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PubMed1989

[The isolation and structure identification of triptotriterpenic acid C].

A new ursolic-type acid named triptotriterpenic acid C was obtained from the total glycosides extracted from the root of Tripterygium wilfordii Hook.f. Its structure was inferred from chemical reaction, IR, 1HNMR, 13CNMR and MS spectral data. The structure and stereochemistry of this compound was confirmed to be 3 beta,22 alpha-dihydroxy-delta 12-ursene-30-oic acid by X-ray crystallo-diffraction analysis of its methyl ester.

Chemical Phenomena↗
PubMedDate not supplied

Triterpenic acids and flavonoids from Satureja parvifolia. Evaluation of their antiprotozoal activity.

Bioassay-guided fractionation of a Satureja parvifolia MeOH extract led to the isolation of eriodictyol, luteolin and ursolic and oleanolic acids as its active components against Plasmodium falciparum K1. This is the first time these compounds are reported as constituents of S. parvifolia. Ursolic acid showed an IC50 of 4.9 microg/ml, luteolin 6.4 microg/ml, oleanolic acid 9.3 microg/ml and eriodictyol 17.2 microg/ml. Antiplasmodial activity of eriodictyol and luteolin is reported here for the first time. Besides, the four compounds showed activity against P. falciparum 3D7 strain and Trypanosoma brucei rhodesiense. Eriodictyol showed moderate activity on all the parasites but was the most selective compound as a result of its rather low cytotoxicity (IC50 174.2 microg/ml) on the mammalian KB cell line.

Animals↗
PubMed2006

Trypanocidal activity of triterpenes from Arrabidaea triplinervia and derivatives.

Ethanol extract from Arrabidaea triplinervia leaves showed in vitro activity (ED100 5.0 mg/ml) against trypomastigotes of Trypanosoma cruzi, the etiologic agent of Chagas; disease. Bioactivity-directed fractionation of this extract led to the isolation of ursolic and oleanolic acids as trypanocidal compounds besides pomolic acid (not tested) and alpinetine (inactive). A series of natural and synthetic derivatives of ursolic and oleanolic acids was simultaneously assayed for structure activity relationships (SAR) studies. Ursolic acid (ED100 0.4 mg/ml) was four times more active than oleanolic acid (ED100 1.6 mg/ml). The presence of free hydroxy and/or carboxy groups is necessary for the trypanocidal activity as could be deduced from the effect of the acetates, methyl ester, and aldehyde derivatives.

Animals↗
PubMed2001

[HPLC determination of oleanolic acid and llrolic acid in Chinese medicinal herbs].

OBJECTIVE: To develop a new method for simultaneous determination of oleanolic acid and llrolic acid in Chinese medicinal herbs at the same time. METHOD: HPLC was carried out on a Shim-pack CLC-ODS column using MeOH-H2O-HOAc-TEA (83:17:0.04:0.02). RESULT AND CONCLUSION: The average recovery of oleanolic acid and llrolic acid was 103.3 +/- 2.07% and 102.7% +/- 0.65% respectively.

Chromatography, High Pressure Liquid↗
PubMed2006

Topical anti-inflammatory activity of 2alpha-hydroxy pentacyclic triterpene acids from the leaves of Ugni molinae.

Leaf extracts of Ugni molinae Turcz. are used in the Chilean cosmetic industry on the assumption that they have decongestant, regenerative, and anti-aging properties. A bioassay-guided fractionation of this plant material showed that some extracts have potent anti-inflammatory activities. Further fractionation led to the isolation and identification of betulinic acid, a mixture of ursolic and oleanolic acids, and the 2alpha-hydroxy derivatives alphitolic, asiatic, and corosolic acids. The latter three were evaluated in vivo in the mouse ear assay for their topical anti-inflammatory activity, inducing inflammation with either arachidonic acid (AA) or 12-O-tetradecanoylphorbol-13 acetate (TPA). Only corosolic acid was active in the AA assay, with similar potency to nimesulide, but all three triterpene acids inhibited TPA-induced inflammation with potencies comparable to that of indomethacin.

Animals↗
PubMed2002

Antithrombin activity of some constituents from Origanum vulgare.

Aristolochic acid I, aristolochic acid II, and D-(+)-raffinose were isolated from Origanum vulgare. Their inhibition of thrombin and activity against leukemia were evaluated. Aristolochic acid I and II have high inhibition of thrombin activity and were confirmed to possess activity against cancer.

Antineoplastic Agents↗
PubMed2006

Extracts from Pygeum africanum and other ethnobotanical species with antiandrogenic activity.

Extracts from Pygeum africanum, Serenoa repens and Cucurbita pepo are used in the treatment of benign prostatic hyperplasia (BPH) and prostate cancer (PCa). The activity of the androgen receptor (AR) is known to control growth of the prostate. Here, we examined extracts of these plants for their antiandrogenic activity using an AR responsive reporter gene assay for drug discovery. A selective dichloromethane extract from the stem barks of Pygeum africanum revealed the highest antiandrogenic effect. Bioactivity-directed fractionation of this extract led to the isolation of N-butylbenzenesulfonamide (NBBS) indicating that extracts of the stem bark of P. africanum harbour androgen antagonistic activity. This compound may provide a novel approach for the prevention and treatment of BPH and human PCa.

