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Twenty-Nine New Limonoids with Skeletal Diversity from the Mangrove Plant, Xylocarpus moluccensis

Twenty-nine new limonoids—named xylomolins A(1)–A(7), B(1)–B(2), C(1)–C(2), D–F, G(1)–G(5), H–I, J(1)–J(2), K(1)–K(2), L(1)–L(2), and M–N, were isolated from the seeds of the mangrove plant, Xylocarpus moluccensis. Compounds 1–13 are mexicanolides with one double bond or two conjugated double bonds,...

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Autores principales: Zhang, Jianzhi, Li, Wanshan, Dai, Yiguo, Shen, Li, Wu, Jun
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5793086/
https://www.ncbi.nlm.nih.gov/pubmed/29351263
http://dx.doi.org/10.3390/md16010038
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author Zhang, Jianzhi
Li, Wanshan
Dai, Yiguo
Shen, Li
Wu, Jun
author_facet Zhang, Jianzhi
Li, Wanshan
Dai, Yiguo
Shen, Li
Wu, Jun
author_sort Zhang, Jianzhi
collection PubMed
description Twenty-nine new limonoids—named xylomolins A(1)–A(7), B(1)–B(2), C(1)–C(2), D–F, G(1)–G(5), H–I, J(1)–J(2), K(1)–K(2), L(1)–L(2), and M–N, were isolated from the seeds of the mangrove plant, Xylocarpus moluccensis. Compounds 1–13 are mexicanolides with one double bond or two conjugated double bonds, while 14 belongs to a small group of mexicanolides with an oxygen bridge between C1 and C8. Compounds 15–19 are khayanolides containing a Δ(8,14) double bond, whereas 20 and 21 are rare khayanolides containing a Δ(14,15) double bond and Δ(8,9), Δ(14,15) conjugated double bonds, respectively. Compounds 22 and 23 are unusual limonoids possessing a (Z)-bicyclo[5.2.1]dec-3-en-8-one motif, while 24 and 25 are 30-ketophragmalins with Δ(8,9), Δ(14,15) conjugated double bonds. Compounds 26 and 27 are phragmalin 8,9,30-ortho esters, whereas 28 and 29 are azadirone and andirobin derivatives, respectively. The structures of these compounds, including absolute configurations of 15–19, 21–23, and 26, were established by HRESIMS, extensive 1D and 2D NMR investigations, and the comparison of experimental electronic circular dichroism (ECD) spectra. The absolute configuration of 1 was unequivocally established by single-crystal X-ray diffraction analysis, obtained with Cu Kα radiation. The diverse cyclization patterns of 1–29 reveal the strong flexibility of skeletal plasticity in the limonoid biosynthesis of X. moluccensis. Compound 23 exhibited weak antitumor activity against human triple-negative breast MD-MBA-231 cancer cells with an IC(50) value of 37.7 μM. Anti-HIV activities of 1, 3, 8, 10, 11, 14, 20, 23–25, and 27 were tested in vitro. However, no compounds showed potent inhibitory activity.
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spelling pubmed-57930862018-02-06 Twenty-Nine New Limonoids with Skeletal Diversity from the Mangrove Plant, Xylocarpus moluccensis Zhang, Jianzhi Li, Wanshan Dai, Yiguo Shen, Li Wu, Jun Mar Drugs Article Twenty-nine new limonoids—named xylomolins A(1)–A(7), B(1)–B(2), C(1)–C(2), D–F, G(1)–G(5), H–I, J(1)–J(2), K(1)–K(2), L(1)–L(2), and M–N, were isolated from the seeds of the mangrove plant, Xylocarpus moluccensis. Compounds 1–13 are mexicanolides with one double bond or two conjugated double bonds, while 14 belongs to a small group of mexicanolides with an oxygen bridge between C1 and C8. Compounds 15–19 are khayanolides containing a Δ(8,14) double bond, whereas 20 and 21 are rare khayanolides containing a Δ(14,15) double bond and Δ(8,9), Δ(14,15) conjugated double bonds, respectively. Compounds 22 and 23 are unusual limonoids possessing a (Z)-bicyclo[5.2.1]dec-3-en-8-one motif, while 24 and 25 are 30-ketophragmalins with Δ(8,9), Δ(14,15) conjugated double bonds. Compounds 26 and 27 are phragmalin 8,9,30-ortho esters, whereas 28 and 29 are azadirone and andirobin derivatives, respectively. The structures of these compounds, including absolute configurations of 15–19, 21–23, and 26, were established by HRESIMS, extensive 1D and 2D NMR investigations, and the comparison of experimental electronic circular dichroism (ECD) spectra. The absolute configuration of 1 was unequivocally established by single-crystal X-ray diffraction analysis, obtained with Cu Kα radiation. The diverse cyclization patterns of 1–29 reveal the strong flexibility of skeletal plasticity in the limonoid biosynthesis of X. moluccensis. Compound 23 exhibited weak antitumor activity against human triple-negative breast MD-MBA-231 cancer cells with an IC(50) value of 37.7 μM. Anti-HIV activities of 1, 3, 8, 10, 11, 14, 20, 23–25, and 27 were tested in vitro. However, no compounds showed potent inhibitory activity. MDPI 2018-01-19 /pmc/articles/PMC5793086/ /pubmed/29351263 http://dx.doi.org/10.3390/md16010038 Text en © 2018 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Zhang, Jianzhi
Li, Wanshan
Dai, Yiguo
Shen, Li
Wu, Jun
Twenty-Nine New Limonoids with Skeletal Diversity from the Mangrove Plant, Xylocarpus moluccensis
title Twenty-Nine New Limonoids with Skeletal Diversity from the Mangrove Plant, Xylocarpus moluccensis
title_full Twenty-Nine New Limonoids with Skeletal Diversity from the Mangrove Plant, Xylocarpus moluccensis
title_fullStr Twenty-Nine New Limonoids with Skeletal Diversity from the Mangrove Plant, Xylocarpus moluccensis
title_full_unstemmed Twenty-Nine New Limonoids with Skeletal Diversity from the Mangrove Plant, Xylocarpus moluccensis
title_short Twenty-Nine New Limonoids with Skeletal Diversity from the Mangrove Plant, Xylocarpus moluccensis
title_sort twenty-nine new limonoids with skeletal diversity from the mangrove plant, xylocarpus moluccensis
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5793086/
https://www.ncbi.nlm.nih.gov/pubmed/29351263
http://dx.doi.org/10.3390/md16010038
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