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Bioorganic and Medicinal Chemistry 2014-Nov

Thiophenes, polyacetylenes and terpenes from the aerial parts of Eclipata prostrate.

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Feng-Min Xi
Chun-Tong Li
Jun Han
Shi-Shan Yu
Zhi-Jun Wu
Wan-Sheng Chen

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One new bithiophenes, 5-(but-3-yne-1,2-diol)-50-hydroxy-methyl-2,20-bithiophene (2), two new polyacetylenic glucosides, 3-O-b-D-glucopyranosyloxy-1-hydroxy-4E,6E-tetradecene-8,10,12-triyne (8), (5E)-trideca-1,5-dien-7,9,11-triyne-3,4-diol-4-O-b-D-glucopyranoside (9), six new terpenoid glycosides, rel-(1S,2S,3S,4R,6R)-1,6-epoxy-menthane-2,3-diol-3-O-b-D-glucopyranoside (10), rel-(1S,2S,3S,4R,6R)-3-O-(6-O-caffeoyl-b-D-glucopyranosyl)-1,6-epoxy menthane-2,3-diol (11), (2E,6E)-2,6,10-trimethyl-2,6,11-dodecatriene-1,10-diol-1-O-b-D-glucopyranoside (12), 3b,16b,29-trihydroxy oleanane-12-ene-3-O-b-D-glucopyranoside (13), 3,28-di-O-b-D-glucopyranosyl-3b,16b-dihydroxy oleanane-12-ene-28-oleanlic acid (14), 3-O-b-D-glucopyranosyl-(1?2)-b-D-glucopyranosyl oleanlic-18-ene acid-28-O-b-D-glucopyranoside (15), along with fifteen known compounds (1, 3–7, and 16–24), were isolated from the aerial parts of Eclipta prostrata. Their structures were established by analysis of the spectroscopic data. The isolated compounds 1–9 were tested for activities against dipeptidyl peptidase IV (DPP-IV), compound 7 showed significant antihyperglycemic activities by inhibitory effects on DPP-IV in human plasma in vitro, with IC50 value of 0.51 lM. Compounds 10–24 were tested in vitro against NF-jB-luc 293 cell line induced by LPS. Compounds 12, 15, 16, 19, 21, and 23 exhibited moderate anti-inflammatory activities.

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