[The research on the chemical components of Schizonepeta tenuifolia Briq].
Eicosane acid, beta-sitosterol, oleanolic acid, ursolic acid and daucosterol have been firstly isolated and identified from Schizonepeta tenuifolia Briq..
Eicosanoic Acids↗
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Antifeedant activity of some pentacyclic triterpene acids and their fatty acid ester analogues.
The 3-O-fatty acid ester derivatives (C(12)-C(18)) of two pentacyclic triterpenic acids, ursolic acid and oleanolic acid, were synthesized under mild esterification conditions in excellent yields (80-85%) and screened for their antifeedant activity, together with the parent acids, against the agricultural pest tobacco caterpillar larvae (Spodoptera litura F) in a no-choice laboratory study. The Urs-12-ene-28-carboxy-3beta-octadecanoate and olean-12-ene-28-carboxy-3beta-hexadecanoate were found to exhibit exceptionally potent antifeedant activities at 50 microg/cm(2) concentration, even after 48 h.
Animals↗
[Changes in level of organic acids in fructus crataegi after processing].
OBJECTIVE: To compare and analyze the organic acids level in fruit of Crataegus pinnatifida var. major before and after processing. METHOD: The amount of total organic acids and individual citric acid, malate acid, ursolic acid and oleanolic acid in fruit of C. pinnatifida var. major before and after processing were determined by pH titration and HPLC analysis. RESULT: Good linear relationship between peakarea and amount was noted for 0.28-9.02 microg of malate acid, with a correlation coefficient of 0.9998. Regression equation was Y = 2344.7 + 49309.6 X. Good linear relationships between the logarithm of peak area and amount were noted for 0.348-1.74 microg of usolic acid and 0.498-2.48 microg of oleanolic acid, with a correlation coefficient of 0.9998 in each case. Regression equations were Y = 1.3628 X + 5.9508 and Y = 1.4447 X + 5.8236, respectively. CONCLUSION: The lipid-soluble organic acids mostly remain whereas only about 70% of the water-soluble acids remain after processing in fruit of C. pinnatifida var. major.
Citric Acid↗
[Chemical studies on Campylotropis hirtella (Franch. Schindl.)].
From the roots of Campylotropis hirtella 6 compounds were isolated. Based on the extensive spectrae analysis their chemical structures were identified as beta-sitosterol, oleanolic acid, ursolic acid, euscaphic acid, tomentic acid and rosamultin.
Drugs, Chinese Herbal↗
[Studies on chemical constituents in the roots of Rabdosia japonica (Burm.f). Hara var. glaucocalyx (Maxin) Hara].
OBJECTIVE: To isolate and elucidate the chemical constituents in the roots of Rabdosia japonica. METHOD: The constituents were extracted by ether and isolated by chromatography on silica gel and ODS. The structures were determined by IR, H NMR, 13C NMR and MS spectra respectively. RESULT: Four compounds were elucidated as glaucocalgxin A, oleanolic acid, ursolic acid and daucosterol. CONCLUSION: Oleanolic acid and daucosterol were isolated from this plant for the first time.
Diterpenes, Kaurane↗
[Lipid chemical constituents of Salvia sochifolia C. Y. Wu].
OBJECTIVE: To study the lipid chemical constituents of Salvia sochifolia growing in Yunnan province. METHOD: Chromatographic techniques were used to isolate the compounds and the structures were identified by spectral analysis. RESULT: Five compounds were isolated from the plant and identified as 2 alpha, 3 alpha-dihydroxyurs-12-en-28-oic acid, 2 alpha, 3 alpha, 24-trihydroxyurs-12-en-28-oic acid, ursolic acid, daucosterol and beta-sitosterol. CONCLUSION: These compounds were isolated from the plant for the first time.
Plant Roots↗
Apoptosis inducing activity of viscin, a lipophilic extract from Viscum album L.
