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Planta Med 2008; 74(10): 1280-1284
DOI: 10.1055/s-2008-1081291
Natural Products Chemistry
Original Paper
© Georg Thieme Verlag KG Stuttgart · New York

Triterpenoid Saponins from Androsace umbellata and their Anti-proliferative Activities in Human Hepatoma Cells

Ying Wang1 , 2 , Dongmei Zhang1 , 2 , Wencai Ye1 , 2 , Zhiqi Yin3 , Kwok-Pui Fung4 , 5 , Shouxue Zhao3 , Xinsheng Yao1 , 2
  • 1Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou, P. R. China
  • 2Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, Guangzhou, P. R. China
  • 3Department of Phytochemistry, China Pharmaceutical University, Nanjing, P. R. China
  • 4Department of Biochemistry, The Chinese University of Hong Kong, Shatin, Hong Kong, P. R. China
  • 5Institute of Chinese Medicine, The Chinese University of Hong Kong, Shatin, Hong Kong, P. R. China
Further Information

Publication History

Received: February 20, 2008 Revised: May 19, 2008

Accepted: May 23, 2008

Publication Date:
11 July 2008 (online)

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Abstract

Two new triterpenoid saponins, along with five known ones, were isolated from the EtOH extract of the whole plants of Androsace umbellata. The structures of the new triterpenoid saponins were identified as 3-O-{β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→2)]-α-L-arabinopyranosyl}-3β-hydroxy-13β,28-epoxy-16-oxo-oleanan-30-al (1) and 3-O-β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-α-L-arabinopyranosyl-3β-hydroxy-13β,28-epoxy-16-oxo-oleanan-30-al (2) on the basis of their spectral and chemical properties. All these compounds showed significant cytotoxic activities in human hepatoma cells.

Key words

Androsace umbellata - Primulaceae - triterpenoid saponin - antiproliferative activity - human hepatoma cells

References

  • 1 State Administration of Traditional Chinese Medicine of PR China. Shanghai, Shanghai; Science and Technology 1998: 87-9
    Search in Google Scholar
  • 2 Pal B C, Roy G, Mahato S B. Triterpenoid sapogenols from Androsace saxifragifolia: the structure of androsacenol.  Phytochemistry. 1984;  23 1475-9
    CrossrefPubMedSearch in Google Scholar
  • 3 Waltho J P, Williams D H, Mahato S B, Pal B C, Barna J CJ. Structure elucidation of two triterpenoid tetrasaccharides from Androsace saxifragifolia. J Chem Soc [Perkin I] 1986: 1527-31
    Search in Google Scholar
  • 4 Pal B C, Mahato S B. New triterpenoid pentasaccharides from Androsace saxifragifoia. J Chem Soc [Perkin I] 1987: 1963-7
    Search in Google Scholar
  • 5 Teo E K, Fock K M. Hepatocellular carcinoma: an Asian perspective.  Dig Dis. 2001;  19 263-8
    CrossrefPubMedSearch in Google Scholar
  • 6 Taieb J, Barbare J C, Rougier P. Medical treatments for hepatocelluar carcinoma (HCC): what’s next.  Ann Oncol. 2006;  17 (Suppl 10) 308-14
    CrossrefPubMedSearch in Google Scholar
  • 7 Ye W C, He A M, Zhao S X, Che C T. Pulsatilloside C from the roots of Pulsatilla chinensis.  J Nat Prod. 1998;  61 658-9
    CrossrefPubMedSearch in Google Scholar
  • 8 Ye W C, Ou B X, Ji N N, Zhao S X, Ye T, Mckervey M A. et al . Patensin, a saponin from Pulsatilla patens var. multifida.  Phytochemistry. 1995;  39 937-9
    CrossrefPubMedSearch in Google Scholar
  • 9 Ye W C, Ji N N, Zhao S X, Liu J H, Ye T, Mckervey M A. et al . Triterpenoids from Pulsatilla chinensis.  Phytochemistry. 1996;  42 799-802
    CrossrefPubMedSearch in Google Scholar
  • 10 Ye W C, Zhang Q W, Liu X, Che C T, Zhao S X. Oleanane saponins from Gymnema sylyestre.  Phytochemistry. 2000;  53 893-9
    CrossrefPubMedSearch in Google Scholar
  • 11 Hara S, Okabe H, Mihashi K. Gas-liquid chromatographic separation of aldose enantiomers as trimethylsilyl ethers of methyl 2-(polyhydroxyalkyl)thiazolidine-4(R)-carboxylates.  Chem Pharm Bull. 1987;  35 501-6
    CrossrefPubMedSearch in Google Scholar
  • 12 Li Y C, Fung K P, Kwok T T, Lee C Y, Suen Y K, Kong S K. Mitochondrial targeting drug lonidamine triggered apoptosisin doxorubicin-resistant HepG2 cells.  Life Sci. 2002;  72 2729-40
    PubMedSearch in Google Scholar
  • 13 Huang J, Ogihara Y, Zhang H, Shimizu N, Takeda T. Triterpenoid saponins from Ardisia manillata.  Phytochemistry. 2000;  54 817-22
    CrossrefPubMedSearch in Google Scholar
  • 14 Liang B, Tian J K, Xu L J, Yang S L. Triterpenoid saponins from Lysimachia davurica.  Chem Pharm Bull. 2006;  54 1380-3
    CrossrefPubMedSearch in Google Scholar
  • 15 Lavaud C, Massiot G, Barrera J B, Moretti C, Menolivier L L. Triterpene saponins from Myrsine pellucida.  Phytochemistry. 1994;  37 1671-7
    CrossrefPubMedSearch in Google Scholar

Professor Wencai Ye

Institute of Traditional Chinese Medicine and Natural Products

College of Pharmacy

Jinan University

Guangzhou 510632

People’s Republic of China

Phone: +86/20/8522/8369

Fax: +86/20/8522/1559

Email: chywc@yahoo.com.cn