PDF herunterladen
Planta Med 2014; 80(17): 1647-1656
DOI: 10.1055/s-0034-1383123
Natural Product Chemistry
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Hepatoprotective Saikosaponin Homologs from Comastoma pedunculatum

Bao-Song Cui
1   State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, Peopleʼs Republic of China
,
Yong-Qi Qiao
1   State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, Peopleʼs Republic of China
,
Yi Yuan
1   State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, Peopleʼs Republic of China
,
Li Tang
2   College of Life and Environmental Science, Central University for Nationalities, Beijing, Peopleʼs Republic of China
,
Hui Chen
1   State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, Peopleʼs Republic of China
,
Yan Li
1   State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, Peopleʼs Republic of China
,
Shuai Li
1   State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, Peopleʼs Republic of China
› Institutsangaben
Weitere Informationen

Publikationsverlauf

received 22. April 2014
revised 20. Juli 2014

accepted 01. September 2014

Publikationsdatum:
24. September 2014 (online)

Auch verfügbar auf
    Lizenzen und Reprints

Abstract

Eight new triterpenoid saponins, the saikosaponin homologs comastomasaponins A–H (1–8), as well as a known triterpenoid (9) and eight known saponins (10–17) were isolated from the aerial portions of Comastoma pedunculatum. The structures of these compounds were elucidated spectroscopically, and their hepatoprotective activity and cytotoxic activity were evaluated against five human tumor cell lines in vitro. Compounds 1, 5–12, 14, 15, and 17 exhibited potent hepatoprotective activity, and compound 11 displayed cytotoxic activity against HCT-8, Bel-7402, BGC-825, A549, and A2780 human tumor cell lines.

Key words

Gentianaceae - Comastoma pedunculatum - saikosaponin homologs - hepatoprotective activity - cytotoxic activity

Supporting Information

 

