np9b00770_si_001.pdf (13.55 MB)
Protein Tyrosine Phosphatase 1B Inhibitory Iridoids from Psydrax subcordata
journal contribution
posted on 2019-10-16, 19:48 authored by Junfei Zhou, Zhenlong Wu, Bamisaye O. Oyawaluja, Herbert A. B. Coker, Olukemi A. Odukoya, Guangmin Yao, Chun-Tao ChePhytochemical investigation of the
leaves and bark of Psydrax
subcordata has led to the isolation of six new iridoids,
subcordatanols I–V (1–4 and 6) and 1-O-methylcrescentin I (5), along with two known analogues (7 and 8). Among them, subcordatanol I (1) is the first example
of a 3,8-monoepoxy-iridoid featuring a caged 2-oxa-bicyclo[3.2.1]octane
core. The absolute stereochemistry at C-4 of 3, 4, and 6 was established through their acid-catalyzed
reaction products subcordatalactones A (3a), B (4a), and C (6a), respectively. Subcordatanols
I (1) and II (2), as well as subcordatalactones
A (3a) and B (4a), displayed inhibitory
activity against protein tyrosine phosphatase 1B (PTP1B). Enzyme kinetic
studies indicated that 3a and 4a are competitive
inhibitors. A molecular docking study is also reported.
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subcordatanolmonoepoxy-iridoidPTP 1B EnzymebarkanaloguePsydrax subcordata Phytochemical investigationdocking studyacid-catalyzed reaction products subcordatalactonesProtein Tyrosine Phosphatase 1 B Inhibitory Iridoids1- Oprotein tyrosine phosphatase 1 BcoreIImethylcrescentinstereochemistry2-SubcordatanolinhibitoriridoidisolationC -4Psydrax subcordataoxa-bicyclo
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