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At least 325 records · Page 18Linked to original sources

Anti-complementary activity of ursane-type triterpenoids from Weigela subsessilis.

A new ursane-type triterpenoid, weigelic acid (1), and seven known compounds, ursolic acid (2), ilekudinol A (3), corosolic acid (4), ilekudinol B (5), esculentic acid (6), pomolic acid (7), and asiatic acid (8) were isolated from the leaf and stem of Weigela subsessilis. The structure of the new triterpenoid was established as 1beta,2alpha,3alpha,23-tetrahydroxyurs-12-en-28-oic acid on the basis of spectroscopic analyses. In addition, the isolated compounds were evaluated for their anti-complement activity against the classical pathway of the complement system. Of these, compounds 1-2 and 4-8 exhibited anti-complement activity with IC50 values of 152, 90, 130, 51, 56, 4, and 163 microM, respectively, whereas 3 was inactive. This shows that a carboxylic group of ursane-type triterpenoids seems to play an important role in inhibiting the hemolytic activity of human serum against erythrocytes.

Animals↗

Sterol and triterpenoid constituents of Verbena littoralis with NGF-potentiating activity.

Two new sterols, stigmast-5-ene 3beta,4beta,7alpha,22alpha-tetraol (1) and stigmast-5-ene 3beta,7alpha,22alpha-triol (2), were isolated from the aerial parts of a Paraguayan medicinal plant, Verbena littoralis, together with the known compounds ursolic acid (3) and oleanolic acid (4). The structures of 1 and 2 were elucidated by spectroscopic analyses. Compounds 2-4 showed an enhancing activity of nerve growth factor (NGF)-mediated neurite outgrowth in PC12D cells.

Animals↗

A review of natural and modified betulinic, ursolic and echinocystic acid derivatives as potential antitumor and anti-HIV agents.

The aim of this review is to update current knowledge on the betulinic, ursolic and echinocystic acids and their natural and semisynthetic analogs, focussing on their cytotoxic and anti-HIV activities. Then, the last results of the authors' team on unusual semisynthetic derivatives of these triterpenoids will be presented in order to establish structure/activity relationships.

Anti-HIV Agents↗

[Studies on chemical constituents of the roots of Salacia hainanensis].

The chemical constituents of Salacia hainanensis were studied for the first time. Five compounds were isolated from the roots of the plant by silica-gel column chromatography and reverse phase preparative chromatography. Four of them have been identified as friedelin, beta-sitosterol, ursolic acid and mangiferin.

China↗

[Studies on chemical components of Gentiana tizuensis Franch. (I)].

OBJECTIVE: To study the chemical components of Gentiana tizuensis distributed in Qinghai Province. METHOD: Chromatography and spectral analyses were used to isolate the constituents and elucidate their structure. RESULT: Four compounds were isolated and identified as uvaol, L-(+)-l-O-methyl-myo-inositol, ursolic acid,beta-sitosterol. CONCLUSION: All these components were obtained from the plant for the first time.

Gentiana↗

Triterpenes as potential dimerization inhibitors of HIV-1 protease.

HIV-1 protease is a homodimeric enzyme. A beta-sheet consisting of the four terminal segments provides the main driving force for dimerization of the per se inactive protomers. Several short peptides with sequences related to the terminal sequences of the protease are able to inhibit dimerization by blocking the 'interface' part of the monomers. From the structures of such inhibitory peptides a 'pharmacophore' could be derived. By using a prominent distance from this pharmacophore scaffold for a library search (Cambridge Structural Database), non-peptide inhibitors of HIV-1 protease with polycyclic triterpene structure could be found. The IC50 constants of these compounds are near 1 microM. One of the triterpenes, the ursolic acid (Ki = 3.4 microM), was further kinetically analysed (according to Zhang). The shape of the graph confirms the expected mechanism of dimerization inhibition.

Amino Acid Sequence↗

[Studies on constituents in Uncaria macrophylla Wall].

OBJECTIVE: To study the chemical constituents of Uncaria macrophylla. METHOD: Compounds were isolated by Columu Chromatography, and the structures were identified by NMR spectral data and other methods. RESULT AND CONCLUSION: Six compounds were isolated and identified as ursolic acid, 3 beta-6 beta-23-trihydroxyurs-12-en-28-oic acid, 3 beta, 6 beta, 19 alpha-trihydroxyurs-12-en-28-oic acid, epicatechin, beta-sitosterol and daucosterin. All the compounds were isolated for the first time from the plant.

Catechin↗

[Chemical constituents of the leaves of Crataegus scabrifolia (Franch.) Rehd].

OBJECTIVE: To explore the medicinal resources of Crataegus and seek compounds with pharmaceutical effects. METHOD: Column chromatography was employed for the isolation and purification of constituents and the structures were elucidated by spectral analysis and chemical evidence. RESULT: Six compounds were obtained and identified as rutin, hyperoside, vitexin, ursolic acid, daucosterol, and nonacosanol. CONCLUSION: The main constituents of the leaves of Crataegus scabrifolia are flavonoids.

Crataegus↗

Separation of underivatised triterpene acids by capillary supercritical fluid chromatography.

Capillary supercritical fluid chromatography with flame ionisation detection was used for the separation of some underivatised triterpene acids such as betulinic, oleanolic, polpunonic and ursolic acids. Supercritical fluid chromatography showed advantages over capillary gas chromatography since derivatisation was not required and separation was obtained in less than 15 min with high efficiency and good resolving power.

Chromatography, Supercritical Fluid↗

Antiinflammatory activity of Synurus deltoides.

