Stephaoxocanine, a Novel Dihydroisoquinoline Alkaloid from Stephania cepharantha

Abstract

Stephaoxocanine (1), a dihydroisoquinoline alkaloid bearing an oxocane ring, was isolated from the tubers of Stephania cepharantha cultivated in Japan, together with five known alkaloids. The structure was established on the basis of the spectroscopic data of 1 and its dihydro derivative (2), and the absolute configuration was determined by the modified Mosher's method. By comparison of the CD spectral data with that of 2, the revised absolute stereochemistry of excentricine (3) was proposed as 3a.

The genus Stephania (Menispermaceae): Chemical and pharmacological perspectives

“…Stephaoxocanine, stephaoxocanidine, romorphinane, cepharanthine, cepharanoline, steponine, isotetrandrine, berbamine, stecepharine, dehydroreticuline (11), magnoflorine, menisperine, oblongine, cyclanoline, cis-N-methylcapaurine, sinomenine, cephamerphinanine, D-glucopyranoside, 2 -N-methylisotetrandrine, N-methyl stesakine chloride (12), stesakine 9-O-␤-Dglucoside (13), N-methylasimilobine-2-O-␤-D-glucopyranoside (14), cephamonine, aromoline, zippelianine, cepharamine, aknadinine (15), aknadicine (16), cephatonine, (−)-cycleanine (28), obamegine, berbamine, isocorydine, anolobine, cotypalline, stepharine (9), (+)-reticuline (17), obaberine, homoaromoline, fangchinoline, tetrandrine (18), cephamuline Nakamura et al, 1992;Sugimoto et al, 1993Sugimoto et al, , 1988Kashiwaba et al, 1996Kashiwaba et al, , 1997Kashiwaba et al, , 2000Kashiwaba et al, , 1998Kashiwaba et al, , 1994Nakaoji et al, 1997;Tanahashi et al, 2000), berbamine and aromorine (Akasu et al, 1976).…”

6,7-Dimethoxy-1-(4-methoxyphenyl)isochroman

“…Isochroman (3,4-dihydro-1H-benzo[c]pyran) derivatives are found in nature; for example 1,6,8-trihydroxy-3-heptyl-7carboxyisochroman, an antibiotic and topoisomerase II inhibitor from Penicillum sp. (Imamura et al, 2000), pseudodeflectusin, a selective human cancer cytotoxin from Aspergillus pseudodeflectus, (Ogawa et al, 2004) in softwood lignin (Peng et al, 1999) and in the male wing gland pheromone of Aphomia sociella (Kunesch et al, 1987), or as part of complex natural products such as stephaoxocanine (Kashiwaba et al, 1996) and glucoside B (Cameron et al, 1964). 1-Phenyl-and 1-(3-methoxy-4-hydroxy)phenyl-6,7-dihydroxyisochromans have been identified in extra-virgin olive oil and shown to exhibit beneficial antioxidant effects (Lorenz et al, 2005) and antiplatelet activity (Togna et al, 2003).…”

Microwave‐accelerated Synthesis of Some (±)‐1‐Aryl‐5‐chloroisochromans

“…4 Isochroman structures are also part of complex natural products such as stephaoxocanine, 5 a novel dihydroisoquinoline alkaloid from Stephania cepharantha, and glucoside B, an aphid insect pigment derivative. 6 Hydroxy-1-arylisochromans such as 1-phenyl-6,7-dihydroxyisochroman and 1-(3-methoxy-4-hydroxyphenyl)-6,7-dihydroxyisochroman have been identified in extra-virgin olive oil.…”