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Molecules 2012, 17(12), 13960-13968; doi:10.3390/molecules171213960
Article

A New Ursane-Type Nor-Triterpenoid from the Leaves of Eucommia ulmoides Oliv.

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State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China
* Author to whom correspondence should be addressed.
Received: 28 September 2012 / Revised: 6 November 2012 / Accepted: 8 November 2012 / Published: 26 November 2012
(This article belongs to the Section Natural Products)
Download PDF [433 KB, 18 June 2014; original version 18 June 2014]

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, 710 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.
Keywords: Eucommia ulmoides Oliv.; nor-triterpenoid; ulmoidol A; absolute configuration; ECD; PTPIB Eucommia ulmoides Oliv.; nor-triterpenoid; ulmoidol A; absolute configuration; ECD; PTPIB
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Li, C.; Li, L.; Wang, C.; Yang, J.; Ye, F.; Tian, J.; Si, Y.; Zhang, D. A New Ursane-Type Nor-Triterpenoid from the Leaves of Eucommia ulmoides Oliv.. Molecules 2012, 17, 13960-13968.

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