 6 in starksia ) .
comparison of starksia lepicoelia specimens from bahamas from genetically distinct lineages ( see fig . 1 ) : a usnm 399615 , bah 8077 , 25 . 0 mm sl , female b usnm 399617 , bah 8079 , 19 . 0 mm sl , female . photographs by carole baldwin .
named in honor of jeffrey t . williams , smithsonian’s national museum of natural history , in recognition of his work on blennioid fishes , including starksia . jeff’s field - collecting efforts at saba bank , tobago , and turks and caicos resulted in numerous specimens utilized in this study .
comparative material . starksia sluiteri . curacao ( all dna vouchers ) : usnm 399623 , cur 8162 ; usnm 399624 , cur 8226 ; usnm 399625 , cur 8227 ; usnm 399626 , cur 8271 . los roques , venezuela ( not dna vouchers ) : usnm 195750 , 2 specimens . dominica ( not dna vouchers ) : usnm 198263 , 15 . puerto rico ( not a dna voucher ) : usnm 219143 , 1 . antigua ( not a dna voucher ) : uf 11344 , 1 . mexico ( not dna vouchers ) : uf 209342 , 2 . starksia fasciata , turks & caicos islands ( all dna vouchers ) : usnm 399681 , tci9204 ; usnm 399683 , tci 9349 ; usnm 399684 , tci 9350 ; usnm 399685 , tci 9714 . starksia sp . navassa island ( not dna vouchers ) : usnm 361059 , 2 .
other than the diagnostic dorsal - fin spine complement , paraclinus larvae can be distinguished from the similar starksia larvae by the consistent presence of the deep nuchal and deep pelvic melanophores and often the cheek melanophore . deep melanophores , however , are not always visible on well - developed larvae . interestingly , transitional paraclinus larvae collected at night over the reef do not have the metamorphic melanophore patterns over the head typical for transitional starksia larvae and frequent on larvae of malacoctenus and labrisomus . nevertheless , by the morning ( in collections made by unattended crest nets ) , metamorphic melanophores have developed .
color and preserved pigment patterns in starksia robertsoni : a amnh 249667 , 22 . 0 mm sl , female , holotype ( photograph by james van tassell and ross robertson ) b usnm 399911 , pan 1418 , 20 . 0 mm sl , male , paratype ( photograph by carole baldwin ) .
color and preserved pigment patterns in starksia robertsoni : a amnh 249667 , 22 . 0 mm sl , female , holotype ( photograph by james van tassell and ross robertson ) b usnm 399911 , pan 1418 , 20 . 0 mm sl , male , paratype ( photograph by carole baldwin ) .
average ( and range ) kimura two - parameter distance summary for the starksia lepicoelia species complex based on cytochrome c oxidase l ( col ) sequences of individuals represented in the neighbor - joining tree in figure 1 . intraspecific averages are shown in bold ; n / a = no average ( one specimen ) .
male and female color patterns of starksia langi : a usnm 398931 , paratype , blz 8266 , 18 . 0 mm sl , male b usnm 398929 , paratype , blz 8131 , 16 . 0 mm sl , female c–e diagnostic features of preserved starksia langi – ( c and d ) usnm 398931 , paratype , blz 8266 , male , 18 . 0 mm sl , note dark marking on cheek and absence of dark blotch in anterior portion of spinous dorsal fin e usnm 398928 , paratype , blz 8062 , female , 17 . 0 mm sl , note small dark spots on head . photographs by carole baldwin , cristina castillo , and donald griswold .
male and female color patterns of starksia langi : a usnm 398931 , paratype , blz 8266 , 18 . 0 mm sl , male b usnm 398929 , paratype , blz 8131 , 16 . 0 mm sl , female c–e diagnostic features of preserved starksia langi – ( c and d ) usnm 398931 , paratype , blz 8266 , male , 18 . 0 mm sl , note dark marking on cheek and absence of dark blotch in anterior portion of spinous dorsal fin e usnm 398928 , paratype , blz 8062 , female , 17 . 0 mm sl , note small dark spots on head . photographs by carole baldwin , cristina castillo , and donald griswold .
male and female color patterns of starksia greenfieldi : a usnm 398920 , tob 9212 , 15 . 0 mm sl , male b usnm 398922 , tob 9282 , 19 . 0 mm sl , female c–e diagnostic features of preserved starksia greenfieldi - c usnm usnm 398919 , paratype , male , 22 . 0 m sl , note pale spots on head d usnm 320832 , holotype , male , 19 . 0 mm sl , note pale spots on head and dark blotch in anterior portion of spinous dorsal fin e usnm 320829 , female , 22 . 0 mm sl , note pale spots on head . photographs by carole baldwin , cristina castillo , and donald griswold .
male and female color patterns of starksia greenfieldi : a usnm 398920 , tob 9212 , 15 . 0 mm sl , male b usnm 398922 , tob 9282 , 19 . 0 mm sl , female c–e diagnostic features of preserved starksia greenfieldi - c usnm usnm 398919 , paratype , male , 22 . 0 m sl , note pale spots on head d usnm 320832 , holotype , male , 19 . 0 mm sl , note pale spots on head and dark blotch in anterior portion of spinous dorsal fin e usnm 320829 , female , 22 . 0 mm sl , note pale spots on head . photographs by carole baldwin , cristina castillo , and donald griswold .
starksia langi . a male from honduras , usnm 399917 , hon 050 , paratype , 16 . 3 mm sl ( right side , reversed ) b femalefrom panama ( atlantic ) , usnm 399918 , pan 018 , 14 . 5 mm sl c male from isla providencia , colombia , mzusp 107860 , 16 mm sl . photographs by carole baldwin .
starksia langi . a male from honduras , usnm 399917 , hon 050 , paratype , 16 . 3 mm sl ( right side , reversed ) b femalefrom panama ( atlantic ) , usnm 399918 , pan 018 , 14 . 5 mm sl c male from isla providencia , colombia , mzusp 107860 , 16 mm sl . photographs by carole baldwin .
unfortunately , fin - ray counts for the entire genus are similar and broadly overlapping . furthermore , adult markings on starksia are both highly variable and patterns are often shared among species , making identifications particularly challenging . it certainly does not help that males and females often have different sets of markings . much of the variation in appearance occurs in live coloration only and the dearth of live specimens or underwater photographs makes identifications quite difficult .
nemaclinus atelestos , a rare labrisomid found only on deep dropoffs , looks much like the starksia species . it has higher median - fin ray counts , but fewer pectoral - fin rays : d - xxi - xxiii , 7 - 9 a - ii , 18 - 19 and only 11 - 12 pectoral - fin rays . it also has notably long pelvic - fin rays , extending well beyond the origin of the anal fin .
a species of starksia distinguished by the following combination of characters : orbital cirrus present ; belly scaled ; trunk pale to tan ( dark orange / tan to bright orange in life ) , without distinct bars or other markings ; lips without conspicuous white spotting , distinct banding , or dark bars—usually with lightly scattered melanophores in preserved specimens ; total dorsal elements 27 ; total vertebrae usually 32 ; dorsal spines + anal soft rays + vertebrae modally 75 .
male and female color patterns of starksia sangreyae : a usnm 398932 , holotype , blz 5111 , 16 . 0 mm sl , male b usnm 398933 , blz 5033 , 16 . 5 mm sl , female . c–d diagnostic patterns of cheek pigment of preserved female and male – c usnm 276147 , 15 . 0 mm sl , male d usnm 321073 , 18 . 0 mm sl , female . photographs by carole baldwin , cristina castillo , donald griswold , and julie mounts .
male and female color patterns of starksia sangreyae : a usnm 398932 , holotype , blz 5111 , 16 . 0 mm sl , male b usnm 398933 , blz 5033 , 16 . 5 mm sl , female . c–d diagnostic patterns of cheek pigment of preserved female and male – c usnm 276147 , 15 . 0 mm sl , male d usnm 321073 , 18 . 0 mm sl , female . photographs by carole baldwin , cristina castillo , donald griswold , and julie mounts .
