Cissampelos insularis

Chondodendron tomentosum Ruiz and Pavon (Menispermaceae)]141,142] Cissampelos insularis Makino (MenispermaceaeXalso called Paracyclea insularis (Makino) Kudo and Yamamoto (Menispermaceae)]] 131] Cissampelos pareira L. (Menispermaceae)] 189,190]... 

Recently Kondo, Tomita, and Uyeo (55) applied the technique of chromatographic adsorption on alumina to the separation of the alkaloids of Cissampelos insularis Makino and Stephania cepharantha. By this means they isolated, in addition to those known, a new, crystalline, ether-soluble alkaloid whose analysis agreed with that of a bisbenzylisoquinoline alkaloid. This same alkaloid was also found in Chondodendron tomentosum (104) and Stephania capitata Spreng (121). Through a comparison of its properties and that of its derivatives with samples of isochondodendrine dimethyl ether and derivatives provided by Faltis, the Japanese workers (55) established the structure of the new alkaloid as being fully methylated isochondodendrine (LXI). They suggested the names methylisochondodendrine or cycleanine. An attempt to synthesize this alkaloid was not successful (130). Hovrever, by means of sodium and liquid ammonia the compound has been bisected into only one phenolic base whose structure proved to be M-(4 -hydroxybenzyl)-6,7-dimethoxy-iV-methyl-l,2,3,4-tetrahydroisoquinoline (134). This showed that cycleanine (methylisochondodendrine) has the structure (LXI) with both the asymmetric centers levorotatory. 

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