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(20S*,24S*)-25-Hydroxy-20,24-epoxy-A-homo-4-oxadammaran-3-one (Chrysura) isolated from the leaves of Walsura chrysogyne
The title dammarane triterpenoid, C(30)H(50)O(4), assigned the name chrysura, was isolated from an ethyl acetate extract of Walsura chrysogyne leaves (Meliaceae). It has 20S*,24S* relative stereochemistry and an oxepanone ring with two methyl groups at position 4. The two cyclohexane rings adopt ch...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2011
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3238949/ https://www.ncbi.nlm.nih.gov/pubmed/22199798 http://dx.doi.org/10.1107/S1600536811047337 |
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author | Mahmod, Ilya Iryani Kwong, Huey Chong Mohamed Tahir, Mohamed Ibrahim Ismail, Intan Safinar |
author_facet | Mahmod, Ilya Iryani Kwong, Huey Chong Mohamed Tahir, Mohamed Ibrahim Ismail, Intan Safinar |
author_sort | Mahmod, Ilya Iryani |
collection | PubMed |
description | The title dammarane triterpenoid, C(30)H(50)O(4), assigned the name chrysura, was isolated from an ethyl acetate extract of Walsura chrysogyne leaves (Meliaceae). It has 20S*,24S* relative stereochemistry and an oxepanone ring with two methyl groups at position 4. The two cyclohexane rings adopt chair conformations. The cyclopentane and tetrahydrofuran rings have envelope conformations; their mean planes make a dihedral angle of 13.1 (3)°, indicating that the rings are only slightly tilted with respect to each other. There is an intramolecular C—H⋯O hydrogen bond in the molecule, which forms S(6) and S(7) ring motifs. In the crystal, molecules are linked via O—H⋯O and C—H⋯O hydrogen bonds, forming chains propagating along [001] which stack along the b-axis direction. |
format | Online Article Text |
id | pubmed-3238949 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2011 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-32389492011-12-23 (20S*,24S*)-25-Hydroxy-20,24-epoxy-A-homo-4-oxadammaran-3-one (Chrysura) isolated from the leaves of Walsura chrysogyne Mahmod, Ilya Iryani Kwong, Huey Chong Mohamed Tahir, Mohamed Ibrahim Ismail, Intan Safinar Acta Crystallogr Sect E Struct Rep Online Organic Papers The title dammarane triterpenoid, C(30)H(50)O(4), assigned the name chrysura, was isolated from an ethyl acetate extract of Walsura chrysogyne leaves (Meliaceae). It has 20S*,24S* relative stereochemistry and an oxepanone ring with two methyl groups at position 4. The two cyclohexane rings adopt chair conformations. The cyclopentane and tetrahydrofuran rings have envelope conformations; their mean planes make a dihedral angle of 13.1 (3)°, indicating that the rings are only slightly tilted with respect to each other. There is an intramolecular C—H⋯O hydrogen bond in the molecule, which forms S(6) and S(7) ring motifs. In the crystal, molecules are linked via O—H⋯O and C—H⋯O hydrogen bonds, forming chains propagating along [001] which stack along the b-axis direction. International Union of Crystallography 2011-11-12 /pmc/articles/PMC3238949/ /pubmed/22199798 http://dx.doi.org/10.1107/S1600536811047337 Text en © Mahmod et al. 2011 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. |
spellingShingle | Organic Papers Mahmod, Ilya Iryani Kwong, Huey Chong Mohamed Tahir, Mohamed Ibrahim Ismail, Intan Safinar (20S*,24S*)-25-Hydroxy-20,24-epoxy-A-homo-4-oxadammaran-3-one (Chrysura) isolated from the leaves of Walsura chrysogyne |
title | (20S*,24S*)-25-Hydroxy-20,24-epoxy-A-homo-4-oxadammaran-3-one (Chrysura) isolated from the leaves of Walsura chrysogyne
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title_full | (20S*,24S*)-25-Hydroxy-20,24-epoxy-A-homo-4-oxadammaran-3-one (Chrysura) isolated from the leaves of Walsura chrysogyne
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title_fullStr | (20S*,24S*)-25-Hydroxy-20,24-epoxy-A-homo-4-oxadammaran-3-one (Chrysura) isolated from the leaves of Walsura chrysogyne
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title_full_unstemmed | (20S*,24S*)-25-Hydroxy-20,24-epoxy-A-homo-4-oxadammaran-3-one (Chrysura) isolated from the leaves of Walsura chrysogyne
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title_short | (20S*,24S*)-25-Hydroxy-20,24-epoxy-A-homo-4-oxadammaran-3-one (Chrysura) isolated from the leaves of Walsura chrysogyne
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title_sort | (20s*,24s*)-25-hydroxy-20,24-epoxy-a-homo-4-oxadammaran-3-one (chrysura) isolated from the leaves of walsura chrysogyne |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3238949/ https://www.ncbi.nlm.nih.gov/pubmed/22199798 http://dx.doi.org/10.1107/S1600536811047337 |
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