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Secocycloartane Triterpenoidal Saponins from the Leaves of Astragalus membranaceus Bunge
Author(s) -
Kuang Haixue,
Okada Yoshihito,
Yang Bingyou,
Tian Zhenkun,
Okuyama Tohru
Publication year - 2009
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200800341
Subject(s) - chemistry , stereochemistry , hydrolysis , alkaline hydrolysis , diene , organic chemistry , natural rubber
Two new 9,10‐secocycloartane triterpenoidal saponins, named huangqiyenins E ( 1 ) and F ( 2 ) were isolated from the leaves of Astragalus membranaceus Bunge . Enzymatic hydrolysis of 1 and 2 afforded the aglycones huangqiyegenins III ( 3 ) and IV ( 4 ), resp. Further alkaline hydrolysis of 3 provided trideacetylhuangqiyegenin III ( 5 ). Their structures were established by detailed spectroscopic analysis as (3 S ,5 R ,6 S ,10 R ,12 β ,16 β ,24 E )‐26‐( β ‐ D ‐glucopyranosyloxy)‐10,16‐dihydroxy‐4,4,14‐trimethyl‐9,19‐cyclo‐9,10‐secocholesta‐9(11),24‐diene‐3,6,12‐triyl triacetate ( 1 ), (3 S ,5 R ,6 S ,10 R , 16 β ,24 E )‐26‐( β ‐ D ‐glucopyranosyloxy)‐10,16‐dihydroxy‐4,4,14‐trimethyl‐9,19‐cyclo‐9,10‐secocholesta‐9(11), 24‐diene‐3,6‐diyl diacetate ( 2 ), (3 S ,5 R ,6 S ,10 R ,12 β ,16 β ,24 E )‐10,16,26‐trihydroxy‐4,4,14‐trimethyl‐9,19‐cyclo‐9,10‐secocholesta‐9(11),24‐diene‐3,6,12‐triyl triacetate ( 3 ), (3 S ,5 R ,6 S ,10 R ,16 β ,24 E )‐10,16,26‐trihydroxy‐4,4,14‐trimethyl‐9,19‐cyclo‐9,10‐secocholesta‐9(11),24‐diene‐3,6‐diyl diacetate ( 4 ), and (3 S ,5 R , 6 S ,10 R ,12 β ,16 β ,24 E )‐4,4,14‐trimethyl‐9,19‐cyclo‐9,10‐secocholesta‐9(11),24‐diene‐3,6,10,12,16,26‐hexol ( 5 ), resp.