(+)-12alpha-Hydroxysophocarpine, a new quinolizidine alkaloid and related anti-HBV alkaloids from Sophora flavescens.
(+)-12alpha-Hydroxysophocarpine (8), a new quinolizidine alkaloid was isolated from the roots of Sophora flavescens, together with 10 known quinolizidine alkaloids, (+)-oxymatrine (1), (+)-matrine (2), (+)-9alpha-hydroxymatrine (3), (+)-allomatrine (4), (+)-oxysophocarpine (5), (-)-sophocarpine (6), (-)-9alpha-hydroxysophocarpine (7), (+)-lehmannine (9), (-)-13,14-dehydrosophoridine (10), and (-)-anagyrine (11). Their structures were elucidated by spectroscopic methods, and the stereochemistry of 8 was confirmed by X-ray analysis. These alkaloids were tested for anti-hepatitis B virus (HBV) activity in vitro, compounds 5, 6, 9, and 10 showed significant anti-HBV activity with inhibitory potency against HBsAg secretion at 48.3-79.3% and that against HBeAg secretion at 24.6-34.6%.
Ding
Pei-Lan
PL
Department of Pharmacognosy, School of Pharmacy, Fudan University, 138 Yixueyuan Road, Shanghai 200032, PR China.
Liao
Zhi-Xin
ZX
Huang
Hai
H
Zhou
Pei
P
Chen
Dao-Feng
DF
D000470:Alkaloids / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D000956:Antigens, Viral / Q000378:metabolism; D000998:Antiviral Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D045744:Cell Line, Tumor; D006515:Hepatitis B virus / Q000187:drug effects* / Q000378:metabolism; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010946:Plants, Medicinal / Q000737:chemistry; D011807:Quinolizines / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D029909:Sophora / Q000737:chemistry*; D013329:Structure-Activity Relationship
C508852:12-hydroxysophocarpine; D000470:Alkaloids; D000956:Antigens, Viral; D000998:Antiviral Agents; D011807:Quinolizines