Androgen Antagonists↗
PubMed2002

Triterpenes and saponins from Ilex psammophila.

Two new saponins were isolated from the leaves of Ilex psammophila. Their structure was established by chemical and spectroscopic methods as 28-O-beta-D-glucopyranosylester of 20(S)-ilexgenin A ([structure: see text]) and 28-O-beta-D-glucopyranosylester of 20(S)-3beta,19alpha,24-trihydroxyurs-12-ene-23, 28-dioic acid ([structure: see text]).

Brazil↗
PubMed1999

Quantitative determination of hydroxy pentacyclic triterpene acids in vegetable oils.

A simple and precise analytical method for the determination of hydroxy pentacyclic triterpene acids (HPTAs) in vegetable oils was developed. The acidic fraction was isolated by solid-phase extraction using bonded aminopropyl cartridges, and the extract was silylated and analyzed by gas chromatography. Repeatability and recovery of the method were determined. In virgin olive oils, similar amounts of oleanolic (3beta-hydroxyolean-12-en-28-oic) and maslinic (2alpha,3beta-dihydroxyolean-12-ene-28oic) acids and traces of ursolic (3beta-hydroxyurs-12-en-28-oic) acid were found. The main factor affecting HPTA concentration was the oil quality since that increases as the quality decreases, while olive variety, olive ripeness, and oil extraction system had less influence. In crude olive pomace oils, the concentrations were very much higher than in virgin olive oils. During refining processes, total or significant losses of HPTAs were observed. Esterified derivatives of HPTAs were not found.

Chromatography, Gas↗
PubMed2005

Cytotoxic activity and effect on nitric oxide production of tirucallane-type triterpenes.

Hexane extract from the bark of Amphipterygium adstringens, as well as its principal constituents, masticadienonic acid and 3alpha-hydroxymasticadienolic acid, inhibited the growth of five human cancer cell lines. Derivatives of, namely 24,25 S-dihydromasticadienonic acid and masticadienolic acid, were also evaluated. The results showed that both and had greater activity than on colon cancer cell lines. The effects of on the production of nitric oxide (NO) from both resting and lipopolysaccharide-activated macrophages were determined. It was found that and caused an increase in NO release from resting macrophages; in lipopolysaccharide-activated macrophages, only and caused an increase in NO production.

Anacardiaceae↗
PubMed2006

Structure determination of ursene-type triterpenes by NMR techniques.

Two new ursene-type triterpenes, nudicauline A and nudicauline B, have been isolated from Launaea nudicaulis. Their structures have been assigned as 3beta-hydroxy-urs-11-ene (1) and 3beta-acetyl-urs-11-ene (2), respectively, by extensive NMR studies. In addition, olean-11,13(18)-diene (3), 3beta-hydroxy-13(28)-epoxy-urs-11-ene (4) and 3-keto-13(28)-epoxy-urs-11-ene (5) are also reported for the first time from this species.

Asteraceae↗
PubMed1993

Structure-activity relationships of synthetic methyl ursolate glycosides.

From 15 synthetic methyl ursolate glycosides, the di- and tri-glycosides showed much higher haemolytic activity than the monoglycosides. The beta-gentiobioside and the beta-maltotrioside exhibited much stronger antibacterial (Staphylococcus aureus) or antifungal (Trichophyton mentagrophytes) activity than the other glycosides. However, none of them exhibited antibacterial activity against Bacillus subtilis.

Bacteria↗
PubMed2002

Phosphoinositide 3-OH kinase/protein kinase B inhibits apoptotic cell death induced by reactive oxygen species in Saccharomyces cerevisiae.

Apoptosis is a common mode of programmed cell death in multicellular organisms. However, the recent observation of yeast cell death displaying the morphology of apoptosis has suggested the presence of an ancestral cell death machinery. Here we examined apoptotic features induced by reactive oxygen species (ROS) in yeast. Saccharomyces cerevisiae show typical apoptotic features upon exposure to ROS: membrane staining with annexin V and DNA fragmentation by the TUNEL assay. The detection of apoptotic features in yeast strongly support the existence of molecular machinery performing the basic pathways of apoptosis. The phosphoinositide 3-OH kinase (PI3K)/protein kinase B (PKB) signaling pathway has been shown to prevent apoptosis in a variety of cells. It is therefore of interest to determine whether the PI3K/PKB signaling pathway is capable of protecting yeast from apoptosis induced by ROS. We determined that PI3K/PKB is capable of significantly inhibiting ROS-evoked apoptosis in yeast. These results suggest that yeast may provide a suitable model system in which to study the apoptotic signaling pathway elicited by a variety of stimuli.

Apoptosis↗