Planta Med 2013; 79(09): 761-767
DOI: 10.1055/s-0032-1328587
Biological and Pharmacological Activity
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Hepatoprotective Phenolic Glycosides from Gymnema tingens

Jin Tian
1   State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Material Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, Peopleʼs Republic of China
,
Qin-Ge Ma
1   State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Material Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, Peopleʼs Republic of China
,
Jian-Bo Yang
1   State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Material Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, Peopleʼs Republic of China
,
Ai-Guo Wang
1   State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Material Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, Peopleʼs Republic of China
,
Teng-Fei Ji
1   State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Material Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, Peopleʼs Republic of China
,
Yan-Gai Wang
1   State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Material Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, Peopleʼs Republic of China
,
Ya-Lun Su
1   State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Material Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, Peopleʼs Republic of China
› Author Affiliations
Further Information

Publication History

received 13 February 2013
revised 25 February 2013

accepted 17 April 2013

Publication Date:
23 May 2013 (online)

Abstract

Six new phenolic diglycosides, named gymnetinosides A–F (16), were isolated from the ethanolic extract of Gymnema tingens, together with three known diglycosides, sequinoside K (7), khaephuoside B (8), and albibrissinoside A (9). The structures of the new compounds were determined by spectroscopic techniques including 1D-, 2D NMR, mass spectroscopy, and circular dichroism. Compounds 1, 5, and 6 showed hepatoprotective activities against D-galactosamine-induced HL-7702 cell damage.

Supporting Information

 
  • References

  • 1 Porchezhian E, Dobriyal RM. An overview on the advances of Gymnema sylvestre: chemistry, pharmacology and patents. Pharmazie 2003; 58: 5-12
  • 2 Xia YF, Liu X, Yu GD. Advance on the research and development of Gymnema sylvestre . Chin Wild Plant Resour 2000; 19: 1-7
  • 3 Shimizu K, Ozeki M, Iino A, Nakajyo S, Urakawa N, Atsuchi M. Structure-activity relationships of triterpenoid derivatives extracted from Gymnema inodorum leaves on glucose absorption. Jpn J Pharmacol 2001; 86: 223-229
  • 4 Zhang Z, Chen J, Zhou J. Gymnemarosides A and B from Gymnema yunnanense . Yunnan Zhiwu Yanjiu 1991; 13: 75-80
  • 5 Chen J, Qiu S, Zhang Z, Zhou J. The chemical constituents of Gymnema yunnanense . Yunnan Zhiwu Yanjiu 1989; 11: 203-208
  • 6 Yoshikawa K, Matsuchika K, Arihara S, Chang HC, Wang JD. Pregnane glycosides, gymnepregosides A–F from the roots of Gymnema alternifolium . Chem Pharm Bull 1998; 46: 1239-1243
  • 7 Yoshikawa K, Ogata H, Arihara S, Chang HC, Wang JD. Antisweet natural products. XIII. Structures of alternosides I–X from Gymnema alternifolium . Chem Pharm Bull 1998; 46: 1102-1107
  • 8 Yoshikawa K, Matsuchika K, Takahashi K, Tanaka M, Arihara S, Chang HC, Wang JD. Pregnane glycosides, gymnepregosides G–Q from the roots of Gymnema alternifolium . Chem Pharm Bull 1999; 47: 798-804
  • 9 Yoshikawa K, Takahashi K, Matsuchika K, Arihara S, Chang HC, Wang JD. Antisweet natural products. XIV. Structures of alternosides XI–XIX from Gymnema alternifolium . Chem Pharm Bull 1999; 47: 1598-1603
  • 10 Kanchanapoom T, Kasai R, Yamasaki K. Phenolic glycosides from Markhamia stipulata . Phytochemistry 2002; 59: 557-563
  • 11 Kanchanapoom T, Kasai R, Yamasaki K. Phenolic glycosides from Barnettia kerrii . Phytochemistry 2002; 59: 565-570
  • 12 Jung MJ, Kang SS, Jung YJ, Choi JS. Phenolic glycosides from the stem bark glycosides from the stem bark of Albizzia julibrissin . Chem Pharm Bull 2004; 52: 1501-1503
  • 13 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: 501-506
  • 14 Xu F, Morikawa T, Matsuda H, Ninomiya K, Yoshikawa M. Structures of new sesquiterpenes and hepatoprotective constituents from the Egyptian herbal medicine Cyperus longus . J Nat Prod 2004; 67: 569-576
  • 15 Wang J, Di Y, Yang X, Li S, Wang Y, Hao X. Hydroquinone diglycoside acyl esters from the stems of Glycosmis pentaphylla . Phytochemistry 2006; 67: 486-491
  • 16 Lynn DG, Chen RH, Manning KS, Wood HN. The structural characterization of endogenous factors from Vinca rosea crown gall tumors that promote cell division of tobacco cells. Proc Natl Acad Sci USA 1987; 84: 615-619
  • 17 Liu GT. The anti-virus and hepatoprotective effect of bicyclol and its mechanism of action. Chin J New Drug Clin 2001; 10: 325-327