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6α-Acetoxygedunin
The title compound [systematic name: (1S,3aS,4aR,4bS,5S,6R,6aR,10aR,10bR,12aS)-5,6-bis(acetyloxy)-1-(3-furyl)-1,5,6,6a,7,10a,10b,11,12,12a-decahydro-4b,7,7,10a,12a-pentamethyloxireno[c]phenanthro[1,2-d]pyran-3,8(3aH,4bH)-dione], C(30)H(36)O(9), is a limonoid-type triterpene isolated from Aglai...
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Formato: | Texto |
Lenguaje: | English |
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International Union of Crystallography
2009
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2977213/ https://www.ncbi.nlm.nih.gov/pubmed/21583624 http://dx.doi.org/10.1107/S1600536809027998 |
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author | Hofer, Margit Greger, Harald Mereiter, Kurt |
author_facet | Hofer, Margit Greger, Harald Mereiter, Kurt |
author_sort | Hofer, Margit |
collection | PubMed |
description | The title compound [systematic name: (1S,3aS,4aR,4bS,5S,6R,6aR,10aR,10bR,12aS)-5,6-bis(acetyloxy)-1-(3-furyl)-1,5,6,6a,7,10a,10b,11,12,12a-decahydro-4b,7,7,10a,12a-pentamethyloxireno[c]phenanthro[1,2-d]pyran-3,8(3aH,4bH)-dione], C(30)H(36)O(9), is a limonoid-type triterpene isolated from Aglaia elaeagnoidea (A. Juss.) Benth. (Meliaceae) from Queensland, northern Australia. It contains the gedunin core of four trans-fused six-membered rings with an oxirane ring annelated to the fourth ring. A terminal 3-furyl unity and two acetoxy groups in a mutual cis-disposition supplement the molecule. A comparison between the gedunin cores of the title compound, the parent compound gedunin, and three further gedunin derivatives revealed considerable variations in their conformation stemming from the conformational lability of the first screw-boat ring and the third twist-boat ring. A sensitive measure for the third ring is one C—C—C—C torsion angle, which is 14.2 (2)° in the title compound, but varies in other cases from ca 20 to ca −40°. In the crystalline state, 6α-acetoxygedunin shows ten comparatively weak C—H⋯O interactions, with H⋯O distances in the range of 2.33–2.69 Å. |
format | Text |
id | pubmed-2977213 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2009 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-29772132010-12-30 6α-Acetoxygedunin Hofer, Margit Greger, Harald Mereiter, Kurt Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound [systematic name: (1S,3aS,4aR,4bS,5S,6R,6aR,10aR,10bR,12aS)-5,6-bis(acetyloxy)-1-(3-furyl)-1,5,6,6a,7,10a,10b,11,12,12a-decahydro-4b,7,7,10a,12a-pentamethyloxireno[c]phenanthro[1,2-d]pyran-3,8(3aH,4bH)-dione], C(30)H(36)O(9), is a limonoid-type triterpene isolated from Aglaia elaeagnoidea (A. Juss.) Benth. (Meliaceae) from Queensland, northern Australia. It contains the gedunin core of four trans-fused six-membered rings with an oxirane ring annelated to the fourth ring. A terminal 3-furyl unity and two acetoxy groups in a mutual cis-disposition supplement the molecule. A comparison between the gedunin cores of the title compound, the parent compound gedunin, and three further gedunin derivatives revealed considerable variations in their conformation stemming from the conformational lability of the first screw-boat ring and the third twist-boat ring. A sensitive measure for the third ring is one C—C—C—C torsion angle, which is 14.2 (2)° in the title compound, but varies in other cases from ca 20 to ca −40°. In the crystalline state, 6α-acetoxygedunin shows ten comparatively weak C—H⋯O interactions, with H⋯O distances in the range of 2.33–2.69 Å. International Union of Crystallography 2009-07-22 /pmc/articles/PMC2977213/ /pubmed/21583624 http://dx.doi.org/10.1107/S1600536809027998 Text en © Hofer et al. 2009 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 Hofer, Margit Greger, Harald Mereiter, Kurt 6α-Acetoxygedunin |
title | 6α-Acetoxygedunin |
title_full | 6α-Acetoxygedunin |
title_fullStr | 6α-Acetoxygedunin |
title_full_unstemmed | 6α-Acetoxygedunin |
title_short | 6α-Acetoxygedunin |
title_sort | 6α-acetoxygedunin |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2977213/ https://www.ncbi.nlm.nih.gov/pubmed/21583624 http://dx.doi.org/10.1107/S1600536809027998 |
work_keys_str_mv | AT hofermargit 6aacetoxygedunin AT gregerharald 6aacetoxygedunin AT mereiterkurt 6aacetoxygedunin |