bluuebunny/crossref_metadata_2025 huggingface dataset:
Regioisomers of Acylcoumarins from the Flowers of Mammea siamensis
Authors: Mahidol Chulabhorn , Prawat Hunsa , Kaweetripob Wirongrong , Ruchirawat Somsak
Published: March 2019

Chemical exploration of the n-hexane extract of the flowers of Mammea siamensis led to the identification of six new compounds, deacetylmammea E/AC cyclo D (1), deacetylmammea E/AA cyclo D (2), deacetylmammea E/AB cyclo D (3), deacetylmammea E/BC cyclo D (4), deacetylmammea E/BB cyclo D (5), and deacetylmammea E/BA cyclo D (6). The structures of these compounds were elucidated by analysis of the spectral data. The absolute stereochemistry of 1, 5 and 6 were established by the modified Mosher's method.
A Novel Acylated Flavone Glycoside from Andrographis nallamalayana
Authors: Reddy Nimmanapalli P. , Reddy Bandi A.K. , Gunasekar Duvvuru , Blond Alain , Bodo Bernard , Raju Reddy V.
Published: March 2019

A new acylated flavone glycoside, skullcapflavone I 2′- O-β-D-(6″- E-cinnamoyl) glucopyranoside (1), together with two known flavones, 5,2′-dihydroxy-7-methoxyflavone (2) and 5,2′,6′-trihydroxy-7-methoxyflavone-2′- O-β-D-glucopyranoside (3), and two known labdane diterpenoids, 14-deoxy-11,12-didehydroandrographolide (4) and andrographolide (5) were isolated from the whole plant of Andrographis nallamalayana. Structural elucidation of the new compound, as well as of the known compounds was achieved by various NMR techniques including 1H-1H COSY, HSQC, HMBC and ROESY experiments, ESITOF mass spectrometry, acid hydrolysis and saponification studies.
Chemical Constituents of the Fern Chingia sakayensis (Zeiller) Holtt
Authors: Sutoyo Suyatno , Indrayanto Gunawan , Zaini Noor Cholies
Published: March 2019

Five compounds, hexacosyl hexadecanoate (1), β-sitosterol (2), matteucinol (3), kaempferol (4), and matteucinol-7- O-β-D-glucoside (5) were isolated for the first time from the fern Chingia sakayensis (Zeiller) Holtt (Thelypteridaceae). Their structures were elucidated from spectroscopic evidence and by comparison with reported literature data.
Germacranolide Rich Essential Oil from Neolitsea pallens
Authors: Padalia Rajendra C. , Chanotiya Chandan S. , Thakuri Bhawani C. , Mathela Chandra S.
Published: March 2019

The composition of the steam volatile constituents of leaf, fruit and bark of Neolitsea pallens (D. Don) syn. Litsea umbrosa var. consimilis Nees Hook f. syn. L. consimilis Nees were analyzed by GC, GC-MS and NMR spectroscopy. The major constituents of the leaf oil were furanogermenone (30.6%), β-caryophyllene (19.3%) and germacrene D (12.7%), while oxygenated sesquiterpenoids (83.6%) constitute the major proportion of the bark oil, which is dominated by furanogermenone (59.1%), germacrone (9.3%), 10- epi-γ-eudesmol (7.8%) and curcumenol (5.3%). The fruit oil was mainly composed of furanogermenone (54.8%), trans-β-ocimene (8.8%), sabinene (6.4%) and germacrene D (4.0%). The major constituents were isolated and characterized on the basis of NMR spectroscopic data. The furano sesquiterpenoids, the major constituents of N. pallens, are of chemosystematic and commercial importance.
An Expeditious, Multi-gram Isolation Protocol for the Ultrapotent SERCA Inhibitor Thapsigargin
Authors: Pagani Alberto , Pollastro Federica , Spera Silvia , Ballero Mauro , Sterner Olov , Appendino Giovanni
Published: March 2019

A streamlined strategy was developed to obtain a mixture of thapsigargins from the fruits of Thapsia garganica L. The mixture was resolved by RP-silica gel flash chromatography to provide, after trituration with ether, 0.32% thapsigargin (1a) as a white powder. A novel, complex phenylpropanoid (neohelmanthicin D, 2a) was also obtained, and its structure confirmed by semisynthesis.
Isolation and Preparation of ent-2,3-Secobeyer-15-en-2,3-dioic acid, 3-methyl ester- A Natural Product from Spirostachys africana
Authors: Munkombwe Namboole Moses , Dijogadifele Disah , Sabure Ngonye
Published: March 2019

A new secobeyerenoic acid mono ester, ent-2,3-secobeyer-15-en-2,3-dioic acid, 3-methyl ester was isolated from the heartwood of Spirostachys africana and identified using spectroscopic methods. The mono ester was also prepared using two methods; by reacting the known diacid, ent-2,3-secobeyer-15-en-2,3-dioic acid with 1.5 mole equivalency of diazomethane, and methanolysis of ent-2,3-secobeyer-15-en-2,3-dioic anhydride.
Cleistenolide and Cleistodienol: Novel Bioactive Constituents of Cleistochlamys kirkii
Authors: Samwel Stephen , Mdachi Stephen J.M. , Nkunya Mayunga H.H. , Irungu Beatrice N. , Moshi Mainen J. , Moulton Brian , Luisi Brian S.
Published: March 2019

(-)-5-Acetoxy-6-(1-benzoyloxy-2-acetoxyethyl)-pyr-3-en-2-one (cleistenolide) and (-)-2,6-diacetoxy-5-hydroxy-cyclohex-3-enylidenemethyl benzoate (cleistodienol) were isolated as novel antimicrobial and cytotoxic constituents of Cleistochlamys kirkii (Annonaceae), together with ( Z)-(+)-5-(2,3-dihydroxy-propylidene)-5 H-furan-2-one and its acetyl and benzoyl derivatives, (-)-1,6-desoxy-β-senepoxide, pinocembrin and polycarpol. Structural determination was achieved based on spectroscopic and other physical data. The structure of cleistenolide was confirmed by single crystal X-ray crystallographic analysis.
Tropane Alkaloids of the Aerial Parts of Schizanthus tricolor
Authors: Humam Munir , Muñoz Orlando , Christen Philippe , Hostettmann Kurt
Published: March 2019

