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PubMed1992

Chemical Constituents of the Lichen Ramalina hierrensis.

The following compounds have been isolated from the lichen RAMALINA HIERRENSIS, collected on savin, and endemic to the Canary Islands: ursolic acid, iso-arborinol acetate, beta-sitosterol, ergosterol peroxide, cerevisterol, (-)-sandaracopimaric acid, parietin, (+)-usnic acid, (+)-iso-usnic acid, divaricatic acid, atranorin, stictic acid, gangaleodin, variolaric acid, montagnetol, and hierridin. The structures of all compounds were elucidated by physical, spectral, and chemical methods.

Journal Article↗
PubMed2005

A new bisabolane sesquiterpenoid from Euphorbia chrysocoma.

The new sesquiterpenoid (6R)-2-chloro-6-[(1S)-1,5-dimethylhex-4-en-1-yl]-3-methylcyclohex-2-en-1-one (1), together with ten known compounds, (6R)-6-[(1S)-1,5-dimethylhex-4-en-1-yl]-3-methylcyclohex-2-en-1-one (2), bauerenol acetate (3), lupenone (4), alpha-amyrenone (5), beta-sitosterol (6), stigmasterol (7), beta-amyrin (8), ursolic acid (9), betulinic acid (10), scopolin (11), have been isolated from the roots of Euphorbia chrysocoma Lévl. et Vant. Their structures have been elucidated by spectroscopic data.

Euphorbia↗
PubMed2002

Antimicrobial triterpenes from Debregeasia salicifolia.

New triterpene, 3beta-(trans-cinnamoyloxy)-19alpha-hydroxy-urs-12-ene (1) has been isolated from the methanolic fraction of Debregeasia salicifolia, along with uvaol (2), 3beta,19alpha-dihydroxy-urs-12-ene (3), ursolic acid (4), pomolic acid (5), pomolic acid methyl ester (6) and tormentic acid (7) reported for the first time from this species. The compounds (1), (3) and (6) showed significant antimicrobial activity. The structure elucidation was made with the help of extensive 2D NMR spectroscopic techniques.

Animals↗
PubMed2004

Antioxidant iridoid glucosides from Wendlandia formosana.

Two new iridoid glucosides of 10-O-caffeoyl scandoside methyl ester (3), and 6-methoxy scandoside methyl ester (4) besides the known compounds of scandoside methyl ester (1), methyl deacetyl asperulosidate (2), 10-O-caffeoyl daphylloside (5), phytol (6), and ursolic acid (7) were isolated from the leaves of Wendlandia formosana. Structure elucidation of the new iridoid glucosides was based on interpretation of high-resolution 1D and 2D NMR spectral data and chemical conversions. Antioxidant activity of Compounds (1-5) against diphenylpicrylhydrazyl (DPPH) and hydroxyl radical, and peroxynitrite was reported.

Antioxidants↗
PubMed2004

New cycloartenol esters from Ixora coccinea.

The air-dried flowers of Ixora coccinea L. afforded two new cycloartenol esters (1a and 1b), lupeol fatty ester, lupeol, ursolic acid, oleanolic acid, and sitosterol. The structures of 1a and 1b were elucidated by extensive 1D and 2D NMR spectroscopy and MS.

Esters↗
PubMed2004

Yin zi huang, an injectable multicomponent chinese herbal medicine, is a potent inhibitor of T-cell activation.

OBJECTIVES: The clinical efficacy of many multiherbal Traditional Chinese Medicines (TCM) is partially attributable to their immunoregulatory properties. In this study we evaluated the effect of eight commonly used, commercially available multiherbal Chinese medicines on T-cell activation. We focused on Yin Zhi Huang (YZH, an injectable herbal medicine commonly used for the treatment of liver diseases in China), because it was the most potent inhibitor of T-cell activation in our experimental system. The effects of 10 ingredient components of YZH were also evaluated. METHODS: [3H] thymidine incorporation assay was used to assess mouse T-cell proliferation after stimulation with latex beads coated with anti-CD3/CD28 antibodies. CD25, CD69, PD-1, and I-COS expression by purified mouse CD4+ T cells treated with plate-bound anti-CD3 antibody and soluble anti-CD28 antibody was analyzed by fluorescent-activated cell sorter (FACS). Cytokine/chemokine production by human peripheral blood mononuclear cells (PBMC) stimulated with staphylococcal enterotoxin B (SEB) was determined by enzyme-linked immunosorbent assay (ELISA). RESULTS: Among tested herbal medicines, YZH was the most potent inhibitor of T-cell activation. In splenocyte proliferation assays, the inhibitory effect of YZH was dose-dependent, with a 50% inhibition concentration (IC50) of 1:3200-1:1600. Ten (10) purified compounds found in YZH were evaluated for their activity. Among them, ursolic acid (1-10 micromol), luteolin (1-10 micromol), baicalein (1-10 micromol), scopran (5-50 micromol), and crocin (5-50 micromol), exhibited dose-dependent inhibition. YZH also inhibited CD25, CD69, PD-1, and ICOS expression by stimulated mouse CD4+ T cells. In human PBMCs, YZH inhibited SEB-stimulated cytokine (interleukin [IL]-1, IL-2, IL-6, tumor necrosis factor[TNF]-alpha, interferon [IFN]-gamma) and chemokine (IP-10, MCP-1, MIP-1alpha and MIP-1beta) production in a dose-dependent manner. CONCLUSION: Our data show for the first time that YZH is a potent inhibitor of T-cell activation, and this property may be the major mechanism underlying the clinical efficacy of YZH. Our experimental results pave the way for identification of active component(s) and/or analysis of synergistic/additive effect of a YZH ingredient in future studies.

