Isolation and Characterization of Biogenetically Related Highly Oxygenated Nortriterpenoids from Schisandra chinensis

Pre-schisanartanin (1) and schindilactones A−C (2−4) were isolated from Schisandra chinensis. Among them, compound 1 had an unprecedented carbon skeleton. More importantly, the structure features of this compound provided new insight into the biosynthesis of triterpenoids with schisanartane skeleton...

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Published inOrganic letters Vol. 9; no. 11; pp. 2079 - 2082
Main Authors Huang, Sheng-Xiong, Li, Rong-Tao, Liu, Jing-Ping, Lu, Yang, Chang, Ying, Lei, Chun, Xiao, Wei-Lie, Yang, Li-Bin, Zheng, Qi-Tai, Sun, Han-Dong
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 24.05.2007
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Models, Molecular
Molecular Structure
Oxygen - analysis
Oxygen - chemistry
Physical Sciences
Schisandra - chemistry
Science & Technology
Triterpenes - chemistry
LANCIFOLIA
ANTI-HIV ACTIVITY
RING
MICRANDILACTONE-A
UNIQUE SKELETON
MICRANTHA
LIGNANS
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ISSN1523-7060
1523-7052
DOI10.1021/ol070510z

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Summary:Pre-schisanartanin (1) and schindilactones A−C (2−4) were isolated from Schisandra chinensis. Among them, compound 1 had an unprecedented carbon skeleton. More importantly, the structure features of this compound provided new insight into the biosynthesis of triterpenoids with schisanartane skeleton. Their structures were determined by extensive spectroscopic analysis, single-crystal X-ray diffraction, and on the basis of the absolute structure of one related nortriterpenoid (5), which was determined for the first time by a modified Mosher method.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol070510z