The alkaloid profile of the aerial parts of Schizanthus tricolor Grau et Gronbach was investigated by GC-MS. Seventeen alkaloids were detected and are reported in this species for the first time. They were identified by means of retention indices, together with the fragmentation pattern of reference material. 3α-Methylitaconyloxytropane (12) is identified as a new alkaloid.
N-(4-Methylphenyl) benzenepropanamide - the First Isolated Amide from the Genus Paederia
Authors: Bandyopadhyay Debasish , Nayak Anupam , Basak Bidyut , Banerji Avijit , Banerji Julie , Chatterjee Asima , Prangé Thierry , Neuman Alain
Published: March 2019

Investigation of the stem of Paederia foetida (Rubiaceae) resulted in the isolation and characterization of N-( 4-methylphenyl)-benzopropanamide, which was hitherto unknown as a natural product This is the first report of an amide for the genus Paederia.
Chemical Composition and Cytotoxic Activity of the Leaf Essential Oil of Ocotea tonduzii from Monteverde, Costa Rica
Authors: Bansal Anita , Moriarity Debra M. , Takaku Sayaka , Setzer William N.
Published: March 2019

The leaf essential oil of Ocotea tonduzii from Monteverde, Costa Rica has been obtained by hydrodistillation and analyzed by GC-MS. The principal constituents of O. tonduzii leaf oil were the monoterpenes α-pinene (41.4%) and pinene (25.1%) and the sesquiterpenes α-humulene (6.9%), β-caryophyllene (5.8%), and germacrene D (3.8%). O. tonduzii leaf oil was notably cytotoxic on MCF-7, MDA-MB-231, MDA-MB-468, and UACC-257 cells in vitro. The major essential oil components showed cytotoxic activities comparable to doxorubicin ( LC50, 20–70 μg/mL).
In Vitro Plant Growth Promoting Activity of Phyllocladane Diterpenoids Isolated from Callicarpa macrophylla Vahl. in Shoot Cultures of Rauwolfia serpentina
Authors: Goel Manoj K , Kukreja Arun K , Singh Anil K , Khanuja Suman Preet S
Published: March 2019

Phyllocladane diterpenoids, particularly calliterpenone (1) and calliterpenone monoacetate (2), isolated from leaves of Callicarpa macrophylla, produced significantly higher growth and multiplication of in vitro shoot cultures of Rauwolfia serpentina at 0.25 and 0.5 mg/L concentrations, respectively, compared to certain other plant growth regulators (0.1-5.0 mg/L) tested under in vitro conditions. This is the first report of the plant growth promoting activities of 1 and 2 in plant tissue cultures.
Larvicidal Properties of the Three Major Furostanol Saponins of Balanites aegyptiaca Fruit Mesocarp against Aedes agypti Mosquito Larvae
Authors: Chapagain Bishnu P. , Wiesman Zeev
Published: March 2019

Among various biological activities, saponin-rich extracts have been found to be larvicidal against mosquito larvae; however, no study so far has reported using pure furostanol saponins. In this study, three major furostanol saponins: 26-( O-β-D-glucopyranosyl)-3β,22,26-trihydroxyfurost-5-ene 3- O-β-D-glucopyranosyl-(1→4)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside (1), 26-( O-β-D-glucopyranosyl)-22- O-methylfurost-5-ene-3β,26-diol 3- O-β-D-xylopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside (2), and 26-( O-β-D-glucopyranosyl)-22- O-methylfurost-5-ene.3β,26-diol 3- O-β-D-glucopyranosyl-(1→4)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside (3) were isolated from methanol extracts of the fruit mesocarp of Balanites aegyptiaca (L.) Del. (desert date). Their identification was carried out by ESI-MSn and structures were elucidated by 800 MHz 1H NMR spectroscopy. The larvicidal properties of these saponins against the Aedes aegypti mosquito larvae were evaluated. Results suggest that all three saponins possess larvicidal activity, but the activity was found to be related to the structure of the saponins, basically in the C-22 position of the aglycone and in the oligosaccharide chain. A furostanol saponin that presents -OCH3 at the C-22 position compared to an -OH group, and the lack of a xylose molecule compared to its presence is found to be more larvicidal.
Rufforone: A New Styrylpyrone from Sanrafaelia ruffonammari
Authors: Makangara John J. , Hirai Nobuhiro , Inomata Masahiro , Murakami Akira , Ohigashi Hajime
Published: March 2019

A new styrylpyrone, 6-(7-hydroxy-8-methoxystyryl)-4-methoxypyran-2-one (1), together with two known styrylpyrones, 6-(7,8-epoxystyryl)-4-methoxypyran-2-one (2) and 6-(7,8-dihydroxystyryl)-4-methoxypyran-2-one (3) were isolated from the stem bark of Sanrafaelia ruffonammari Verdc. 6-(7,8-Epoxystyryl)-4-methoxypyran-2-one exhibited high inhibitory activity to interferon-γ-induced nitric oxide generation in RAW264.7 macrophages, whereas the other two showed no activity.
Flavonoids from the Fern Chingia sakayensis (Zeiller) Holtt. and Evaluation of Their Cytotoxicity Against Murine Leukemia P-388 Cells
Authors: Sutoyo Suyatno , Indrayanto Gunawan , Zaini Noor Cholies
Published: March 2019

Three flavonoids, pinocembrin (1), farrerol (2) and matteucinol-7- O-α-L-arabinopyranosyl (1→6)-β-D-glucopyranoside (miconioside A) (3), were isolated for the first time from the fern Chingia sakayensis (Zeiller) Holtt (Thelypteridaceae). Their structures were elucidated from spectroscopic evidence and by comparison with reported literature data. All three isolated flavonoids showed only moderate activity against murine leukemia P-388 cells, with IC50 values greater than 100 μg/mL.
Monohydroxyflavones: Distribution Coefficients and Affinities for Reverse-Phase (C18) and Immobilized Artificial Membrane (IAM) Adsorbents
Authors: Whaley William L. , Tseng Jen-Te , Rummel Jeremy D. , Wommack Cody L.
Published: March 2019

