2-hydroxyursolic-acid and euscaphic-acid

Ten compounds were isolated and purified from the peels of gold-red apple (Malus domestica) for the 1st time. The identified compounds are 3β, 20β-dihydroxyursan-28-oic acid (1), 2α-hydroxyoleanolic acid (2), euscaphic acid (3), 3-O-p-coumaroyl tormentic acid (4), ursolic acid (5), 2α-hydroxyursolic acid (6), oleanolic acid (7), betulinic acid (8), linolic acid (9), and α-linolenic acid (10). Their structures were determined by interpreting their nuclear magnetic resonance and mass spectrometry (MS) spectra, and by comparison with literature data. Compound 1 is new, and compound 2 is herein reported for the 1st time for the genus Malus. α-Glucosidase inhibition assay revealed 6 of the triterpenoid isolates as remarkable α-glucosidase inhibitors, with betulinic acid showing the strongest inhibition (IC50 = 15.19 μM). Ultra-performance liquid chromatography-electrospray ionization MS analysis of the fruit peels, pomace, flesh, and juice revealed that the peels and pomace contained high levels of triterpenes, suggesting that wastes from the fruit juice industry could serve as rich sources of bioactive triterpenes.

Topics: alpha-Glucosidases; alpha-Linolenic Acid; Betulinic Acid; Fruit; Glycoside Hydrolase Inhibitors; Magnetic Resonance Spectroscopy; Malus; Oleanolic Acid; Pentacyclic Triterpenes; Spectrometry, Mass, Electrospray Ionization; Triterpenes; Ursolic Acid

To study the chemical constituents from the root of Actinidia chinensis.. The roots of A. chinensis were extracted with 95% EtOH. The EtOH extract was suspended in H2O and extracted with petroleum ether, EtOAc and BuOH successively. The compounds were isolated with column chromatography from the EtOAc fraction, and elucidated on the basis of spectral analysis(MS, IR, 1H-NMR, 13C-NMR).. Seven compounds were isolated from the root of A. chinensis, and the structures were identified as 2alpha-hydroxyoleanolic acid (1), 2alpha-hydroxyursolic acid (2), euscaphic acid (3), 23-hydroxyursolic acid (4), 3beta-O-acetylursolic acid (5), ergosta4, 6, 8, (14), 22-tetraen-3-one (6), beta-steriol (7).. All the compounds were obtained from the root of A. chinensis for the first time.

Topics: Actinidia; Oleanolic Acid; Plant Roots; Plants, Medicinal; Sitosterols; Triterpenes

In order to determine the mechanism of triterpenes, a class of secondary metabolites in plants, in modulating progression of vascular atherosclerotic lesions, we isolated three ursane triterpenoids (euscaphic acid, tormentic acid and 2alpha-hydroxyursolic acid) from aerial part of Salvia miltirrhiza Bge. and fed LDLr(-/-) mice the isolated compounds at a dose of 10 mg/kg p.o. for 24 weeks.. The treated mice were raised with a cholesterol-enriched (1.25%) diet. Implying serum and aorta MCP-1 analysis, we found that all mice treated with the compounds exhibited a significant reduction of whole body and vascular inflammation.. The reduction of macrophage cells' number in aortic atherosclerotic lesions suggests that triterpenes treatment results in the development of a more stable plaque phenotype. Analysis of the structure-activity relationships demonstrates that compounds with a beta-orientated hydrogen-bond forming group at C-3 exhibit more potent anti-atherogenic effect than the alpha-counterpart on the development of atherosclerosis and xanthoma. However, the biological activities of the compounds are significantly reduced when they have C-19 hydrogen-bonds.. These Results suggest that down-regulation of MCP-1 is the main mechanism for antiatherogenic activity of triterpenes and MCP-1 might play important roles in the development of atherosclerosis and xanthoma.

Topics: Animals; Aorta; Atherosclerosis; Chemokine CCL2; Cholesterol; Diet, Atherogenic; Female; Male; Mice; Mice, Knockout; Receptors, LDL; Salvia; Structure-Activity Relationship; Triglycerides; Triterpenes; Xanthomatosis

To study the chemical constituents of the herb of Ludwigia octovalvis.. Chemical constituents were isolated by the repeated silica gel column chromatography, and their structures were elucidated by the physicochemical properties and spectral analysis.. Thirteen compounds were obtained and determined as follows: beta-sitosterol (1), oleanolic acid (2), 2alpha-hydroxy ursolic acid (3), tormentic acid (4), daucosterol (5), maltol (6), luteolin (7), quercetin (8), apigenin (9), methyl brevifolincarboxylate (10), gallic acid (11), 3, 4, 8, 9, 10-pentahydroxydibenzo[b, d]pyran-6-one (12), and ellagic acid (13).. Compounds 3, 4, 6-13 were isolated from the plant for the first time. And compounds 3, 4, 6, 10, 12 were obtained from the genus for the first time.

Topics: Molecular Structure; Onagraceae; Plants, Medicinal; Pyrones; Triterpenes

Seven triterpenes (1-7), i.e., betulinic acid 1, ursolic acid 2, oleanolic acid 3, 3-O-caffeoyloleanolic acid 4, euscaphic acid 5, 2 alpha-hydroxyursolic acid 6 and maslinic acid 7 were isolated from the stem bark extract of P. intermedius as active principles responsible for the cytotoxicity against five cultured human tumor cell lines, i.e., A549 (non small cell lung), SK-OV-3 (ovary), SK-MEL-2 (melanoma), XF498 (central nerve system) and HCT-15 (colon), in vitro.

Topics: Antineoplastic Agents, Phytogenic; Betulinic Acid; Humans; Magnetic Resonance Spectroscopy; Oleanolic Acid; Pentacyclic Triterpenes; Plant Stems; Rosales; Triterpenes; Tumor Cells, Cultured; Ursolic Acid