euscaphic-acid and pomolic-acid

Two new triterpenoids, maquatic acid (1), a 2,3-seco-triterpene having an acetal in its A-ring, and 3-Ο-benzoyltormentic acid (2), were isolated from underground parts of Mentha aquatica, in addition to twelve known compounds, tormentic acid (3), 1-Ο-benzoylhyptadienic acid (4), 3-epi-ursolic acid (5), hyptadienic acid (6), 3-epi-maslinic acid (7), 3-epi-tormentic acid (8), ursolic acid (9), β-sitosterol (10), oleanolic acid (11), pomolic acid (12), micromeric acid (13) and 21α-hydroxyursolic acid (14) from aerial and underground parts of the plant. Compounds 4-6, 8, 13 and 14 have been isolated from the genus Mentha for the first time.

Topics: Mentha; Molecular Structure; Oleanolic Acid; Plant Extracts; Plants, Medicinal; Triterpenes; Ursolic Acid

From the methanol extract of the fruits of the blackberry (Rubus allegheniensis Port.), four triterpenoids - pomolic acid (1), tormentic acid (2), euscaphic acid (3) and 1β-hydroxyeuscaphic acid (4) - were isolated, while six triterpenoids - 2, 3, myrianthic acid (5), ziyu glycoside II (6), sericic acid (7) and 19-hydroxy-2,3-secours-12-ene-2,3,28-trioic acid 3-methyl ester (8) - were obtained from the methanol extract of the leaves of this plant. Their structures were determined on the basis of spectral data. Compounds 1-8 were examined for their inhibitory activities on foam cell formation in human monocyte-derived macrophages induced by acetylated low-density lipoproteins at a 50 μM concentration. Among the tested compounds, 1 showed the strongest activity, with the inhibitory effect being 90%. The inhibitory activities of 2-8 were evaluated to be 30%, 32%, 33%, 4%, 48%, 4% and 24%, respectively. Further, the structure-activity relationship of these compounds was investigated.

Topics: Arteriosclerosis; Foam Cells; Fruit; Glycosides; Humans; Lipoproteins, LDL; Macrophages; Molecular Structure; Oleanolic Acid; Plant Leaves; Rubus; Structure-Activity Relationship; Triterpenes

To investigate the chemical constituents from the roots of Rubus parvifolius.. The chemical constituents were isolated by silica gel column chromatography, Sephadex LH-20, as well as preparative high performance liquid chromatography. Their structures were identified on the basis of physicochemical properties and NMR analysis.. Six comounds were isolated and identified as 3-O-Acetyl-11α, 12α-epoxy-oleanan-28,β-olide( I ) ,3-O-Acetyl-pomolic acid( II ), Ursolic acid( Ill),Ursolic acid acetate (1V ), Euscaphic acid ( V) and β-Sitosterol ( VI).. Compounds I , II and IV are isolated from Rubus parvifolius for the first time.

Topics: Chromatography, High Pressure Liquid; Magnetic Resonance Spectroscopy; Oleanolic Acid; Plant Roots; Rubus; Sitosterols; Triterpenes; Ursolic Acid

Ellagic acid (1), 3,3'-di-O-methylellagic acid (2), 3,3',4-tri-O-methylellagic acid (3), isovitexin (4), kaempferol 3-O-beta-D-glucuronide methyl ester (5), quercetin 3-O-alpha-L-arabinopyranosyl-(1-->6)-beta-D-galactopyranoside (6), ursolic acid, pomolic acid, tormentic acid, euscaphic acid, euscaphic acid 28-O-beta-D-glucopyranoside, and maslinic acid were isolated from the AcOEt- and BuOH-soluble MeOH extract of Duchesnea chrysantha (whole plant). The isolates were subjected to in vitro bioassays to evaluate their inhibitory activity on rat-lens aldose reductase (RLAR) and formation of advanced glycation end products (AGEs). The ellagic acids and flavonoids, compounds 1-6, exhibited moderate inhibitory effects on RLAR. However, compounds 1 and 4-6 showed excellent inhibitory activities towards the formation of AGEs. This is the first report that 4 and 6 exhibit inhibitory activity towards AR and AGEs formation.

Topics: Aldehyde Reductase; Animals; Apigenin; Ellagic Acid; Glycation End Products, Advanced; Glycosides; Lens, Crystalline; Molecular Structure; Oleanolic Acid; Quercetin; Rats; Rats, Sprague-Dawley; Rosaceae; Stereoisomerism; Structure-Activity Relationship; Triterpenes; Ursolic Acid

To investigate the chemical constituents from the fruit of Rosa bella and its bioactivity.. The compounds were isolated from the methanol extract by column chromatography, then identified by 1H, 13C NMR and by comparison with authentic samples. The unorganized hoptoad heart was used for testing the contracting force of cardiac muscle and enzymology for measuring the bloody lipid of serum in rats.. Seven compounds were isolated and identified as pomolic acid, tiliroside, euscaphic acid, daucosterol, quercetin, oleanolic acid and beta-sitosterol, respectively. In the concentration of 0.4-1.0 mg.ml-1, the methanol extract had obvious cardiotonic effect. While at 400 mg.kg-1, there are no obvious effect to the TC, HDL-ac and TG of serum in rats.. The isolated compounds may be the active components of this plant.

Topics: Animals; Benzopyrans; Bufo bufo; Cholesterol; Flavonoids; Fruit; Lipoproteins, HDL; Male; Myocardial Contraction; Oleanolic Acid; Plants, Medicinal; Rats; Rats, Wistar; Rosa; Triglycerides; Triterpenes

Oleanolic acid (1) was identified as an anti-HIV principle from several plants, including Rosa woodsii (leaves), Prosopis glandulosa (leaves and twigs), Phoradendron juniperinum (whole plant), Syzygium claviflorum (leaves), Hyptis capitata (whole plant), and Ternstromia gymnanthera (aerial part). It inhibited HIV-1 replication in acutely infected H9 cells with an EC50 value of 1.7 microg/mL, and inhibited H9 cell growth with an IC50 value of 21.8 microg/mL [therapeutic index (T. I.) 12.8]. Pomolic acid, isolated from R. woodsii and H. capitata, was also identified as an anti-HIV agent (EC50 1.4 microg/mL, T. I. 16.6). Although ursolic acid did show anti-HIV activity (EC50 2.0 microg/mL), it was slightly toxic (IC50 6.5 microg/mL, T. I. 3.3). A new triterpene (11) was also isolated from the CHCl3-soluble fraction of R. woodsii, though it showed no anti-HIV activity. The structure of 11 was determined to be 1beta-hydroxy-2-oxopomolic acid by spectral examination. Based on these results, we examined the anti-HIV activity of oleanolic acid- or pomolic acid-related triterpenes isolated from several plants. In addition, we previously demonstrated that derivatives of betulinic acid, isolated from the leaves of S. claviflorum as an anti-HIV principle, exhibited extremely potent anti-HIV activity. Accordingly, we prepared derivatives of oleanolic acid and evaluated their anti-HIV activity. Among the oleanolic acid derivatives, 18 demonstrated most potent anti-HIV activity, with an EC50 value of 0. 0005 microg/mL and a T. I. value of 22 400.

Topics: Anti-HIV Agents; Cell Line; Humans; Oleanolic Acid; Plants, Medicinal; Triterpenes; Viral Plaque Assay