# Menispermaceae

Menispermaceae (botanical Latin: 'moonseed family' from Greek mene 'crescent moon' and sperma 'seed') is a family of flowering plants. The alkaloid tubocurarine, a neuromuscular blocker and the active ingredient in the 'tube curare' form of the dart poison curare, is derived from the South American liana Chondrodendron tomentosum, which belongs to this family. Several other South American genera belonging to the family have been used to prepare the 'pot' and 'calabash' forms of curare. The family contains 78 genera with some 440 species, which are distributed throughout low-lying tropical areas with some species present in temperate and arid regions.

## Description

* Twining, ever-growing and woody climbing plants, winding anti-clockwise (Stephania winds clockwise) and vines; rarely upright shrubs or small trees. Rarer still herbaceous plants or epiphytes (Stephania cyanantha), perennial or deciduous, with simple to uni-serrate hairs.
* Alternating, spiral leaves; simple, whole, dentate, lobed to palmatifid (bi- o trifoliate in Burasaia), frequently peltate, petiolated, petiole frequently pulvinate at both extremes, without stipules, sometimes with spines derived from the petioles (Antizoma), venation, parallelodromous, penninerved or frequently palmatinerved, bifacial, rarely isofacial; in Angelisia and Anamirta, with hydathodes derived from trichomes. Domatia present in five genera as pits or hair tufts. Various types of stomata, frequently cyclocytic.
* Rapidly-growing stems with trilacunar nodes. Phylloclades are present in Cocculus balfourii.
* Dioecious plants, sometimes perfect flowers in Tiliacora acuminata and Parabaena denudata.
* Inflorescences in racemiform, paniculate or thyrse with partial inflorescences in a capituliform cyme or pseudo-umbel; multifloral, rarely single or paired flowers; axillary, or on sharp branches or cauliflorous trunks; females frequently less branched.
* Flowers small, regular to zygomorphic (Antizoma, Cyclea, Cissampelos); cyclic to irregularly spiral; hypogynous, basically trimers. Receptacle sometimes with developed gynophore. Sepals (1-)3-12 or more, usually in (1-)2(-many) whorls of three, rarely six; free to slightly fused; imbricate or valvate, sometimes less numerous in female flowers. Petals numbering 0–6, in two whorls of three, rarely of six; free or fused, frequently holding the opposite stamen; sometimes less numerous in female flowers. Androecium of (1-)3-6(-40) stamens free of the perianth, free or fused together in 2–5, fasciculate or monadelphous, introrse, dehiscence along longitudinal, oblique or transversal slits. Female flowers sometimes with staminodes. Gynoecium apocarpous, superior, of (1-)3-6(-32) carpels, usually oppositipetalous, stigma apical, dry, papillous, ovules 2 per carpel, anatropous, hemianatropous to campilotropous, uni- or bitegmic, crassinucellate, the superior epitropous and fertile, the inferior apotropous and abortive, placentation marginal ventral. Male flowers sometimes with carpelodes.
* Fruits are compound; each unit in a straight or flattened, asymmetric drupe; more or less stipitate (rarely only one developed); non coalescing; exocarp sub-coriaceous or membranous, mesocarp pulpy, fleshy or fibrous, endocarp woody to petrous, rough, tuberous, echinate or ribbed, often with a recess in the placenta called a condyle.
* Seeds slightly curved or spiral (Limaciopsis, Spirospermum), with endosperm absent or present, totally or only ventrally ruminate or not ruminate, oleaginous, embryo straight or curved, with two cotyledons flat or cylindrical, leafy or fleshy, divaricate or applied.
* Pollen tricolpate, without operculum nor ribs, tectum perreticulate columellate, endexine granular; or the pollen can be colporate (Abuta), syncolporate (Tinospora), pororate or hexa-cryptoporate (with 6 apertures).
* Chromosomal number: x = 11, 13, 19, 25. 2n can be up to 52.

## Ecology

It is thought that the cauliflorous species are pollinated by small bees, beetles or flies although there are no direct observations of this. Birds disperse the purple or black drupes, for example Sayornis phoebe (a tyrant flycatcher) eats the fruit of Cocculus. In Tinospora cordifolia a lapse of 6–8 weeks has been observed between fertilization and the first zygotic cell division.
The Menispermaceae predominantly inhabit low elevation tropical forests (up to 2,100m), where they are climbers, but some genera and species have adapted to arid locations (Antizoma species have adapted to the South African deserts or Cebatha balfourii and its phylloclades have adapted to the climate on the island of Socotra) and other temperate climates. C3 photosynthesis has been recorded in Menispermum.

