The stereochemistry of ledol from Renealmia chrysotrycha: An NMR study

Maria Auxiliadora C. Kaplan; Helena R.L. Pugialli; Daise Lopes; Hugo E. Gottlieb

doi:10.1016/s0031-9422(00)00291-0

The stereochemistry of ledol from Renealmia chrysotrycha: An NMR study

Maria Auxiliadora C. Kaplan
, Helena R.L. Pugialli
, Daise Lopes
, Hugo E. Gottlieb

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

31 Scopus citations

Abstract

From the leaves of Renealmia chrysotrycha (Zingiberaceae), we isolated a sesquiterpene alcohol for which spectral data suggested the structure of a 10-aromadendranol. A meticulous NMR investigation, based mainly on vicinal proton-proton coupling constants and NOE interactions, and confirmed by a molecular mechanics calculation, established its relative stereochemistry as that of ledol. This finding resolves several recent literature ambiguities. Three known compounds (aromadendrene, cis-calamenene and palustrol) were also isolated. (C) 2000 Elsevier Science Ltd.

Original language	English
Pages (from-to)	749-753
Number of pages	5
Journal	Phytochemistry
Volume	55
Issue number	7
DOIs	https://doi.org/10.1016/s0031-9422(00)00291-0
State	Published - 8 Dec 2000

Keywords

Ledol
NMR determination of stereochemistry
Renealmia chrysotrycha
Sesquiterpene alcohol
Zingiberaceae

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10.1016/s0031-9422(00)00291-0

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abstract = "From the leaves of Renealmia chrysotrycha (Zingiberaceae), we isolated a sesquiterpene alcohol for which spectral data suggested the structure of a 10-aromadendranol. A meticulous NMR investigation, based mainly on vicinal proton-proton coupling constants and NOE interactions, and confirmed by a molecular mechanics calculation, established its relative stereochemistry as that of ledol. This finding resolves several recent literature ambiguities. Three known compounds (aromadendrene, cis-calamenene and palustrol) were also isolated. (C) 2000 Elsevier Science Ltd.",

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AU - Kaplan, Maria Auxiliadora C.

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AU - Lopes, Daise

AU - Gottlieb, Hugo E.

PY - 2000/12/8

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AB - From the leaves of Renealmia chrysotrycha (Zingiberaceae), we isolated a sesquiterpene alcohol for which spectral data suggested the structure of a 10-aromadendranol. A meticulous NMR investigation, based mainly on vicinal proton-proton coupling constants and NOE interactions, and confirmed by a molecular mechanics calculation, established its relative stereochemistry as that of ledol. This finding resolves several recent literature ambiguities. Three known compounds (aromadendrene, cis-calamenene and palustrol) were also isolated. (C) 2000 Elsevier Science Ltd.

KW - Ledol

KW - NMR determination of stereochemistry

KW - Renealmia chrysotrycha

KW - Sesquiterpene alcohol

KW - Zingiberaceae

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The stereochemistry of ledol from Renealmia chrysotrycha: An NMR study

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