Distribution coefficients (D) were measured for flavone, monohydroxyflavones, and monomethoxyflavones equilibrated between 1-octanol and aqueous buffer (50 mM MOPS, pH=7.4). The values of LogD were used to determine substitution constants referred to as π values. Hydroxyl groups at the 3 or 5 position of flavone had positive π values (increased hydrophobicity) while hydroxyl groups at other positions had negative π values (increased hydrophilicity). For each monohydroxyflavone, chromatographic capacity factors (k’) were determined for both reverse phase (C-18) and immobilized artificial membrane (IAM) columns. For the IAM column, relatively large k’ values were observed for both 3-hydroxyflavone and 5-hydroxyflavone indicating that hydroxyl groups at positions 3 and 5 of flavones promote high affinities for phospholipid structures. These results should aid in refinement of quantitative structure activity relationships (QSAR's) that are useful for drug development based on flavonoids as lead compounds.
Neighboring Group Participation in 12,20-Dioxopregnanes
Authors: Matyas Libor , Pohl Radek , Kasal Alexander
Published: March 2019

12,20-Dioxo-5α-pregnan-3β-yl acetate, obtained from hecogenin, was treated with NaH in DMSO to yield the bridged cyclopropano ketone, 3β-hydroxy-12α,21-cyclo-12β,21-methano-5α,17α-pregnan-20-one. In tert-BuOH the reaction leads to 3β-hydroxy-12,21-cyclo-5α-pregn-12,21-en-20-one. Experimental data prove that the new methylene group of the cyclopropane ring came from DMSO.
A New 9,11-Secosterol from the Vietnamese Sea Soft Coral, Sarcophyton Mililatensis, Increases the Function of Osteoblastic MC3T3-E1 Cells
Authors: Van Minh Chau , Cuong Nguyen Xuan , Tuan Tran Anh , Choi Eun Mi , Kim Young Ho , Van Kiem Phan
Published: March 2019

Chemical investigation of the Vietnamese soft coral Sarcophyton mililatensis resulted in the isolation of a new 9,11-secosterol, sarcomilasterol (1), along with two known polyhydroxylated sterols, sarcoaldesterol B (2) and ergosta-1β,3β,5α,6β-tetraol (3). Their structures were established on the basis of NMR spectroscopic and MS experiments. Compound 1 (3 μM) significantly increased the growth of MC3T3-E1 cells and caused a significant elevation of alkaline phosphatase activity and nodules mineralization compared to those of the control (P<0.05). These results suggest that compound 1 has a direct stimulatory effect on bone formation in vitro and may contribute to the prevention of osteoporosis.
Flavonoid Diversity of Saussurea and Serratula Species in Tien Shan Mountains
Authors: Kusano Katsumi , Iwashina Tsukasa , Kitajima Junichi , Mishio Tamaki
Published: March 2019

Nine Saussurea species, S. alberti, S. elegans, S. gnaphalodes, S. involucrata, S. konuroba, S. kuschakewiczii, S. leucophylla, S. schanginiana and S. sordida, and Serratula lyratifolia from the Tien Shan Mountains and adjacent area were chemically characterized for flavonoids. Thirty-one flavonoids and one hydroquinone were isolated from the leaves of these species and identified from mass spectrometric, UV, 1H and 13C NMR spectroscopic data, by characterization of hydrolyzates, and direct TLC and HPLC comparisons with authentic samples as kaempferol 3-O-rutinoside (1), quercetin 3-O-rutinoside (2), isorhamnetin 3-O-rutinoside (3), quercetin 3-O-glucoside (4), quercetin 3-O-galactoside (5), kaempferol 5-O-glucoside (6), kaempferol 7-O-glucoside (7), quercetin 5-O-glucoside (8), quercetin 7-O-glucoside (9), isorhamnetin 5-O-glucoside (10), luteolin (11), hispidulin (12), nepetin (13), selagin 7-methyl ether (14), selagin (15), velutin (16), luteolin 7-methyl ether (17), jaceosidin (18), apigenin 7-O-rutinoside (19), apigenin 7-O-glucoside (20), luteolin 7-O-rutinoside (21), luteolin 7-O-glucoside (22), luteolin 7-O-galactoside (23), luteolin 7-O-glucuronide (24), hispidulin 7-O-glucoside (25), nepetin 7-O-glucoside (26), luteolin 5-O-glucoside (27), isovitexin (28), apigenin 6,8-di-C-glycoside (29), isoorientin (30), luteolin 8-C-glycoside (31), and arbutin (32). The nine surveyed Saussurea species differed in their flavonoid composition. It was shown that the genus is not only morphologically, but also chemically diversified.
Alkaloids from an Undescribed Thorectid Sponge (Porifera: Dictyoceratida) from the Northern Marianas
Authors: Ankietty Sridevi , Kelly Michelle , Slattery Marc
Published: March 2019

Bioassay guided investigation of an undescribed thorectid sponge from Saipan in the Commonwealth of the Northern Marianas Islands resulted in the isolation of two new fascaplysin related alkaloids (2 and 3), along with the known 10-bromofascaplysin (1). The structures of the isolated metabolites were unambiguously established based on extensive NMR spectroscopic (1H, 13C, COSY, HMQC and HMBC) and MS analyses.
Composition and Antinociceptive Activity of the Essential Oil from Protium Heptaphyllum Resin
Authors: Rao Vietla S. , Maia Juliana L. , Oliveira Francisco A. , Lemos Thelma L.G. , Chaves Mariana H. , Santos Flavia A.
Published: March 2019

The chemical composition of the essential oil from Protium heptaphyllum resin was analyzed by GC/MS and the oil examined for antinociceptive activity in chemical and thermal tests. Fourteen compounds were characterized, representing 95.8% of the total essential oil, with the monoterpenes α-phellandrene (10.4%), α-terpinene (13.7%) and 1,8-cineole (58.7%) as major components. Oral administration of the essential oil (50 and 100 mg/kg) significantly inhibited chemical nociception induced by capsaicin and formalin in mice. In rats, the oil also effectively enhanced the radiant heat-induced tail-flick latency response at a dose of 100 mg/kg. However, the essential oil, at either dose, was ineffective against thermal pain in the hot-plate test.
Chemical Composition and Antibacterial Activity of the Essential Oil of Baccharis latifolia Pers. and B. Prunifolia H. B. &K. (Asteraceae)
Authors: Rojas Janne , Velasco Judith , Rojas Luis B. , Díaz Tulia , Carmona Juan , Morales Antonio
Published: March 2019

