(−)- and (+)-Securidanes A and B, Natural Triarylmethane Enantiomers: Structure and Bioinspired Total Synthesis

Two pairs of enantiomers, (−) and (+)-securidanes A (1 and 2) and B (3 and 4) featuring unprecedented triarylmethane (TAM) skeletons, were isolated from Securidaca inappendiculata. Their structures were established by spectroscopic data, X-ray crystallography, and CD analysis. A plausible biosynthet...

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Detalles Bibliográficos
Autores principales: Zhou, B., Liu, D. X., Yuan, X. J., Li, J. Y., Xu, Y. C., Li, J., Li, Y., Yue, J. M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: AAAS 2018
Materias:
Research Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6750104/
https://www.ncbi.nlm.nih.gov/pubmed/31549026
http://dx.doi.org/10.1155/2018/2674182
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author Zhou, B.
Liu, D. X.
Yuan, X. J.
Li, J. Y.
Xu, Y. C.
Li, J.
Li, Y.
Yue, J. M.
author_facet Zhou, B.
Liu, D. X.
Yuan, X. J.
Li, J. Y.
Xu, Y. C.
Li, J.
Li, Y.
Yue, J. M.
author_sort Zhou, B.
collection PubMed
description Two pairs of enantiomers, (−) and (+)-securidanes A (1 and 2) and B (3 and 4) featuring unprecedented triarylmethane (TAM) skeletons, were isolated from Securidaca inappendiculata. Their structures were established by spectroscopic data, X-ray crystallography, and CD analysis. A plausible biosynthetic pathway for 1−4 based on the co-isolated precursors was proposed. Bioinspired total synthesis of 1−4 was completed in high yield, which in turn corroborated the biosynthetic hypothesis. Compounds 1−4 showed good inhibition against protein tyrosine phosphatase 1B (PTP1B). The molecular docking demonstrated that the strongest inhibitor 3 (IC(50) = 7.52 μM) reaches deeper into the binding pocket and has an additional H-bond.
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spelling pubmed-67501042019-09-23 (−)- and (+)-Securidanes A and B, Natural Triarylmethane Enantiomers: Structure and Bioinspired Total Synthesis Zhou, B. Liu, D. X. Yuan, X. J. Li, J. Y. Xu, Y. C. Li, J. Li, Y. Yue, J. M. Research (Wash D C) Research Article Two pairs of enantiomers, (−) and (+)-securidanes A (1 and 2) and B (3 and 4) featuring unprecedented triarylmethane (TAM) skeletons, were isolated from Securidaca inappendiculata. Their structures were established by spectroscopic data, X-ray crystallography, and CD analysis. A plausible biosynthetic pathway for 1−4 based on the co-isolated precursors was proposed. Bioinspired total synthesis of 1−4 was completed in high yield, which in turn corroborated the biosynthetic hypothesis. Compounds 1−4 showed good inhibition against protein tyrosine phosphatase 1B (PTP1B). The molecular docking demonstrated that the strongest inhibitor 3 (IC(50) = 7.52 μM) reaches deeper into the binding pocket and has an additional H-bond. AAAS 2018-09-05 /pmc/articles/PMC6750104/ /pubmed/31549026 http://dx.doi.org/10.1155/2018/2674182 Text en Copyright © 2018 B. Zhou et al. https://creativecommons.org/licenses/by/4.0/ Exclusive licensee Science and Technology Review Publishing House. Distributed under a Creative Commons Attribution License (CC BY 4.0).
spellingShingle Research Article
Zhou, B.
Liu, D. X.
Yuan, X. J.
Li, J. Y.
Xu, Y. C.
Li, J.
Li, Y.
Yue, J. M.
(−)- and (+)-Securidanes A and B, Natural Triarylmethane Enantiomers: Structure and Bioinspired Total Synthesis
title (−)- and (+)-Securidanes A and B, Natural Triarylmethane Enantiomers: Structure and Bioinspired Total Synthesis
title_full (−)- and (+)-Securidanes A and B, Natural Triarylmethane Enantiomers: Structure and Bioinspired Total Synthesis
title_fullStr (−)- and (+)-Securidanes A and B, Natural Triarylmethane Enantiomers: Structure and Bioinspired Total Synthesis
title_full_unstemmed (−)- and (+)-Securidanes A and B, Natural Triarylmethane Enantiomers: Structure and Bioinspired Total Synthesis
title_short (−)- and (+)-Securidanes A and B, Natural Triarylmethane Enantiomers: Structure and Bioinspired Total Synthesis
title_sort (−)- and (+)-securidanes a and b, natural triarylmethane enantiomers: structure and bioinspired total synthesis
topic Research Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6750104/
https://www.ncbi.nlm.nih.gov/pubmed/31549026
http://dx.doi.org/10.1155/2018/2674182
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