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


ABSTRACT: 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 ?M) reaches deeper into the binding pocket and has an additional H-bond.

SUBMITTER: Zhou B 

PROVIDER: S-EPMC6750104 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature

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

Zhou B B   Liu D X DX   Yuan X J XJ   Li J Y JY   Xu Y C YC   Li J J   Li Y Y   Yue J M JM  

Research (Washington, D.C.) 20180905


Two pairs of enantiomers, (-) and (+)-securidanes A (<b>1</b> and <b>2</b>) and B (<b>3</b> and <b>4</b>) featuring unprecedented triarylmethane (TAM) skeletons, were isolated from <i>Securidaca inappendiculata</i>. Their structures were established by spectroscopic data, X-ray crystallography, and CD analysis. A plausible biosynthetic pathway for <b>1</b>-<b>4</b> based on the co-isolated precursors was proposed. Bioinspired total synthesis of <b>1</b>-<b>4</b> was completed in high yield, whic  ...[more]

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