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PubMed2005

Radical-scavenging activities of new hydroxylated ursane triterpenes from cv. Annurca apples.

Two new ursolic acid triterpene derivatives, compounds 2 and 3, have been isolated from cv. Annurca apple fruit, a high-quality apple variety widely cultivated in southern Italy, together with the known 2-oxopomolic acid (1). The new compounds were identified by means of different spectroscopic techniques as 3-epi-2-oxopomolic acid (= (3alpha)-3,19-dihydroxy-2-oxours-12-en-28-oic acid; 2) and (1alpha)-1-hydroxy-3-oxours-12-en-28-oic acid (3). Compounds 1-3 were tested for their radical-scavenging activities with the aid of a 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay (Fig. 2). All three constituents showed activities similar to that of the reference antioxidant alpha-tocopherol (vitamin E).

Free Radical Scavengers↗
PubMed2005

A new xanthone glycoside and antioxidant constituents from the rhizomes of Swertia speciosa.

From the rhizomes of Swertia speciosa, a traditional medicinal plant from the Himalayan region of Uttaranchal (North India), a new constituent, 6-hydroxy-3,5-dimethoxy-1-[(6-O-beta-D-xylopyranosyl-beta-D-glucopyranosyl)oxy]-9H-xanthen-9-one (8), was isolated, together with nine known compounds. Their structures were elucidated on the basis of chemical, physical, and spectroscopic evidence. Both the acetone and MeOH extracts, as well as the known constituents ursolic acid (5) and 1,5,8-trihydroxy-3-methoxy-9H-xanthen-9-one (6) exhibited potent antioxidant activities in different biological assays (Table 2).

Antioxidants↗
PubMed2004

Triterpenoids from Salvia wagneriana.

From the exudate of Salvia wagneriana Polak, beside the known ursolic acid, two pentaoxygenated triterpenoids were isolated. Their structures were determined as 3-oxo-11alpha,19beta,20,22beta-tetrahydroxy-lupane (1) and 3beta,11alpha,19beta,20,22beta-pentahydroxy-lupane (2) using a combination of one- and two-dimensional NMR techniques.

Chromatography, Thin Layer↗
PubMed1979

Chemical constituents of Echites hirsuta (Apocynaceae).

A phytochemical investigation of an ethanolic extract of the whole plant of Echites hirsuta (Apocynaceae) resulted in the isolation and identification of the flavonoids naringenin, aromadendrin (dihydrokaempferol), and kaempferol; the coumarin fraxetin; the triterpene ursolic acid; and the sterol glycoside sitosteryl glucoside.

Chromatography, Gel↗
PubMed2004

Antifungal constituents of Clytostoma ramentaceum and Mansoa hirsuta.

Ethanol extracts of Clytostoma ramentaceum Bur. & K. Schum and Mansoa hirsuta DC. (Bignoniaceae) inhibited the growth of standardized cultures of Aspergillus niger and Fusarium oxysporum, at concentrations of 400 microg and 500 microg, in bioautographic assays. The activity-guided fractionation of C. ramentaceum extract afforded ursolic acid and 2-(3',4'-dihydroxyphenyl) ethanol, both active against the test fungi (100 microg). These compounds are reported for the first time in C. ramentaceum and were not detected in M. hirsuta extract, according to HPLC analysis. The bioguided study of M. hirsuta resulted in five active fractions (100 to 200 microg), whose GC-MS analysis allowed us to identify 11 compounds, mostly alkanols and alkanodiols, that may be regarded as the antifungal constituents of M. hirsuta.

Antifungal Agents↗
PubMed2005

A rapid screening method for detecting active compounds against erythromycin-resistant bacterial strains of Finnish origin.

A rapid and simple microdilution technique on 96-well microplate based on turbidimetry was optimized and validated for screening of antimicrobial activity against erythromycin-resistant bacterial strains of Streptococcus pyogenes and Staphylococcus simulans isolated from Finnish patients. Using S. pyogenes ATCC 12351 as reference strain the developed method was evaluated by reproducibility measurements and using parameters typically employed for screening methods, i.e. signal-to-background, signal-to-noise and a screening-window coefficient, the Z' factor. The method was further used for screening a group of natural compounds and their synthetic derivatives against resistant bacterial strains. Of these, octyl and dodecyl gallates, and usnic and ursolic acids were the most active. The described method is a rapid, homogeneous, cost-effective and easy-to-perform system for screening of new potential antimicrobial agents in drug discovery.

Anti-Bacterial Agents↗
PubMed2005

Inhibitory effect on TNF-alpha-induced IL-8 production in the HT29 cell of constituents from the leaf and stem of Weigela subsessilis.

Twelve compounds were isolated from the MeOH extract of the leaf and stem of the Korean endemic plant Weigela subsessilis L. H. Bailey. Their chemical structures were elucidated on the basis of physicochemical and spectroscopic data and by comparison with those of published literatures. These compounds were identified as three sterols, beta-sitosterol acetate (2), betasitosterol (3), daucosterol (11), eight triterpenoids, squalene (1), ursolic acid (4), ilekudinol A (5), corosolic acid (6), ilekudinol B (7), esculentic acid (8), pomolic acid (9), asiatic acid (10), and one iridoid glycoside, alboside I (12). This is the first report pertaining to the isolation of these compounds from Weigela subsessilis L. H. Bailey. In addition, three compounds 7, 9, and 12 were found to display a strong inhibitory effect on the production of IL-8 in the HT29 cells stimulated by TNF-alpha.

Caprifoliaceae↗
PubMed2002

Brine shrimp lethality of the compounds from Phryma leptostachya L.

Brine shrimp assay-guided fractionation and isolation of the EtOAc soluble fraction of Phryma leptostachya L. (Phrymacaceae) gave two active compounds, phrymarolin II (1) and ursolic acid (2), which were identified by physicochemical and spectroscopic methods. Compound 1 exhibited potent lethality with LD50 value of 0.0013 microg/ml, whereas 2 showed moderate lethality with LD50 value of 27.0 microg/ml against brine shrimp. The cytotoxic activities of 1 and 2 were also evaluated against one murine and five human cancer cell lines employing the sulforhodamin B (SRB) method. Compound 2 exhibited cytotoxic activity against L1210 and SK-MEL-2 cells with ED50 values of 3.70 and 9.27 mg/ml, respectively, whereas 1 was devoid of any cytotoxic activity against all cancer cells tested.

Animals↗
PubMed2006

Bioactive principles in the bark of Pilidiostigma tropicum.

The crude dichloromethane bark extract of Pilidiostigma tropicum (Myrtaceae) from north Queensland, Australia, shows antibacterial and cytotoxic activity. Bioactivity-directed separation led to the isolation of rhodomyrtoxin B and ursolic acid-3-p-coumarate as the biologically active materials. The structures of these compounds were elucidated on the basis of spectral analysis. The intercalation interaction of rhodomyrtoxin B with DNA was investigated using molecular mechanics and ab initio molecular-orbital techniques. A favorable pi-pi interaction between rhodomyrtoxin B and the cytosine-guanine base pair is predicted, but the orientation of the interaction cannot be predicted based on frontier molecular orbitals.

Amsacrine↗
PubMed1996

Matesaponin 5, a highly polar saponin from Ilex paraguariensis.

The structure of matesaponin 5, a novel saponin isolated from the leaves of the Ilex paraguariensis, was established as ursolic acid-3-0-{beta-D-glucopyranosyl-(1->3)-[alpha-L-rhamnopyranosyl-(1->2)]-alpha-L- arabino pyranosyl}-(28->1)-beta-D-glucopyranosyl-(1->4)-beta-D-glucopyranosyl-(1 ->6)-beta-D-glucopyranosyl] ester.

Carbohydrate Conformation↗
PubMed2004

New lupane triterpenoids from Solidago canadensis that inhibit the lyase activity of DNA polymerase beta.

Bioassay-directed fractionation of a methyl ethyl ketone extract of Solidago canadensis L. (Asteraceae), using an assay to detect the lyase activity of DNA polymerase beta, resulted in the isolation of the four new lupane triterpenoids 1-4 and the seven known compounds lupeol, lupeyl acetate, ursolic acid, cycloartenol, cycloartenyl palmitate, alpha-amyrin acetate, and stigmasterol. The structures of the new compounds were established as 3beta-(3R-acetoxyhexadecanoyloxy)-lup-20(29)-ene (1), 3beta-(3-ketohexadecanoyloxy)-lup-20(29)-ene (2), 3beta-(3R-acetoxyhexadecanoyloxy)-29-nor-lupan-20-one (3), and 3beta-(3-hetohexadecanoyloxy)-29-nor-lupan-20-one (4), respectively, on the basis of extensive 1D and 2D NMR spectroscopic interpretation and chemical modification studies. All 11 compounds were inhibitory to the lyase activity of DNA polymerase beta.

DNA Polymerase beta↗
PubMed2004

Phytochemical and antiinflammatory studies on Terminalia catappa.

The antiinflammatory activity of Terminalia catappa leaves ethanolic extract was studied using 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced ear edema in acute and chronic models. A bioassay-oriented fractionation procedure showed that the activity concentrates in the chloroform fraction. Ursolic acid (1) and 2alpha,3beta,23-trihydroxyurs-12-en-28-oic acid (2), isolated from the chloroform fraction, exhibited strong antiinflammatory activities. The results suggest that the triterpenic acids 1 and 2 are responsible for the antiinflammatory activity of T. catappa leaves.

Acute Disease↗
PubMed2005

Bioactivity guided isolation of antimicrobial compounds from Lythrum salicaria.

Lythrum salicaria extracts showed activity against the phytopathogenic fungus Cladosporium cucumerinum and activity against the bacteria Staphylococcus aureus, Proteus mirabilis and Microccocus luteus. Bioautography on thin-layer chromatograms was used to isolate the two antifungal triterpenoids oleanolic and ursolic acid. The hexahydroxydiphenoyl ester vescalagin was isolated as active principle of the antibacterial activity. Furthermore, the flavon-C-glucosides vitexin, isovitexin, orientin and isoorientin were isolated.

Anti-Bacterial Agents↗
PubMed2006

alpha-Glucosidase inhibitory activity of the methanolic extract from Tournefortia hartwegiana: an anti-hyperglycemic agent.

Tournefortia hartwegiana is a Mexican medicinal plant that is used for the treatment of diabetes, diarrhea and kidney pain. In a previous investigation, the methanolic extract of Tournefortia hartwegiana (METh) showed significant hypoglycemic and anti-diabetic properties on normoglycemic and alloxanized rats. In this context, the purpose of the present study was to establish one of the possible modes of action of METh to induce anti-diabetic activity. METh (310mg/kg) effect on alpha-glucosidase activity was investigated. METh intragastric administration was conducted to determine oral glucose tolerance test (OGTT), using different substrates: glucose, sucrose and maltose. The increase in plasma glucose level was significantly suppressed (P<0.05) by the extract after substrates administration. On the other hand, METh inhibited alpha-glucosidase activity in vitro, in a concentration-dependent manner (IC(50) of 3.16mg/mL). These results suggest that METh might exert its anti-diabetic effect by suppressing carbohydrate absorption from intestine, and thereby reducing the post-prandial increase of blood glucose. On the other hand, the bio-guided fractionation of this extract led to the isolation of: beta-sitosterol (1), stigmasterol (2), lupeol (3), ursolic acid (4), oleanolic acid (5), saccharose (6) and myo-inositol (7), using various chromatographic techniques.

Animals↗
PubMed2006

Lipid peroxidation, cyclooxygenase enzyme and tumor cell proliferation inhibitory compounds in Cornus kousa fruits.

The genus Cornus is well known for its medicinal properties. Bioassay-guided isolation and characterization of C. kousa fruits afforded kaempferol 3-O-rhamnoside (1), myricetin 3-O-rhamnoside (2), kaempferol 3-O-glucoside (3), cornin (4) and stenophyllin (5) in addition to ursolic acid and beta-sitosterol. These compounds are isolated for the first time from C. kousa. Compounds 1-5 inhibited Fe(2+) catalyzed lipid peroxidation by 63%, 57%, 61%, 53%, and 51%, at 23, 22, 23, 129, and 108 microM, respectively. Similarly, they inhibited COX-1 and -2 enzymes activities by 24% and 47%, 40% and 37%, 20% and 37%, 52% and 63%, and 48% and 55% respectively, at 231, 215, 226, 258, and 217 microM, respectively. At 129 microM, compound 4 displayed growth inhibition of HCT-116 (colon), MCF-7 (breast), NCI-H460 (lung), SF-268 (central nervous system CNS), and AGS (stomach) human tumor cell lines by 31%, 29%, 40%, 9%, and 28%, respectively. Similarly, compound 5 inhibited the growth of colon, breast, lung, CNS, and stomach tumor cell lines by 0%, 27%, 35%, 16%, and 27%, respectively, at 108 microM.

Antineoplastic Agents, Phytogenic↗
PubMed2005

Cladocalol, a pentacyclic 28-nor-triterpene from Eucalyptus cladocalyx with cytotoxic activity.

A formylated triterpene named cladocalol has been isolated from the leaves of Eucalyptus cladocalyx, together with ursulolactone acetate, ursolic acid, 3 beta-acetate-12,20(29)-lupadien-28-oic acid, beta-sitosterol and the known flavonoid eucalyptine. Their structures were mainly established by extensive NMR studies (1H NMR, 13C NMR, DEPT, 1H-1H COSY, HSQC, HMBC) and mass spectroscopy as well as by X-ray crystallographic analysis. In this paper, we report on the cytotoxic effect induced by cladocalol and its derivatives on the myeloid leukemia cell line HL-60.

Antineoplastic Agents, Phytogenic↗
PubMed2006

Ontogenetic variation in chemical and physical characteristics of adaxial apple leaf surfaces.

The reaction of plants to environmental factors often varies with developmental stage. It was hypothesized, that also the cuticle, the outer surface layer of plants is modified during ontogenesis. Apple plantlets, cv. Golden Delicious, were grown under controlled conditions avoiding biotic and abiotic stress factors. The cuticular wax surface of adaxial apple leaves was analyzed for its chemical composition as well as for its micromorphology and hydrophobicity just after unfolding of leaves ending in the seventh leaf insertion. The outer surface of apple leaves was formed by a thin amorphous layer of epicuticular waxes. Epidermal cells of young leaves exhibited a distinctive curvature of the periclinal cell walls resulting in an undulated surface of the cuticle including pronounced lamellae, with the highest density at the centre of cells. As epidermal cells expanded during ontogenesis, the upper surface showed only minor surface sculpturing and a decrease in lamellae. With increasing leaf age the hydrophobicity of adaxial leaf side decreased significantly indicated by a decrease in contact angle. Extracted from plants, the amount of apolar cuticular wax per area unit ranged from only 0.9 microgcm(-2) for the oldest studied leaf to 1.5 microgcm(-2) for the youngest studied leaf. Differences in the total amount of cuticular waxes per leaf were not significant for older leaves. For young leaves, triterpenes (ursolic acid and oleanolic acid), esters and alcohols were the main wax components. During ontogenesis, the proportion of triterpenes in total mass of apolar waxes decreased from 32% (leaf 1) to 13% (leaf 7); absolute amounts decreased by more than 50%. The proportion of wax alcohols and esters, and alkanes to a lesser degree, increased with leaf age, whereas the proportion of acids decreased. The epicuticular wax layer also contained alpha-tocopherol described for the first time to be present also in the epicuticular wax. The modifications in the chemical composition of cuticular waxes are discussed in relation to the varying physical characteristics of the cuticle during ontogenesis of apple leaves.

Malus↗
PubMed2006

Beccaridiol, an unusual 28-nortriterpenoid from the leaves of Diplectria beccariana.

A C29-triterpene, beccaridiol (1), a dihydrochalcone natural product, 2',4'-dihydroxy-3-(4-methoxyphenyl)-propiophenone (2), as well as three known compounds, 4'-hydroxy-1',2'-dihydro-beta-ionone, 4'-O-methyldavidigenin (3), and ursolic acid, have been isolated from an EtOAc-soluble extract of the leaves of Diplectria beccariana. Beccaridiol (1) was characterized as an ursane-type 28-nortriterpene possessing an unusual aromatic E-ring by spectroscopic data interpretation. The relative configuration of this unusual isolate was established by analyzing the observed NOESY NMR correlations, and the absolute stereochemistry of 1 was then determined based on the circular dichroism (CD) spectrum of its 2,3-di-p-bromobenzoate (1b) derivative. All isolates were evaluated for their potential cancer chemopreventive properties utilizing a cell culture assay to determine quinone reductase induction.

Enzyme Induction↗