male and female color patterns of starksia weigti : a usnm 399648 , holotype , blz 5010 , 25 . 0 mm sl , male b blz 6121 ( no voucher ) , 18 . 0 mm sl , female c–d close - up views of diagnostic spotting on lips in life – c blz 6120 , 24 . 0 mm sl ( no voucher ) , male d usnm 399650 , blz 5193 , 24 . 0 mm sl , female . photographs by carole baldwin and julie mounts .
male and female color patterns of starksia weigti : a usnm 399648 , holotype , blz 5010 , 25 . 0 mm sl , male b blz 6121 ( no voucher ) , 18 . 0 mm sl , female c–d close - up views of diagnostic spotting on lips in life – c blz 6120 , 24 . 0 mm sl ( no voucher ) , male d usnm 399650 , blz 5193 , 24 . 0 mm sl , female . photographs by carole baldwin and julie mounts .
a species of starksia distinguished by the following combination of characters : no orbital cirrus ; trunk with irregular dark blotches on pale background ; pectoral - fin base with relatively straight margins defining pale gap that separates two dark blotches ; cheek with distinctive dark and pale markings : anterior portion of cheek with prominent dark blotch , anteroventral and posterior margins of blotch well defined by pale regions ; posterior pale area on cheek bordered posteriorly by thin , dark , anteroventral - to - posterodorsal streak of pigment along distal edge of preopercle .
a species of starksia distinguished by the following combination of characters : orbital cirrus present ; belly scaled ; trunk pale ( pale red in life ) , without distinct bars or other markings ; lips peppered with white spots in life ; lacrimal region with single row of small white spots in life ; jaws usually with lightly scattered melanophores in preserved specimens , without distinct banding or dark bars ; entire gular region usually covered with scattered melanophores ; total dorsal elements usually 27 ; total vertebrae usually 32 ; dorsal spines + anal soft rays + vertebrae modally 75 .
specimens used in this study were collected from barbados , belize , bahamas , curacao ( netherland antilles ) , florida , honduras , panama ( atlantic ) , saba bank ( netherland antilles ) , st . thomas ( u . s . virgin islands ) , tobago ( trinidad and tobago ) , and turks and caicos . that material and additional museum specimens examined are listed in the appropriate species and comparisons sections . starksia specimens included in the genetic analysis but not in the species accounts are tabulated in appendix 1 . institutional abbreviations for collections follow sabaj pérez ( 2010 ) .
a species of starksia distinguished by the following combination of characters : orbital cirrus present ; belly scaled ; trunk pale to dark tan ( dark orange / tan to bright orange in life ) , without distinct bars or other markings ; lips without conspicuous white spotting in life ; ventral surface of lower jaw of males with one to three dark blotches or bars in preserved specimens , lips without distinct banding or dark bars ; dorsal - fin elements usually xx , 7 – 27 total ; vertebrae usually 10 + 22 = 32 ; dorsal spines + anal soft rays + vertebrae modally 75 .
a species of starksia distinguished by the following combination of characters : orbital cirrus present ; two rows of prominent , very dark blotches on side of body , at least some of those in lower row vertically elongate to oval , rarely round ; males with dark , fat , crescent - shaped marking on cheek and without dark blotch on anterior portion of spinous dorsal fin ; females with scattered dark spots on lower half of head and on pectoral - fin base ; first anal - fin spine in males two - thirds to three - quarters length of male genital papilla ; belly naked .
a species of starksia distinguished by the following combination of characters : orbital cirrus present ; two to three rows of dark blotches on side of body , blotches in middle row ( or ventral row if only two rows ) mostly circular , never vertically elongate or oval ; white ( or pale ) , mostly round spots ( absence of melanophores against a darker background ) on at least portions of cheek , opercle , and gular region , this spotting pattern more prominent in males ; males with dark blotch of pigment on anterior portion of spinous dorsal fin ; first anal - fin spine one - half to three - quarters length of male genital papilla ; belly naked .
there is a quite consistent count of 13 caudal - fin segmented rays in the blennioids , 7 dorsal and 6 ventral , with a variable number of procurrent rays . procurrent - ray counts usually vary within species by one , and usually there is one additional procurrent ray in the dorsal series than in the ventral series . among the labrisomids , paraclinus have the fewest , with only 4 or 5 , while starksia typically have 5 or 6 , and malacoctenus and labrisomus have 6 to 10 . although the numerical differences can be slight , the procurrent rays look distinctly more crowded in the latter genera . other blennioid families can also be distinguished : chaenopsids have few , from 3 to 5 , while the tripterygiid enneanectes have 6 to 8 .
specimens examined ranging from 12 . 0 to 19 . 0mm sl ; hl 25–32 % sl ( 32 % in holotype ) ; genital - papilla length in 15 . 0 - mm sl paratype 0 . 3 mm , one - fourth length of first anal spine ( broken ) ; papilla adhered to spine proximally . note : the presence of a small but measurable genital papilla on 15 . 0 - mm sl paratype suggests that it is a male : although female starksia sometimes have a small genital papilla , the 19 mm female holotype does not . as noted below , the 15 mm paratype has a pupil - size dark spot at posterior base of anal fin , which usually characterizes females . we tentatively recognize this paratype as a male .
comparative material . starksia lepicoelia . bahamas ( dna vouchers ) : usnm 399615 , bah 8077 ; usnm 399616 , bah 8078 ; usnm 399617 , bah 8079 . bahamas ( not dna vouchers ) : usnm 399923 , 1 specimen ; usnm 399924 , 1 ; usnm 399925 , 1 ; usnm 399926 , 1 ; usnm 399927 , 9 ; usnm 399928 , 1 ; usnm 399929 , 1 ; usnm 399930 , 1 ; usnm 399931 , 1 ; usnm 399932 , 1 ; usnm 399933 , 1 ; usnm 399934 , 1 ; usnm 399921 , 1 ; usnm 399922 , 1 ; usnm 386919 , 3 specimens ; usnm 386972 , 15 ; usnm 386383 , 1 ; usnm 386402 , 8 ; usnm 386651 , 2 ; usnm 386581 , 3 ; usnm 386500 , 4 ; usnm 387026 , 3 ; usnm 386244 , 13 ; usnm 387069 , 6 ; usnm 399618 , 1 ; usnm 399614 , 2 ; turks and caicos islands ( dna vouchers ) : usnm 399638 , tci 9291 ; usnm 399639 , tci 9292 ; usnm 399640 , tci 9293 ; usnm 399641 , tci 9294 ; usnm 399636 , tci 9112 ; turks and caicos islands ( not dna vouchers ) : usnm 399637 , 7 ; usnm 399642 , 1 . navassa island ( not dna vouchers ) : usnm 359448 , 5 ; usnm 359699 , 19 . u . s . virgin islands , st . croix ( not dna vouchers ) : uf 149809 , 11 ; uf 149815 , 33 ; uf 149814 , 10 .
