Chiral Resolution and Absolute Configuration of a Pair of Rare Racemic Spirodienone Sesquineolignans from Xanthium sibiricum

A pair of racemic spirodienone neolignan enantiomers, (±)-sibiricumin A, were isolated from the extract of the fruits of Xanthium sibiricum. The resolution of (+)- and (−)-sibiricumin A was achieved by chiral HPLC. The absolute configurations of the racemes were assigned by X-ray and by electronic c...

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Published inOrganic letters Vol. 16; no. 20; pp. 5406 - 5409
Main Authors Shi, Yusheng, Liu, Yunbao, Li, Yong, Li, Li, Qu, Jing, Ma, Shuanggang, Yu, Shishan
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.10.2014
Amer Chemical Soc
Subjects
Animals
Chemistry
Chemistry, Organic
Chromatography, High Pressure Liquid
Circular Dichroism
Crystallography, X-Ray
Leukocytes - drug effects
Lignans - chemistry
Lignans - isolation & purification
Lipopolysaccharides - pharmacology
Molecular Conformation
Molecular Structure
Nitric Oxide - biosynthesis
Physical Sciences
Rats
Science & Technology
Spiro Compounds - chemistry
Spiro Compounds - isolation & purification
Stereoisomerism
Xanthium - chemistry
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Abstract A pair of racemic spirodienone neolignan enantiomers, (±)-sibiricumin A, were isolated from the extract of the fruits of Xanthium sibiricum. The resolution of (+)- and (−)-sibiricumin A was achieved by chiral HPLC. The absolute configurations of the racemes were assigned by X-ray and by electronic circular dichroism (ECD). This experiment is the first unambiguous determination of the absolute configuration of spirodienone neolignan.
AbstractList A pair of racemic spirodienone neolignan enantiomers, (±)-sibiricumin A, were isolated from the extract of the fruits of Xanthium sibiricum. The resolution of (+)- and (-)-sibiricumin A was achieved by chiral HPLC. The absolute configurations of the racemes were assigned by X-ray and by electronic circular dichroism (ECD). This experiment is the first unambiguous determination of the absolute configuration of spirodienone neolignan.
A pair of racemic spirodienone neolignan enantiomers, (±)-sibiricumin A, were isolated from the extract of the fruits of Xanthium sibiricum. The resolution of (+)- and (−)-sibiricumin A was achieved by chiral HPLC. The absolute configurations of the racemes were assigned by X-ray and by electronic circular dichroism (ECD). This experiment is the first unambiguous determination of the absolute configuration of spirodienone neolignan.
A pair of racemic spirodienone neolignan enantiomers, (+/-)-sibiricumin A, were isolated from the extract of the fruits of Xanthium sibiricum. The resolution of (+)- and (-)-sibiricumin A was achieved by chiral HPLC. The absolute configurations of the racemes were assigned by X-ray and by electronic circular dichroism (ECD). This experiment is the first unambiguous determination of the absolute configuration of spirodienone neolignan.
Author Yu, Shishan
Li, Li
Liu, Yunbao
Qu, Jing
Shi, Yusheng
Ma, Shuanggang
Li, Yong
AuthorAffiliation State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica
Chinese Academy of Medical Sciences and Peking Union Medical College
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Snippet A pair of racemic spirodienone neolignan enantiomers, (±)-sibiricumin A, were isolated from the extract of the fruits of Xanthium sibiricum. The resolution of...
A pair of racemic spirodienone neolignan enantiomers, (+/-)-sibiricumin A, were isolated from the extract of the fruits of Xanthium sibiricum. The resolution...
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SubjectTerms Animals
Chemistry
Chemistry, Organic
Chromatography, High Pressure Liquid
Circular Dichroism
Crystallography, X-Ray
Leukocytes - drug effects
Lignans - chemistry
Lignans - isolation & purification
Lipopolysaccharides - pharmacology
Molecular Conformation
Molecular Structure
Nitric Oxide - biosynthesis
Physical Sciences
Rats
Science & Technology
Spiro Compounds - chemistry
Spiro Compounds - isolation & purification
Stereoisomerism
Xanthium - chemistry
Title Chiral Resolution and Absolute Configuration of a Pair of Rare Racemic Spirodienone Sesquineolignans from Xanthium sibiricum
URI http://dx.doi.org/10.1021/ol502649a
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