Detection of antiproliferative activity and bioactivity-guided fractionation of viscin, a lipophilic extract from Viscum album L., led to the isolation of betulinic acid, oleanolic acid and ursolic acid as active components. Viscin, betulinic acid, oleanolic acid and ursolic acid inhibited growth and induced apoptotic cell death in Molt4, K562 and U937 leukaemia cells. The growth inhibitory effect of viscin was more pronounced in Molt4 and U937 cells (IC50 (concentration that inhibited cell proliferation by 50%): 118 +/- 24 and 138 +/- 24 microg mL(-1)) than in K562 cells (IC50: 252 +/- 37 microg mL(-1)). Oleanolic acid was the least effective in all cell lines (7.5-45.5% inhibition at 10 microg mL(-1)) and ursolic acid the most active in Molt4 and U937 cells (81.8 and 97.8% inhibition, respectively, at 5 microg mL(-1)). A dose-dependent loss of membrane phospholipid asymmetry associated with apoptosis was induced in all cell lines as shown in flow cytometry by the externalization of phosphatidylserine and morphological changes in cell size and granularity. There were differences in individual cell lines' response towards the apoptosis-inducing effect of viscin, betulinic acid, oleanolic acid and ursolic acid. The triterpenoids beta-amyrin, beta-amyrinacetate, lupeol, lupeolacetate, beta-sitosterol and stigmasterol, and the fatty acids oleic acid, linoleic acid, palmitic acid and stearic acid were also present in the lipophilic extract.
Antineoplastic Agents, Phytogenic↗
Biological activity of some naturally occurring resins, gums and pigments against in vitro LDL oxidation.
Naturally occurring gums and resins with beneficial pharmaceutical and nutraceutical properties were tested for their possible protective effect against copper-induced LDL oxidation in vitro. Chiosmastic gum (CMG) (Pistacia lentiscus var. Chia resin) was the most effective in protecting human LDL from oxidation. The minimum and maximum doses for the saturation phenomena of inhibition of LDL oxidation were 2.5 mg and 50 mg CMG (75.3% and 99.9%, respectively). The methanol/water extract of CMG was the most effective compared with other solvent combinations. CMG when fractionated in order to determine a structure-activity relationship showed that the total mastic essential oil, collofonium-like residue and acidic fractions of CMG exhibited a high protective activity ranging from 65.0% to 77.8%. The other natural gums and resins (CMG resin 'liquid collection', P. terebinthus var. Chia resin, dammar resin, acacia gum, tragacanth gum, storax gum) also tested as above, showed 27.0%-78.8% of the maximum LDL protection. The other naturally occurring substances, i.e. triterpenes (amyrin, oleanolic acid, ursolic acid, lupeol, 18-a-glycyrrhetinic acid) and hydroxynaphthoquinones (naphthazarin, shikonin and alkannin) showed 53.5%-78.8% and 27.0%-64.1% LDL protective activity, respectively. The combination effects (68.7%-76.2% LDL protection) of ursolic-, oleanolic- and ursodeoxycholic- acids were almost equal to the effect (75.3%) of the CMG extract in comparable doses.
Cholesterol, LDL↗
The cytotoxic principles of Solanum incanum.
In continuation of work on Solanum incanum a new steroidal alkaloid glycoside has been isolated from the fresh berries, which is named incanumine, and characterized as O(3)-[beta-D-xylopyranosyl-(1----3glu)-[beta-D-xylopyranosyl-(1--- -4rha)- alpha-L-rhamnopyranosyl-(1----4)]-beta-D-glucopyranosyl)-solasodine++ +. Solamargine, solasodine, ursolic acid, and ursolic acid derivatives (3-O-palmitoyl ursolic acid, 3-O-crotonyl ursolic acid, 3-O-propionyl ursolic acid) exhibited significant cytotoxic effects against human PLC/PRF/5 cells in vitro. Esterification of ursolic acid with aliphatic acids clearly enhanced the cytotoxic effects against human PLC/PRF/5 cells in vitro.
Animals↗
Triterpenoids from the flower of Campsis grandiflora K. Schum. as human acyl-CoA: cholesterol acyltransferase inhibitors.
The flower of Campsis grandiflora K. Schum. was extracted with 80% aqueous MeOH, and the concentrated extract was partitioned with EtOAc, n-BuOH and H2O. From the EtOAc fraction, seven triterpenoids were isolated through the repeated silica gel, ODS column chromatographies and preparative HPLC. From the result of physico-chemical data including NMR, MS and IR, the chemical structures of the compounds were determined as 3beta-hydroxyolean-12-en-28-oic acid (oleanolic acid, 1), 3beta-hydroxyurs-12-en-28-oic acid (ursolic acid, 2), 3beta-hydroxyurs-12-en-28-al (ursolic aldehyde, 3), 2alpha,3beta-dihydroxyolean-12-en-28-oic acid (maslinic acid, 4), 2alpha,3beta-dihydroxyurs-12-en-28-oic acid (corosolic acid, 5), 3beta,23-dihydroxyurs-12-en-28-oic acid (23-hydroxyursolic acid, 6) and 2alpha,3beta,23-trihydroxyolean-12-en-28-oic acid (arjunolic acid, 7). These teriterpenoids were isolated for the first time from this plant. Also, compounds 4, 5, 6, and 7 revealed relatively high hACAT-1 inhibitory activity with the value of 46.2+/-1.1, 46.7+/-0.9, 41.5+/-1.3 and 60.8+/-1.1% at the concentration of 100 microg/mL, respectively.
