Journal
RESEARCH
Volume 2018, Issue -, Pages -Publisher
AMER ASSOC ADVANCEMENT SCIENCE
DOI: 10.1155/2018/2674182
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Funding
- National Natural Science Foundation [21532007, U1302222, 81321092]
- Foundation from the MOST of China [2012CB721105]
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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 mu M) reaches deeper into the binding pocket and has an additional H-bond.
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