Epiaschantin

Anti-platelet aggregation alkaloids and lignans from Hernandia nymphaeifolia.[Pubmed:10821052]

Planta Med. 2000 Apr;66(3):251-6.

A new aporphine, N-(N-methylcarbamoyl)-O-methyl-bulbocapnine (1), together with seven known compounds, (-)-5'-methoxypodorhizol (2), a mixture of beta-sitosterone (3) and stigmasta-4,22-dien-3-one (4), a mixture of 3 beta-hydroxystigmast-5-en-7-one (5) and 3 beta-hydroxystigmasta-5,22-dien-7-one (6), and a mixture of 6 alpha-hydroxystigmast-4-en-3-one (7) and 6 alpha-hydroxystigmasta-4,22-dien-3-one (8), were isolated in continuing studies on the trunk bark of Formosan Hernandia nymphaeifolia. The structures of these compounds were determined through spectral analyses. In addition, the previously reported six alkaloids, laurotetanine, oxohernagine, thalicarpine, reticuline, (+)-vateamine-2'-beta-N-oxide, (+)-hernandaline and six lignans, (+)-Epiaschantin, (+)-epimagnolin, (+)-epiyangambin, (-)-hernone, (-)-yatein, (-)-deoxypodophyllotoxin were demonstrated to have anti-platelet aggregation activity.

New dimeric aporphine alkaloids and cytotoxic constituents of Hernandia nymphaeifolia.[Pubmed:9000885]

Planta Med. 1996 Dec;62(6):528-33.

Three minor new dimeric aporphine alkaloids, oviisocorydine (1), ovihernangerine (2), and oxohernandaline (3), along with four known alkaloids, (+)-hernandaline, (+)-thallcarpine, (+)-N-methylovigerine, and N-methylcorydaldine, and five known lignans, (+)-epimagnolin, (+)-Epiaschantin, (+)-epiyangambin, (-)-deoxypodophyllotoxin, and (-)-yatein, have been additionally isolated from the trunk bark of Hernandia nymphaeifolia. The structures of these compounds were elucidated by spectroscopic methods. Among forty-four isolates obtained till now, nine compounds, hernandonine (4), hernanymphine (5), demethylsonodione (6), (+)-ovigerine (7), (+)-N-methylovigerine (8), N-formyldehydroovigerine (9), 4-methoxyoxohernandaline (10), (-)-deoxypodophyllotoxin (11), and (-)-yatein (12) showed significant cytotoxic activities (ED50 values < 1 microgram/ml) against P-388, KB16, A549, and HT-29 cell lines.

Antineoplastic agents. 522. Hernandia peltata (Malaysia) and Hernandia nymphaeifolia (Republic of Maldives).[Pubmed:14987061]

J Nat Prod. 2004 Feb;67(2):214-20.

Bioassay (P388 lymphocytic leukemia cell line and human tumor cell lines)-guided separation of the extracts prepared from the tropical and coastal trees Hernandia peltata (Malaysia) and Hernandianymphaeifolia (Republic of Maldives) led to the isolation of a new lignan designated as hernanol (1) and 12 previously known lignans: (-)-deoxypodophyllotoxin (2), deoxypicropodophyllin (3), (+)-Epiaschantin (4), (+)-epieudesmin (5), praderin (6), 5'-methoxyyatein (7), podorhizol (8), deoxypodorhizone (9), bursehernin (10), kusunokinol (11), clusin (12), and (-)-maculatin (13). The oxidative cyclization (with VOF(3)) of lignans 8, 9, and 10 resulted in a new and unusual benzopyran (14), isostegane (15), and a new dibenzocyclooctadiene lactone (16), respectively. The structure and relative stereochemistry of hernanol (1) and lignans 3, 7, 8, 9, 10, 11, and 12 were determined by 1D and 2DNMR and HRMS analyses. The structures and absolute stereochemistry of structures 2, 4, 5, 6, 13, 14, 15, and 16 were unequivocally determined by single-crystal X-ray diffraction analyses. Evaluation against the murine P388 lymphocytic leukemia cell line and human tumor cell lines showed podophyllotoxin derivatives 2 and 3 to be strong cancer cell line growth inhibitors and substances 4, 5, 8, and 15 to have marginal cancer cell line inhibitory activities. Seven of the lignans and one of the synthetic modifications (14) inhibited growth of the pathogenic bacterium Neisseria gonorrhoeae.