Animals↗
PubMed2002

Inhibitory activity of minor polyphenolic and nonpolyphenolic constituents of olive oil against in vitro low-density lipoprotein oxidation.

The minor polyphenolic and nonpolyphenolic constituents of olive oil were examined, in various doses, against copper ion-induced low-density lipoprotein (LDL) oxidation and were found, in optimal doses (final concentration, 10 microM or 20 microM), to have remarkable biological activity, contributing to that previously reported for the major phenolic compounds. The main phytosterols, beta-sitosterol, campesterol, and stigmasterol, were found to have 43.8%, 37.3%, and 33.4% LDL mean protection (MP) activity, respectively, while free cholesterol exhibited 43.2% MP. The triterpenoid derivative compounds, ursolic acid, uvaol, and oleanolic acid, had similar MP activities of 50.5%, 46.8%, and 46.0%, respectively. Tocopherol (Toc) isomers exhibited an increasing effect in the following order: alpha-Toc (33.6%) < beta-Toc (36.1%) < gamma-Toc (42.9%) < delta-Toc (46.0%). The flavonoid polyphenols, quercetin, luteolin, and rutin, exhibited the highest activities--46.8%, 49.5%, and 53.7% MP, respectively, comparable to the 49.0% MP activity found for oleuropein. These findings indicate the relative independence of LDL protection activity in regard to structural differences among the involved compounds. A relation to the Mediterranean diet is also demonstrated.

Antioxidants↗
PubMed1999

Protective effects of triterpene compounds against the cytotoxicity of cadmium in HepG2 cells.

The effects of triterpene compounds on cadmium toxicity were investigated in HepG2 cells. Ten triterpene compounds were examined, namely, betulin, soyasapogenol A, soyasapogenol B, ursolic acid, uvaol, oleanolic acid, friedelin, glycyrrhizin, 18alpha-glycyrrhetinic acid, and 18beta-glycyrrhetinic acid, and betulin, soyasapogenol A, and uvaol were found to reduce the toxicity of CdCl(2). In particular, betulin almost completely abolished the cytotoxicity of CdCl(2) at concentrations as low as 0. 1 microg/ml. The effects of betulin were particularly apparent when added to the culture medium before the addition of CdCl(2). Moreover, when HepG2 cells were incubated with betulin and then incubated in fresh betulin-free medium before the addition of CdCl(2), the toxic effects of cadmium were reduced. Betulin had no significant effect on the intracellular accumulation of cadmium, nor did it bind to cadmium, at least not in a test tube. When HepG2 cells were treated first with cycloheximide or actinomycin D, the subsequent protective effect of betulin against cadmium toxicity was significantly reduced, suggesting that betulin might protect cells against cadmium toxicity by inducing the synthesis of a certain protein or proteins. The synthesis of metallothionein, a protein that is known to reduce the toxicity of heavy metals, was not induced by betulin. However, using the differential display method, we confirmed that betulin promoted the expression of several genes. Our findings suggest that betulin might reduce cadmium toxicity by promoting the synthesis of certain proteins that protect cells against the toxic effects of cadmium.

Cadmium↗
PubMed2004

Suppression of the nuclear factor-kappaB activation pathway by spice-derived phytochemicals: reasoning for seasoning.

The activation of nuclear transcription factor kappaB has now been linked with a variety of inflammatory diseases, including cancer, atherosclerosis, myocardial infarction, diabetes, allergy, asthma, arthritis, Crohn's disease, multiple sclerosis, Alzheimer's disease, osteoporosis, psoriasis, septic shock, and AIDS. Extensive research in the last few years has shown that the pathway that activates this transcription factor can be interrupted by phytochemicals derived from spices such as turmeric (curcumin), red pepper (capsaicin), cloves (eugenol), ginger (gingerol), cumin, anise, and fennel (anethol), basil and rosemary (ursolic acid), garlic (diallyl sulfide, S-allylmercaptocysteine, ajoene), and pomegranate (ellagic acid). For the first time, therefore, research provides "reasoning for seasoning."

