(-)- 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 μM) reaches deeper into the binding pocket a

SUBMITTER: Zhou B 

PROVIDER: S-EPMC6750104 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature