Abstract
A new ursane-type nortriterpenoid, (11S,12S)-4-methyl-11,12-epoxy-2-hydroxy-3-oxoursa-1,4-dine-28-oic acid γ-lactone (1), named ulmoidol A, together with ten known compounds: ulmoidol (2), corosolic acid (3), 2α,3α-dihydroxy-24-nor-4(23),12-oleanadien-28-oic acid (4), oleanolic acid (5), ursolic acid (6), cycloart-3β, 25-diol (7), foliasalacioside B1 (8), (6R,7E,9R)-9-hydroxy-4,7-megastigmadien-3-one-9-O-α-L-arabinopyranosyl-(1→6)-β-D-glucopyranoside (9), (6R,7E,9R)-9-hydroxy-4,7-megastigma-dien-3-one-9-O-β-D-xylopyranosyl-(1→6)-β-D-glucopyranoside (10), and quercetin 3-O-sambubioside (11) were isolated from the leaves of Eucommia ulmoides Oliv. The structure of compound 1 was determined by extensive spectroscopic analysis, and its absolute configuration was determined by CD experiments and a computational method. Compounds 3, 4, 7–10 were isolated from this plant for the first time. Compounds 3 and 4 showed inhibition to PTPIB activities, with IC50 values of 0.69 and 3.98 μM, respectively.
Highlights
Eucommia ulmoides Oliv. mainly grows along the Yangtze River and in southern China
Recombinant human GST-protein tyrosine phosphatase 1B (PTP1B) protein was overexpressed by hGST-PTP1B-BL21 E. coli and purified by GST affinity chromatography
The reagent pNPP was used as substrate for the measurement of PTP1B activity
Summary
Mainly grows along the Yangtze River and in southern China. Its bark has traditionally been applied in China as an antihypertensive, diuretic, sedative, tonic and nourishing agent [1]. The extract of its leaves showed activities against hypertension and bacteria [2,3]. As part of a program to study the chemical diversity of traditional Chinese medicines and their biological effects, an ethanol extract of E. ulmoides has been investigated. EtOAc-soluble portion of the ethanol extract of E. ulmoides (Figure 1). Compounds 3 and 4 showed inhibition to PTPIB activities with IC50 values of 0.69 and 3.98 μM, respectively
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