Biological Factors↗
PubMed2002

In vitro screening for antitumour activity of Clinopodium vulgare L. (Lamiaceae) extracts.

Aqueous extract of Clinopodium vulgare L. showed strong antitumour activity when tested in vitro on A2058 (human metastatic melanoma), HEp-2 (epidermoid carcinoma, larynx, human) and L5178Y (mouse lymphoma) cell lines-6 h after treatment disintegration of the nuclei and cell lysis started. Applied at a concentration of 80 microg/ml it reduced the cell survival to 1.0, 5.6 and 6.6%, respectively. The concentrations of aqueous extract inhibiting the growth of A2058, HEp-2 and L5178Y cells by 50% (IC50 values) were calculated to be 20, 10 and 17.8 microg/ml respectively. Two groups of active substances were detected: the first one, probably combining glycosides, influenced adhesion, while the second one caused massive cell vacuolisation. The chloroform extract, which contained ursolic acid and gentriacontan had also cytotoxic, however a little bit weaker effect. All changes observed were irreversible.

Animals↗
PubMed2005

Cytochrome P450 2D6 (CYP2D6) inhibitory constituents of Catharanthus roseus.

The MeOH-soluble fraction of the water extract of Catharanthus roseus from Indonesia, having shown potent inhibitory activity on the metabolism mediated by CYP2D6, was subjected to activity-guided isolation to yield two triterpenes, ursolic acid (1) and oleanolic acid (2), and three alkaloids, vindoline (3), ajmalicine (4), and serpentine (5). The isolated compounds were tested for their inhibitory activity on the metabolism mediated by CYP3A4 or CYP2D6 using [N-methyl-14C]erythromycin or [O-methyl-14C]dextromethorphan as a substrate, respectively. Ajmalicine (4) and serpentine (5) showed very potent inhibitory activity against CYP2D6 with IC50 values of 0.0023 and 3.51 microM, respectively. All isolated compounds showed weak or no inhibition against CYP3A4. On time-, concentration-, and NADPH-dependent assay, serpentine (5) appear to be the mechanism-based inhibitor for CYP2D6 enzyme in which the inhibition was irreversible and driven by catalytic process. K(I) and k(inact) values for serpentine (5) were 0.148 microM and 0.090 min-1, respectively. On the other hand, ajmalicine (4) showed no time-dependent inhibition or reversible inhibition, and thus appear to be not mechanism-based inhibitor.

Catharanthus↗
PubMed1991

Biologically active constituents of Melaleuca leucadendron: inhibitors of induced histamine release from rat mast cells.

Chloroform and methanol extracts of the fruits of Melaleuca leucadendron strongly inhibited histamine release from rat mast cells induced by compound 48/80 or concanavalin A. Ursolic acid, a triterpene, was the most active compound contained in the chloroform extract and two stilbenes, piceatannol and oxyresveratrol, were isolated as active compounds from the methanol extract. Several other stilbenes and related compounds were examined to obtain information on the structure activity relationships of stilbenes.

Animals↗
PubMed1993

Two new 2-arylbenzofuran derivatives from hypoglycemic activity-bearing fractions of Morus insignis.

Ethyl acetate- and n-butanol-soluble fractions of the leaves of Morus insignis showed a significant hypoglycemic activity on streptozotocin (STZ)-induced hyperglycemic rats. From these hypoglycemic activity-showing fractions, two new compounds, mulberrofuran U (2) and moracin M-3-O-beta-D-glucopyranoside (3) were isolated, along with six known compounds [beta-sitosterol, beta-sitosterol-3-O-beta-glucopyranoside, ursolic acid, moracin M (1), kaempferol-3-O-beta-glucopyranoside and quercetin-3-O-beta-glucopyranoside] and the structures of the new compounds were determined by spectroscopic and chemical methods.

Animals↗
PubMed2001

Latifolosides I and J, two new triterpenoid saponins from the bark of Ilex latifolia.

Two new triterpenoid saponins, latifoloside I (1), 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl 3beta,21alpha,28-trihydroxy-urs-12-ene 21-O-beta-D-glucopyranoside; latifoloside J (2), 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl-3beta,21alpha-dihydroxy-ursolic acid 21-O-beta-D-glucopyranoside, along with two known compounds, latifoloside C (3) and latifoloside E (4), were isolated from the bark of Ilex latifolia THUNB. Structure assignments were established on the basis of spectroscopic data and chemical evidence.

Carbohydrate Conformation↗
PubMed2004

Search for constituents with neurotrophic factor-potentiating activity from the medicinal plants of paraguay and Thailand.