The essential oils from leaves of Baccharis latifolia and B. prunifolia collected in January 2006 were analyzed by GC/MS. The yields of oils extracted by hydrodistillation were 0.27 and 0.29% for B. latifolia and B. prunifolia, respectively. Sixteen (B. latifolia) and twenty nine (B. prunifolia) components were identified by comparison of their mass spectra with the Wiley GC-MS Library data and by their retention indices (RI). The identified products may be divided into four different groups: monoterpenes (9.0% B. latifolia; 43.9% B. prunifolia), oxygenated monoterpenes (0.8% B. latifolia; 5.4% B. prunifolia), sesquiterpenes (20.4% B. latifolia; 45.9% B. prunifolia) and oxygenated sesquiterpenes (69.8% B. latifolia; 1.9% B. prunifolia). The oils showed antibacterial activity only against Gram positive bacteria, with MIC values for Staphylococcus aureus (ATCC 25923) of 80 μg/mL (B. latifolia) and Enterococcus faecalis (ATCC 29212) of 90 μg/mL and 260 μg/mL (B latifolia and B. prunifolia, respectively).
Biological Activity and Composition of the Essential Oil of Tetrataenium Nephrophyllum (Apiaceae) from Iran
Authors: Sonboli Ali , Kanani Mohammad Reza , Yousefzadi Morteza , Mojarrad Mehran
Published: March 2019

The aerial parts of Tetrataenium nephrophyllum were collected at the flowering stage, hydrodistilled, and the essential oil was analyzed by GC and GC-MS. Forty components accounting for 97.9% of the total oil were identified. Germacrene D (38.5%), 2-ethylhexyl acetate (11.2%), n-octyl 2-methylbutanoate (9.2%) and geranyl isovalerate (8.3%) were the major constituents. Sesquiterpene hydrocarbons (51.3%) and aliphatic esters (40.4%) were found to be the main group of compounds. The antimicrobial activity of the essential oil of T. nephrophyllum was determined against seven Gram-positive and Gram-negative bacteria (Bacillus subtilis, Enterococcus faecalis, Staphylococcus aureus, S. epidermidis, Escherichia coli, Pseudomonas aeruginosa and Klebsiella pneumoniae), as well as three fungi (Candida albicans, Saccharomyces cerevisiae and Aspergillus niger). The bioassay showed that the oil exhibited moderate to high antimicrobial activity.
Essential Oil from Chenopodium ambrosioides as a Promising Antileishmanial Agent
Authors: Fidalgo Lianet Monzote
Published: March 2019

Chenopodium ambrosioides has been used traditionally against parasitic diseases. The essential oil of the plant is a complex mixture of compounds with a rich structural diversity. This review focuses on recent evaluation of the essential oil from C. ambrosioides as a promising antileishmanial agent. The tested product showed activity against promastigotes and amastigotes of Leishmania amazonensis and L. donovani. An optimal dose of 30 mg/Kg was effective by intraperitoneal and oral routes in experimental cutaneous leishmaniasis. The chenopodium oil had a moderate toxicity against peritoneal macrophages of BALB/c mice and no side effects were detected in animals treated by the oral route. Isolates of L. amazonensis from treated mice were susceptible to the essential oil. Synergic effects were observed when the essential oil was incubated in conjunction with pentamidine on L. amazonensis promastigote cultures. Future studies focusing on formulation, toxicity and mechanism of action may help in the development of chenopodium oil as a new antileishmanial drug.
Recent Advances of Biologically Active Substances from the Marchantiophyta
Authors: Asakawa Yoshinori
Published: March 2019

The Marchantiophyta (liverworts) produce a number of terpenoids, aromatic compounds and acetogenins, several of which show interesting biological properties, such as antimicrobial, antifungal, allergenic contact dermatitis, insecticide, insect antifeedant, cytotoxic, piscicidal, muscle relaxing, plant growth regulatory, anti-HIV and DNA polymerase β inhibitory, anti-obesity and neurotrophic activities. The isolation and chemical structures of the active compounds are discussed.
New cis-Chrysanthenyl Esters from Eryngium planum L
Authors: Korbel Emilia , Bighelli Ange , Kurowska Anna , Kalemba Danuta , Casanova Joseph
Published: March 2019

cis-Chrysanthenyl hexanoate and cis-chrysanthenyl octanoate, two new natural esters from Eryngium planum L., have been spectroscopically characterized.
Synergistic Antifungal Activities of Thymol Analogues with Propolis
Authors: Chen Chi-Pien , Shen Ai-Yu
Published: March 2019

In this study, an attempt was made to elucidate the combined effect of thymol analogues with propolis on fungi that are involved in human diseases. Antifungal activity of thymol analogues was examined by the agar dilution method, using antibiotic medium-3-enriched with 0.2% dextrose. The activity of thymol analogues against Penicillium rastrickii appeared to be more marked than against Candida albicans and Saccharomyces cerevisiae. Various thymol analogues and propolis, when tested alone, did not exhibit significant inhibitory activity. However, in the presence of sub-inhibitory concentrations of propolis, the relative antifungal potency of the thymol analogues was greatly enhanced. Natural thymol was found to be superior to the synthetic thymol analogues. In particular, the MIC of thymol was considerably reduced (191-fold) against Candida albicans by combination with propolis. This study highlights the potential of the combination of either thymol or synthetic thymol analogues with propolis to inhibit fungi.
Synthesis and Antibacterial Activity of Highly Oxygenated 1,8-Cineole Derivatives
Authors: Villecco Margarita B. , Catalán Julieta V. , Vega Marta I. , Garibotto Francisco M. , Enriz Ricardo D. , Catalán César A. N.
Published: March 2019

Seventeen mono-, di- and trifunctionalized 1,8-cineole derivatives carrying OH, OAc, keto and lactone functions at C-5, C-8 and C-9 were synthesized from 1,8-cineole with fair to excellent yields. The antibacterial activity of these synthetic compounds against Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa and Staphylococcus aureus using the agar dilution method was examined. Lactones 1,3-dimethyl-2-oxabicyclo[2.2.2]octan-8- endo-acetyloxy-5→9-olide (15) and 1,3-dimethyl-2-oxabicyclo[2.2.2]octan-8- endo-ol-5→9-olide (16) showed the highest antibacterial activity against all the three Gram negative bacteria assayed. A structure-activity relationship (SAR) study on the oxygenated 1,8-cineole derivatives has allowed a model to be proposed for the recognition of the minimal structural requirements for the antimicrobial effect.
Myrsicorianol, A New Prenylated Benzoic Acid Derivative from Myrsine Coriacea
Authors: Amaro-Luis Juan Manuel , Koteich-Khatib Sonia , Carrillo-Rodríguez Freddy , Bahsas Alí
Published: March 2019