## Phytochemistry

The family contains a wide range of benzylisoquinoline compounds (alkaloids) and lignans such as furofuran, flavones and flavonols and some proanthocyanidins. The most notable are the wide variety of alkaloids derived from benzyltetrahydroisoquinoline and aporphine, which accumulate as dimers, as well as the alkaloids derived from morphinan and from hasubanan and other diverse types of alkaloid such as derivative of aza-fluoranthene. Sesquiterpenes such as picrotoxin and diterpenes such as clerodane diterpene are also present, while the triterpenes are scarce and where present are similar to oleanane. Ecdysone steroids have also been found. Some species are cyanogenic.

## Uses

The Menispermaceae have been used in traditional pharmacopeia and drugs have been formulated from these plants that are of great use in modern medicine. These drugs are based on alkaloids and include tubocurarine from curare, a poison used by indigenous South American tribes on their poison darts, that is obtained from species of Curarea, Chondrodendron, Sciadotenia, and Telitoxicum. A similar poison was used in Asia that was obtained from species of Anamirta, Tinospora, Coscinium, and Cocculus. Tubocurarine and its synthetic derivatives are used to relax muscles during surgical interventions. The roots of "kalumba" or "colombo" (Jateorhiza palmata) are used in Africa for stomach problems and against dysentery. Species of Tinospora are used in Asia as antipyretics, the fruit of Anamirta cocculus is used to poison fish and birds and the stems of Fibraurea are used to dye fabric yellow. The South East Asian species Coscinium fenestratum, a local Thai remedy for stomach ailments (which contains berberine and related alkaloids) was recently implicated in mass harvesting operations to prepare extracts usable as precursors in the manufacture of the drug MDMA.

## Fossil record

The Middle Cretaceous genus Callicrypta from Siberia has been placed into Menispermaceae. The Paleocene fossil record for the family includes at least 11 genera identified from compression leaf fossils found in Alaska and 15 genera and approximately 22 different Menispermaceae species identified from the Early Eocene London Clay. The London Clay genera Eohypserpa and Tinomiscoidea named by Reid & Chandler (1933) from mineralized nuts and additional three genera Atriaecarpum, Davisicarpum, and Palaeosinomenium were later described by Chandler (1961, 1978). Additional species from those genera were identified in the Clarno nut beds by Scott and Manchester respectively.
Menispermaceae is one of the most diverse families found in the Middle Eocene Clarno nut beds of central Oregon. Species belonging to thirteen different genera, mostly extinct, have been described based on cast or permineralized fruit and nut fossils from the beds, and four different foliage types are known from associated compression fossils. Chandlera and Odontocaryoideae were described by Scott (1954), while Manchester (1994) described Curvitinospora and Thanikaimonia.

## Phylogeny and internal classification

The APG IV system (2016; unchanged from the prior systems of 1998, 2003, and 2009) recognizes this family and places it with the eudicots order Ranunculales. Their trimerous flower structure is similar to the Lardizabalaceae and Berberidaceae, although they differ from them in other important characteristics. The APW (Angiosperm Phylogeny Website) considers that they form part of the Order Ranunculales, and that they are a sister group on the branch formed by the Lardizabalaceae and Berberidaceae families in a reasonably advanced clade of the order. Kinship with the Berberidaceae is further borne out by similarities in phytochemistry e.g. in the presence of berberine and related alkaloids. It is a medium-sized family of 78 genera totaling 420 extant species, mostly of climbing plants. The great majority of the genera are tropical, but with a few (notably Menispermum and Cocculus) reaching temperate climates in eastern North America and eastern Asia.
The genetic factors within Menispermaceae are very narrow resulting in many genera with one or a few species. According to Kessler (1993) there wasn't sufficient data from genetic studies to evaluate subfamily and tribal division into five tribes (see Kessler, 1993, in the References section). As such, division was fundamentally based on morphologic characteristics of the seeds with doubts as to whether the tribes are monophyletic. Further molecular research compiled and conducted by the Angiosperm Phylogeny Group has clarified many of the interrelationships of the family.

