Planta Med 2011; 77(7): 754-758
DOI: 10.1055/s-0030-1250569
Natural Product Chemistry
Original Papers
© Georg Thieme Verlag KG Stuttgart · New York

Three New Terpenoid Indole Alkaloids from Catharanthus roseus

Lei Wang1 , 2 , Yu Zhang1 , Hong-Ping He1 , Qiang Zhang1 , Shi-Fei Li1 , 2 , Xiao-Jiang Hao1
  • 1State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, The Chinese Academy of Sciences, Kunming, P. R. China
  • 2Graduate School of Chinese Academy of Sciences, Beijing, P. R. China
Further Information

Publication History

received Sept. 15, 2010 revised October 21, 2010

accepted October 26, 2010

Publication Date:
23 November 2010 (online)

Abstract

Three new terpenoid indole alkaloids, vidolicine (1), normacusine B N-oxide (2), and lochnerine N-oxide (3), together with seven known ones (410), were isolated from whole plants of Catharanthus roseus. Their structures were elucidated by spectroscopic methods (NMR, MS, UV, and IR). Cytotoxic activities of these isolates (110) were evaluated, but only compound 8 was active against HL-60, SMMC-7721, and A549 cell lines.

References

  • 1 van Der Heijden R, Jacobs D I, Snoeijer W, Hallard D, Verpoorte R. The Catharanthus alkaloids: pharmacognosy and biotechnology.  Curr Med Chem. 2004;  11 607-628
  • 2 Usia T, Watabe T, Kadota S, Tezuka Y. Cytochrome P450 2D6 (CYP2D6) inhibitory constituents of Catharanthus roseus.  Biol Pharm Bull. 2005;  28 1021-1024
  • 3 Singh D K, Srivastava B, Sahu A. Spectrophotometric determination of Rauwolfia alkaloids: estimation of reserpine in pharmaceuticals.  Anal Sci. 2004;  20 571-573
  • 4 Pereira D M, Ferreres F, Oliveira J M A, Gaspar L, Faria J, Valentão P, Sottomayor M, Andrade P B. Pharmacological effects of Catharanthus roseus root alkaloids in acetylcholinesterase inhibition and cholinergic neurotransmission.  Phytomedicine. 2010;  17 646-652
  • 5 Zhou H, He H P, Kong N C, Wang T J, Hao X J. Indole alkaloids from the leaves of Anthocephalus chinensis.  Helv Chim Acta. 2008;  91 2148-2152
  • 6 Zhou H, He H P, Kong N C, Wang Y H, Liu X D, Hao X J. Three new indole alkaloids from the leaves of Kopsia officinalis.  Helv Chim Acta. 2006;  89 515-519
  • 7 Zhou H, He H P, Luo X D, Wang Y H, Yang X W, Di Y T, Hao X J. Three new indole alkaloids from the leaves of Alstonia scholaris.  Helv Chim Acta. 2005;  88 2508-2512
  • 8 Zhang Z, Di Y T, Wang Y H, Mu S Z, Fang X, Zhang Y, Tan C J, Zhang Q, Yan X H, Guo J, Li C S, Hao X J. Gelegamines A–E: five new oxindole alkaloids from Gelsemium elegans.  Tetrahedron. 2009;  65 4551-4556
  • 9 Monks A, Scudiero D, Skehan P, Shoemaker R, Paull K, Vistica D, Hose C, Langley J, Cronise P, Vaigro W. Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines.  J Natl Cancer Inst. 1991;  83 757-766
  • 10 Reed L J, Muench H. A simple method of estimating fifty percent endpoint.  Am J Hyg. 1938;  27 493-497
  • 11 Weissberger I, Taylor E C. Indoles: the monoterpenoid indole alkaloids. New York; Wiley-Interscience 1983: 357
  • 12 Wenkert E, Cochran D W, Hagaman E W, Schell F M, Neuss N, Katner A S, Potier P, Kan C, Plat M, Koch M, Mehri H, Poisson J, Kunesch N, Rolland Y. Carbon-13 nuclear magnetic resonance spectroscopy of naturally occurring substances. XIX. Aspidosperma alkaloids.  J Am Chem Soc. 1973;  95 4990-4995
  • 13 Bruneton J, Cavé A. The carbon-20 stereochemistry of pandoline and epipandoline.  Tetrahedron Lett. 1976;  17 3567-3570
  • 14 Éles J, Kalaus G, Greiner I, Kajtár-Peredy M, Szabó P, Keserû G M, Szabó L, Szántay C. Synthesis of vinca alkaloids and related compounds. 100. Stereoselective oxidation reactions of compounds with the aspidospermane and quebrachamine ring system. First synthesis of some alkaloids containing the epoxy ring1a.  J Org Chem. 2002;  67 7255-7260
  • 15 Jokela R, Lounasmaa M. 1H- and 13C-NMR spectral data of five sarpagine-type alkaloids.  Heterocycles. 1996;  43 1015-1020
  • 16 Abaul J, Philogène E, Bourgeois P, Mérault G, Poupat C, Ahond A, Potier P. Alcaloïdes indoliques de Rauvolfia biauriculata.  J Nat Prod. 1986;  49 829-832
  • 17 Bruneton J, Cavé A. The carbon-20 stereochemistry of pandoline and epipandoline.  Tetrahedron Lett. 1976;  39 3567-3570
  • 18 Wang F P. The alkaloid chemistry. Beijing; Chemical Industry Press 2008: 305
  • 19 Marvin G, Janice S. Perivine.  Tetrahedron Lett. 1964;  42 3105-3111

Prof. Xiao-Jiang Hao

State Key Laboratory of Phytochemistry and Plant Resources in West China
Kunming Institute of Botany, the Chinese Academy of Sciences

Kunming 650204

People's Republic of China

Phone: +86 87 15 22 32 63

Fax: +86 87 15 22 30 70

Email: haoxj@mail.kib.ac.cn

>