title: New indole glucosides as biosynthetic intermediates of camptothecin from the fruits of Camptotheca acuminata.
abstract: Six new indole glucosides (1-6) and fifteen known alkaloids (7-21) were isolated from the fruit of Camptotheca acuminata. The planar structures of 1-6 were determined on the basis of spectroscopic data analysis and their absolute configurations were established by CD. The isolated indole glucosides showed a clear biosynthetic pathway of camptothecin (7), which started from tryptamine and secologanin and was proposed by synthetic chemists previously. Particularly, compound 1 supplemented the process of the transformation from pumiloside (20) or 3-epi-pumiloside (21) to camptothecin (7). In addition, camptothecin 10-O-β-D-glucopyranoside (13) and norcamptothecin (17), synthesized in the early structural modification of 7, were first isolated from the natural resources. The new compounds 1-6 were screened for their in vitro cytotoxicity but they did not show any exciting result.
authors.affiliation: State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing, 210009, People's Republic of China; School of Pharmacy, Yancheng Teachers University, Yancheng, Xiwang Road, 224051, People's Republic of China.
authors.forename: Peng
authors.initials: P
authors.lastname: Wang
authors.affiliation: State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing, 210009, People's Republic of China. Electronic address: luojun1981ly@163.com.
authors.forename: Jun
authors.initials: J
authors.lastname: Luo
authors.affiliation: State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing, 210009, People's Republic of China.
authors.forename: Xiao-Bing
authors.initials: XB
authors.lastname: Wang
authors.affiliation: State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing, 210009, People's Republic of China.
authors.forename: Bo-Yi
authors.initials: BY
authors.lastname: Fan
authors.affiliation: State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing, 210009, People's Republic of China. Electronic address: cpu_lykong@126.com.
authors.forename: Ling-Yi
authors.initials: LY
authors.lastname: Kong
mesh_terms: D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification; D029769:Camptotheca / Q000737:chemistry*; D002166:Camptothecin / Q000096:biosynthesis*; D002681:China; D005638:Fruit / Q000737:chemistry*; D005960:Glucosides / Q000737:chemistry* / Q000302:isolation & purification; D007211:Indoles / Q000737:chemistry* / Q000302:isolation & purification; D015394:Molecular Structure
chemical_list: D000470:Alkaloids; D005960:Glucosides; D007211:Indoles; D002166:Camptothecin
keywords: Biosynthesis; Camptotheca acuminata; Camptothecin; Indole glucoside