Abstract
A new polyacetylene glycoside, (5R)-6E-tetradecene-8,10,12-triyne-1-ol-5-O-β-glucoside (1), was isolated from the flower of Coreopsis lanceolata (Compositae), together with two known compounds, bidenoside C (10) and (3S,4S)-5E-trideca-1,5-dien-7,9,11-triyne-3,4-diol-4-O-β-glucopyranoside (11), which were found in Coreopsis species for the first time. The other known compounds, lanceoletin (2), 3,2′-dihydroxy-4-3′-dimethoxychalcone-4′-glucoside (3), 4-methoxylanceoletin (4), lanceolin (5), leptosidin (6), (2R)-8-methoxybutin (7), luteolin (8) and quercetin (9), were isolated in this study and reported previously from this plant. The structure of 1 was elucidated by analyzing one-dimensional and two-dimensional nuclear magnetic resonance and high resolution-electrospray ionization-mass spectrometry data. All compounds were tested for their dipeptidyl peptidase IV (DPP-IV) inhibitory activity and compounds 2-4, 6 and 7 inhibited DPP-IV activity in a concentration-dependent manner, with IC50 values from 9.6 to 64.9 μM. These results suggest that C. lanceolata flower and its active constituents show potential as therapeutic agents for diseases associated with type 2 diabetes mellitus.
Highlights
Coreopsis is a perennial plant belonging to the Compositae family [1]
Additional signals for a methyl group at δH 2.02 (3H, s, H-14)/δc 4.6 (C-14) and six acetylene carbons at δc 81.3 (C-13), 75.4 (C-8), 74.0 (C-9), 64.6 (C-12), 67.4 (C-11) and 59.0 (C-10) indicated the presence of a 1,3,5-heptatriyne group, which was attached at the trans-olefin group by the 1 H-13 C HMBC NMR correlations of H-7/C-9 and H-14/C-12
This study provides the first demonstration of the compounds responsible for the dipeptidyl peptidaseIV (DPP-IV) inhibitory activity of the C. lanceolata flower
Summary
Coreopsis is a perennial plant belonging to the Compositae family [1]. It was planted for decoration on the roadsides in North America, Asia and Oceania regions [2,3,4]. C. lanceolata, C. tinctoria and C. drummondii are generally Coreopsis plants distributed all around Korea [5]. C. lanceolate are ornamental plants commonly found in Korea in spring and summer. In the previous phytochemical studies on C. lanceolata, phenolics, flavonoids (aurones, chalcones, flavaons, flanavol) and acetylene compounds have been isolated from this plant [5,6,7,8,9,10,11,12]
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