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Four New Bisbenzylisoquinoline Alkaloids from the Root of Stephania Tetrandra (Fen-Fang Ji)

1988; Elsevier BV; Volume: 27; Issue: 5 Linguagem: Inglês

10.3987/com-88-4498

1881-0942

Tatsunori Ogino, Toshitsugu Sato, Hiroshi Sasaki, Masao Chin, Hiroshi Mitsuhashi,

Ziziphus Jujuba Studies and Applications

Four new bisbenzylisoquinoline (BBI) alkaloids named fenfangjines A, B, C and D were isolated from the root of Stephania tetrandra S. Moore, the Chinese traditional medicine "Fen-Fang-Ji", along with thirteen known alkaloids (1-11).The chemical structures of fenfangjines A, B, C and D were respectively determined to be I , I , ( ) and (17) by spectral analyses and chemical methods.The Chinese traditional medicine "Fen-Fang-Ji", the root of Stephania tetrandra S. Moore (Menispermaceae), demonstrated to have antiinflamatory, antiallergic and hypotensive effects in experimental animals.'The main alkaloid tetrandrinell) wasshown to be effective to hypertension in a clinical test.The methanolic extract of the root and its following alkaloidal fraction showed the inhibitory activitiesZ against angiotensin converting enzyme I (ACE).Repeated chromatographic separation of alkaloidal fraction gave thirteen known alkaloids, tetrandrine (A) ,3'4 fangchinoline (2) ,4'5 tetrandrine 2'-N-a-oxide (A), tetrandrine 2'-N-0-oxide (4) , 2-N-methyltetrandrinium chloride (XI ,' 2'-N-methyltetrandrinium chloride (61 ,' 2,2'-N,N-dimethyltetrandrinium dichloride ( l ) , cycleanine (8) ,4'9 cyclanoline chloride (z), "lo stephenanthrine (s) , l1 magnoflorine chloride ( G I , 9.12 alkaloid AA-l(X) ,I3 oblongine chloride(=) ,14 and four new bisbenzylisoquinoline (BBI) derivatives named fenfangjines A ( * ) , B(g1, C(E) and D ( g ) .Their yields are 0.0014%, 0.006%, 0.008% and 0,005%, respectively.The active concentrations of BBI alkaloids as inhibitors of ACE are all in the 1 0 -~-1 0 -~~ range.This communication discribes the structural elucidations of fenfangjines A(e), El(%), C(g) and D(E1. Me0HO q& OH / OMe