euscaphic-acid and maslinic-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

Corosolic acid (CRA), maslinic acid (MA), and tormentic acid (TA) are three kind of bioactive constituents of Eriobotrta japonica leaves. In this study, plasma protein binding model prediction suggested that the binding ability to HSA was CRA>MA>TA. Furthermore, fluorescence spectroscopy confirmed this prediction. The results from emission and time resolved fluorescence studies revealed that the emission quenching of HSA with CRA, MA, and TA were all initiated by static quenching mechanism. From molecular docking results and site marker competitive experimental results it was possible to make good estimates about CRA, MA, and TA mainly bound to subdomain IIA of HSA. 3D fluorescence, FT-IR and CD spectra indicated that the local conformation of HSA molecules was affected by the presence of CRA, MA, and TA, but at different extents.

Topics: Binding Sites; Circular Dichroism; Eriobotrya; Humans; Molecular Docking Simulation; Plant Leaves; Protein Binding; Protein Structure, Tertiary; Serum Albumin; Spectrometry, Fluorescence; Spectroscopy, Fourier Transform Infrared; Triterpenes

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

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 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

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