Cytotoxic bisbenzylisoquinoline alkaloids from the roots of Cyclea racemosa.
Six new bisbenzylisoquinoline alkaloids, racemosidines A-C (1-3) and racemosinines A-C (4-6), and four known compounds were isolated from the roots of Cyclea racemosa. Compound 1 is the first bisbenzylisoquinoline alkaloid reported that has diphenyl ether bridges at C-11/C-7' and C-8/C-12' and a benzyl-phenyl ether bridge at C-7/C-11'. Structures and absolute configurations of 1-6 were established by interpretation of spectroscopic data and confirmed by X-ray crystallographic analysis of representative compounds. Compounds 1-3 exhibited significant cytotoxicity against HCT-8 and BEL-7402 tumor cells, and compound 1 was also cytotoxic against A2780 tumor cells.
Wang
Jian-Zhong
JZ
Department of Chemistry of Medicinal Natural Products, West China College of Pharmacy, Sichuan University, No. 17, Duan 3, Renmin Nan Road, Chengdu, People's Republic of China.
Chen
Qiao-Hong
QH
Wang
Feng-Peng
FP
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D044182:Benzylisoquinolines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D018360:Crystallography, X-Ray; D031604:Cyclea / Q000737:chemistry*; D004354:Drug Screening Assays, Antitumor; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D006801:Humans; D007546:Isoquinolines; D008968:Molecular Conformation; D015394:Molecular Structure; D018517:Plant Roots / Q000737:chemistry
D000470:Alkaloids; D000972:Antineoplastic Agents, Phytogenic; D044182:Benzylisoquinolines; D004365:Drugs, Chinese Herbal; D007546:Isoquinolines; C551565:racemosinine C; C551561:racemosidine B; C551563:racemosinine A; C551560:racemosidine A; C551562:racemosidine C; C551564:racemosinine B