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A New Ursane-Type Nor-Triterpenoid from the Leaves of Eucommia ulmoides Oliv.
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; in revised form: 6 November 2012 / Accepted: 8 November 2012 / Published: 26 November 2012
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.
Keywords: Eucommia ulmoides Oliv.; nor-triterpenoid; ulmoidol A; absolute configuration; ECD; PTPIB
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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.
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(12):13960-13968.
Li, Chuangjun; Li, Li; Wang, Chao; Yang, Jingzhi; Ye, Fei; Tian, Jinying; Si, Yikang; Zhang, Dongming. 2012. "A New Ursane-Type Nor-Triterpenoid from the Leaves of Eucommia ulmoides Oliv.." Molecules 17, no. 12: 13960-13968.