[reaction: see text] A facile approach for the conversion of a spirostan saponin into its furostan counterpart, as illustrated by the transformation of dioscin to methyl protodioscin (and its 26-thio-analogue), has been developed.
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Carbohydr Res
January 2015
Beijing Institute of Radiation Medicine, No. 27 Tai-ping Road, Haidian District, Beijing 100850, China. Electronic address:
In this study seven strains of the genus Arthrobacter were screened by biotransformation to discover glycosylating patterns on steroid saponins. A strain of Arthrobacter nitroguajacolicus (CPCC 203516) was found to have the ability of fructosylation. Crude enzyme of the strain was extracted for the further study of conversion characteristics and patterns.
View Article and Find Full Text PDFChem Pharm Bull (Tokyo)
May 2012
Faculty of Medical and Pharmaceutical Scieces, Sojo University, 4-22-1 Ikeda, Kumamoto 860-0082, Japan.
A spirosolane derivative possessing a hydroxyl group at C-23, esculeogenin A, a sapogenol of tomato saponin, was found to be easily converted into the corresponding pregnane derivative by refluxing with aqueous pyridine. Therefore, introduction of a hydroxyl group into the C-23 of diosgenin (as representative of spirostane derivatives) and solasodine (as representative of spirosolane derivatives) was attempted by the reaction of NaNO(2)-BF(3) · Et(2)O. In diosgenin, the objective compound was obtained by the reaction in AcOH.
View Article and Find Full Text PDFOrg Lett
June 2006
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, China.
[reaction: see text] A facile approach for the conversion of a spirostan saponin into its furostan counterpart, as illustrated by the transformation of dioscin to methyl protodioscin (and its 26-thio-analogue), has been developed.
View Article and Find Full Text PDFNat Prod Res
April 2006
Laboratório de Química de Plantas Medicinais, Núcleo de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro, PO Box 68045, CEP 21944-971, Rio de Janeiro, Brazil.
A new steroidal saponin was isolated from the leaves of Agave shrevei. Its structure was established as 3-[O-beta-D-glucopyranosyl-(1-->2)-O-[O-beta-D-glucopyranosyl-(1-->4)-O-[O-beta-D-glucopyranosyl-(1-->6)]-O-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranosyl)-oxy]-(3beta,5alpha,25R)-spirostane. The structural identification was performed using detailed analyses of 1H- and 13C-NMR spectra including 2D NMR spectroscopic techniques (COSY, HETCOR, HMBC, and HMQC) and chemical conversions.
View Article and Find Full Text PDFZ Naturforsch C J Biosci
June 2005
Núcleo de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro, Centro de Ciências da Saúde, 21944-970, P.O. Box 68045, Rio de Janeiro, Brasil.
A new steroidal saponin, 3-{(O-6-deoxy-a-L-mannopyranosyl-(1 --> 4)-O-beta-D-glucopyranosyl-(1 --> 3)-O-[O-beta-D-glucopyranosyl-(1 --> 3)-beta-D-glucopyranosyl-(1 --> 2)]-O-beta-D-glucopyranosyl-(1 --> 4)-beta-D-galactopyranosyl)oxy}-6-hydroxy-(3beta,5alpha,6alpha,25R)-spirostan-12-one, was isolated from Agave brittoniana Trel. The structure was determined by extensive NMR spectroscopy studies and chemical conversions. Its effects on the Na+-ATPase and (Na+ + K+)-ATPase activities of the proximal tubule from pig kidney were evaluated.
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