A new prenylated benzoic acid derivative, named myrsicorianol (1), was isolated from the fruits of Myrsine coriacea and its structure was determined by spectral analysis, including 1D- and 2D-NMR experiments. Myrsinoic acid A and a mixture of the p-benzoquinones, embelin, rapanone and 2,5-dihydroxy-3-pentadecyl-1,4-benzoquinone (homorapanone) were also obtained from the fruits, whilst the bark afforded myrsinoic acid A, myrsinoic acid B, 3-(3′,7′-dimethyl-2′,6′-octadienyl)-4-hydroxybenzoic acid and 3-(3′,7′-dimethyl-2′,6′-octadienyl)-4-methoxybenzoic acid.
Enantiodifferentiation by 1H and 13C NMR Spectroscopy (Dirhodium Method) – Selectivity of Oxygen Functionalities
Authors: Gómez Edison Díaz , Antus Sándor , Ferenczi Renáta , Rys Barbara , Stankiewicz Anna , Duddeck Helmut
Published: March 2019

Chiral carbonyl compounds can easily be enantiodifferentiated by the dirhodium method. The rhodium atoms reveal a remarkable selectivity in binding to oxygen atoms, which is of great advantage for discriminating chiral polyoxygenated natural products. Amides are the strongest ligands followed by ketones and esters; ethers and alcohols/phenols are even less effective. This sequence is rationalized by electronic charges at the oxygen atoms, as obtained from density functional calculations.
Substrate Specificity of a Cationic Peptidase from Bromelia Hemisphaerica L
Authors: Isabel Cortés-Vázquez Ma. , Luis Muñoz-Sánchez José , Roberto Briones-Martínez
Published: March 2019

A cationic peptidase, named hemisphaericin-C, has been purified from the juice of Bromelia hemisphaerica fruits by ammonium sulfate precipitation, gel filtration on Sephadex G-75 and cationic exchange chromatography on carboxymethyl cellulose (CMC), to yield a single 24 kDa band on SDS-polyacrylamide gel electrophoresis (SDS-PAGE), which showed esterase and proteolytic activities. The esterase activity was inhibited by E-64, leupeptin, and cystatin, but not by EDTA. Characterization of the primary specificity of hemisphaericin-C showed activity towards substrates specific for chymotrypsin: N-succinyl-L-Phe- p-nitroanilide (PHE pNA) and N-benzoyl-L-Tyr- p-nitroanilide (TYR pNA), and those for trypsin: N-benzoyl-L-arg- p-nitroanilide (BA pNA) to a lower degree. The higher selectivity, assessed by Vmax/Km, was obtained for PHE pNA, the substrate containing the aromatic lateral chain amino acid at the P1 position. The preference of hemisphaericin-C for PHE pNA gives a clue in the search for a chymotrypsin-like peptidase from a vegetal source.
Essential Oils from Bolivia. X. Asteraceae: Gnaphalium Viravira Molina
Authors: Arze Javier B Lopez , Collin Guy , Garneau François-Xavier , Jean France-Ida , Gagnon Hélène
Published: March 2019

The chemical composition of the essential oil obtained from Gnaphalium viravira growing in the high valley region of Bolivia, Province of Cochabamba, was determined by a combination of GC and GC/MS measurements. The composition of the oil is dominated by non oxygenated terpenes. The main products are limonene, α-copaene, β-caryophyllene, geranyl-α-terpinene, and geranyl- p-cymene. Oxygenated monoterpenes account for less than 10%.
Reactivity of Several Reactive Oxygen Species (ROS) with the Sesquiterpene Cacalol
Authors: Jiménez-Estrada Manuel , Reyes-Chilpa Ricardo , Navarro-Ocaña Arturo , Arrieta-Báez Daniel
Published: March 2019

To analyze the antioxidant effects of cacalol we determined its reactivity with different reactive oxygen species (ROS). Cacalol gave rise to cacalone by a specific site reaction with a hydroxyl radical. Singlet oxygen reacted only with the double bond of the furan ring, causing its rupture. On the other hand, ozone reacted with all double bonds in cacalol affording 2-methyl-hexanedioic acid as an end product. No reaction was observed with either superoxide or hydrogen peroxide. The potential antioxidant effect of cacalol as a scavenger of hydroxyl radical and singlet oxygen could be related to its function in the plant roots.
Aporphine Alkaloids from Guatteria stenopetala (Annonaceae)
Authors: Rodríguez María , Bastidas Elsy , Rodríguez Mildred , Lucena Edgar , Castillo Anibal , Hasegawa Masahisa
Published: March 2019

Guatteria species (Annonaceae) are rich in isoquinoline alkaloids that contain a restricted β-phenethylamine moiety and thus have potential as monoamine oxidase (MAO) inhibitors for the treatment of Alzheimer's and Parkinson's diseases. Three aporphine alkaloids have been isolated from G. stenopetala, the known oxoaporphine dicentrinone (1), and two novel compounds, N-methyldicentrinone (2) and 4,5-dioxodehydrodicentrine (3). Their inhibitory effects on MAO-B were evaluated, but none of them was significantly active.
Effect on Hantavirus Replication of Resins from Heliotropium Species and Other Selected Compounds
Authors: Gaona René Torres , Araya Héctor Galeno , Canobra Brenda Modak
Published: March 2019

The present investigation on Heliotropium species was carried out in an attempt to detect possible replication inhibitors of Hantavirus variety Andes. Using the plaque inhibition assay, we have evaluated a group of compounds and resins isolated from Heliotropium species. The antiviral activity was determined between the concentration range 2.5-40.0 μg/mL. Antiviral activity was detected in all the tested resins, particularly that of H. huascoense, with an EC50 value of 12.5 μg/mL. Of the pure compounds tested, the aromatic geranyl derivative filifolinone was the most active. The EC50 value of this compound, 11.3 μg/mL, was similar to that of the control, ribavirin. However, these substances were not selective, but this screening has served to identify those compounds with most promise.
Total Synthesis of 5-(5–Ethenyl-2-Methoxyphenyl)–3-Furancarboxaldehyde and Related Compounds
Authors: León–Galeana Leticia , Luis Ángel Maldonado G.
Published: March 2019

