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Xyloccensin E
The title compound (also known as phragmalin triacetate), C(35)H(42)O(14), is a phragmalin-type limonoid extracted from X. rumphii. The molecule consists of eight rings with the orthoacetate group bridged at positions 1, 8 and 9. The two five-carbocyclic rings (A (1) and A (2)) and the dioxolane ri...
Autores principales: | , , , , |
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Formato: | Texto |
Lenguaje: | English |
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International Union of Crystallography
2010
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2979606/ https://www.ncbi.nlm.nih.gov/pubmed/21579436 http://dx.doi.org/10.1107/S1600536810016582 |
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author | Sarigaputi, Chanin Teerawatananond, Thapong Pengpreecha, Somchai Muangsin, Nongnuj Pudhom, Khanitha |
author_facet | Sarigaputi, Chanin Teerawatananond, Thapong Pengpreecha, Somchai Muangsin, Nongnuj Pudhom, Khanitha |
author_sort | Sarigaputi, Chanin |
collection | PubMed |
description | The title compound (also known as phragmalin triacetate), C(35)H(42)O(14), is a phragmalin-type limonoid extracted from X. rumphii. The molecule consists of eight rings with the orthoacetate group bridged at positions 1, 8 and 9. The two five-carbocyclic rings (A (1) and A (2)) and the dioxolane ring (G) adopt a distorted envelope conformation. The 1,3-dioxane ring (E) exists in a chair conformation. The six-carbocyclic rings (B and C) exhibit a twisted-boat conformation. The lactone ring has a half-chair conformation and the furan ring is planar (r.m.s. deviation = 0.002 Å). Rings A (1)/B, A (2)/B, B/C, C/D and C/G are all cis-fused. The two acetoxy groups attached to ring B and the furan ring attached to the lactone ring are in equatorial positions. The porous crystal packing exhibits voids of 688 Å(3) and weak intermolecular C—H⋯O interactions. The absolute configuration was assigned on the basis of literature data. |
format | Text |
id | pubmed-2979606 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2010 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-29796062010-12-30 Xyloccensin E Sarigaputi, Chanin Teerawatananond, Thapong Pengpreecha, Somchai Muangsin, Nongnuj Pudhom, Khanitha Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound (also known as phragmalin triacetate), C(35)H(42)O(14), is a phragmalin-type limonoid extracted from X. rumphii. The molecule consists of eight rings with the orthoacetate group bridged at positions 1, 8 and 9. The two five-carbocyclic rings (A (1) and A (2)) and the dioxolane ring (G) adopt a distorted envelope conformation. The 1,3-dioxane ring (E) exists in a chair conformation. The six-carbocyclic rings (B and C) exhibit a twisted-boat conformation. The lactone ring has a half-chair conformation and the furan ring is planar (r.m.s. deviation = 0.002 Å). Rings A (1)/B, A (2)/B, B/C, C/D and C/G are all cis-fused. The two acetoxy groups attached to ring B and the furan ring attached to the lactone ring are in equatorial positions. The porous crystal packing exhibits voids of 688 Å(3) and weak intermolecular C—H⋯O interactions. The absolute configuration was assigned on the basis of literature data. International Union of Crystallography 2010-05-15 /pmc/articles/PMC2979606/ /pubmed/21579436 http://dx.doi.org/10.1107/S1600536810016582 Text en © Sarigaputi et al. 2010 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 Sarigaputi, Chanin Teerawatananond, Thapong Pengpreecha, Somchai Muangsin, Nongnuj Pudhom, Khanitha Xyloccensin E |
title | Xyloccensin E |
title_full | Xyloccensin E |
title_fullStr | Xyloccensin E |
title_full_unstemmed | Xyloccensin E |
title_short | Xyloccensin E |
title_sort | xyloccensin e |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2979606/ https://www.ncbi.nlm.nih.gov/pubmed/21579436 http://dx.doi.org/10.1107/S1600536810016582 |
work_keys_str_mv | AT sarigaputichanin xyloccensine AT teerawatananondthapong xyloccensine AT pengpreechasomchai xyloccensine AT muangsinnongnuj xyloccensine AT pudhomkhanitha xyloccensine |