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

(−)- 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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Main Authors: B. Zhou, D. X. Liu, X. J. Yuan, J. Y. Li, Y. C. Xu, J. Li, Y. Li, J. M. Yue
Format: Article
Language:English
Published: American Association for the Advancement of Science 2018-01-01
Series:Research
Online Access:http://dx.doi.org/10.1155/2018/2674182
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spelling doaj-c1e793542fe34888a0ef4037b0de2e712020-11-25T02:14:51ZengAmerican Association for the Advancement of ScienceResearch2639-52742018-01-01201810.1155/2018/2674182(−)- and (+)-Securidanes A and B, Natural Triarylmethane Enantiomers: Structure and Bioinspired Total SynthesisB. Zhou0D. X. Liu1X. J. Yuan2J. Y. Li3Y. C. Xu4J. Li5Y. Li6J. M. Yue7State Key Laboratory of Drug Research,Shanghai Institute of Materia Medica,Chinese Academy of Sciences,555 Zuchongzhi Road, Shanghai 201203,ChinaState Key Laboratory of Applied Organic Chemistry,College of Chemistry and Chemical Engineering,Lanzhou University,Lanzhou 730000,ChinaState Key Laboratory of Drug Research,Shanghai Institute of Materia Medica,Chinese Academy of Sciences,555 Zuchongzhi Road, Shanghai 201203,ChinaState Key Laboratory of Drug Research,Shanghai Institute of Materia Medica,Chinese Academy of Sciences,555 Zuchongzhi Road, Shanghai 201203,ChinaState Key Laboratory of Drug Research,Shanghai Institute of Materia Medica,Chinese Academy of Sciences,555 Zuchongzhi Road, Shanghai 201203,ChinaState Key Laboratory of Drug Research,Shanghai Institute of Materia Medica,Chinese Academy of Sciences,555 Zuchongzhi Road, Shanghai 201203,ChinaState Key Laboratory of Applied Organic Chemistry,College of Chemistry and Chemical Engineering,Lanzhou University,Lanzhou 730000,ChinaState Key Laboratory of Drug Research,Shanghai Institute of Materia Medica,Chinese Academy of Sciences,555 Zuchongzhi Road, Shanghai 201203,ChinaTwo 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 (IC50 = 7.52 μM) reaches deeper into the binding pocket and has an additional H-bond.http://dx.doi.org/10.1155/2018/2674182
collection DOAJ
language English
format Article
sources DOAJ
author B. Zhou
D. X. Liu
X. J. Yuan
J. Y. Li
Y. C. Xu
J. Li
Y. Li
J. M. Yue
spellingShingle B. Zhou
D. X. Liu
X. J. Yuan
J. Y. Li
Y. C. Xu
J. Li
Y. Li
J. M. Yue
(−)- and (+)-Securidanes A and B, Natural Triarylmethane Enantiomers: Structure and Bioinspired Total Synthesis
Research
author_facet B. Zhou
D. X. Liu
X. J. Yuan
J. Y. Li
Y. C. Xu
J. Li
Y. Li
J. M. Yue
author_sort B. Zhou
title (−)- 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_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_sort (−)- and (+)-securidanes a and b, natural triarylmethane enantiomers: structure and bioinspired total synthesis
publisher American Association for the Advancement of Science
series Research
issn 2639-5274
publishDate 2018-01-01
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 (IC50 = 7.52 μM) reaches deeper into the binding pocket and has an additional H-bond.
url http://dx.doi.org/10.1155/2018/2674182
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