A short and unambiguous total synthesis of furans 2a-c, natural products isolated from the roots of Trichogonia prancii, is described. Some differences in melting points and 1H NMR spectroscopic data were found when compared with those published for the natural products, which can be attributed to typographical errors in the original papers.
In vitro Antiprotozoal Activity and Chemical Composition of Ambrosia tenuifolia and A. scabra Essential Oils
Authors: Sülsen Valeria P. , Cazorla Silvia I. , Frank Fernanda M. , Di Leo Lira Paola M. R. , Anesini Claudia A. , GutierrezYapu David , GiménezTurba Alberto , Bandoni Arnaldo L. , Malchiodi Emilio L. , Muschietti Liliana V. , Martino Virginia S.
Published: March 2019

The in vitro antimalarial, trypanocidal and leishmanicidal activities and the chemical composition of Ambrosia tenuifolia and A. scabra essential oils were investigated. The oils, obtained by hydrodistillation of the aerial parts, showed significant antimalarial activity against the chloroquine sensitive (F32) and the chloroquine resistant (W2) strains of Plasmodium falciparum with 50% inhibitory concentration (IC50) values ranged from 2.8 to 7 μg/mL. Against Trypanosoma cruzi epimastigotes, only A. tenuifolia exerted slight activity (IC50 = 59.7 μg/mL). None of the essential oils showed toxicity towards Leishmania mexicana. Cytotoxicity for murine T-lymphocytes was compared with the parasiticidal activity by using the selectivity index (SI) ratio. The chemical composition of A. tenuifolia and A. scabra essential oils was analyzed by GC-FID-MS. Thirty-eight and twenty-four compounds were identified in A. tenuifolia and A. scabra, respectively. The major constituents of A. tenuifolia oil were germacrene D (22.9%) and bicyclogermacrene (14.2%), while the oil of A. scabra contained limonene (22.0%), caryophyllene oxide (13.8%) and ( E)-caryophyllene (13.5%). This is the first time that the antiprotozoal activity of both oils and the chemical composition of A. scabra essential oil have been reported.
Synthesis of Marine Indole Alkaloids from Flustra foliacea
Authors: Morales-Ríos Martha S. , Suárez-Castillo Oscar R.
Published: March 2019

Brominated natural indoles are frequently reported metabolites of marine seaweeds. The bryozoan Flustra foliacea has been a rich source of brominated indole alkaloids bearing prenyl or isoprenyl substituents at various positions. Because interest in the chemistry of these marine alkaloids is steadily growing and shows unique promise in the discovery of new important medicinal drugs, the methods which have been employed towards their total synthesis are reviewed in detail.
Simultaneous Determination of Vitexin Rhamnoside and Vitexin Glucoside in Rats by Liquid Chromatography Coupled with Mass Spectrometry
Authors: Liang MingJin , Zhang WeiDong , Zhang Chuan , Shen YunHeng , Wang XiaoLin , Wang Xiangwei
Published: March 2019

The purpose of the present study was to evaluate the pharmacokinetic interaction of vitexin rhamnoside (vitexin 2″-α-L-rhamnopyranosyl) and vitexin glucoside (vitexin 2″-β-D-glucopyranosyl) in rats by using a high performance liquid chromatography coupled with tandem mass spectrometry quantitative detection method (LC-MS/MS). The method was validated at the concentration range of 5 - 5000 ng/mL for both vitexin rhamnoside and vitexin glucoside with the regression equations Y = 0.00181X - 0.000955 ( r > 0.998) and Y = 0.000788X - 0.000373 ( r > 0.997), respectively. The methodological studies (including linearity, intra-assay / inter-assay accuracy and precision) of these two components were investigated. The pharmacokinetic parameters of these two components were compared, which demonstrated their pharmacokinetic variance, especially when they were administrated simultaneously.
Quantitative Determination of Ecdysteroids in Sida rhombifolia L. and various other Sida Species Using LC-UV, and their Anatomical Characterization
Authors: Avula Bharathi , Joshi Vaishali , Wang Yan-Hong , Jadhav Atul N. , Khan Ikhlas A.
Published: March 2019

The genus Sida is used extensively in herbal medicine. A simple and specific analytical method for the quantitative determination of ecdysteroids in S. rhombifolia is reported. The ecdysteroids were separated with an acetonitrile (0.1% acetic acid)-water (0.1% acetic acid) gradient at a flow rate of 1.0 mL per minute. The HPLC separation was performed on a Synergi Polar-RP reversed phase column and operated at 35°C. Detection was performed at 247 nm. The method facilitated the quantification of seven ecdysteroids [20-hydroxyecdysone-3- O-β-D-glucopyranoside (1), 20-hydroxyecdysone (2), 2-deoxy ecdysone-3- O-β-D-glucopyranoside (3), pterosterone-3- O-β-D-glucopyranoside (4), ecdysone-3- O-β-D-glucopyranoside (5), ecdysone (6), and 20-hydroxy-(25-acetyl)-ecdysone-3- O-β-D-glucopyranoside (7)] in aerial parts of S. rhombifolia. The LOD and LOQ for compounds 1–7 were found to be in the range from 0.07-0.1 μg/mL and 0.3–0.5 μg/mL, respectively. In the present study, a micro-morphological description of S. rhombifolia is provided. The developed method was used for the determination of ecdysteroids in various other species of Sida, which were compared both micro-morphologically and chemically.
Phytochemical Analysis of Nunavik Rhodiola rosea L
Authors: Filion Vicky J. , Saleem Ammar , Rochefort Guy , Allard Marc , Cuerrier Alain , Arnason John T.
Published: March 2019

This is the first report on the phytochemistry of Nunavik (Québec, Canada) populations of Rhodiola rosea L., a medicinal plant widely used in Eurasia as a tonic and adaptogen. The wild harvested rhizome of the Nunavik populations contained the marker phytochemicals (salidroside, rosarin, rosavin and rosin) reported in authentic Eurasian material, although in lesser amount. Phytochemical profiling by HPLC of the Nunavik populations also showed the presence of new marker compounds not found in the Eurasian material. For quantitative analysis of the phytochemicals, method validation was undertaken, and the marker phytochemicals were measured in the rhizome, leaf, stem, and seeds. The rhizome showed the highest amount of salidroside and rosavins, as well as the highest total phytochemical content. Consequently, the rhizome remains the most medicinally valuable part of R. rosea.
Assessment of 1H NMR Spectroscopy for Specific Metabolite Fingerprinting of Angelica sinensis
Authors: Su Dongmin , Han Jinglan , Yu Shishan , Qin Hailin
Published: March 2019

