New indole glucosides as biosynthetic intermediates of camptothecin from the fruits of Camptotheca acuminata

  • Fitoterapia. 2015 Jun:103:1-8. doi: 10.1016/j.fitote.2015.03.004.
Peng Wang  1 ,  Jun Luo  2 ,  Xiao-Bing Wang  3 ,  Bo-Yi Fan  3 ,  Ling-Yi Kong  4
Affiliations
  • 1. 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.
  • 2. 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: [email protected].
  • 3. 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.
  • 4. 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: [email protected].
PMID: 25771119 DOI: 10.1016/j.fitote.2015.03.004
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.

Keywords
Biosynthesis; Camptotheca acuminata; Camptothecin; Indole glucoside.
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