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Clionasterol Glucoside and Acylated Clionasterol Glucosides from Oplismenus burmannii
Author(s) -
Verma Surjeet,
Kumar Shiv,
Srivastava Santosh Kumar,
Darokar Mahendra P.
Publication year - 2014
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.201300484
Subject(s) - chemistry , arachidic acid , glucoside , aglycone , oleic acid , fatty acid , stereochemistry , acylation , organic chemistry , palmitic acid , glycoside , biochemistry , medicine , alternative medicine , pathology , catalysis
A new clionasterol glucoside, clionasterol‐[(1'→3α)‐ O ‐β‐D]‐glucopyranoside ( 1 ), a new acylated clionasterol glucoside, clionasterol‐[6'‐ O ‐acyl‐(1'→3β)‐O‐b‐D]‐glucopyranoside ( 2 ) and clionasterol ( 3 ) were isolated from the aerial parts of Oplismenus burmannii . The nature and length of fatty acid acyl chains in 2 was identified by alkaline methanolysis of compound 2 . The aglycone fraction on GC‐MS analysis showed three peaks in GC at t R 49.86 (82.1%), 51.13 (13.3%) and 56.53 (4.6%) min, which were characterized as arachidic acid methyl ester ( a ) oleic acid methyl ester ( b ) and 12‐methyltetradecanoic acid methyl ester ( c ) respectively. Thus 2 was characterized as a mixture of three new compounds, clionasterol‐[6'‐ O ‐eicosanoyl‐(1'→3β)‐ O ‐β‐D]‐glucopyranoside ( 2a ), clionasterol‐[6'‐ O ‐(8Z)‐octa‐deca‐9‐enoyl‐(1'→3β)‐ O ‐β‐D]‐glucopyranoside ( 2b ) and clionasterol‐[6'‐ O ‐(12‐methyltetradecanoyl)‐(1'→3β)‐ O ‐β‐D]‐glucopyranoside ( 2c ).