Dicarabrones A and B, a Pair of New Epimers Dimerized from Sesquiterpene Lactones via a [3 + 2] Cycloaddition from Carpesium abrotanoides

Dicarabrones A and B, a pair of epimers possessing a new skeleton featuring a cyclopentane ring connecting two sesquiterpene lactone units, were isolated from the whole plant of Carpesium abrotanoides L. Their full structures were established on the basis of spectroscopic data and were further confi...

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Published inOrganic letters Vol. 17; no. 7; pp. 1656 - 1659
Main Authors Wu, Jiewei, Tang, Chunping, Chen, Lan, Qiao, Yan, Geng, Meiyu, Ye, Yang
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 03.04.2015
Amer Chemical Soc
Subjects
Asteraceae - chemistry
Chemistry
Chemistry, Organic
Crystallography, X-Ray
Cycloaddition Reaction
Dimerization
Lactones - chemistry
Lactones - isolation & purification
Molecular Structure
Physical Sciences
Science & Technology
Sesquiterpenes - chemistry
Sesquiterpenes - isolation & purification
DENSITY FUNCTIONALS
CARBONYLS
THERMOCHEMICAL KINETICS
CYCLOPROPANE 1,1-DIESTERS
STRATEGY
CONSTRUCTION
CROSS-CYCLOADDITION
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Summary:Dicarabrones A and B, a pair of epimers possessing a new skeleton featuring a cyclopentane ring connecting two sesquiterpene lactone units, were isolated from the whole plant of Carpesium abrotanoides L. Their full structures were established on the basis of spectroscopic data and were further confirmed by single-crystal X-ray crystallography. They were presumably biosynthesized from two sesquiterpenoid monomers through a [3 + 2] cycloaddition. Dicarabrones A and B showed moderate effects on HL-60 cells with IC50 values of 9.1 and 8.2 μM, respectively.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b00371