Chemical constituents from the fruit of Gardenia jasminoides and their inhibitory effects on nitric oxide production

Three new iridoid glycosides, 6″-O-trans-caffeoylgenipin gentiobioside (1), genipin 1-O-β-d-apiofuranosyl (1→6)-β-d-glucopyranoside (2), genipin 1-O-α-d-xylopyranosyl (1→6)-β-d-glucopyranoside (3), three new monocyclic monoterpenoids, jasminoside R (4), jasminoside S (5), jasminoside T (6), together with nine known iridoid glycosides (7–15) and three crocetin glycosides (16–18), were isolated from the fruit of Gardenia jasminoides. Their chemical structures were established mainly by 1D and 2D NMR techniques and mass spectrometry. Inhibitory effects of the isolated compounds on nitric oxide production in lipopolysaccaride-activated macrophages were evaluated. Compounds 8 and 18 showed strong inhibitory activity on NO production with IC50 values of 11.14 ± 0.67 and 5.99 ± 0.54 μM, respectively.

Graphical abstractThree new iridoid glycosides (1–3), three new monocyclic monoterpenoids (4–6), were isolated from the fruit of Gardenia jasminoides, together with 12 known compounds. Following structural elucidation, they were evaluated for inhibitory activities against LPS-induced NO production in RAW 264.7 macrophages.Figure optionsDownload full-size imageDownload as PowerPoint slide