Bignoniaceae↗
Antihypertensive, antiatherosclerotic and antioxidant activity of triterpenoids isolated from Olea europaea, subspecies africana leaves.
For the first time a biossay-directed study of triterpenoids isolated from the leaves of Olea europaea from Greece, from wild African olive and from a cultivar of O. europaea grown in Cape Town was reported. The experiment was undertaken since our preliminary analyses showed that the African wild olive leave is rich in triterpenoids and contain only traces of the glycoside oleuropein, which is typical for the European olive leaves. The isolate of the African wild olive leaves (AO) used in the experiments was found to contain 0.27% 1:1 mixture of oleanolic acid and ursolic acid, named oleuafricein. The isolate of Greek olive leaves (GO) was found to contain 0.71% oleanolic acid, and the Cape Town cultivar (CT) contained 2.47% oleanolic acid. No ursolic acid was found in either GO or CT. The antihypertensive, diuretic, antiatherosclerotic, antioxidant and hypoglycemic effects of authentic oleanolic and ursolic acid and the three isolates (GO, AO and CT) were studied on Dahl salt-sensitive (DSS), insulin-resistant rat genetic model of hypertension. All three isolates, in a dose 60 mg/kg b.w. for 6 weeks treatment, prevented the development of severe hypertension and atherosclerosis and improved the insulin resistance of the experimental animals. GO, OA and CT isolates could provide an effective and cheap treatment of this particular, most common type of salt-sensitive hypertension in the African population.
Animals↗
Proposed active constituents of Dipladenia martiana.
3Beta-O-beta-D-glucopyranosylsitosterol, pomolic acid, ursolic acid, epicatechin, kaempferol, kaempferol-3-O-beta-D-glucopyranoside (astragalin), quercetin-7-O-beta-D-glucopyranoside, quercetin-7-O-beta-D-galactopyranoside and quebrachitol were isolated by chromatographic fractionation of the methanol extract from the aerial parts of Dipladenia martiana (Apocynaceae). The hexane extract yielded lupeol and sitostenone. These compounds are likely to be responsible for the therapeutic effects.
Apocynaceae↗
Selective inhibition of cyclic AMP-dependent protein kinase by amphiphilic triterpenoids and related compounds.
A set of plant- and animal-derived amphiphilic triterpenoids have been shown to be potent and selective inhibitors of the catalytic subunit of rat liver cyclic AMP-dependent protein kinase (cAK). Thus plant-derived 18 alpha- and 18 beta-glycyrrhetinic acid, ursolic acid, oleanolic acid and betulin and animal-derived lithocholic acid, 5-cholenic acid and lithocholic acid methyl ester are inhibitors of cAK with IC50 values (concentrations for 50% inhibition) in the range 4-20 microM. These compounds are ineffective or relatively ineffective as inhibitors of various other eukaryote signal-regulated protein kinases namely wheat embryo Ca(2+)-dependent protein kinase (CDPK), avian calmodulin-dependent myosin light chain kinase (MLCK) and rat brain Ca(2+)- and phospholipid-dependent protein kinase C (PKC). These naturally occurring triterpenoids have a common structural motif involving polar residues located at opposite ends of an otherwise non-polar triterpenoid nucleus. A variety of triterpenoids not possessing this structural motif are relatively inactive as inhibitors of cAK and of CDPK, PKC and MLCK. The terpenoid amphiphilic compound crocetin is also a potent and relatively selective inhibitor of cAK (IC50 value for cAK 3.0 microM). 12-Hydroxystearic acid and 10-hydroxydecanoic acid do not inhibit CDPK, PKC or MLCK but are selective inhibitors of cAK (IC50 values 127 and 138 microM, respectively), consistent with a simple model for amphiphile inhibition of cAK involving two polar groups separated by a non-polar region. However, laurylgallate and 15-pentadecanolide are also potent and selective inhibitors of cAK (IC50 values 1.5 and 20 microM, respectively) although the structures of both of these compounds involve a large non-polar portion associated with only one polar region. Crocetin and the plant-derived amphiphilic triterpenoids described here are the most potent non-aromatic plant-derived inhibitors of cAK yet found.
