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 in | Organic letters Vol. 16; no. 20; pp. 5406 - 5409 |
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Main Authors | , , , , , , |
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17.10.2014
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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. |
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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 |
AuthorAffiliation_xml | – name: Chinese Academy of Medical Sciences and Peking Union Medical College – name: State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica |
Author_xml | – sequence: 1 givenname: Yusheng surname: Shi fullname: Shi, Yusheng – sequence: 2 givenname: Yunbao surname: Liu fullname: Liu, Yunbao – sequence: 3 givenname: Yong surname: Li fullname: Li, Yong – sequence: 4 givenname: Li surname: Li fullname: Li, Li – sequence: 5 givenname: Jing surname: Qu fullname: Qu, Jing – sequence: 6 givenname: Shuanggang surname: Ma fullname: Ma, Shuanggang – sequence: 7 givenname: Shishan surname: Yu fullname: Yu, Shishan email: yushishan@imm.ac.cn |
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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 |
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