Constituents of Coreopsis lanceolata Flower and Their Dipeptidyl Peptidase IV Inhibitory Effects

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 and two dimensional nuclear 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.

Metabolite Profiling and Dipeptidyl Peptidase IV Inhibitory Activity of Coreopsis Cultivars in Different Mutations

“…tinctoria (known as snow chrysanthemum) and C . lanceolata [ 3 , 5 , 6 , 12 , 26 , 27 , 28 , 29 ]. Moreover, its mass spectrum was compared to that in Waters Traditional Medicine Library that is built in UNIFI software (Waters, Milford, MA, USA) and MassBank available online (a public database for sharing mass spectral data) [ 30 , 31 ].…”

“…lanceolata and C . tinctoria , in particular [ 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 ]. Diverse types of flavonoids, such as aurone, chalcone, flavanone, and flavanol have been identified from C .…”

“…In addition, unique polyacetylene compounds have also been found in these plants [ 10 , 12 , 13 ]. Various pharmacological activities such as anticancer [ 2 , 5 ], antioxidant [ 6 , 14 , 15 , 16 , 17 , 18 ], anti-inflammatory [ 6 , 10 , 19 ], and anti-diabetic effects [ 8 , 12 ] have been reported of compounds isolated from C . lanceolata and C .…”

A Comprehensive Review and Perspective on Natural Sources as Dipeptidyl Peptidase-4 Inhibitors for Management of Diabetes

“…A methanol extract of the flowers of C. lanceolata was found to inhibit DPP-4 activity by 87.2%. Among the various compounds isolated, compounds 2 – 4 , 6 , and 7 inhibited DPP-4 in a concentration-dependent manner, with IC 50 values ranging from 9.6 to 64.9 µM [ 91 ], which suggests that flowers of C. lanceolata and their active components have potential for the treatment of T2DM.…”

Microbial Transformation of Flavonoids in Cultures of Mucor hiemalis

“…25 In our previous study on Coreopsis lanceolata, several types of flavonoids were isolated as flavone, flavonol, flavanone, chalcones, and aurone. 26 As part of our search for new derivatives and/or enhancers of bioactivity and bioavailability through microbial transformation, we performed biotransformations of isolates 1 and 2 from C. lanceolata and commercially available compounds (3-10) with similar structures to those isolated, in cultures of Mucor hiemalis KCTC 26779, which has been an efficient biocatalyst for microbial glycosylation in our studies. [27][28][29] As a result, one compound (8) was successfully converted into a new metabolite (11) by the microbial transformation (Figure 1).…”