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the unusual genus stathmonotus is still considered chaenopsid even though their dorsal fin is made up of all spines and they can have scales . some labrisomids of paraclinus also have a dorsal fin made up of all spines ; fortunately the larvae of the two genera are easily distinguished by morphology .
labrisomid larvae generally resemble those of the other blennioid families of reef fishes - they can be distinguished easily from larvae of the combtooth blennies ( family blenniidae ) , which have fewer dorsal - fin spines than soft rays and blunt snouts at all stages ( labrisomids have twice as many dorsal - fin spines as rays ( or more ) and pointed snouts as larvae ) . larvae of the blennioid triplefins ( family tripterygiidae ) have three separate dorsal fins and distinctive markings and the stargazers ( family dactyloscopidae ) have relatively foreshortened anterior bodies and curled - up pelvic fins .
larval labrisomids are superficially similar to the larvae of gobies and scarids , which also often have a similar anal - fin row of melanophores and are very common in collections and are about the same size as labrisomid larvae . however , those larvae notably have many fewer dorsal - fin spines , short and / or fused pelvic fins , and narrowed or oddly - shaped eyes , while later - stage labrisomids have long thread - like pelvic fins and large round eyes . larval gerreids ( mojarras ) are also common and can be mistaken for labrisomid larvae , however they have silvery abdominal linings . larval grunts ( haemulidae ) often have an anal - fin row of melanophores and can resemble earlier - stage labrisomids , but they develop a notably short anal fin and characteristic tail spots .
there is sufficient divergence in appearance among labrisomid larvae in the region to identify most later - stage larvae to species and all to the genus level . the exceptions are those species recently shown by dna sequencing to be made up of sets of closely - related species that can be hard to distinguish , even as adults ( i . e . cryptic species ) . some labrisomids , unlike most other reef fishes , have benthic eggs and short larval lives which promote reproductive isolation and genetic divergence within the region . as a result , there can be a proliferation of cryptic species and lineages and quite complex phylogeography . the larvae and juveniles of cryptic species would be expected to be almost identical and are thus pooled into a type for that species complex in the descriptions below .
the diagnosis paragraph under each species listed in the following sections describes the criteria that confirm the species designation for a larval type , usually the fin - ray counts , narrowing the possibilities to one or a few species and sometimes a morphological feature to distinguish among the remainder . of course , a dna - sequence match is the ultimate confirmation . a sequence match has been used for many of the taxa described below , indicated by the notation ( dna ) .
the analogues section briefly describes how to distinguish larvae at particular stages from other similar - appearing species , highlighting which of the characters - fin - ray counts , melanophore patterns , morphology , or various combinations thereof - are most useful for each comparison . in most cases , especially for late - stage larvae , these features can rapidly narrow down an id to the species level .
some diagnostic characters are more easily visible on larvae than on larger fishes . one of the more obscure characters that is useful for distinguishing among the numerous blennioid families and genera is the number of procurrent rays in the caudal fin . these accessory rays are defined as the non - segmented rays anterior to the large segmented caudal - fin rays . the transparency of fish larvae allows for an easy assessment of the number of procurrent caudal - fin rays . adjustment of the transmitted - light angle highlights bony tissues well . fortunately , the caudal - fin rays are usually preserved in otherwise - damaged larvae and they can provide diagnostic information for identifications when little else is available .
labrisomid larvae share , to varying degrees , a basic set of melanophores that develop progressively after hatching and are very useful for identifying larvae at least to genus and often to species . the timing of the development of each marking can be somewhat variable within a species , resulting in a variety of patterns on earlier - stage larvae that preclude a simple key to species identification . late and pre - transitional larvae typically have their full complement of larval melanophores , making identifications at these larger sizes somewhat easier . during transition , however , larval melanophores begin to disappear and metamorphic melanophore patterns develop . metamorphic melanophores consist primarily of intricate patterns of small surface melanophores , usually starting on the head and spreading over the body to form the juvenile markings . this transitional sequence is also variably timed , promoting a proliferation of intermediate melanophore complements that can easily lead to the impression of a greater number of species than are actually present .
note : a number of other melanophores are present at specific , and often diagnostic , locations on the larvae of particular species ( or groups of species ) and are discussed under the genus or species descriptions in the next sections .
these dorsal melanophores shield the brain and are near the surface , usually on the meningeal membrane or over the skull . they can best be labeled by the quadrant of the brain they overlie , i . e . the forebrain , the smaller lobes forming a triangle between the eyes , and the large midbrain ( optic ) lobes , behind the eyes (


phyllodesmium is a genus of predatory sea slugs , aeolid nudibranchs , marine gastropod molluscs in the family facelinidae .

these nudibranchs occur in the tropical indo-pacific ocean and warm temperate waters of japan , tasmania and south africa .

the nudibranchs in this genus often show extraordinary mimicry , each species very closely resembling its prey species , which are octocorals , a kind of soft coral .

some of the species are also unusual in that they are able to utilize zooxanthellae from their prey , in a symbiotic relationship that provides them with extra nutrition from photosynthesis , hence they are commonly called " solar-powered " sea slugs ( also see the sacoglossa ) .

phyllodesmium

information on phyllodesmium spp . from : delisse m . ortiz , october 7 , 1999
this species is very similar in appearance to phyllodesmium hyalinum , another species found in association with the soft coral xenia . see phyllodesmium hyalinum , for distinguishing features of the two species .
phyllodesmium poindimiei , from bare island , sydney from : n . missenden , september 19 , 2005
figure 11 : effect of phyllodesmium metabolites in different concentrations on predation by canthigaster soland . . .
phyllodesmium poindimiei ? from sydney from : p . zylstra & h . rothenfluh , june 18 , 2000
figure 12 : phylogenetic tree of octocorals relevant as putative food sources for phyllodesmium spp . phylogram . . .
phyllodesmium poindimiei is a species of sea slug , an aolid nudibranch , a marine gastropod mollusk in the family facelinidae .
phyllodesmium briareum is a species of sea slug , an aolid nudibranch , a marine gastropod mollusk in the family facelinidae .
phyllodesmium opalescens is a species of small sea slug , an aolid nudibranch , a marine gastropod mollusk in the family facelinidae .
upper : phyllodesmium crypticum angourie , northern new south wales , australia . october 1979 . length 5cm . photo : bill rudman . lower : section through a tentacle of the soft coral xenia showing the pouches of symbiotic zooxanthellae ( stained red ) . xenia is the preferred food of phyllodesmium crypticum . photo : bill rudman .
the coral nudibranch , phyllodesmium horridum , is a species of sea slug , specifically an aeolid nudibranch . it is a marine gastropod mollusc in the family facelinidae .
rudman , w . b . , 2001 ( august 9 ) phyllodesmium horridum ( macnae , 1954 ) . [ in ] sea slug forum . australian museum , sydney .
the aeolid nudibranch genus phyllodesmium ( mollusca : gastropoda ) is reviewed , three new species are described and further information on the biology , anatomy and distribution on the eight previously known species is reported . the genus ennoia bergh , 1896 is considered a synonym of phyllodesmium and the type species ennoia briareus redescribed . the genus phyllodesmium is unique amongst the aeolids in feeding on octocoral cnidarians . this has led to the evolution of nudibranch - zooxanthellae symbioses , zooanthellae being obtained from the octocoral prey . the adaptations developed throughout the genus are described and possible relationships between the species proposed .
more information : moore , elizabeth and terrence gosliner . 2014 . additions to the genus phyllodesmium , with a phylogenetic analysis and its implications to the evolution of symbiosis . the veliger 51 : 237 - 251 .
as its name suggests , phyllodesmium crypticum is a very cryptic species , well - camouflaged amongst the colonies of the soft - coral xenia in which it lives and on which it feeds . this is another of the many species of aeolid which store zooxanthellae from their food , presumably obtaining nourishment when they photosynthesise . the large sacs of zooxanthellae found in the tentacles of xenia are clearly the source of phyllodesmium ' s zooxanthellae .
rudman w . b . ( 1991 ) further studies on the taxonomy and biology of the octocoral - feeding genus phyllodesmium ehrenberg , 1831 ( nudibranchia : aeolidoidea ) . journal of molluscan studies 57 : 167 - 203
baba , k . ( 1991 ) taxonomical study on some species of the genus phyllodesmium from cape muroto - misaki , shikoku and okinawa province , southern japan ( nudibranchia : facelinidae ) . venus , 50 , 109–123 .