  • References

  • 1 Northwest Institute of Plateau Biology, Chinese Academy of Sciences. Tibetan medicine glossary. Xining: Qinghai Peopleʼs Publishing House; 1991: 106
    Suche in Google Scholar
  • 2 Zhang X, Zhao YZ, Zhang ZX. Classification and distribution of Comastoma (Gentianaceae) in Helan Mountains in China by floristic, ecological and geographical approaches. For Stud China 2007; 9: 147-151
    CrossrefPubMedSuche in Google Scholar
  • 3 Fan SF, Hu BL, Ding JY, Sun HF. Study on the chemical constituents of Comastoma pulmonarium (Turcz.) Toyohuni. Acta Bot Sin 1988; 30: 303-307
    PubMedSuche in Google Scholar
  • 4 Tang L, Cui J, Zhou SX. Xanthones from Comastomu pedunculatum . Chem Nat Compd 2009; 45: 733-734
    CrossrefPubMedSuche in Google Scholar
  • 5 Tang L, Xu XM, Rinderspacher KA, Cai CQ, Ma Y, Long CL, Feng JC. Two new compounds from Comastoma pedunculatum . J Asian Nat Prod Res 2011; 13: 895-900
    CrossrefPubMedSuche in Google Scholar
  • 6 Tang L, Xu XM, Liu Y, Wang YR, Long CL, Feng JC. Phytochemical constituents of Comastomu pedunculatum . Chem Nat Compd 2013; 49: 381-382
    CrossrefPubMedSuche in Google Scholar
  • 7 Zhang XF. Xanthone glycosides in Gentianaceae of Qinghai-Tibet plateau. Stud Plant Sci 1999; 6: 320-322
    PubMedSuche in Google Scholar
  • 8 Yuan Y, Cui BS, Zhang Y, Li S. Xanthones of Comastoma pedunculatum . China J Chin Mater Med 2010; 35: 1577-1579
    PubMedSuche in Google Scholar
  • 9 Qiao YQ, Yuan Y, Cui BS, Zhang Y, Chen H, Li S, Li Y. New xanthone glycosides from Comastoma pedunculatum . Planta Med 2012; 78: 1591-1596
    Thieme ConnectPubMedSuche in Google Scholar
  • 10 Qiao YQ, Cui BS, Tang L, Liu JB, Li S. Chemical constituents of n-BuOH extract of Comastoma pedunculatum . China J Chin Mater Med 2012; 37: 2360-2365
    PubMedSuche in Google Scholar
  • 11 Ding JK, Fujino H, Kasai R, Fujimoto N, Tanaka O, Zhou J, Matsuura H, Fuwa T. Chemical evaluation of Bupleurum species collected in Yunnan, China. Chem Pham Bull 1986; 34: 1158-1167
    CrossrefPubMedSuche in Google Scholar
  • 12 Benito PB, Martínez MJA, Sen AMS, Gómez AS, Matellano LF, Contreras SS, Lanza AMD. In vivo and in vitro anti-inflammatory activity of saikosaponins. Life Sci 1998; 63: 1147-1156
    CrossrefPubMedSuche in Google Scholar
  • 13 Kato M, Pu MY, Isobe KI, Iwamoto T, Nagase F, Lwin T, Zhang YH, Hattori T, Yanagita N, Nakashima I. Characterization of the immunoregulatory action of saikosaponin-d. Cell Immunol 1994; 159: 15-25
    CrossrefPubMedSuche in Google Scholar
  • 14 Chiang LC, Ng LT, Liu LT, Shieh DE, Lin CC. Cytotoxicity and anti-hepatitis B virus activities of saikosaponins from Bupleurum species. Planta Med 2003; 69: 705-709
    Thieme ConnectPubMedSuche in Google Scholar
  • 15 Miyase T, Matsushima Y. Saikosaponin homologues from Clinopodium spp. The structures of clinoposaponins XII–XX. Chem Pharm Bull 1997; 45: 1493-1497
    CrossrefPubMedSuche in Google Scholar
  • 16 Yamamoto A, Miyase T, Ueno A, Maeda T. Clinoposaponins I–V, new oleanane-triterpene saponins from Clinopodium gracile O. Kuntze. Chem Pharm Bull 1993; 41: 1270-1274
    CrossrefPubMedSuche in Google Scholar
  • 17 Barreroa AF, Haïdoura A, Sedqui A, Mansour AI, Rodíguez-García I, López A, Muñoz-Dorado M. Saikosaponins from roots of Bupleurum gibraltaricum and Bupleurum spinosum . Phytochemistry 2000; 54: 741-745
    CrossrefPubMedSuche in Google Scholar
  • 18 Ishii H, Nakamura M, Seo S, Tori K, Tozvo T, Yoshimura Y. Isolation, characterization, and nuclear magnetic resonance spectra of new saponins from the roots of Bupleurum falcatum L. Chem Pharm Bull 1980; 28: 2367-2383
    CrossrefPubMedSuche in Google Scholar
  • 19 Tanaka T, Nakashima T, Ueda T, Tomii K, Kouno I. Facile discrimination of aldose enantiomers bv reversed-phase HPLC. Chem Pharm Bull 2007; 55: 899-901
    CrossrefPubMedSuche in Google Scholar
  • 20 Ebata N, Nakajima K, Hayashi K, Okada M, Maruno M. Saponins from the root of Bupleurum falcatum . Phytochemistry 1996; 41: 895-901
    CrossrefPubMedSuche in Google Scholar
  • 21 Yamamoto A, Suzuki H, Miyase T, Ueno A, Maeda T. Clinoposaponins VI and VIII, two oleanane-triterpene saponins from Clinopodium micranthum . Phytochemistry 1993; 34: 485-488
    CrossrefPubMedSuche in Google Scholar
  • 22 Liu GT. The anti-virus and hepatoprotective effect of bicyclol and its mechanism of action. Chin J New Drugs 2001; 10: 325-327
    PubMedSuche in Google Scholar