Structure elucidation of new oleanane-type glycosides from three species of Acanthophyllum

被引:13
作者
Timite, Gaoussou [1 ]
Mitaine-Offer, Anne-Claire [1 ]
Miyamoto, Tomofumi [2 ]
Ramezani, Mohammad [3 ]
Rustaiyan, Abdolhossein [4 ]
Mirjolet, Jean-Francois [5 ]
Duchamp, Olivier [5 ]
Lacaille-Dubois, Marie-Aleth [1 ]
机构
[1] Univ Bourgogne, Lab Pharmacognosie, UMIB, Fac Pharm,UPRES EA 3660, F-21079 Dijon, France
[2] Kyushu Univ, Grad Sch Pharmaceut Sci, Fukuoka 8128582, Japan
[3] Mashhad Univ Med Sci, Sch Pharm, Dept Pharmacognosy & Biotechnol, Mashhad, Iran
[4] Shahid Beheshty Univ, Dept Chem, Tehran, Iran
[5] Oncodesign, F-21076 Dijon, France
关键词
NMR; (1)H; (13)C; 2D NMR; triterpene saponins; gypsogenic acid; Caryophyllaceae; Acanthophyllum; TRITERPENE SAPONINS; SQUARROSUM;
D O I
10.1002/mrc.2577
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
From the roots of three species of Acanthophyllum (Caryophyllaceae), two new gypsogenic acid glycosides, 1 and 2, were isolated, 1 from A. sordidum and A. lilacinum, 2 from A. elatius and A. lilacinum, together with three known saponins, glandulosides B and C, and SAPO50. The structures of 1 and 2 were established mainly by 2D NMR techniques as 23-O-beta-D-galactopyranosylgypsogenic acid-28-O-beta-D-glucopyranosyl-(1 -> 3)-[beta-D-glucopyranosyl-(1 -> 6)]-beta-D-galactopyranoside (1) and gypsogenic acid-28-O-beta-D-glucopyranosyl-(1 -> 3)-[beta-D-glucopyranosyl-(1 -> 6)]-beta-D-galactopyranoside (2). The cytotoxicity of several of these saponins was evaluated against two human colon cancer cell lines (HT-29 and HCT 116). Copyright (C) 2010 John Wiley & Sons, Ltd.
引用
收藏
页码:370 / 374
页数:5
相关论文
共 8 条
  • [1] CARMICHAEL J, 1987, CANCER RES, V47, P936
  • [2] Isolation and structure elucidation of a highly haemolytic saponin from the Merck saponin extract using high-field gradient-enhanced NMR techniques
    Delay, C
    Gavin, JA
    Aumelas, A
    Bonnet, PA
    Roumestand, C
    [J]. CARBOHYDRATE RESEARCH, 1997, 302 (1-2) : 67 - 78
  • [3] Glandulosides A-D, triterpene saponins from Acanthophyllum glandulosum
    Gaidi, G
    Miyamoto, T
    Ramezani, M
    Lacaille-Dubois, MA
    [J]. JOURNAL OF NATURAL PRODUCTS, 2004, 67 (07): : 1114 - 1118
  • [4] Two new biologically active triterpene saponins from Acanthophyllum squarrosum
    Gaidi, G
    Miyamoto, T
    Rustaiyan, A
    Laurens, V
    Lacaille-Dubois, MA
    [J]. JOURNAL OF NATURAL PRODUCTS, 2000, 63 (11): : 1497 - 1502
  • [5] Three new acylated triterpene saponins from Acanthophyllum squarrosum
    Gaidi, G
    Miyamoto, T
    Rustaiyan, A
    Lacaille-Dubois, MA
    [J]. JOURNAL OF NATURAL PRODUCTS, 2001, 64 (07): : 920 - 924
  • [6] New triterpene saponins from Acanthophyllum pachystegium
    Haddad, M
    Miyamoto, T
    Ramezani, M
    Lacaille-Dubois, MA
    [J]. HELVETICA CHIMICA ACTA, 2004, 87 (01) : 73 - 81
  • [7] Two new biologically active triterpenoidal saponins acylated with salicylic acid from Albizia adianthifolia
    Haddad, M
    Miyamoto, T
    Laurens, V
    Lacaille-Dubois, MA
    [J]. JOURNAL OF NATURAL PRODUCTS, 2003, 66 (03): : 372 - 377
  • [8] Triterpene saponins from the roots of Clematis chinensis
    Mimaki, Y
    Yokosuka, A
    Hamanaka, M
    Sakuma, C
    Yamori, T
    Sashida, Y
    [J]. JOURNAL OF NATURAL PRODUCTS, 2004, 67 (09): : 1511 - 1516