rudman , w . b . ( 1991 ) further studies on the taxonomy and biology of the octocoral - feeding genus phyllodesmium ehrenberg , 1831 ( nudibranchia , aeolidacea ) . journal of molluscan studies , 57 , 167–203 .
rudman w . b . ( 1991 ) further studies on the taxonomy and biology of the octocoral - feeding genus phyllodesmium ehrenberg , 1831 ( nudibranchia : aeolidoidea ) . journal of molluscan studies 57 : 167 - 203 .
dear ingo , sorry it has taken me a while to post this message . it is indeed a spectacular xenia mimic , perhaps not quite as good as phyllodesmium sp . 11 , but almost . best wishes , bill rudman
moore e . & gosliner t . ( 2014 ) . additions to the genus phyllodesmium , with a phylogenetic analysis and its implications to the evolution of symbiosis . the veliger . 51 ( 4 ) : 237 - 251 . [ details ]
phyllodesmium briareum , like other species of phyllodesmium , feeds on soft corals and is very well camouflaged when crawling over or nestled between the polyps of the doft coral it is feeding on . it is reported to feed on a number of species of briareid soft coral including solenopodium stelleri and briareum stecheri ( sensu macfadyen , 1936 ) . it is also reported from pachyclavularia violacea a mat forming soft coral with purplish trunks and greenish brown polyps ( see rie nakano ' s message below ) .
rudman , w . b . ( 1991 ) . further studies on the taxonomy and biology of the octocoral - feeding genus phyllodesmium ehrenberg , 1831 ( nudibranchia : aeolidoidea ) . journal of molluscan studies . 57 : 167 - 203 . [ details ]
rudman w . b . ( 1991 ) .
further studies on the taxonomy and biology of the octocoral - feeding genus phyllodesmium ehrenberg , 1831 ( nudibranchia : aeolidacea )
. journal of molluscan studies 57 ( 2 ) : 167–203 . abstract .
burghardt i . & goslinert . m . 2006 . phyllodesmium rudmani ( mollusca : nudibranchia : aeolidoidea ) , a new solar powered species from the indo - west pacific with data on its symbiosis with zooxanthellae . zootaxa 1308 : 31 - 47 [ details ]
graceful
solar - powered
phyllodesmium sp . nudibranch in the surge . raja ampat . these are very difficult to spot if they are not moving . it is hard to imagine how they make any forward progress . i love to watch them try !
ortiz , d . m . & gosliner , t . m . ( 2003 ) a new species of phyllodesmium ehrenberg , 1831 ( mollusca , nudibranchia ) from the tropical indo - pacific . proceedings of the california academy of sciences , 54 , 161–168 .
reference : • rudman , w . b . ( 1991 ) further studies on the taxonomy and biology of the octocoral - feeding genus phyllodesmium ehrenberg , 1831 ( nudibranchia : aeolidoidea ) . journal of molluscan studies , 57 ( 2 ) : 167 - 203 .
avila , c . , ballesteros , m . , slattery , m . & paul , v . j . ( 1998 ) phyllodesmium guamensis ( nudibranchia , aeolidoidea ) , a new species from guam ( micronesia ) . journal of molluscan studies , 64 , 147–160 .
burghardt , i . and wägele , h . ( 2004 ) a new solar powered species of the genus phyllodesmium ehrenberg , 1831 ( mollusca : nudibranchia : aeolidoidea ) from indonesia with analysis of its photosynthetic activity and notes on biology . zootaxa , 596 : 1 - 18 .
moore e . & gosliner t . ( 2014 ) . additions to the genus phyllodesmium , with a phylogenetic analysis and its implications to the evolution of symbiosis . the veliger . 51 ( 4 ) : 237 - 251 . page ( s ) : 238 - 242 [ details ]
( of ennoia bergh , 1896 ) rudman , w . b . ( 1991 ) . further studies on the taxonomy and biology of the octocoral - feeding genus phyllodesmium ehrenberg , 1831 ( nudibranchia : aeolidoidea ) . journal of molluscan studies . 57 : 167 - 203 . [ details ]
( of myrrhine bergh , 1905 ) rudman , w . b . ( 1991 ) . further studies on the taxonomy and biology of the octocoral - feeding genus phyllodesmium ehrenberg , 1831 ( nudibranchia : aeolidoidea ) . journal of molluscan studies . 57 : 167 - 203 . [ details ]
phyllodesmium jakobsenae is another species of phyllodesmium which lives in , feeds on , and mimics the soft coral xenia by the shape and colour of its cerata . it is solar - powered , retaining some of the soft corals zooxanthellae which continue to photosynthesise in the ceratal digestive gland cells . probably the most characteristic external feature of this species is the shape of the cerata , which have a basal cylindrical , stalk - like , region which becomes broader and flatter toward the tip . in this upper region there is a central pale vein - like region flanked on each side by a broad brown flattened blade . on the upper , sunlit , side of the blade are spherical structures in which the zooxanthellae are ' farmed ' . of the phyllodesmium which farm photosynthesising zooxanthellae , this is the only one we know that has no branching of the digestive gland in the body wall . it is reported to grow to 30 mm in length .
dear bill , i would like to provide the forum some pictures and info about the new phyllodesmium species that heike wägele and i described last year . phyllodesmium jakobsenae is a
solar - powered
species and is very cryptic . it lives in xenia soft corals and its cerata mimic the polyps of xenia . p . jakobsenae feeds on the soft coral and retains some of the corals ' zooxanthellae photosynthetic active inside their digestive glandular cells ( for further details see our publication ) . we only found them close to bunaken island / sulawesi , but i ' ve heard that some people also found them in the philippines , so it might have a wider distribution .
burghardt i . , schrödl m . & wägele h . 2008 . three new solar powered species of the genus phyllodesmium ehrenberg , 1831 ( mollusca : nudibranchia : aeolidoidea ) from the tropical indopacific with analysis of their photosynthetic activity and notes on biology . journal of molluscan studies , 74 ( 3 ) : 277 - 292 [ details ]
this is one of the species of phyllodesmium that does not harbour zooxanthellae in its tissues . the colour of the digestive glands ducts in the cerata is a deep pink in specimens i have observed . it has been found feeding on the telestacean soft coral carijoa . note the branching in the digestive gland ducts , a common feature in species of the genus .
defense strategy using sequestered soft coral metabolites has been discussed for the members of the genus phyllodesmium , however , there are only few studies supporting this hypothesis . besides our earlier study [ 12 ] reporting a feeding deterrent activity of 4 - oxochatancin ( 16 ) , only a study by slattery et al . [ 15 ] could show an antifeedant effect of a secondary metabolite sequestered by phyllodesmium . in the latter study , acetoxypukalide , which was sequestered by p . guamensis from its prey corals sinularia spp . , successfully deterred the omnivorous pufferfish canthigaster solandri under laboratory conditions at 0 . 5 % of dry mass in artificial food . the concentration chosen was at least an order of magnitude lower , than found in the body tissues of p . guamensis .
as you will see from the bernard picton ' s photo on the right , p . briareum is one of the species of phyllodesmium which has a symbiotic relationship with zooxanthella . the rows of brown specks in the photo are one - celled plants [ zooxanthellae ] which are nurtured in specialised ducts of the aeolid ' s digestive gland , where they continue to grow , reproduce and photosynthesise , providing nutrients for the aeolid .
in our former study in 2014 , relying on uplc - hrms data only , we assumed that isosarcophines 8 and 9 and sarcophytonin b ( 6 ) could be present in the p . longicirrum extract . in the current investigation we were able to isolate these metabolites and demonstrate the informative value of the preliminary uplc–hrms analysis . further investigations on alcyonacean and / or phyllodesmium chemistry may thus lead to the isolation and full characterization of the putative biscembranoids .