### Chasmantheroideae

Burasaieae
* Aspidocarya J. D. Hooker & Thomson
* Borismene Barneby
* Burasaia Thouars
* Calycocarpum Torrey & A. Gray
* Chasmanthera Hochst.
* †Chandlera Scott
* Chlaenandra Miquel
* Dialytheca Exell & Mendonça
* Dioscoreophyllum Engler
* Diploclisia Miers
* Disciphania Eichler
* Fibraurea Loureiro
* Hyalosepalum Troupin
* Jateorhiza Miers
* Kolobopetalum Engler
* Leptoterantha Troupin
* Odontocarya Miers (including Synandropus)
* Orthogynium Baillon
* Parabaena Miers
* Paratinospora Wei Wang
* Penianthus Miers
* Platytinospora (Engler) Diels
* Rhigiocarya Miers
* Sarcolophium Troupin
* Sphenocentrum Pierre
* Syntriandrium Engler
* Tinomiscium J. D. Hooker & Thomson
* Tinospora Miers (including Fawcettia F. Muell.)
Coscinieae
* Anamirta Colebrooke
* Arcangelisia Beccari
* Coscinium Colebrooke

### Menispermoideae

Anomospermeae
* Abuta Aublet
* Anomospermum Miers
* Caryomene Barneby & Krukoff
* Diploclisia Miers
* Echinostephia (Diels) Domin
* Elephantomene Barneby & Krukoff (including Cionomene)
* Elissarrhena Miers
* Hypserpa Miers
* Legnephora Miers
* Orthomene Barneby & Krukoff
* Parapachygone Forman
* Pericampylus Miers
* Rupertiella Wei Wang & R. Ortiz
* Sarcopetalum F. Mueller
* Telitoxicum Moldenke
Cissampelidae
* Antizoma Miers
* Cissampelos L.
* Cyclea Wight
* Perichasma Miers
* Stephania Loureiro
Limacieae
* Limacia Loureiro
Menispermeae
* Menispermum L.
* Sinomenium Diels
Pachygoneae
* Cebatha Forssk.
* Cocculus de Candolle
* Haematocarpus Miers
* Hyperbaena Bentham
* Nephroia Lour.
* Pachygone Miers
Spirospermeae
* Limaciopsis Engler
* Rhaptonema Miers
* Spirospermum Thouars
* Strychnopsis Baillon
Tiliacoreae
* Albertisia Beccari
* Anisocycla Baillon
* Beirnaertia Troupin
* Carronia F. Mueller
* Chondrodendron Ruiz & Pavón
* Curarea Barneby & Krukoff
* Eleutharrhena Forman
* Macrococculus Beccari
* Pleogyne Miers
* Pycnarrhena J. D. Hooker & Thomson
* Sciadotenia Miers
* Synclisia Bentham & J. D. Hooker
* Syrrheonema Miers
* Tiliacora Colebrooke
* Triclisia Bentham & J. D. Hooker
* Ungulipetalum Moldenke

#### Incertae sedis

* †Callicrypta

## Gallery

* Menispermum canadense, foliage and flowers. Frick Park, Pittsburgh.
* Menispermum canadense (Canada moonseed) : ripe fruit and crescent moon-shaped seeds.
* Chondrodendron tomentosum : Coloured plate from Bentley and Trimen's Medicinal Plants
* The Abuta species A. selloana : line drawing from Engler's Das Pflanzenreich.
* Cocculus orbiculatus in fruit. Real Jardín Botánico de Madrid.
* Anamirta cocculus : illustration from Köhler's Medizinal Pflanzen.
* Anomospermum : A. schomburgkii : anatomical study from the Flora Brasiliensis of von Martius and Eichler.
* Cissampelos pareira: illustration from Blanco's Flora de Filipinas.
* Coscinium fenestratum 'yellow vine' : plate from Curtis's Botanical Magazine.
* The Stephania species S. venosa in flower, Gothenburg Botanical Garden.
* Thai villagers harvesting large, medicinal root tuber of Stephania venosa.
* Stephania japonica in fruit, Mc.Kay Reserve, NSW, Australia.
* Jateorhiza palmata illustration from Köhler's Medizinal Pflanzen.
* Foliage of Tinospora cordifolia.