Planta Med 2005; 71(4): 355-361
DOI: 10.1055/s-2005-864103
Original Paper
Natural Product Chemistry
© Georg Thieme Verlag KG Stuttgart · New York

Six New Triterpenoid Saponins from the Root and Stem Bark of Cephalanthus occidentalis

Zhizhen Zhang1 , Shiyou Li1 , Shanmin Zhang2
  • 1Center for Medicinal Plant Research, Arthur Temple College of Forestry, Stephen F. Austin State University, Nacogdoches, Texas, USA
  • 2Sealy Center for Structural Biology, Department of Physiology and Biophysics, University of Texas Medical Branch, Galveston, Texas, USA
Further Information

Publication History

Received: July 8, 2004

Accepted: October 14, 2004

Publication Date:
27 April 2005 (online)

Abstract

From the root and stem bark of Cephalanthus occidentalis L., a common American wetland species, six new triterpenoid saponins (1 - 6), together with 29 known compounds were isolated and identified. On the basis of spectroscopic analysis and chemical degradation, the structures of new compounds were elucidated as 3-O-β-glucopyranosylcincholic acid (1), cincholic acid 28-O-β-glucopyranosyl ester (2), 3-O-β-glucopyranosyl-(1→4)-β-fucopyranosylcincholic acid (3), 3-O-β-glucopyranosyl-(1→4)-β-fucopyranosylcincholic acid 28-O-β-glucopyranosyl ester (4), 3-O-β-glucopyranosylcincholic acid 28-O-α-arabinopyranosyl-(1→2)-β-glucopyranosyl ester (5), and 3-O-β-glucopyranosylquinovic acid 28-O-α-arabinopyranosyl-(1→2)-β-glucopyranosyl ester (6).

References

  • 1 Harris M. Botanical North America. New York; HarperResource 2003: pp 162-4
  • 2 Phillipson J D, Hemingway S R. Indole and oxindole alkaloids from Cephalanthus occidentalis .  Phytochemistry. 1974;  13 2621-2
  • 3 Fairman K R. The glycosides and alkaloids of Cephalanthus occidentalis L. Ph. D. Dissertation. Storrs; The University of Connecticut 1970
  • 4 Zhang Z Z, Li S Y, Zhang S M, Liang C, Gorenstein D, Beasley R S. New camptothecin and ellagic acid analogues from the root bark of Camptotheca acuminata .  Planta Medica. 2004;  70 1216-21
  • 5 Li S Y. A system for increasing the production of indole and quinoline alkaloids, particularly camptothecins and related compounds, from plants. R. O. China Invention Patent 162 720 2002
  • 6 Rumbero-Sanchez A, Vazquez P. A non-triterpene glycoside from Isertia haenkeana and a 13C NMR study of cincholic acid.  Phytochemistry. 1991;  30 623-6
  • 7 Jimeno M L, Rumbero-Sanchez A, Vazquez P. 1H and 13C NMR spectra of pyrocincholic acid.  Phytochemistry. 1995;  40 899-901
  • 8 Poellmann K, Gagel S, Hani M, Elgamal A, Shaker K H, Seifert K. Triterpenoid saponins from the roots of Zygophyllum species.  Phytochemistry. 1997;  44 485-9
  • 9 Kang W Y, Wang J S, Yang X S, Hao X J. Triterpenoid saponins from Luculia pincia Hook.  Chin J Chem. 2003;  21 1501-5
  • 10 Aquino R, De Tommasi N, De Simone F, Pizza C. Triterpenes and quinovic acid glycosides from Uncaria tomentosa .  Phytochemistry. 1997;  45 1035-40
  • 11 Arriaga F J, Rumbero-Sanchez A, Vazquez P. Two triterpene glycosides from Isertia haenkeana .  Phytochemistry. 1990;  29 209-13
  • 12 Fan G J, He Z S. Triterpenoid glycosides from Adina rubella .  Phytochemistry. 1997;  44 1139-43
  • 13 Kitajima M, Hashimoto K, Yokoya M, Takayama H, Sandoval M, Aimi N. Two new nor-triterpene glycosides from Peruvian ”Uña de Gato” (Uncaria tomentosa).  J Nat Prod. 2003;  66 320-3
  • 14 Arbain D, Byrne L T, Putra M M, Sargent M V, Syarif M. A new glucoalkaloid from Uncaria glabrata . J Chem Soc Perkin Trans 1 1992: 665-6
  • 15 Achenbach H, Benirschke M. Confirmation of the absolute configuration of dolichantoside and isodolichantoside by synthesis from (-)-secologanin.  Phytochemistry. 1997;  44 1387-90
  • 16 Zhang Z Z, ElSohly H N, Jacob M R, Pasco D S, Walker L A, Clark A M. New indole alkaloids from the bark of Nauclea orientalis .  J Nat Prod. 2001;  64 1001-5
  • 17 Waterman P G, Zhong S. Vallesiachotamine and isovallesiachotamine from the seeds of Strychnos tricalysioides .  Planta Medica. 1982;  45 28-30
  • 18 Solis P N, Wright C W, Gupta M P, Phillipson J D. Alkaloids from Cephaelis dichroa .  Phytochemistry. 1993;  33 1117-9
  • 19 Kitajima J, Kamoshita A, Ishikawa T, Takano A, Fukuda T. Glycosides of Atractylodes ovata .  Chem Pharm Bull. 2003;  51 1106-8
  • 20 Tsukamoto H, Hisada S, Nishibe S. Coumarin and secoiridoid glucosides from bark of Olea africana and Olea capensis .  Chem Pharm Bull. 1985;  33 396-9
  • 21 Sati S P, Chaukiyal D C, Sati O P, Yamada F, Ono M. 2D NMR structure elucidation of a new coumarin glycoside from Xeromphis spinosa .  J Nat Prod. 1989;  52 376-9
  • 22 Boros C A, Stermitz F R. Iridoids. An updated review. Part I.  J Nat Prod. 1990;  53 1055-147

Shiyou Li, PhD

Center for Medicinal Plant Research

Arthur Temple College of Forestry

Stephen F. Austin State University

Nacogdoches

Texas 75962-6109

USA

Phone: +1-936-468-2071

Fax: +1-936-468-2489

Email: lis@sfasu.edu