references : • rudman , w . b . ( 1981 ) the anatomy and biology of alcyonarian feeding aeolid opisthobranch molluscs and their development of symbiosis with zooxanthellae . zoological journal of the linnean society , 72 : 219 - 262 . • rudman , w . b . ( 1991 ) further studies on the taxonomy and biology of the octocoral - feeding genus phyllodesmium ehrenberg , 1831 ( nudibranchia : aeolidoidea ) . journal of molluscan studies , 57 ( 2 ) : 167 - 203 .
wagner d . , kahng s . e . & toonen r . j . ( 2009 ) .
observations on the life history and feeding ecology of a specialized nudibranch predator ( phyllodesmium poindimiei ) , with implications for biocontrol of an invasive octocoral ( carijoa riisei ) in hawaii
. journal of experimental marine biology and ecology 372 ( 1 - 2 ) : 64 - 74 . doi : 10 . 1016 / j . jembe . 2009 . 02 . 007 . pdf .
fish may represent the main , however not the only potential predation threat to slugs . the omnivorous echinodermata , crustacea and cephalopoda could also consider phyllodesmium as possible prey . whether the compounds , proven defensive against fish predation in this study function as deterrents towards other organisms , has yet to be shown . even if the furanocembranoids represent the protection against omnivorous fish , it is possible that some of the numerous secondary metabolites found in this study could be useful against a wider range of predators .
figure 11 : effect of phyllodesmium metabolites in different concentrations on predation by canthigaster solandri ( n = 8–40 , depending on availability ) . experiments were repeated twice with compounds 10–12 in all tested concentrations , twice with 16 at 1 % and 2 % and three times at 0 . 5 % . mean values with sd are displayed . significance of deterrence was shown with fisher´s exact test ( p < 0 . 05 for 10 , 12 and 16 , calculated for each trial separately ) . control pellets were 100 % eaten for each trial .
only few chemical investigations were undertaken on phyllodesmium species [ 10 - 15 ] , describing mostly terpenoid secondary metabolites . indirect evidence suggests that these compounds are sequestered from the respective octocorallian prey organisms . in rare cases , the ecological function of some of these metabolites as deterrent agents was demonstrated , e . g . , acetoxypukalide from p . guamensis [ 15 ] and 4 - oxochatancin ( 16 ) in p . longicirrum [ 12 ] were shown to cause a significant feeding deterrence under laboratory conditions at concentration levels below natural abundance in the sea slug bodies .
in summary , chemical investigation of a single large p . longicirrum specimen resulted in isolation of 19 secondary metabolites of terpenoid origin . taking the metabolites detected by uplc–hrms analysis also into account , p . longicirrum demonstrates an unprecedented level of secondary metabolite diversity . the herein studied p . longicirrum sequesters its secondary metabolites most probably from the chemistry - rich s . glaucum species complex , in contrary to a previously reported investigated p . longicirrum . the defensive role of the major diterpenoid constituents ( 10 , 12 and 16 ) as feeding deterrent agents against tropical omnivorous fish c . solandri was shown in laboratory assays , providing further strong evidence for the use of chemical protection strategy within the scarcely investigated aeolidoidean genus phyllodesmium .
references : • coll , j . c . , bowden , b . f . , tapiolas , d . m . , willis , r . h . , djura , p . . streamer , m . & trott , l . ( 1985 ) studies of australian soft corals - xxxv . the terpenoid chemistry of soft corals and its implications . tetrahedron , 41 ( 6 ) : 1085 - 1092 . • rudman , w . b . ( 1981 ) the anatomy and biology of alcyonarian feeding aeolid opisthobranch molluscs and their development of symbiosis with zooxanthellae . zoological journal of the linnean society , 72 : 219 - 262 . • rudman , w . b . ( 1991 ) further studies on the taxonomy and biology of the octocoral - feeding genus phyllodesmium ehrenberg , 1831 ( nudibranchia : aeolidoidea ) . journal of molluscan studies , 57 ( 2 ) : 167 - 203 .
figure 12 : phylogenetic tree of octocorals relevant as putative food sources for phyllodesmium spp . phylogram of sarcophyton and lobophytum , based on a consensus phylogram of mcfadden et al . [ 54 ] . only the sarcophyton clade with species investigated with regard to secondary metabolites are given in detail . the two other clades from the original phylogram are only indicated ; lobophytum and the mixed clade consisting of sarcophyton and lobophytum species . numbers indicate the number of specimens that represent the respective branch . note that the single specimen of s . cherbonnieri groups with 4 specimens of s . glaucum . s . glaucum is not monophyletic , but is represented with several independent clades . the dots at the terminal branches of s . glaucum in the tree indicate that secondary metabolites are described from this species , but it is not known , from which clade . species in bold indicate that secondary metabolites were described .
phyllodesmium longicirrum is the largest aeolidoidean species known to date , and extremely rich in terpenoid chemistry . herein we report the isolation of a total of 19 secondary metabolites from a single specimen of this species , i . e . , steroids 1–4 , cembranoid diterpenes 5–13 , complex biscembranoids 14 and 15 , and the chatancin - type diterpenes 16–19 . these compounds resemble those from soft corals of the genus sarcophyton , of which to date , however , only s . trocheliophorum is described as a food source for p . longicirrum . fish feeding deterrent activity was determined using the tropical puffer fish canthigaster solandri , and showed activity for ( 2 s ) - isosarcophytoxide ( 10 ) , cembranoid bisepoxide 12 and 4 - oxochatancin ( 16 ) . determining the metabolome of p . longicirrum and its bioactivity , makes it evident that this seemingly vulnerable soft bodied animal is well protected from fish by its chemical arsenal .
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upper : the sacoglossan placida cf . dendritica showing the green network of ducts which contain the green chloroplasts from its algal food . lower : the aeolid nudibranch pteraeolidia ianthina which
farms
colonies of brown single - celled algae ( zooxanthellae ) in its body . photos : bill rudman .
for further information : • zooxanthellae symbiosis references . • zooxanthellae - what are they ? • zooxanthellae - in cnidarians • zooxanthellae - in nudibranchs • chloroplast symbiosis references . • aspects of coral feeding • chloroplast symbiosis research • sacoglossan feeding • feeding on palythoa
rudman , w . b . , 1998 ( october 11 ) solar - powered sea slugs .
' solar - powered ' sea slugs from : caroline r . cripe , september 4 , 2001
the solar - powered ' ruffled sea slug ' from : molly e . hagan , december 5 , 1999
nudibranchs in symbiosis with zooxanthellae from : j . e . austin , november 9 , 1998
your
solar - powered
sea slugs . from : amanda lindsey , october 11 , 1998
zooxanthellae in nudibranchs from : j . e . austin , october 11 , 1998
ehrenberg c . g . ( 1828 - 1831 ) . in : f . g . hemprich & c . g . ehrenberg , symbolae physicae seu icones et descriptiones animalium evertebratorum sepositis insectis quae ex itinere per africam borealem et asiam occidentalem , novae aut illustrate redierunt . decas i mollusca . berlin . vol . 1 ( plates ) [ 1828 ] , vol . 2 ( text , 126 pp . ) [ 1831 ] . , available online at urltoken page ( s ) : folio h [ page 3 ] [ details ]
( of ennoia bergh , 1896 ) bergh , l . s . r . ( 1896 ) . eolidiens d ' amboine . revue suisse de zoologie . 4 ( 2 ) : 385 - 394 . , available online at urltoken page ( s ) : 392 [ details ]
( of myrrhine bergh , 1905 ) bergh , l . s . r . ( 1905 ) . die opisthobranchiata der siboga - expedition . siboga - expeditie . 50 : 1 - 248 , pls 1 - 20 . , available online at urltoken page ( s ) : 226 [ details ]
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upper : southern end of sek island , madang , march 1987 . [ 20mm long preserved - wam391 - 87 ] . photo : f . e . wells , lower : closeup of animals showing the development of ducts in the body wall and cerata to nurture zooxanthellae , which can be seen as lines of brown specks . animal 25mm long alive , tambuli beach , mactan is , cebu , 20m , march 1983 , on solenopodium stelleri ( fam : briareidae ) philippines , march 1983 . photo : b . e . picton
the name briareus was apparently given to it by bergh because of its association with the soft coral briareum .
