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A pair of new enantiomers of xanthones from the stems and leaves of Cratoxylum cochinchinense

BACKGROUND: The simple and caged xanthones from Clusiaceae showed significant antineoplastic activity. This study aims to identify structural diverse xanthones and search for novel antitumor natural products from this family plants. METHODS: The structures of new compounds 1a and 1b were elucidated...

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Autores principales: Jia, Cuicui, Gong, Chi, Chen, Hong, Pu, Jing, Li, Dahong, Li, Zhanlin, Hua, Huiming
Formato: Online Artículo Texto
Lenguaje:English
Publicado: BioMed Central 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6441139/
https://www.ncbi.nlm.nih.gov/pubmed/30976295
http://dx.doi.org/10.1186/s13020-019-0235-z
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author Jia, Cuicui
Gong, Chi
Chen, Hong
Pu, Jing
Li, Dahong
Li, Zhanlin
Hua, Huiming
author_facet Jia, Cuicui
Gong, Chi
Chen, Hong
Pu, Jing
Li, Dahong
Li, Zhanlin
Hua, Huiming
author_sort Jia, Cuicui
collection PubMed
description BACKGROUND: The simple and caged xanthones from Clusiaceae showed significant antineoplastic activity. This study aims to identify structural diverse xanthones and search for novel antitumor natural products from this family plants. METHODS: The structures of new compounds 1a and 1b were elucidated mainly through comprehensive NMR and MS spectroscopic data, and their absolute configurations were determined by the comparison of the experimental and calculated electronic circular dichroism. RESULTS: A pair of new xanthone enantiomers, (+)- and (−)-cracochinxanthone A (1a and 1b), along with thirty known analogues (2–31), were isolated from extracts of the stems and leaves of C. cochinchinense. Preliminary biological assay of some isolates against HL-60, PC-3, and MDA-MB-231 cancer cell lines. CONCLUSION: Some isolated xanthones exhibited high sensitivity against three human malignant cell lines and the structure–activity relationship study showed that the prenyl and geranyl units may play an important role in antitumor activity. ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (10.1186/s13020-019-0235-z) contains supplementary material, which is available to authorized users.
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spelling pubmed-64411392019-04-11 A pair of new enantiomers of xanthones from the stems and leaves of Cratoxylum cochinchinense Jia, Cuicui Gong, Chi Chen, Hong Pu, Jing Li, Dahong Li, Zhanlin Hua, Huiming Chin Med Research BACKGROUND: The simple and caged xanthones from Clusiaceae showed significant antineoplastic activity. This study aims to identify structural diverse xanthones and search for novel antitumor natural products from this family plants. METHODS: The structures of new compounds 1a and 1b were elucidated mainly through comprehensive NMR and MS spectroscopic data, and their absolute configurations were determined by the comparison of the experimental and calculated electronic circular dichroism. RESULTS: A pair of new xanthone enantiomers, (+)- and (−)-cracochinxanthone A (1a and 1b), along with thirty known analogues (2–31), were isolated from extracts of the stems and leaves of C. cochinchinense. Preliminary biological assay of some isolates against HL-60, PC-3, and MDA-MB-231 cancer cell lines. CONCLUSION: Some isolated xanthones exhibited high sensitivity against three human malignant cell lines and the structure–activity relationship study showed that the prenyl and geranyl units may play an important role in antitumor activity. ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (10.1186/s13020-019-0235-z) contains supplementary material, which is available to authorized users. BioMed Central 2019-03-29 /pmc/articles/PMC6441139/ /pubmed/30976295 http://dx.doi.org/10.1186/s13020-019-0235-z Text en © The Author(s) 2019 Open AccessThis article is distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The Creative Commons Public Domain Dedication waiver (http://creativecommons.org/publicdomain/zero/1.0/) applies to the data made available in this article, unless otherwise stated.
spellingShingle Research
Jia, Cuicui
Gong, Chi
Chen, Hong
Pu, Jing
Li, Dahong
Li, Zhanlin
Hua, Huiming
A pair of new enantiomers of xanthones from the stems and leaves of Cratoxylum cochinchinense
title A pair of new enantiomers of xanthones from the stems and leaves of Cratoxylum cochinchinense
title_full A pair of new enantiomers of xanthones from the stems and leaves of Cratoxylum cochinchinense
title_fullStr A pair of new enantiomers of xanthones from the stems and leaves of Cratoxylum cochinchinense
title_full_unstemmed A pair of new enantiomers of xanthones from the stems and leaves of Cratoxylum cochinchinense
title_short A pair of new enantiomers of xanthones from the stems and leaves of Cratoxylum cochinchinense
title_sort pair of new enantiomers of xanthones from the stems and leaves of cratoxylum cochinchinense
topic Research
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6441139/
https://www.ncbi.nlm.nih.gov/pubmed/30976295
http://dx.doi.org/10.1186/s13020-019-0235-z
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