5-O-Coumaroylquinic acid

Flavonoids from Hypericum patulum enhance glucose consumption and attenuate lipid accumulation in HepG2 cells.[Pubmed:34378802]

J Food Biochem. 2021 Sep;45(9):e13898.

Hypericum patulum has been used as a folk medicine for its varied therapeutic effects including antifungal, wound-healing, spasmolytic, stimulant, hypotensive activities. The water decoction is drank as tea could treat cold, infantile malnutrition. The present study aims to isolate the constituents of the plant and investigate their effects on the glucose consumption in insulin-resistant HepG2 cells, furthermore, lipid metabolism in oleic acid (OA)-treated HepG2 cells was also studied. The phytochemical investigation of the plant led to the isolation of eleven compounds, and their structures were identified by spectroscopic analysis as n-dotriacontanol (1), shikimic acid (2), 1-O-caffeoylquinic acid methyl ester (3), 5-O-caffeoylquinic acid methyl ester (4), 5-O-Coumaroylquinic acid methyl ester (5), 5-O-caffeoylquinic acid butyl ester (6), quercetin-3-O-alpha-L-rhamnoside (7), quercetin (8), quercetin-3-O-(4-methoxy)-alpha-L-rahmnopyranosyl (9), hyperoside (10), and rutin (11). The results revealed that compounds 7, 9, and 10 could enhance glucose consumption significantly in hyperglycemia induced HepG2 cells and insulin-resistant HepG2 cells. In addition, the western blotting analysis result exhibited that compounds 7, 9, and 10 in high concentration (5 muM, H) group could dramatically upregulate the expression of PPARgamma protein, and even the effect of them had no significant difference compared with that of rosiglitazone. Furthermore, compounds 9 and 10 in middle concentration (2.5 muM, M) group and H group could dramatically promote triglyceride metabolism and decrease TG content in OA-treated HepG2 cells, and even in H group, reactive oxygen species (ROS) level were significantly decreased compared with model group. PRACTICAL APPLICATIONS: Hypericum patulum is a well-known plant of the genera Hypericum for its varied preventive and therapeutic potential activities. To study the chemical constituents and their effects on glucose and lipid metabolism in vitro, we detected glucose consumption in insulin-resistant HepG2 cells, triglyceride content and reactive oxygen species level in OA-treated HepG2 cells. In addition, PPARgamma protein was also detected by western blotting analysis in the study. Compounds 1, 2, 3, 5, 6, 9, 10, and 11 were isolated from the plant for the first time. Quercetin-3-O-(4"-methoxy)-alpha-L-rahmnopyranosyl (9) and hyperoside (10) had potential therapeutic benefit against glucose and lipid metabolic disease. Therefore, this study might have certain guiding significance for further research and development of H. patulum.

Simultaneous Determination of 10 Bioactive Components of Lophatherum gracile Brongn by HPLC-DAD.[Pubmed:25527702]

J Chromatogr Sci. 2015 Jul;53(6):963-7.

A high-performance liquid chromatography method coupled with diode array detection (HPLC-DAD) was developed for simultaneous determination of two coumarins and eight flavonoids in Lophatherum gracile Brongn (Gramineae), namely 5-O-Coumaroylquinic acid (i), 4-O-coumaroylquinic acid (ii), luteolin 6-C-beta-d-galactopyranosiduronic acid (1-->2)-beta-d-glucopyranoside (iii), 7-O-beta-d-glucopyranosyl-6-C-alpha-l-arabinopy ranoside (iv), isoorientin (v), swertiajaponin (vi), luteolin 6-C-beta-d-galactopyranosiduronic acid (1-->2)-alpha-l-arabinopyranoside (vii), Saponaretin (viii), swertisin (ix) and apigenin 6-C-beta-d-galactopyranosiduronic acid (1-->2)-alpha-l-arabinopyranoside (x). The analysis was performed on Cosmosil MS-II C18 column (250 x 4.6 mm, 5 microm) with gradient elution of 0.1% aqueous acetic acid and acetonitrile. The detection wavelength was 330 nm. The developed method was able to determine the bioactive compounds with excellent resolution, precision and recovery. The validated method was successfully applied for the analysis of the 10 bioactive compounds in n samples from different cultivated regions. The results indicated that the developed method can be used as a suitable quality control method for L. gracile.