Isolation, characterization and antimicrobial activities of polyacetylene glycosides from Coreopsis tinctoria Nutt.

Polyacetylene glycosides, (6Z, 12E)-tetradecadiene-8,10-diyne-1-ol-3(R)-O-ß-D-glucopyranoside (trivially named coreoside E) and (6Z, 12E)-tetradecadiene-8,10-diyne-1-ol-3(R)-O-ß-L-arabinopyranosyl-(1 â†’ 2)-ß-D-glucopyranoside (trivially named coreoside F), were isolated from buds of Coreopsis tinctoria Nutt., together with one known compound, coreoside B. Their chemical structures were elucidated by extensive spectroscopic analysis and on the basis of their chemical reactivities. Coreoside E exhibited high levels of antimicrobial activity against Staphylococcus aureus and Bacillus anthracis with minimum inhibitory concentrations of 27 ± 0.27 and 18 ± 0.40 µM, respectively, whereas coreoside F and coreoside B showed weak antimicrobial activity against S. aureus and B. anthracis.

Polyacetylenes from capitulum of Coreopsis tinctoria / 中草药

Objective: To study the chemical constituents in the capitulum of Coreopsis tinctoria. Methods: The constituents were separated and purified by AB-8 macroporous resin, silica gel, Sephadex LH-20, ODS column chromatography, and preparative HPLC. The structures were elucidated on the basis of chemical evidences, spectroscopic methods, and optical rotation data. The new compound was evaluated for its inhibitory activity against LPS-activated NO production in BV-2 microglial cells using the Griess assay. Results: Five polyacetylenes were obtained from the fraction of 50% ethanol extract of C. tinctoria identified as (3S)-(6E,12E)-tetradecadiene-8,10-diyne-1-ol-3-O-β-D-glucopyranoside (1),(2S)-(3Z,11E)-decadiene-5,7,9-triyne-1,2-diol (2),(2R)-(3E,5E,11E)-triene-7,9-diyne-1,2-diol (3),(E)-7-phenyl-2-heptene-4,6-diyn-1-ol (4), and (Z)-7-phenyl-2-heptene-4,6-diyn-1-ol (5). Conclusion: Compound 1 is a new polyacetylene glycoside named coreoside E and shows weak anti-inflammatory activity. Compounds 3 and 5 are isolated from the plants of C. tinctoria for the first time.