The 1H NMR fingerprints of fractionated non-polar extracts (CSPD A) from the roots of Angelica sinensis of six different specimens were assigned by comparison with the 1H NMR spectra of the isolated pure compounds. The 1H NMR fingerprints showed exclusively characteristic resonance signals of the major constituents of the plant. The 1H NMR fingerprint established for an authentic sample of A. sinensis can be used for authenticating A. sinensis species.
Steroidal Glycosides from the Seeds of Hyoscyamus niger L
Authors: Lunga Irina , Bassarello Carla , Kintia Pavel , Shvets Stepan , Piacente Sonia , Pizza Cosimo
Published: March 2019

The investigation of the steroidal glycosides of the seeds of Hyoscyamus niger L. led to the isolation of two new spirostane saponins (2, 6) together with seven known glycosides with either furostane or spirostane aglycones. On the basis of chemical and spectroscopic evidence, the structures of 2 and 6 were elucidated as (25 R)-5α-spirostan-3β-ol 3- O-β-D-glucopyranosyl-(1→3)-β-D-galactopyranoside (2) and (25 R)-5α-spirostan-3β-ol 3- O-β-D-glucopyranosyl-(1→3)-[β-D-glucopyranosyl-(1→2)]-β-D-galactopyranoside (6). The given compounds have been found for the first time in the genus Hyoscyamus.
Sideroxylin from Miconia Ioneura: Monohydrate Crystal Structure from High Resolution X-Ray Powder Diffraction
Authors: Pagola Silvina , Tracanna María I. , Amani Sara M. , González Ana M. , Raschi Ana B. , Romano Elida , Benavente Alba M. , Stephens Peter W.
Published: March 2019

High resolution X-ray powder diffraction has been used to obtain the crystal structure of sideroxylin ( 4H-1-Benzopyran-4-one,5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-6,8-dimethyl) monohydrate, (C18H16O5).H2O, isolated from the bioactive ethyl acetate extract of Miconia ioneura Griseb (Melastomataceae) leaves. The crystal structure was determined using direct space methodology based on the simulated annealing algorithm. Thermogravimetric analysis shows that the material dehydrates while heated from room temperature to ~150°C.
Flavonoid Constituents of Carduncellus Mareoticus (Del.) Hanelt and their Biological Activities
Authors: Shabana Marwan M. , El-Sherei Moshera M. , Moussa Mohamed Y. , Sleem Amany A. , Abdallah Hosam M.
Published: March 2019

The total ethanolic extract (TEE) of Carduncellus mareoticus (Del.) Hanelt showed antioxidant and antihyperlipidemic activities, which were attributed to the ethyl acetate fraction (EAF). Also TEE showed potent cytotoxic activity against a cervix cancer cell line (IC50 = 5 μg/mL) and moderate activity against a breast cancer cell line. Chemical investigation of EAF led to the isolation of a new flavonoid, 8-hydroxy-5-methoxyluteolin 7- O-β-D-glucopyranoside (11), along with ten known metabolites (1–10). Three of these compounds, isorhamnetin 3- O-β-D-glucopyranoside (7), luteolin 3′- O-β-D-glucopyranoside (8), and eriodictyol 7- O-β-D-glucopyranoside (9) are reported for the first time from the genus Carduncellus, and two compounds, chrysoeriol 7- O-β-D-glucopyranoside (6), and luteolin 7- O-β-D-glucopyranoside (10), for the first time from C. mareoticus. The rest of the isolated compounds, chrysoeriol (1), luteolin (2), quercetin (3), kaempferol 3- O-α-L-arabinopyranoside (4), and kaempferol 3- O-β-D-glucopyranoside (5) have been previously reported from the genus.
Essential Oil Composition of Two Subspecies of Nepeta Glomerulosa Boiss. from Iran
Authors: Javidnia Katayoun , Miri Ramin , Rezazadeh Shaghayegh Rasteh , Soltani Mohammad , Khosravi Ahmad Reza
Published: March 2019

Essential oil compositions of Nepeta glomerulosa Boiss. subsp. glomerulosa and N. glomerulosa subsp. stapfiana (Bornm. ex Rech. f.) Rech. f., each gathered from two different locations, have been investigated by GC and GC/MS. 1,8-Cineole was the major compound in the oils of both collections of subspecies glomerulosa (27.4%, 30.6%), and was also a major constituent of subspecies stapfiana (14.9%, 17.8%). However, caryophyllene oxide was the predominant compound for both oils of subspecies stapfiana (32.0%, 24.1%). From the chemotaxonomic point of view, the two members of each subspecies comprised a separate group with a considerable distance from the other two, and the morphological differences of these two subspecies were well reflected in their essential oil compositions.
Furanolabdane Diterpene Glycosides from Eremostachys Laciniata
Authors: Delazar Abbas , Modarresi Masoud , Nazemiyeh Hossein , Fathi-Azad Fatemeh , Nahar Lutfun , Sarker Satyajit D.
Published: March 2019

Three furanolabdane diterpene glycosides, phlomisoside II (1), eremostachiin (2) and β-D-glucopyranosyl ester of phlomisoic acid (3, named laciniatiin), the latter being a new natural product, were isolated from the methanol extract of the rhizomes of Eremostachys laciniata. The structures of these compounds were elucidated by spectroscopic means.
Triterpenoids from Anthocleista grandiflora (Gentianaceae)
Authors: Magadula Joseph J. , Mulholland Dulcie A. , Crouch Neil R.
Published: March 2019

The stem bark of Anthocleista grandiflora (Gentianaceae) has yielded five triterpenoids, baruol, 3-deacetylmongolenin, anthocleistone, 6-ketoanthocleistone and lupenone together with scopoletin and (+)-de- O-methyllasiodiplodin. 3-Deacetyl-mongolenin was isolated from the leaves while the root bark yielded, in addition to the above compounds, the secoiridoid, sweroside.
Chemical Composition of the Essential Oils of Centaurea Sicana and C. Giardinae Growing Wild in Sicily
Authors: Formisano Carmen , Rigano Daniela , Senatore Felice , Bruno Maurizio , Rosselli Sergio , Raimondo Francesco Maria , Spadaro Vivienne
Published: March 2019