known from tropical eastern australia , but possibly more widely spread in the western pacific .
reference : • rudman , w . b . ( 1981 ) the anatomy and biology of alcyonarian - feeding aeolid opisthobranch molluscs and their development of symbiosis with zooxanthellae . zoological journal of the linnean society 72 : 219 - 262 .
how it made the top 10 : for this sea slug , the top 10 competition was more than a beauty contest . it is a “missing link” between sea slugs that feed on hydroids and those specializing on corals . gastropods do not get more photogenic than sea slugs whose graceful lines and vivid coloration make them beauties of the deep . this new species , which photographs in shades of blue , red and gold , also contributed to a better understanding of the origin of an unusual symbiosis in other species of the genus . related sea slugs have multi - branched guts in which algae called zooanthellae live . these algae have a primary symbiotic relationship with the corals on which the sea slugs feed . once sequestered in the gut , the photosynthetic algae produce nutrients of benefit to the host . the newly identified species is an inch long , more or less ( 17 - 28 mm ) , and resides in the japanese islands .
etymology : the name refers to the spiny appearance of papillae on the surface of the rhinophores or paired smelling organs at front end of body .
esf is committed to the accessibilty of all online materials . if you have any issues , contact web @ urltoken for a prompt solution .
burn , r . f . ( 2006 ) . a checklist and bibliography of the opisthobranchia ( mollusca : gastropoda ) of victoria and the bass strait area , south - eastern australia . museum victoria science reports . 10 : 1–42 . , available online at urltoken [ details ]
to biodiversity heritage library ( 4 publications ) to biological information system for marine life ( bismal ) to encyclopedia of life to sea slug forum ( via archive . org )
right : animal ( 10cm long ) crawling over porites colony . indonesia . lower left : ceras showing the white ducts of the digestive gland radiating out to the brown
gardens
of symbiotic zooxanthellae . photo : bill rudman . lower right : section through the a ceras showing the ducts leading to the zooxanthellae
gardens
at the surface of the ceras . ( zooxanthellae stained red . ) photo : bill rudman .
bunaken island , north sulawesi , indonesia . intertidal . length : up to 30 mm . 12 july 2003 . intertifal coral reef with patches of sea grass . lower photo showing animal nestling in xenia colony . photographer : michael schrödl
la perouse , sydney , new south wales , australia , august 1979 . photo : john fields .
this article is part of the thematic series
lipids : fatty acids and derivatives , polyketides and isoprenoids
.
marine gastropods , of which approximately 150 . 000 are known , mostly are protected by a shell . however , shell reduction or even loss is common within several marine heterobranchia clades , which were united under the name opisthobranchia in former times [ 1 ] . to compensate this lack of physical protection , alternative defensive strategies , such as the production of calcareous needles or acidic sulfates , and sequestration or de novo synthesis of toxic metabolites emerged within the opisthobranch taxa [ 2 - 5 ] . adaptations and mimicry , which help to hide in habitats is frequent in marine gastropods , as obvious from very diverse and spectacular phenotypes [ 1 , 6 ] .
herein we report on the secondary metabolome of a single specimen of p . longicirrum , including the structure elucidation of the new metabolites 1 , 5 , 9 , 14 and 15 , and show the fish feeding deterrent activity of the major metabolites 10 and 12 .
from the ethanolic extract of p . longicirrum the ethyl acetate - soluble organic compounds were analyzed . a first fractionation was achieved by vacuum liquid chromatography ( vlc ) on reversed - phase material yielding 11 fractions . 1 h nmr analysis of these indicated the presence of chemically diverse secondary metabolites in the major fractions 3–8 , whereas the hydrophilic fractions 1 and 2 merely contained sugars and the lipophilic ones , i . e . , 9–11 simple lipids .
detailed uplc–hrms investigation was thus performed with the vlc fractions 3–8 . the resulting uplc chromatograms ( supporting information file 1 , figures s47–52 ) were extremely complex and gave an impression on the multi - faceted metabolome of this animal . the majority ( except 4 and 17 ) of the subsequently isolated and characterized secondary metabolites ( 1 – 19 , figure 1 ) could be assigned to the detected m / z values ( supporting information file 1 , table s7a ) , e . g . , prominent ms data were associated with the presence of metabolites with a molecular weight of 362 da , relating to 4 - oxochatancin ( 16 ) or 1 - oxo - 9 - hydroisochatancin ( 18 ) . peaks with retention times around 14 min in the chromatograms of vlc 5 and 6 contained a metabolite showing an m / z of 319 . 23 ( m + h ) and 341 . 21 ( m + na ) , which indicated the presence of bisepoxide 12 , having a molecular weight of 318 . 45 da . a mass charge ratio of 475 . 39 ( m + h − h 2 o ) and 493 . 39 ( m + h ) , found for the peak with a retention time of 14 . 7 min of the uplc - chromatogram of vlc fraction 7 , is characteristic for the secosteroid 1 or the polyhydroxylated steroid 4 , both with a molecular weight of 492 da .
more importantly , uplc–hrms investigations produced also some peaks with m / z values that cannot be linked to isolated compounds 1 – 19 . thus , in vlc fraction 7 and 8 an m / z value of 287 . 24 ( m + h ) indicates most probably the presence of the instable sarcophytonin a with a molecular weight of 286 . 23 da [ 16 ] . vlc fractions 7 and 8 also contain m / z values characteristic for steroid constituents of sarcophyton soft corals that could not be isolated in the current study , e . g . , m / z 397 . 35 ( m + h ) suggests the presence of a steroid compound reported by kobayashi et al . from sarcophyton glaucum [ 17 ] with a molecular mass of 396 da as outlined in table s7b ( supporting information file 1 ) . detailed analysis of the uplc–hrms data also revealed the presence of m / z 711 . 39 ( m + h ) and 669 . 44 ( m + h ) in vlc fractions 6 and 7 . these values would fit to not yet reported biscembranoids , containing compound 5 as a possible biogenetic precursor , with a suggested molecular mass of 710 and 668 da ( see supporting information file 1 , table s7b ) .
notable is the occurrence of numerous peaks containing m / z values attributable to isomers of the isolated metabolites . besides the isosarcophines 8 and 9 with a molecular weight of 316 da , m / z values 317 . 21 ( m + h ) were also detected in the chromatograms of the fractions vlc 6 and 7 in different chromatographic peaks ( t r : 12 . 0 , 12 . 7 , 14 . 0 , 15 . 9 min ) indicating the presence of further possible cembranoid isomers as shown in table s7a ( supporting information file 1 ) . the m / z values ( m + h , 739 . 44 ) attributable to the isobisglaucumlides b ( 14 ) and c ( 15 ) are also found at four different retention times of the uplc chromatograms , suggesting the presence of the further isomeric metabolites . these findings highlight the amazingly complex and diverse metabolome of p . longicirrum .
regarding the reported secondary metabolites of p . longicirrum 20–22 , figure 2 by coll et al . [ 13 ] , only compound 22 with a molecular weight of 304 da resulting in an m / z of 305 . 25 ( m + h ) may be present in vlc 8 ( see supporting information file 1 , figure s7b ) . however , there are about 20 further cembranoids described from sarcophyton spp . with a molecular weight of 304 da , making this assessment very tentative . it can , however be stated that the p . longicirrum specimen investigated in this study either belongs to a different chemotype or has different food preference than the one investigated by coll and co - workers [ 13 ] .
