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Anisocycla cymosa Troupin Protologue Bull. Jard. Bot. Etat 19: 416 (1949). Family Menispermaceae Origin and geographic distribution Anisocycla cymosa is endemic to DR Congo. Uses An aqueous extract of the leaves and roots is used in DR Congo as a tonic and analgesic, e.g. against rheumatic pains and stomach-ache. Properties From the roots the bisbenzylisoquinoline alkaloids 2’-norcocsoline, cocsoline-N-oxide and 12-O-methylcocsoline-N-oxide have been isolated, as well as a number of alkaloids of various structures, including anisocycline, palmatine, liriodenine, remrefidine, 1,2-dehydroapateline, 1,2-dehydrotelobine and trilobine. The bisbenzylisoquinoline alkaloids 2-norobaberine-2’-β-N-oxide, 2-norobaberine, daphnandrine, coclobine, anisocycline, palmatine, and remrefidine have been isolated from seeds. Their role in neurochemistry is being studied. The leaves contain N-O-dimethylthaicanine, N-methylthaicanine, N-methyltetrahydropalmatine, anisocycline, palmatine, and stephenanthrine. Botany Dioecious liana; stem up to 5 cm in diameter; bark with circular leaf scars. Leaves arranged spirally, simple and entire; petiole up to 6 cm long, thin, grooved; blade broadly ovate to elliptical, 6–10 cm × 3–6.5 cm, base rounded to slightly cordate, apex acuminate, glabrous, pinnately veined with 3–5 pairs of lateral veins. Inflorescence an axillary, many-flowered cyme, single or paired, 2–8 cm long, reddish hairy. Flowers unisexual, small; pedicel short; sepals 9 in 3 whorls, yellowish hairy, sepals of outer and middle whorls 0.5–1.5 mm long, 3 inner sepals 2–3 mm × 1–1.5 mm; petals broadly ovate, c. 1.5 mm long, narrowing to the base, glabrous; male flowers with 9–18 stamens c. 3 mm long, filaments fused; female flowers with superior ovary composed of 3 free carpels 2–4 mm long, styles cylindrical, glabrous. Fruit composed of 1–3 drupes; stone bony. Anisocycla comprises 6 species, 4 in continental Africa and 2 in Madagascar. Anisocycla grandidieri Baill. is endemic to northern Madagascar, where it occurs below 500 m altitude. A very bitter decoction of its yellow roots is used to cure diseases of the kidneys and the bladder. Sap from the roots is used as a coagulant. The roots contain the bisbenzylisoquinoline alkaloids epistephanine, stebisimine, trilobine and 12’-O-demethyltrilobine. Epistephanine and stebisimine have shown spasmolytic activity in isolated guinea-pig ileum. Anisocycla jollyana (Pierre) Diels is a climbing shrub occurring in fringing forest from Equatorial Guinea to western DR Congo. It does not have recorded medicinal uses, but its chemistry was researched because its close relative Anisocycla cymosa contains many interesting alkaloids. The roots of Anisocycla jollyana contain a great variety of bisbenzylisoquinoline alkaloids and dioxine alkaloids, including cycleanine, limacusine, apateline and isochondrodendrine and its derivatives fastrine and jollyanine. From the leaves the secodibenzylisoquinolines secojollyanine and secohomoaromaline have been isolated, as have several bisbenzylisoquinoline alkaloids. Ecology Anisocycla cymosa occurs on sandy riversides and in fringing forest around open vegetation in the humid forest belt. Genetic resources and breeding Too little is known about Anisocycla cymosa to assess its genetic vulnerability. Prospects Additional research on the phytochemistry and pharmacology of Anisocycla cymosa and the other Anisocycla species seems warranted in view of the uses and the numerous bioactive constituents. Major references • Kanyinda, B., Diallo, B., Vanhaelen-Fastre, R. & Vanhaelen, M., 1989. Benzylisoquinoline alkaloids from Anisocycla cymosa roots. Planta Medica 55(4): 394. • Kanyinda, B., Vanhaelen-Fastre, R. & Vanhaelen, M., 1993. A new bisbenzylisoquinoline-N-oxide alkaloid from seeds of Anisocycla cymosa. Journal of Natural Products 56(4): 618–620. • Kanyinda, B., Vanhaelen-Fastre, R., Vanhaelen, M. & Ottinger, R., 1992. Identification by two-dimensional NMR spectroscopy of two new benzylisoquinoline alkaloids from leaves of Anisocycla cymosa. Journal of Natural Products 55(5): 607–612. • Kanyinda, B., Vanhaelen-Fastre, R., Vanhaelen, M. & Ottinger, R., 1993. Bisbenzylisoquinoline alkaloids from Anisocycla cymosa roots. Journal of Natural Products 56(6): 957–960. • Troupin, G., 1962. Monographie des Menispermaceae africaines. Mémoires in-8. Académie Royale des Sciences d’Outre-Mer, Classe des Sciences Naturelles et Médicales, Nouvelle série 8(2), Brussels, Belgium. 313 pp. Other references • Boissier, J.R., Combes, G., Pernet, R. & Dumont, C., 1975. Menispermaceae alkaloids of Madagascar: Cissampelos pareira, Cyclea madagascariensis, Anisocycla grandidieri, and Spirospermum penduliflorum. Lloydia 28(3): 191–198. • Boiteau, P., Boiteau, M. & Allorge-Boiteau, L., 1999. Dictionnaire des noms malgaches de végétaux. 4 Volumes + Index des noms scientifiques avec leurs équivalents malgaches. Editions Alzieu, Grenoble, France. • Kanyinda, B., Vanhaelen-Fastre, R. & Vanhaelen, M., 1995. Benzylisoquinoline alkaloids from Anisocycla jollyana leaves. Journal of Natural Products 58(10): 1587–1589. • Kanyinda, B., Vanhaelen-Fastre, R., Vanhaelen, M. & Ottinger, R., 1996. Two new secobisbenzylisoquinoline alkaloids from the leaves of Anisocycla jollyana. Journal of Natural Products 59(5): 498–500. • Kanyinda, B., Vanhaelen-Fastre, R., Vanhaelen, M. & Ottinger, R., 1997. Two new isochondodendrine-type alkaloids from the roots of Anisocycla jollyana. Journal of Natural Products 60(11): 1121–1124. • Schlittler, E. & Weber, N., 1972. Alkaloids of Anisocyclea grandidieri (Menispermaceae). Helvetica Chimica Acta 55(6): 2061–2064. • Thanikaimoni, G., 1986. Evolution of Menispermaceae. Canadian Journal of Botany 64: 3130–3133. • Vauquelin, G., De Keyser, J., Kanyinda, B. & Vanhaelen, M., 1989. (±)Tetrahydroanisocycline and (±)tetrahydropalmatine binding to D1 and D2 dopaminergic receptors in human putamen. Neurochemistry International 15(3): 321–324. Author(s)
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