Stephania hernandifolia

Stephania hernandifolia Walp. Aknadicine C19H23NOs (345) 156 -200° (EtOH) 23-25... 

Stephania hernandifolia (Willd.) Walp. (Menispermaceae) [also called Stephania discolor Spreng. (Menispcrmaceae)][249]... 

There are four alkaloids that are imino alkaloids in ring B (that is 3,4-dihydroisoquinolines) 3, 4 -dihydrostephasubine (295) from Stephania hernandifolia... 

There are but two alkaloids in this small group, ( t-)-epistephanine (40) from three species (capitata, hernandifolia, and japonica) and one variety of these species (Japonica var. australis) of Stephania (Menispermaceae), and oxoepistephanine (47a) from Stephania hernandifolia (Menispermaceae). The two compounds differ only in the presence of the carbonyl function at the a carbon in oxoepistephanine. These alkaloids appear lo be restricted in distribution to Stephania species. 

There are two alkaloids that are racemic mixtures cycleadrine (58) [(+/-) - fangchinoiine] from Cyclea barbaia and C. peltata (Menispermaceae) and (+/-)-tetrandrine (77) from the same two plants, as well as from Isopyrum thalictroides (Ranunculaceae) and Stephania hernandifolia (Menispermaceae). Menisidine (65) is likely a fangchinoiine isomer and menisine (66) is likely a (+)-tetrandrine stereoisomer. These latter two alkaloids were isolated from Stephania tetrandra (Menispermaceae). Oxofangchirine (349) is a benzyltetrahydoisoquinoline-benzylisoquinolone alkaloid from Stephania tetrandra (Menispermaceae). The stereochemistry at C( 1) is not defined. 

Sinoacutine and pallidine are found in Corydalis incisa (Pers.) (Fumariaceae)/ and the former alkaloid is also found in Stephania glabra (Menispermaceae). The chlorine-containing alkaloids acutumine and acutumidine are present in Menispermum canadense L. (Menispermaceae), and a full paper describing the isolation and structural elucidation of these two bases has been published. Hernandine (194) and hernandifoline (195) have been obtained from Stephania hernandifolia. 

Ray AB, Chattopadhyay S, Tripathi RM, Gambhir SS et al. 1979 Isolation and pharmacological action of epistephanine, an alkaloid of Stephania hernandifolia. Planta Med 35 167-173... 

Investigation of the cytoxic agents of Stephania hernandifolia showed that both enantiomorphs and the racemic modification of tetrandrine (X) have significant in vivo activity against W 256. With a therapeutic index of greater than 2, ( )-tetrandrine warrants preclinical pharmacological study [53, 54]. A new synthetic route to the tetrandrine skeleton has been recently reported [55]. 

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