The essential oils of Centaurea sicana (S) and C. giardinae (G) were studied by GC and GC-MS. Thirty constituents for S, representing 81.5% of the total oil, and 24 compounds for G (94.2% of the total) were identified. The oils were rich in sesquiterpenoids (47.9% for S and 54.7% for G) and hydrocarbons (25.9% for S and 31.7% for G). Germacrene D (13.3%), ( E)-β-farnesene (8.3%), nonacosane (7.3%), heptacosane (6.5%) and phytol (6%) were recognized as the main constituents for S, while caryophyllene oxide (17.7%), nonacosane (14.5%), germacrene D (11.5%), caryophyllene (11.2%) and heptacosane (10.3%) were the main compounds for G.
Neo-Clerodane Diterpenoids from Verbenaceae: Structural Elucidation and Biological Activity
Authors: Castro Amaya , Coll Josep
Published: March 2019

This review focuses on the occurrence and structural elucidation of neo-clerodane type diterpenes from Verbenaceae (no matter if recently reclassified based on phylogenetic research) and the semisynthetic compounds of closely related structure obtained. Biological activities of crude extracts and isolated diterpenes will be briefly discussed.
Evaluation of the Activities of Five Essential Oils against the Stored Maize Weevil
Authors: Odeyemi Oluwakemi O. , Masika Patrick , Afolayan Anthony J.
Published: March 2019

The contact, repellent and fumigation effects of essential oils from Tagetes minuta L., Mentha longifolia L., Rosmarinus officinalis L., Helichrysum odoratissimum L. and Pelargonium graveolens L. were investigated against maize weevil, S. zeamais (Motschulsky) (Colepotera: Curculionidae). The effects of the oils were dose-dependent with gradual increases in insect mortality as the oil concentrations increased. For the contact bioassay, the oils of T. minuta and M. longifolia acted rapidly, causing 100% mortality within two days after treatment at 0.375 and 0.50 μL/g grain concentrations, respectively. The repellent effect of these two oils against S. zeamais was also well pronounced. A Percentage Repellency (PR) value of more than 90% was obtained for the two oils, which puts them in the highest repellency class V. The level of repellency caused by the essential oils of R. officinalis, H. odoratissimum and P. graveolens were 51.1%, 49.4% and 51.7%, respectively. However, most of the oils demonstrated very low fumigation activity against the weevil. For the fumigation bioassay, all the oil concentrations tested did not achieve insect mortality more than 12.5%, even six days after treatment, except for the oil of M. longifolia that exhibited over 70% mortality at 32 μL/L of air. The present study revealed that the essential oils of R. officinalis, H. odoratissimum and P. graveolens had weak contact and fumigation effects against S. zeamais.
The Bark Essential Oil Composition and Chemotaxonomical Appraisal of Cedrelopsis Grevei H. Baillon from Madagascar
Authors: Rakotobe Miarantsoa , Menut Chantal , Andrianoelisoa Hanitriniaina Sahondra , Rahajanirina Voninavoko , De Chatelperron Philippe Collas , Roger Edmond , Danthu Pascal
Published: March 2019

Cedrelopsis grevei is an aromatic and endemic tree of Madagascar. Its essential oil, resulting from its bark, and known under the name katrafay oil, is used in Madagascar in traditional medicine and in aromatherapy in the areas of the North. The chemical composition of this oil shows a great variability. This work proposed to study some determinants of this variability. Sampling was carried out tree by tree, in six representative sites of the distribution area of the species, followed by distillation and analysis by GC-MS. Twenty one samples were thus analyzed and 71 molecules were identified in at least one sample. A principal components analysis was performed considering the thirteen principal compounds identified in these essential oils. Four chemical patterns were distinguished. The first is characterized by eudesmane skeletons, mainly represented by selinenes (3.4-17.2%) and eudesmols (9.9-37.8% and 0-11.1% for the α- and γ- isomers, respectively); the second is rich in α-pinene (2.1-30.0%) and copaborneol (4.7-20.0%); the third is dominated by α-copaene (5.9-11.8%) and ishwarane (13.7-22.1%), and the last by cadinane skeletons (cadinenes 0.5-35.2%, T-muurolol 0-11.8% and α-cadinol 0-6.7%). Variable amounts of α-bisabolol were found in samples belonging to these four groups. Our study indicates a linkage between the zone of gathering and the essential oil chemical composition. There was not much variability between trees in the same zone, but there were big differences from one zone to another. These results make it possible to propose methods for sustainable collection and durable management of the species.
Essential Oil Compounds for Thrips Control – a Review
Authors: Koschier Elisabeth H.
Published: March 2019

This review covers aspects of putting essential oil compounds to use either as allelochemicals that manipulate the host selection process of Thysanopteran pest species or as botanical insecticides that kill these pests. Thysanoptera (thrips) make an especially interesting case study in this field, because their increasing economic impact puts some urgency on the development of novel control strategies, especially strategies that incorporate natural compounds. Known facts about the host selection behaviour of thrips are briefly summarized, and methods for the evaluation of thrips responses to volatile and non-volatile plant compounds are outlined. Recent results on the search for attractive and repellent volatiles and for feeding and/or oviposition deterrent essential oil compounds are listed in detail and their potential for use in control strategies against thrips pests is discussed. An overview of plant essential oils used either for insecticidal spraying treatments of crops or for fumigation of crops in greenhouses or fumigation chambers completes the picture of bioactivities. Finally, an outlook on the perspectives for future control strategies against thrips pests is given, including thoughts on the direction of further research needed to fully evaluate the thrips control potential of plant essential oils.
Chemodiversity of Artemisia Dracunculus L. from Kyrgyzstan: Isocoumarins, Coumarins, and Flavonoids from Aerial Parts
Authors: Bhutia Tshering D. , Valant-Vetschera Karin M.
Published: March 2019

A new accession of Artemisia dracunculus L., originating from Kyrgyzstan, has been analyzed for the first time regarding organ-specific accumulation of lipophilic compounds. Differences were found between leaves, stems, and inflorescences. Exudates obtained from aerial parts yielded only flavanones (eriodictyol, naringenin and their methyl ethers), while the coumarins herniarin and scoparone and biosynthetically unrelated isocoumarins (artemidin, dracumerin) were found to be tissue components. The chemosystematic significance of observed accumulation tendencies is shortly discussed, and other chemodiversity aspects are briefly addressed.