Ancistrocladus heyneanus

Two naphthalene-isoquinoline groups of alkaloids, ancistrocladidine (53) and ancistrotectorine (54), were isolated from Ancistrocladus heyneanus Wall [295], and A. tectorius (Lour.) Merr [296], respectively. The members of the plant family, ancistrocladaceae, are distributed in tropical Asia and Western Africa. Some are regarded as traditionally medicinal plants. The root of A. tectorius has been used to treat dysentery and malaria [296],... 

Yang et al. [118] reported the isolation and characterization of a novel naphthy-lisoquinoline alkaloid, ancisheynine (104) from the aerial part of Ancistrocladus heyneanus. The alkaloid is interesting in that it contains a previously undescribed N-2-C-8 linkage between the naphthyl and isoquinoline subunits, the presence of which was established with long-range correlation data. 

Ancisheynin, a novel naphthylisoquinolinium alkaloid from Ancistrocladus heyneanus. Plants of the genera Ancistrocladaceae and Dinocophyllaceae are rich sources of naphthylisoquinoline alkaloids that vary in the degree of hydroxylation and 0-methylation. Butler and co-workers reported the isolation and structural characterization of a novel naphthylisoquinolinium alkaloid, ancisheynine (102) from Ancistrocladus heyneanus. The authors used long-range HMBC data to confirm the... 

Naphthalenoisoquinolines.—A new base related to the unusual alkaloid (—)-ancistrocladine is (— )-ancistrocladinine (233), also found in Ancistrocladus heyneanus Wall. (Ancistrocladaceae), and which corresponds to ( —)-l,2-dehydroancistrocladine. " ... 

The unique substitution pattern of ancistrocladine (1), however, which was first isolated by Govindachari from the Indian liana Ancistrocladus heyneanus Wall. (Ancistrocladaceae) (4), can barely be brought into line with such a conventional isoquinoline biosynthesis. Its unprecedented structure, for which it was termed the most unusual of all the isoquinoline alkaloids (5), makes obvious that its biosynthesis must also differ from that of all other tetrahydroiso-quinoline alkaloids by starting not from aromatic amino acids, but from poly-ketide precursors, as first proposed by Govindachari (6). 

Due to the brilliant, pioneering work by Govindachari and his colleagues at the CIBA Research Centre in Bombay, Ancistrocladus heyneanus Wall, is the most thoroughly investigated of all the Ancistrocladaceae. From the roots of this liana, a new alkaloid was isolated in nearly 1% yield, named ancistrocladine, and analyzed as C25H29O4N, as also confirmed by the mass spectrum (M" " = 407)... 

Ancisheynine (434) was the first characterized atropisomeric N-C linked naphthylisoquinolinium alkaloid (03TL5827). It was isolated from Ancistrocladus heyneanus. The extract presented no optical rotation. The nature of counter anion was not determined. 

Bringmann, G. et al., Betulinic acid isolation from Triphyophyllum peltatum and Ancistrocladus heyneanus, antimalarial activity, and crystal structure of the benzyl ester, Planta Med., 63, 255, 1997. Fujioka, T. et al.. Anti-AIDS agents, 11. Betulinic acid and platanic acid as anti-HIV principles from Syzigium claviflorum, and the anti-HIV activity of structurally related triterpenoids, J. Nat. Prod., 57, 243, 1994. 

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