Synurus deltoides Aiton, Nakai, is an edible plant that has been used as a folk medicine for treating inflammatory disorders. This investigation was carried out to establish the antiinflammatory activity of this plant material using a 75% ethanol extract from the aerial part of S. deltoides. Against the acute inflammatory animal model of mouse croton oil-induced ear oedema assay, the extract did not show significant inhibition at 100-800 mg/kg by oral administration. On the other hand, the extract showed considerable inhibition against the chronic inflammatory animal model of rat adjuvant-induced arthritis (25% inhibition at 100 mg/kg/day) while prednisolone exerted 40% inhibition at 10 mg/kg/day. In addition, S. deltoides possessed strong analgesic activity (IC50 = 50 mg/kg) in the acetic acid-induced writhing test. From the extract, ursolic acid and scopoletin were successfully isolated and their contents were found to be 0.31% and 0.37% (w/w), respectively, based on the dried extract by HPLC analysis. All the results obtained indicate that this plant material may be used beneficially as an antiinflammatory agent having analgesic action.

Acetic Acid↗

Constituents of Eriobotrya japonica. A study of their antiviral properties.

The CHCl3 extract of Eriobotrya japonica from an Italian source was shown to contain four new triterpene esters, namely, 23-trans-p-coumaroyltormentic acid [1], 23-cis-p-coumaroyltormentic acid [2], 3-O-trans-caffeoyltormentic acid [3], and 3-O-trans-p-coumaroylrotundic acid [4], in addition to three common ursolic acid derivatives 5, 6, and 7. An investigation of the antiviral properties of compounds 1-7 revealed that only 3 significantly reduced rhinovirus infection. The compounds were ineffective towards human immunodeficiency virus type 1 (HIV-1) and Sindbis virus replication.

Antiviral Agents↗

Triterpene acids from the leaves of Perilla frutescens and their anti-inflammatory and antitumor-promoting effects.

Nine triterpene acids, viz., six of the ursane type, ursolic acid (1), corosolic acid (2), 3-epicorosolic acid (3), pomolic acid (4), tormentic acid (5) and hyptadienic acid (6), and three of the oleanane type, oleanolic acid (7), augustic acid (8) and 3-epimaslinic acid (9), among which 1 constituted the most predominant triterpene acid, were isolated and identified from ethanol extracts of the leaves of red perilla [Perilla frutescens (L.) Britton var. acuta Kudo] and green perilla [P. frutescens (L.) Britton var. acuta Kudo forma viridis Makino]. These eight compounds, 1, 2, 4-9, were evaluated for their inhibitory effects on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation (1 microg/ear) in mice. All the compounds tested showed a marked anti-inflammatory effect, with a 50% inhibitory dose (ID50) of 0.09-0.3 mg per ear. In addition, an evaluation against the Epstein-Barr virus early antigen (EBV-EA) activation induced by TPA showed five compounds, 1-3, 5 and 9, with a potent inhibitory effect on EBV-EA induction (91-93% inhibition at 1x10(3) mol ratio/TPA). Furthermore, compound 5 exhibited strong antitumor-promoting activity in an in vivo two-stage carcinogenesis test of mouse tumor by using 7,12-dimethylbenz(a)anthracene (DMBA) as an initiator and TPA as a promoter.

9,10-Dimethyl-1,2-benzanthracene↗

Constituents of Carapa guianensis Aubl. (Meliaceae).

Nine compounds were isolated from the EtOH extraction of the twig of Carapa guianensis Aubl. On the basis of spectroscopic methods, their structures were elucidated as 1,3-di-benzene carbon amine-2-octadecylic acid-glyceride (1), hexacosanoic acid-2,3-dihydroxy-glyceride (2), ursolic acid (3), naringenin (4), scopoletin (5), 3,4-dihydroxymethylbenzoate (6), 2,6-dihydroxymethylbenzoate (7), tetratriacontanoic acid (8), triacontanoic acid (9) respectively. Among them 1 was new, 2 was firstly isolated from nature, and 3-9 were obtained from this plant for the first time.

Chemical Phenomena↗

[Studies on chemical constituents of Salvia roborowskii Maxim].

OBJECTIVE: To study the chemical constituents from Salvia roborowskii Maxim. METHODS: Chromatography and spectroscopic analysis were employed to isolate and elucidate the chemical constituents in the plant. RESULTS: Six compounds were isolated and elucidated as lupeol (I), 11 beta-hydroxy-lupeol(II),3 beta-acetyl-11 beta-hydroxy-lupeol(III), ursolic acid (IV), beta-sitosterol(V), daucosterol (VI). CONCLUSION: I approximately VI were isolated from this plant for the first time.

Chromatography, Thin Layer↗

[Fat soluble constituents of the leaves of Vaccinium bracteatum Thunb].

Four compounds were isolated from the fat soluble fraction of the leaves of Vaccinium bracteatum and identified as friedelin (I), epifriedelinol (II), beta-sitosterol(III) and ursolic acid(IV) by IR, NMR and MS. Compound III and IV are isolated from the leaves of this plant for the first time.

Drugs, Chinese Herbal↗

[Chemical studies on Pyrrosia gralla (Gies.) Ching].

From Pyrrosia gralla four compounds were isolated and identified stigmasterol(I), ursolic acid (II), mangiferin(III) and sucrose(IV) by physical and chemical means. Compounds I and II were obtained from Pyrrosia for the first time.

Drugs, Chinese Herbal↗

[Studies on chemical constituents of Ilex Merr].

OBJECTIVE: To further probe into the chemical composition of Ilex hainanensis. METHOD: Compound isolation was affected on the basis of the EtOAc soluble fraction of the ethanolic extract from the leaves of the plant. RESULT: Four compounds were obtained and by physico-chemical and spectroscopic methods identified as ursolic acid, ilexgenin A, ilexsaponin A1 and beta-sitosterol-3-O-beta-D-glucoside. CONCLUSION: All the four compounds were isolated from the plant for the first time.

Ilex↗