figure 2 : structures of secondary metabolites from p . longicirrum as described by coll et al . in 1985 [ 13 ] .
figure 2 : structures of secondary metabolites from p . longicirrum as described by coll et al . in 1985 [ 13 ] .
detailed chemical investigation of p . longicirrum including structure elucidation of the new metabolites 1 , 5 , 9 , 14 , 15 and stereochemical assignment of 12
repeated fractionation of vlc fractions 5–8 resulted in the isolation of a range of secondary metabolites , i . e . , four steroids 1–4 , nine cembranoid diterpenes 5–13 and two biscembranoids 14 and 15 , as well as four polycyclic diterpenes of the chatancin type 16–19 [ 12 ] . compounds 1 and 5 are new chemical structures . the same applies to the biscembranoids 14 and 15 , which however show close resemblance to bisglaucumlides b and c [ 18 ] , but differ in their stereochemistry from the latter . since no studies regarding the stereochemical features of the cembranoid bisepoxide 12 were published to date , we propose here its relative configuration . figure 1 summarizes all metabolites found during this investigation . it is noteworthy , that the previously reported cembranoid diterpenes ( see figure 2 , compounds 20–22 ) from p . longicirrum by coll et al . [ 13 ] were not isolated from the complex secondary metabolome of the investigated specimen , although the uplc–hrms data ( see above ) suggest that cembranoid alcohol 22 may be present .
compound 1 was isolated as amorphous white solid . the specific optical rotation was measured in chloroform ( c 0 . 1 ) , giving [ α ] d 20 −21 . 0 . the molecular formula c 30 h 52 o 5 was established by a hrms measurement , which yielded m / z 515 . 3694 [ m + na ] for the molecular ion . the ring double bond equivalent ( rde ) was calculated to be five . the ir spectrum revealed the presence of hydroxy groups ( broad band at 3360 cm −1 ) and a keto function ( sharp band at 1697 cm −1 ) .
the planar structure of 1 was established by extensive nmr experiments ( 1 h , 13 c nmr , cosy , dept , hsqc and hmbc ( see supporting information file 1 , table s1 ) . the 13 c nmr spectrum showed 30 resonances attributable to 7 methyl , 9 methylene and 8 methine groups . a 13 c nmr resonance at 218 . 4 ppm confirmed the keto group ( c - 9 ) , whereas a primary alcohol moiety was evident from a 13 c nmr resonance at δ c 59 . 1 ( c - 11 ) . further oxygenated carbons , i . e . , c - 3 , c - 5 and c - 6 gave rise to 13 c nmr resonances at δ c 68 . 0 , 80 . 7 and 75 . 7 , respectively . proton carbon assignments were done according to correlations obtained in a hsqc experiment . the absence of 13 c nmr resonances for sp 2 hybridized carbons for c = c bonds , together with a rde of five indicated the presence of several rings in 1 , likely of steroid origin . the latter is supported by characteristically shielded 1 h nmr resonances at δ h 0 . 54 and δ h −0 . 05 ( both dd , h 2 - 30 ) as well as a multiplet at δ h 0 . 32 ( h - 22 ) for a cyclopropyl group , as typically found in gorgosterols [ 19 , 20 ] .
a 1 h , 1 h cosy experiment led to partial structures which could be combined using hmbc correlations . spin system a included h 2 - 1 to h 2 - 4 , whereas h - 6 through to h - 30 formed spin system b ( see figure 3 ) . the connection of partial structures a and b was established from hmbc correlations , i . e . , from the resonances of h - 4 to c - 5 and c - 6 , as well as h - 6 to c - 5 . the position of the c - 9 ketone function was established due to hmbc correlations from resonances of h 2 - 7 and h - 8 to c - 9 . the decaline system was finally confirmed by the heteronuclear long range correlations of the resonances from h 3 - 19 . of the five degrees of unsaturation one is ascribed to a keto function , another one to the cyclopropane ring in the side chain , and two further ones to the decaline ring , thus requiring a further ring in 1 . considering this , a secosterol backbone was likely . also , the 13 c nmr resonance of the oxygenated methylene at δ c 59 . 1 ( c - 11 ) is characteristic for marine - derived secosterols [ 21 ] . the 1 h - 1 h spin system c only including h 2 - 11 and h 2 - 12 was connected to the partial structure b via long range correlations from h 3 - 18 to c - 12 , c - 13 , c - 14 and c - 17 . this also established the still required ring d . finally , the complete gorgosterol side chain could be elucidated by connection of the 1 h , 1 h spin system d with b using hmbc correlations from h 3 - 28 to c - 23 and from h 3 - 29 to c - 22 , c - 23 , c - 24 and c - 30 ( see figure 3 ) .
figure 3 : significant 1 h , 1 h cosy correlations as found in compound 1 .
the nmr data ( supporting information file 1 , table s1 ) of compound 1 resembled most closely those of epoxy - secosterols isolated from the gorgonian pseudopterogorgia americana [ 22 ] and from the soft coral pachyclavularia violacea ( now briareum violaceum [ 23 ] ) by anta et al . ( [ 24 ] , figure 4 ) . however , the 13 c nmr chemical shifts of c - 5 and c - 6 in compound 1 ( δ c 80 . 7 and δ c 75 . 7 , respectively ) differ from shifts for the equivalent carbons in epoxy - secogorgosterol reported by naz et al . ( δ c 61 . 0 and δ c 60 . 4 , respectively ; [ 22 ] ) and from those of the epoxy - secosterol reported by anta et al . ( δ c 65 . 5 and δ c 58 . 1 , respectively ; [ 24 ] ) . the downfield shift , observed for these carbons in 1 , results from the cleavage of the epoxide ring , and 13 c values around δ c 70–80 as observed for 1 are characteristic for hydroxylated carbons .
figure 4 : secosterols [ 22 , 24 ] related to 3β , 5α , 6β - trihydroxy - 9 - oxo - 9 , 11 - secogorgostan - 11 - ol ( 1 ) from p . longicirrum .
the relative stereochemistry of the secogorgosterol 1 was established by analysis of 1 h , 1 h coupling constants , noesy data , and comparison of nmr spectral data with those of similar compounds [ 22 , 24 ] . an equatorial orientation of the oh - group at c - 3 was evident , since h - 3 displayed 1 h , 1 h coupling constants to the vicinal axial h - 2β and h - 4β of 12 hz and to the equatorial h - 2α and h - 4α of 6 hz . noe correlations of h - 3 to h - 1α , h - 2α and h - 4α indicate thus an α - orientation of axial h - 3 and a β - orientation of the equatorial hydroxy group at c - 3 . the identical 13 c nmr shift of c - 3 ( δ c 68 . 0 ) with the reported value [ 24 ] supports this orientation .