20 medicinal plants of Paraguay and 3 medicinal plants of Thailand were examined on nerve growth factor (NGF)-potentiating activities in PC12D cells. The trail results demonstrated that the methanol extracts of four plants, Verbena littoralis, Scoparia dulcis, Artemisia absinthium and Garcinia xanthochymus, markedly enhanced the neurite outgrowth induced by NGF from PC12D cells. Furthermore, utilizing the bioactivity-guided separation we successfully isolated 32, 4 and 5 constituents from V. littoralis, S. dulcis and G. xanthochymus, respectively, including nine iridoid and iridoid glucosides (1-9), two dihydrochalcone dimers (10 and 11), two flavonoids and three flavonoid glycosides (12-16), two sterols (17 and 18), ten triterpenoids (19-28), five xanthones (29-33), one naphthoquinone (34), one benzenepropanamide (35), four phenylethanoid glycosides (36-39) and two other compounds (40 and 41). Among which, 15 compounds (1-4, 10-11, 14-18, 29-31 and 34) were new natural products. The results of pharmacological trails verified that littoralisone (1), gelsemiol (5), 7a-hydroxysemperoside aglucone (6), verbenachalcone (10), littorachalcone (11), stigmast-5-ene 3beta,7alpha,22alpha-triol (18), ursolic acid (19), 3beta-hydroxyurs-11-en-28,13beta-olide (24), oleanolic acid (25), 2alpha,3beta-dihydroxyolean-12-en-28-oic acid (26), 1,4,5,6-tetrahydroxy-7,8-di(3-methylbut-2-enyl)xanthone (29), 1,2,6-trihydroxy-5-methoxy-7-(3-methylbut-2-enyl)xanthone (30), 1,3,5,6-tetrahydroxy-4,7,8-tri(3-methyl-2-butenyl)xanthone (31), 12b-hydroxy-des-D-garcigerrin A (32), garciniaxanthone E (33) and (4R)-4,9-dihydroxy-8-methoxy-alpha-lapachone (34) elicited marked enhancement of NGF-mediated neurite outgrowth in PC12D cells. These substances may contribute to the basic study and the medicinal development for the neurodegenerative disorder.

Animals↗
PubMed1989

[Studies on the constituents of Leucoseptrum stellipillum].

Flavonoids, triterpenoids, and steroids were isolated from the leaves of Leucoseptrum stellipillum (MIQ). Kitamura et Murata and identified as apigenin, luteolin, chrysoeriol, ursolic acid, pomolic acid, tormentic acid, beta-sitosterol, and beta-sitosterol glucoside by comparison of their spectral data with those of authentic specimens. Among these compounds, the triterpenoids showed significant antibacterial activities against Streptococcus mutans.

Bacteria↗
PubMedDate not supplied

Major constituents of the foliar epicuticular waxes of species from the Caatinga and Cerrado.

The epicuticular waxes of leaves of four species (Aspidosperma pyrifolium, Capparis yco, Maytenus rigida and Ziziphus joazeiro) from the Caatinga, (a semi-arid ecosystem of Northeast Brazil) and four species (Aristolochia esperanzae, Didymopanax vinosum, Strychnos pseudoquina and Tocoyena formosa) from the Cerrado, (a savanna ecosystem covering one third of the Brazilian territory), were analyzed. Six species contained a high content (above 60 microg x cm(-2)) of wax, four of them from the Caatinga. Triterpenoids and n-alkanes were the most frequent and abundant constituents found in the species from both habitats. The distribution of n-alkanes predominated by homologues with 27, 29, 31 and 33 carbon atoms, displayed no consistent differences between species from the two habitats. Lupeol, beta-amyrin, epifriedelinol and ursolic acid were the triterpenoids found. Triterpenoids clearly predominate over alkanes in the waxes from the Cerrado species. The waxes of two evergreen species from the Caatinga yielded n-alkanes as predominant constituents. A comparison of foliar epicuticular waxes of native plants from ecosystems with different hydric constraints is discussed.

Alcohols↗
PubMed1998

[Isolation and identification of Triterpenoid compounds in the fruits of Chaenomeles lagenaria (Loisel.) Koidz].

OBJECTIVE: The fruit of Chaenomeles lagenaria is a commonly used drug in Chinese traditional medicine. It is especially effective on rheumatism. The current work is to find out the chemical basis of its pharmacological activity. METHOD: All compounds were extracted with organic solvents and separated by silica gel column or thin layer chromatography, and then purified by recrystalization. The structures were elucidated on the basis of chemical reactions and spectral data analysis. RESULT: In addition to the compounds reported in our previous work, three triterpenoid compounds were separated and identified as 3-O-acetyl ursolic acid, 3-O-acetyl pomolic acid and betulinic acid respectively. CONCLUSION: It is obvious that triterpenoid compounds are dominant among the chemical constituents of C. lagenaria. But it is still to be clarified whether they are the chemical basis of the drug's pharmacological activity.

Drugs, Chinese Herbal↗