Amino Acid Sequence↗
Role of chemopreventive agents in cancer therapy.
Tumorigenesis or carcinogenesis is a multi-step process that is induced primarily by carcinogens leading to the development of cancer. Extensive research in the last few years has revealed that regular consumption of certain fruits and vegetables can reduce the risk of acquiring specific cancers. Phytochemicals derived from such fruits and vegetables, referred to as chemopreventive agents include genistein, resveratrol, diallyl sulfide, S-allyl cysteine, allicin, lycopene, capsaicin, curcumin, 6-gingerol, ellagic acid, ursolic acid, silymarin, anethol, catechins and eugenol. Because these agents have been shown to suppress cancer cell proliferation, inhibit growth factor signaling pathways, induce apoptosis, inhibit NF-kappaB, AP-1 and JAK-STAT activation pathways, inhibit angiogenesis, suppress the expression of anti-apoptotic proteins, inhibit cyclooxygenase-2, they may have untapped therapeutic value. These chemopreventive agents also have very recently been found to reverse chemoresistance and radioresistance in patients undergoing cancer treatment. Thus, these chemopreventive agents have potential to be used as adjuncts to current cancer therapies.
Anticarcinogenic Agents↗
Simultaneous determination of key bioactive components in Hedyotis diffusa by capillary electrophoresis.
A capillary zone electrophoresis (CZE) method based on systematic one-variable-at-a time approach was developed for the analysis of four important bioactive components (geniposidic acid, ursolic acid, quercetin and p-coumaric acid) in the extract of Hedyotis diffusa (HD). Separations were carried out in a fused-silica capillary tube with peak detection at 214 nm. Good separation was achieved using a 20 mM borate buffer containing 5% acetonitrile as organic modifier and pH adjusted to 10.0. Operating voltage was 15 kV and temperature was maintained at 25 degrees C while hydrodynamic injection was 5s. A good linearity, with correlation coefficients in the ranges of 0.997-0.999 was obtained in the calibration curves of each standard. Relative standard deviation (R.S.D.) of migration time was between 0.32 and 0.70% and deviation of corrected peak area was between 8.84 and 11.99%. These results indicate that this method could be used for rapid and simultaneous analysis of the bioactive components in HD and other herbal products.
Buffers↗
Abietane diterpenoids and triterpenoic acids from Salvia cilicica and their antileishmanial activities.
Bioguided-fractionation of an acetone extract of the roots of Salvia cilicica (Lamiaceae) led to isolation of two new diterpenes, 7-hydroxy-12-methoxy-20-nor-abieta-1,5(10),7,9,12-pentaen-6,14-dione and abieta-8,12-dien-11,14-dione (12-deoxy-royleanone), together with oleanolic acid, ursolic acid, ferruginol, inuroyoleanol and cryptanol. Their structures were determined spectroscopically, which included HREIMS and 2D NMR spectroscopic analysis. The new abietane derivatives showed appreciable in vitro antileishmanial activity against intracellular amastigote forms of both Leishmania donovani (IC(50) values of 170 and 120 nM, respectively) and Leishmania major (IC(50) values of 290 and 180 nM, respectively). The triterpenoic acids were found to be potently active against amastigote (IC(50) values of 7-120 nM) and moderately active against promastigote stages (IC(50) values of 51-137 nM) of the two Leishmania species.
Abietanes↗
A new secoiridoid glycoside from Lonicera angustifolia.
A new secoiridoid glycoside, 6'-O-beta-apiofuranosylsweroside (1), together with the known compounds sweroside, loganin, beta-sitosterol, oleanolic acid, ursolic acid and methyl-4-hydroxy benzoate have been identified from the leaves of Lonicera angustifolia. The structure of the new compound has been elucidated on the basis of spectroscopic and chemical evidence.
Glucosides↗
Sessiline, a new nitrogenous compound from the fruits of Acanthopanax sessiliflorus.
A new nitrogenous compound, named sessiline [5-(5-oxo-pyrrolidin-2-yloxymethyl)-furan-2-carbaldehyde (1)], was isolated from the fruits of Acanthopanax sessiliflorus, together with (-)-sesamin, scoparone, protocatechuic acid, ursolic acid, hyperin and 5-hydroxymethylfurfural by CC. The structures of these compounds were elucidated by physico-chemical and spectral analysis.
Aldehydes↗