title: Aglaiabbrevins A-D, New Prenylated Bibenzyls from the Leaves of Aglaia abbreviata with Potent PTP1B Inhibitory Activity.
abstract: Four new prenylated bibenzyls, named aglaiabbrevins A-D (2, 4-6), were isolated from the leaves of Aglaia abbreviata, along with two known related analogues, 3,5-dihydroxy-2-[3,7-dimethyl-2(E),6-octadienyl]bibenzyl (7) and 3,5-dihydroxy-2-(3-methyl-2-butenyl)bibenzyl (8). The structures of the new compounds were elucidated on the basis of extensive spectroscopic experiments, mainly one and two dimensional (1D- and 2D)-NMR, and the absolute configuration of 5 was determined by the measurement of specific rotation. The isolated compounds were evaluated for their protein tyrosine phosphatase-1B (PTP1B) inhibitory activity. The results showed that compounds 5-7 exhibited more potent PTP1B inhibitory effects with IC50values of 2.58±0.52, 2.44±0.35, and 2.23±0.14 µM, respectively, than the positive control oleanolic acid (IC50=2.74±0.20 µM). On the basis of the data obtained, these bibenzyls with the longer C-2 prenyl groups may be considered as potential lead compounds for the development of new anti-obesity and anti-diabetic agents. Also, the PTP1B inhibitory effects for prenylated bibenzyls are being reported for the first time.
authors.affiliation: School of Pharmacy, Nanchang University.
authors.forename: Pan
authors.initials: P
authors.lastname: Sun
authors.forename: Chang-Sheng
authors.initials: CS
authors.lastname: Jiang
authors.forename: Yi
authors.initials: Y
authors.lastname: Zhang
authors.forename: Ai-Hong
authors.initials: AH
authors.lastname: Liu
authors.forename: Tong-Jun
authors.initials: TJ
authors.lastname: Liang
authors.forename: Jia
authors.initials: J
authors.lastname: Li
authors.forename: Yue-Wei
authors.initials: YW
authors.lastname: Guo
authors.forename: Jian-Mei
authors.initials: JM
authors.lastname: Jiang
authors.forename: Shui-Chun
authors.initials: SC
authors.lastname: Mao
authors.forename: Bin
authors.initials: B
authors.lastname: Wang
mesh_terms: D031602:Aglaia / Q000737:chemistry*; D001632:Bibenzyls / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D006801:Humans; D015394:Molecular Structure; D018515:Plant Leaves / Q000737:chemistry*; D054562:Protein Tyrosine Phosphatase, Non-Receptor Type 1 / Q000037:antagonists & inhibitors* / Q000378:metabolism; D013329:Structure-Activity Relationship
chemical_list: D001632:Bibenzyls; D004791:Enzyme Inhibitors; C516607:PTPN1 protein, human; D054562:Protein Tyrosine Phosphatase, Non-Receptor Type 1