Planta Med 2010; 76(3): 291-294
DOI: 10.1055/s-0029-1186063
Natural Product Chemistry
Letters
© Georg Thieme Verlag KG Stuttgart · New York

Cholestane Glycosides and Trihydroxy Fatty Acids from the Rhizomes of Dioscorea septemloba

Xue-Ting Liu1 , 2 , Zhen-Zhong Wang3 , Wei Xiao3 , Hui-Wu Zhao3 , Biao Yu1
  • 1State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, P. R. China
  • 2Department of Chemistry, University of Wisconsin–La Crosse, La Crosse, WI, USA
  • 3Jiangsu Kanion Pharmaceutical Co., Jiangsu, P. R. China
Further Information

Publication History

received June 9, 2009 revised July 15, 2009

accepted July 21, 2009

Publication Date:
25 August 2009 (online)

Abstract

Two new steroidal glycosides, named dioseptemlosides I (1) and J (2), along with two known trihydroxy fatty acids, (12Z,15Z)-9,10,11-trihydroxy-12,15-octadecadienoic acid (3) and (12Z)-9,10,11-trihydroxy-12-octadecenoic acid (4), were isolated from the rhizomes of Dioscorea septemloba. Their structures were determined by HRESIMS, 1D and 2D NMR experiments, physical data, and chemical methods. The antitumor activity of compounds 1-4 was evaluated against three tumor cell lines and all of them were inactive at a concentration of 10 µM.

References

  • 1 Liu X T, Wang Z Z, Xiao W, Zhao H W, Hu J, Yu B. Cholestane and spirostane glycosides from the rhizomes of Dioscorea septemloba.  Phytochemistry. 2008;  69 1411-1418
  • 2 He X J, Qiao A M, Wang X L, Liu B, Jiang M M, Su L, Yao X S. Structural identification of methyl protodioscin metabolites in rats' urine and their antiproliferative activities against human tumor cell lines.  Steroids. 2006;  71 828-833
  • 3 Hu K, Dong A J, Yao X S, Kobayashi H, Iwasaki S. Antineoplastic agents I. Three spirostanol glycosides from rhizomes of Dioscorea collettii var. hypoglauca.  Planta Med. 1996;  62 573-575
  • 4 Hu K, Yao X S. The cytotoxicity of methyl protoneodioscin (NSC-698791) against human cancer cell lines in vitro.  Anticancer Res. 2002;  22 1001-1005
  • 5 Kawasaki T, Yamauchi T, Yamauchi R. Kikuba saponin. (1). (Saponins of Japanese Dioscoreaceae. X.).  Chem Pharm Bull. 1962;  10 698-702
  • 6 Yin J, Kouda K, Tezuka Y, Tran Q L, Miyahara T, Chen Y, Kadota S. Steroidal glycosides from the rhizomes of Dioscorea spongiosa.  J Nat Prod. 2003;  66 646-650
  • 7 Haraguchi M, Santos A P Z, Young M C M, Paulo E. Steroidal prosapogenins from Dioscorea olferslana.  Phytochemistry. 1994;  36 1005-1008
  • 8 Kuroda M, Mimaki Y, Ori K, Sakagami H, Sashida Y. Steroidal glycosides from the bulbs of Ornithogalum thyrsoides.  J Nat Prod. 2004;  67 1690-1696
  • 9 Kuroda M, Mimaki Y, Yokosuka A, Sashida Y. Cholestane glycosides from the bulbs of Galtonia candicans and their cytotoxicity.  Chem Pharm Bull. 2001;  49 1042-1046
  • 10 Agrawal P K, Jain D C, Gupta R K, Thakur R S. Carbon-13 NMR spectroscopy of steroidal sapogenins and steroidal sponins.  Phytochemistry. 1985;  24 2479-2496
  • 11 Benavides A, Napolitano A, Bassarello C, Carbone V, Gazzerro P, Malfitano A, Saggese P, Bifulco M, Piacente S, Pizza C. Oxylipins from Dracontium loretense.  J Nat Prod. 2009;  72 813-817
  • 12 Gao J M, Wang C Y, Zhang A L, Liu J K. A new trihydroxy fatty acid from the Ascomycete, Chinese truffle Tuber indicum.  Lipids. 2001;  36 1365-1370
  • 13 Dilika F, Bremner P D, Meyer J J M. Antibacterial activity of linoleic and oleic acids isolated from Helichrysum pedunculatum: a plant used during circumcision rites.  Fitoterapia. 2000;  71 450-452
  • 14 Prost I, Dhondt S, Rothe G, Vicente J, Rodriguez M J, Kift N, Carbonne F, Griffiths G, Esquerré-Tugayé M T, Rosahl S, Castresana C, Hamberg M, Fournier J. Evaluation of the antimicrobial activities of plant oxylipins supports their involvement in defense against pathogens.  Plant Physiol. 2005;  139 1902-1913

Prof. Dr. Biao Yu
Dr. Xue-Ting Liu

Shanghai Institute of Organic Chemistry
State Key laboratory of Biooganic and Natural Products Chemistry

354 Fenglin road, Shanghai

200032 Shanghai

China

Phone: + 86 21 54 92 51 31

Fax: + 86 21 64 16 61 28

Email: liuxueting_cn@hotmail.com

    >