Cargando…

(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...

Descripción completa

Detalles Bibliográficos
Autores principales: Mahmod, Ilya Iryani, Kwong, Huey Chong, Mohamed Tahir, Mohamed Ibrahim, Ismail, Intan Safinar
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2011
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
_version_ 1782219090482429952
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
title_full (20S*,24S*)-25-Hy­droxy-20,24-ep­oxy-A-homo-4-oxadammaran-3-one (Chrysura) isolated from the leaves of Walsura chrysogyne
title_fullStr (20S*,24S*)-25-Hy­droxy-20,24-ep­oxy-A-homo-4-oxadammaran-3-one (Chrysura) isolated from the leaves of Walsura chrysogyne
title_full_unstemmed (20S*,24S*)-25-Hy­droxy-20,24-ep­oxy-A-homo-4-oxadammaran-3-one (Chrysura) isolated from the leaves of Walsura chrysogyne
title_short (20S*,24S*)-25-Hy­droxy-20,24-ep­oxy-A-homo-4-oxadammaran-3-one (Chrysura) isolated from the leaves of Walsura chrysogyne
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
work_keys_str_mv AT mahmodilyairyani 20s24s25hydroxy2024epoxyahomo4oxadammaran3onechrysuraisolatedfromtheleavesofwalsurachrysogyne
AT kwonghueychong 20s24s25hydroxy2024epoxyahomo4oxadammaran3onechrysuraisolatedfromtheleavesofwalsurachrysogyne
AT mohamedtahirmohamedibrahim 20s24s25hydroxy2024epoxyahomo4oxadammaran3onechrysuraisolatedfromtheleavesofwalsurachrysogyne
AT ismailintansafinar 20s24s25hydroxy2024epoxyahomo4oxadammaran3onechrysuraisolatedfromtheleavesofwalsurachrysogyne