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 IC(50) values of 11.14±0.67 and 5.99±0.54 μM, respectively.

Peng K ，Yang L ，Zhao S ，Chen L ，Zhao F ，Qiu F ... -  《-》

2-methyl-L-erythritol glycosides from Gardenia jasminoides.

Two new glycosides, 2-methyl-L-erythritol-4-O-(6-O-trans-sinapoyl)-β-D-glucopyranoside (1) and 2-methyl-L-erythritol-1-O-(6-O-trans-sinapoyl)-β-D-glucopyranoside (2), along with two known triterpenoids (3-4), four quinic acid derivatives (5-8) and one flavonoid (9) were isolated from the fruit of Gardenia jasminoides. Their structures were elucidated through MS and 2D NMR experiments (HMQC and HMBC). Inhibitory effects of the isolated compounds on nitric oxide production in lipopolysaccharide-activated macrophages were evaluated. Though 2-methyl-D-erythritol and its glycosides have been reported in a few references, this is the first report about 2-methyl-L-erythritol glycosides. Based on this finding, we propose that 2-methyl-L-erythritol might be a new intermediate in the non-mevalonate biosynthesis of terpenoids.

Yang L ，Peng K ，Zhao S ，Zhao F ，Chen L ，Qiu F ... -  《-》

Pyronane monoterpenoids from the fruit of Gardenia jasminoides.

Chen QC ，Youn U ，Min BS ，Bae K ... -  《-》

Iridoid and bis-iridoid glucosides from the fruit of Gardenia jasminoides.

Three new iridoid glucosides, 6″-O-trans-feruloylgenipin gentiobioside (1), 2'-O-trans-caffeoylgardoside (2), jasmigeniposide A (3), and one new bis-iridoid glucoside, jasmigeniposide B (4), along with six known analogues (5-10), were isolated from the fruit of Gardenia jasminoides. Their structures were established on the basis of spectroscopic analyses and chemical methods. Anti-virus activity of isolated compounds were evaluated in vitro and only compound 9 showed moderate inhibitory activity against H1N1 with 50% effective concentration (EC50) value of 104.36 μM, and selective index (SI) value greater than 4.79.

Li HB ，Yu Y ，Wang ZZ ，Dai Y ，Gao H ，Xiao W ，Yao XS ... -  《-》

Chemical constituents from the fruits of Gardenia jasminoides Ellis.

A new lignan glucoside, (+)-(7S,8R,8'R)-lyoniresinol 9-O-β-D-(6″-O-trans-sinapoyl)glucopyranoside (1), and a new iridoid glucoside, 10-O-trans-sinapoylgeniposide (2), together with eight known compounds, were isolated from the fruits of Gardenia jasminoides Ellis. The structures of the isolates were elucidated by extensive spectroscopic studies, including UV, IR, 1D and 2D NMR, ESI-MS, HR-ESI-MS, and CD experiments. The short-term-memory-enhancement activities of some compounds were evaluated on an Aβ transgenic drosophila model.

Yu Y ，Feng XL ，Gao H ，Xie ZL ，Dai Y ，Huang XJ ，Kurihara H ，Ye WC ，Zhong Y ，Yao XS ... -  《-》