Determination of the three-dimensional structure of Gynoside A in solution using NMR and molecular modeling

Molecules

Volumn 12, Issue 4, 2007, Pages 907-916

  Li, Qian ^a   Yao, Zhi Hong ^b   Shi, Yan Hong ^c   Liu, Xin ^a   Yao, Xin Sheng ^b   Ye, Wen Cai ^a,b  

^a CHINA PHARMACEUTICAL UNIVERSITY   (China)

^b JINAN UNIVERSITY   (China)

^c SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

Gynoside A; Molecular modeling; NMR; Triterpenoid glycoside

Indexed keywords

DIMETHYL SULFOXIDE; GYNOSIDE A; PLANT EXTRACT; PROTON; PYRIDINE; PYRIDINE DERIVATIVE; SAPONIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; GYNOSTEMMA; METABOLISM; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PLANT LEAF;

CHEMISTRY; DIMETHYL SULFOXIDE; GYNOSTEMMA; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PLANT EXTRACTS; PLANT LEAVES; PROTONS; PYRIDINES; SAPONINS;

EID: 34247857625     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/12040907     Document Type: Article

References (18)

1. Cho, J.Y.; Yoo, E.S.; Cha, B.C.; Park, H.J; Rhee, M.H.; Han, Y.N. The inhibitory effect of triterpenoid glycosides originating from Sanguisorba officinalis on tissue factor activity and the production of TNF-α. Planta Medica 2006, 72, 1279-1284.
2. Popovich, D.G.; Kitts, D.D. Anticancer activity of ginseng and soy saponins. In Nutrition and Cancer Prevention; Awad, A.B.; Bradford, P.G., (Eds.); Taylor and Francis: Boca Raton, FL, 2006; pp. 457-483.
3. Sugishita, E.; Amagaya, S.; Ogihara, Y. Structure-activity studies of some oleanane triterpenoid glycosides and their related compounds from the leaves of Tetrapanax papyriferum on antiinflammatory activities. J. Pharmacobio-Dynam. 1982, 5, 379-87.
4. Rao, A.V.; Gurfinkel, D.M. The bioactivity of saponins: triterpenoid and steroidal glycosides. Drug Metab. Drug Interact. 2000, 17, 211-235.
5. Liu, X.; Ye, W.C.; Mo, Z.Y.; Hsiao, W.L. Five New Ocotillone-Type Saponins from Gynostemma pentaphyllum. J. Nat. Prod. 2004, 67, 1147-1151.
6. Gao, J.H.; Shi, G.B.; Song, G.Q.; Shao, Y.; Zhou, B.N. Further NMR Investigation and Conformational Analysis of an Acylated Flavonol Glucorhamnoside. Magn. Reson. Chem. 1996, 34, 249-254.
7. Hudson, B.P.; Hudson; Barton, J.K. Solution Structure of a Metallointercalator Bound Site Specifically to DNA. J. Am. Chem. Soc. 1998, 120, 6877-6888.
8. Goddard, T.D.; Kneller, D.G. SPARKY 3; University of California: San Francisco, CA, 2006.
9. Wüthrich, K.; Billeter, M.; Braun, W. Pseudo-structures for the 20 common amino acids for use in studies of protein conformations by measurements of intramolecular proton-proton distance constraints with nuclear magnetic resonance J. Mol. Biol. 1983, 169, 949-961.
10. Wüthrich, K. NMR of Proteins and Nucleic Acids; Wiley: New York, 1986.
11. Steinmetz, W.E.; Sadowshy, J.D.; Rice, J.S.; Roberts, J.J.; Bui, Y.K. Determination of the aqueous-phase structure of 6-O-methylerythromycin from NMR constraints. Magn. Reson. Chem. 2001, 39, 163.
12. 2O from NMR constraints. Magn. Reson. Chem. 2005, 43, 16-20.
13. Liu, S.B.; Shi, Y.H.; Zhang, Q.W.; Song, G.Q. Conformational study of fosinopril sodium in solution using NMR and molecular modeling. Magn. Reson. Chem. 2003, 41, 609-614.
14. Shi, YH, Song, YL, Li, Q, Song, GQ. Binding affinity difference induced by the stereochemistry of the sulfoxide bridge of the cyclic peptide inhibitors of Grb2-SH2 domain: NMR studies for the structural origin. Biochim. Biophys. Res. Commu. 2005, 330, 1254-1261.
15. Hyperchem 7.5 Master manual: Release 7 for Windows; Hypercube Inc.: Florida, USA, 2002.
16. Lins, L.; Brasseur, R.; Malaisse, W.J.; Biesemans, M.; Verheyden, P.; Willem, R. Importance of the hydrophobic energy: structural determination of a hypoglycemic drug of the meglitinide family by nuclear magnetic resonance and molecular modeling, Biochem. Pharmacol. 1996, 52, 1155-1168.
17. Gao, J.H.; Shi, G.B.; Song, G.Q.; Chen, K.X.; Ji, R.Y. Conformational studies of Asterin B and C in solution by NMR. II. Conformational analysis by NMR and molecular dynamic simulations. Acta Chim. Sin. 1996, 54, 702-708.
18. Crystallographic data for the compound Gynoside A reported in this paper have been deposited with the Cambridge Crystallographic Data Center and allocated the deposition number CCDC 200550. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(0)-1223-336033 or e-mail:deposit@ccdc.cam.ac.uk]