1 h nmr measurements in pyridine - d 5 led to a further downfield shift of the deshielded h - 3 resonance to δ h 4 . 81 ( compared with δ h 4 . 00 in meoh - d 4 ) . this shift is explained by a 1 , 3 axial–axial interaction with the 5α hydroxy group [ 25 , 26 ] , demonstrating the α - orientation of the substituent at the bridge head carbon c - 5 . noes between the resonances for h - 2β as well as h - 1β to h 3 - 19 showed the latter to be β - orientated , and thus the trans configuration of the decaline system . the 1 h nmr signal at δ h 3 . 66 for h - 6 exhibited noe correlation with h - 4α ( δ h 1 . 70 , m ) indicating β - orientation of the equatorial oh - group at c - 6 . contrary to the reported epoxy - secosteroid by naz et al . [ 22 ] , no noe was observed between the resonances of h - 6 and β - oriented h 3 - 19 confirming the β - orientation of the hydroxy group at c - 6 ( see figure 5 ) .
figure 5 : conformational structure of 1 ( key noesy correlations are indicated with blue arrows ; coupling constants crucial for the determination of the orientation of the 3 - oh group are shown ) .
figure 5 : conformational structure of 1 ( key noesy correlations are indicated with blue arrows ; coupling cons . . .
noe correlations between h 3 - 19 and h - 8 , as well as between h - 8 and h 3 - 18 showed the β - orientation of the methyl groups ch 3 - 18 , ch 3 - 19 and of the proton at c - 8 , which is in accordance with reported stereochemistry for the related metabolites of this compound - class [ 21 , 22 ] . free rotation along the bond between c - 8 and c - 14 is unlikely because of the bulky substituents on ring d . noe correlations were observed between α - oriented h - 14 and h - 17 demonstrating β - orientation of the gorgosterol side chain . 13 c nmr shifts for the carbons of the side chain ( c - 20 to c - 30 : δ c 36 . 3 , 21 . 4 , 33 . 3 , 26 . 9 , 52 . 2 , 33 . 4 , 22 . 7 , 21 . 9 , 15 . 8 , 14 . 7 , 22 . 2 ) were almost identical with those reported by naz et al . ( c - 20 to c - 30 : δ c 34 . 9 , 20 . 8 , 31 . 9 , 25 . 9 , 50 . 5 , 31 . 4 , 22 . 3 , 21 . 5 , 15 . 2 , 14 . 2 , 21 . 2 ) [ 22 ] . the relative stereochemistry of the gorgosterol side chain was thus suggested to be the same . for the compound 1 we propose the name 3β , 5α , 6β - trihydroxy - 9 - oxo - 9 , 11 - secogorgostan - 11 - ol .
chemical structures of the polyhydroxylated steroids 2 – 4 were established by comparison of the nmr and ms data obtained in our laboratory ( supporting information file 1 , figures s6–11 ) with the reported values [ 27 , 28 ] .
compound 5 was isolated as colorless oil ( 1 . 5 mg ) . the specific optical rotation was measured in chloroform ( c 0 . 09 ) , and yielded [ α ] d 20 + 3 . 5 . the molecular formula of compound 5 was deduced by hrms–esi ( m + na 355 . 2244 da ) to be c 21 h 32 o 3 . ring double bond equivalents ( rde ) were calculated to be six . the ir spectrum of compound 5 showed absorptions for carbonyl bonds at 1700 cm −1 and 1679 cm −1 , indicating the presence of ketone and / or ester functions .
extensive nmr measurements ( 1 h , 13 c nmr , cosy , dept , hsqc and hmbc , see supporting information file 1 , table s2 ) revealed the presence of a methoxy group ( δ h 3 . 71 3h , δ c 52 . 1 ) , an ester carbonyl ( δ c 170 . 0 , c - 18 ) and a keto group ( δ c 211 . 3 , c - 2 ) . the 13 c nmr spectrum of compound 5 contained a total of 21 resonances attributable to 5 methyl , 6 methylene , 5 methine and 5 quaternary carbons as indicated by a dept 135 experiment . six characteristic shifts in the 13 c nmr spectrum at δ c 130 . 5 ( c - 4 ) and 142 . 8 ( c - 5 ) , 121 . 6 ( c - 7 ) and 136 . 9 ( c - 8 ) , 127 . 0 ( c - 11 ) and 135 . 4 ( c - 12 ) pointed towards three carbon–carbon double bonds . together with two carbonyls ( at c - 2 and c - 18 ) one rde accountable to a ring remained , and suggested a cembrane - class diterpene .
the proton resonances could be unambiguously assigned to those of directly attached carbons by a hsqc measurement , and afterwards the fragments of the molecule were elucidated using a cosy experiment . thus , the cosy data showed correlations of the resonances h 3 - 16 , h 3 - 17 and h - 1 to h - 15 , forming an isopropyl moiety . together with cosy correlations from h - 1 over h 2 - 14 to h 2 - 13 spin system a was established . two further smaller fragments were established via cosy correlations from h - 5 to h - 7 ( b ) , and from h - 9 to h - 11 ( c ) . these subunits could be assigned to a 14 - membered cembrane skeleton according to couplings detected in the hmbc experiment . key heteronuclear long range correlations for assembling the complete structure were from h 3 - 20 to c - 11 , c - 12 and c - 13 connecting fragments a and c . the fragments b and c were then connected according to hmbc cross peaks of the methyl group resonance h 3 - 19 with quaternary c - 8 and with c - 7 and c - 9 ( see figure 6 ) .
figure 6 : structure of cembranoid 5 . 1 h , 1 h spin systems ( a , b and c ) are indicated in bold , arrows show key hmbc correlations .
figure 6 : structure of cembranoid 5 . 1 h , 1 h spin systems ( a , b and c ) are indicated in bold , arrows show key h . . .
the absence of a further 1 h , 1 h spin system required heteronuclear long range correlations for the elucidation of the remaining structural features and the closure of the cembrane ring . methylene group ch 2 - 3 exhibited hmbc correlations with resonances of the keto at c - 2 , sp 2 quaternary carbon c - 4 and tertiary carbon c - 5 and with the ester carbonyl c - 18 . due to the deshielded nature and large 1 h - coupling constant ( signals of both protons appear as doublets , j = 17 . 7 hz at δ h 3 . 49 and 3 . 64 ) of the 1 h nmr resonance of the h 2 - 3 , the position of the methylene group between keto carbonyl c - 2 and the quaternary sp 2 carbon c - 4 was very likely . the methyl ester moiety could be localized at c - 4 due to long range correlation of the - och 3 resonance with ester carbonyl c - 18 and quaternary c - 4 . a hmbc cross peak between the resonances of h - 1 and c - 2 established the 14 - membered cembranoid ring .
the e - geometries at olefinic double bonds δ 7 , 8 and δ 11 , 12 were easily deduced from the 13 c nmr upfield shifts of the methyl group resonances ch 3 - 19 ( δ c 16 . 0 ) and ch 3 - 20 ( δ c 15 . 2 ) . the deshielded resonance of h - 5 ( δ h 7 . 08 ) indicated e - geometry of the olefinic double bond δ 4 , 5 [ 29 ] .
figure 7 : compound 5 and the most closely related cembranoids from soft corals .
known compounds 6–8 , 10 , 11 and 13 were unambiguously identified comparing the obtained 1 h and 13 c nmr spectral data with the literature reports [ 31 - 36 ] .
repeated hplc separation of vlc fraction 7 firstly led to two metabolites , which could not be structurally analyzed due to their instability . it was noted however , that two stable degradation products resulted and could be isolated , i . e . , compounds 8 and 9 . the planar structure of 8 and 9 was established as that of isosarcophine by 1d and 2d nmr data ( 1 h , 13 c , cosy , hsqc and hmbc ) . specific optical rotation measurements in chloroform ( c 0 . 1 each substance ) yielded [ α ] d 20 values of + 92 . 0 for 8 and −38 . 0 for 9 . due to the close similarity of the 1 h and 13 c nmr data ( supporting information file 1 , table s3 ) compounds 8 and 9 were supposed to be stereoisomers . nmr spectral data of compound 8 were identical with those of ( + ) - isosarcophine ( [ α ] d 20 + 235 . 3 ) reported by kusumi et al . [ 32 ] , so 8 is established as ( + ) - isosarcophine . the configuration at c - 2 for 8 and 9 was established with the help of cd experiments ( supporting information file 1 , figures s22 and s27 ) . according to kobayashi et al . [ 31 ] ( s ) configuration at c - 2 in furanocembranoids causes a negative cotton effect at 246 nm like we obtained for compound 8 , which is thus ( 2 s ) - isosarcophine . the cd spectrum of 9 was the inverse of 8 and displayed a positive cotton effect at 246 nm demonstrating that 8 and 9 are diastereomers . thus , compound 9 is 2 r - isosarcophine .