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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 Metabolites)
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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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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