Novel O-glycosidic gossypol isomers and their bioactivities.

作者: Juanjuan Yin , Limei Jin , Feng Chen , Xi Wang , Alex Kitaygorodskiy

DOI: 10.1016/J.CARRES.2011.06.031

关键词:

摘要: Abstract Novel glycosidic gossypol analogs, 7,7′-gossypol diglucoside tetraacetate GS1 , 6,7′-gossypol GS2 diglycoside GS1′ GS2′ were obtained by the ultrasound-assisted reaction of potassium salt with 2,3,4,6-tetra- O -acetyl-α- d -glucopyranosyl bromide under PTC conditions and fully characterized 1D NMR ( 1 H NMR, 13 C DEPT, NOE), 2D (HMBC, HMQC), FTIR, HRMS HPLC. The anticancer activities, cytotoxic effects as well anti-trypanosomal activities these novel gossypols explored suggest that glycosides could be used to develop new candidates for drugs agents.

参考文章(24)
K. Zh. Rezhepov, Kh. L. Ziyaev, N. I. Baram, A. I. Ismailov, F. G. Kamaev, A. M. Saiitkulov, Synthesis and Interferon-Inducing Activity of Azo-Derivatives of Gossypol and Its Imines Chemistry of Natural Compounds. ,vol. 38, pp. 319- 322 ,(2002) , 10.1023/A:1021613705698
S.A. Talipov, B.T. Ibragimov, X-Ray Crystal Structure of Four Inclusion Complexes of the Novel Host Gossindane: An Oxidation Product of Gossypol Journal of Inclusion Phenomena and Macrocyclic Chemistry. ,vol. 33, pp. 27- 38 ,(1999) , 10.1023/A:1008054114773
Gregory R. Moe, Tamara S. Bhandari, Becca A. Flitter, Vaccines containing de-N-acetyl sialic acid elicit antibodies protective against neisseria meningitidis groups B and C. Journal of Immunology. ,vol. 182, pp. 6610- 6617 ,(2009) , 10.4049/JIMMUNOL.0803677
X. S. Liang, A. J. Rogers, C. L. Webber, T. J. Ormsby, M. E. Tiritan, S. A. Matlin, C. C. Benz, Developing gossypol derivatives with enhanced antitumor activity. Investigational New Drugs. ,vol. 13, pp. 181- 186 ,(1995) , 10.1007/BF00873798
Roger J. Radloff, Lorraine M. Deck, Robert E. Royer, David L. Vander Jagt, Antiviral activities of gossypol and its derivatives against herpes simplex virus type II Pharmacological Research Communications. ,vol. 18, pp. 1063- 1073 ,(1986) , 10.1016/0031-6989(86)90023-8
R Kaminsky, E Zweygarth, Feeder layer-free in vitro assay for screening antitrypanosomal compounds against Trypanosoma brucei brucei and T. b. evansi. Antimicrobial Agents and Chemotherapy. ,vol. 33, pp. 881- 885 ,(1989) , 10.1128/AAC.33.6.881
Roswitha H. Haas, David A. Shirley, The Oxidation of Gossypol. II. Formation of Gossypolone with Ferric Chloride Journal of Organic Chemistry. ,vol. 30, pp. 4111- 4113 ,(1965) , 10.1021/JO01023A031
Offie Porat, Effects of gossypol on the motility of mammalian sperm Molecular Reproduction and Development. ,vol. 25, pp. 400- 408 ,(1990) , 10.1002/MRD.1080250414