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. 2012 Nov 26;17(12):13960-8.
doi: 10.3390/molecules171213960.

A new ursane-type nor-triterpenoid from the leaves of Eucommia ulmoides Oliv

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A new ursane-type nor-triterpenoid from the leaves of Eucommia ulmoides Oliv

Chuangjun Li et al. Molecules. .

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 IC(50) values of 0.69 and 3.98 μM, respectively.

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Figures

Figure 1
Figure 1
Structures of compounds 111.
Figure 2
Figure 2
Key HMBC and ROESY correlations of 1.
Figure 3
Figure 3
The optimized geometry of compound 1 and two possible structures 1a and 1b.
Figure 4
Figure 4
Comparison of theoretical and experimental ECD and UV spectra of compound 1.
Figure 5
Figure 5
Inhibition of Compounds 3 (A) and 4 (B) on PTP1B activity in vitro.

References

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