Terpenes from leaves of Guarea macrophylla (Meliaceae).

The dichloromethane extract from the leaves of Guarea macrophylla (Meliaceae) was submitted to adsorption chromatography. Guai-6-en-10beta-ol, isopimara-7,15-dien-2alpha-ol and cycloarta-23,25-dien-3-one were isolated and identified by spectroscopic data, mainly by 1H and 13C NMR analyses; eight other known terpenoids were also isolated.

7Beta-oxygenated limonoids from Trichilia elegans ssp. elegans.

Five 7beta- and 7alpha-oxygenated obacunone-type limonoids were obtained on reinvestigation of the seeds of Trichilia elegans ssp. elegans: 7-deoxo-7beta-acetoxykihadanins A and B, 7-deoxo-7beta-hydroxykihadanins A and B and 7-deoxo-7alpha-hydroxykihadanin A, the last three being isolated after acetylation procedures as their mono- and/or diacetate derivatives. This is the first report of the natural occurrence of C-7 beta-substituted limonoids without any oxygenated function at C-6. The structures of these compounds have been established on the basis of 1D- and 2D-NMR spectral techniques, ESI-mass spectrum and X-ray crystallographic data.

Antifungal polysulphides from Petiveria alliacea L.

Bioactivity-directed fractionation of the CH(2)Cl(2)/MeOH (2:1, v/v) extract of the roots of Petiveria alliacea, using mutant yeast strains of Saccharomyces cerevisiae and fungi Cladosporium cladosporioides and C. sphaerospermum led to the isolation of dipropyl disulphide (1), dibenzyl sulphide (2), dibenzyl disulphide (3), dibenzyl trisulphide (4), dibenzyl tetrasulphide (5), benzylhydroxymethyl sulphide (6) and di(benzyltrithio) methane (7). Of these, 5-7 are new compounds and this is the first report of the natural occurrence of 2 and 3.

Diterpene from Baccharis trimera with a relaxant effect on rat vascular smooth muscle.

A bioassay monitored fractionation of a chloroform extract from the aerial parts of Baccharis trimera yielded a mixture that blocked the Ca2+-induced contractions of KCl- depolarized rat portal vein preparations. Pharmacological tests of two pure compounds isolated from the mixture revealed the dilactonic clerodane diterpene as the active compound.

Antimicrobial activity of kaurenoic acid derivatives substituted on carbon-15.

The antibacterial and antifungic activities of two kaurenic acids, ent kaurenoic acid and cinnamoylgrandifloric acid isolated from a hexane extract of aerial parts of Mikania laevigata, were investigated and compared with the activities of other kaurenic acid derivatives substituted on carbon-15. Only acetylgrandifloric acid (ent-kaur-16-en-15 alpha-acetyloxy-19-oic) and its epimer xylopic acid (ent-kaur-16-en-15 beta-acetyloxy-19-oic) displayed significant antibacterial activity at concentrations greater than or equal to 250 micrograms/ml, the 15 alpha epimer being the most active.

Antimitotic action of extracts of Petiveria alliacea on sea urchin egg development.

The hydroethanol extract of the roots of Petiveria alliacea L. (Phytolaccaceae) has been investigated previously as an antitumor agent against mouse Ehrlich ascites. The extract and its methanol, butanol and ether fractions exhibited an antimitotic effect on sea urchin egg development. The aqueous fraction did not produce inhibition of cell cleavage. At the first cleavage the inhibition, at the lowest concentration (10 micrograms/ml), produced by the ether fraction was 42%, whereas the inhibition produced by the total extract and by the other fractions was only 5 to 10% showing that the ether fraction was the most active. Even at higher concentrations the butanol and methanol fractions inhibit the cleavage about 30%. At the first cleavage, the ED50 of the hydroethanol extract and of the ether fraction were 45.02 and 12.40 micrograms/ml, respectively. Furthermore, in the second cleavage, the hydroethanol extract was about twice as potent as the methanol or butanol fractions (ED50 of 22.40, 44.80 and 54.10 micrograms/ml, respectively).

Effect of ursolic acid from epicuticular waxes of Jacaranda decurrens on Schizaphis graminum.

Ursolic acid from Jacaranda decurrens showed toxicity and feeding deterrency towards the greenbug Schizaphis graminum. Biological activity was determined by analyzing ursolic acid effects on the survival, reproductive index, and population growth rate of the greenbug. Survival and reproductive index decreased in direct proportion to ursolic acid content in the diet. The population growth rate decreased markedly when the aphids were fed on barley leaves sprayed with ursolic acid dissolved in DMSO, in comparison to leaves sprayed only with DMSO. The feeding behavior of the greenbug was also affected by ursolic acid. Ingestion time on diet with 0.1 mM was reduced about 30% in relation to the ingestion time on control diet.

Analgesic activity of a triterpene isolated from Scoparia dulcis L. (Vassourinha).

Analgesic and anti-inflammatory activities of water (WE) and ethanolic (EE) extracts of Scoparia dulcis L. were investigated in rats and mice, and compared to the effects induced by Glutinol, a triterpene isolated by purification of EE. Oral administration (p.o.) of either WE or EE (up to 2 g/kg) did not alter the normal spontaneous activity of mice and rats. The sleeping time induced by sodium pentobarbital (50 mg/kg, i.p.) was prolonged by 2 fold in mice pretreated with 0.5 g/kg EE, p.o. Neither extract altered the tail flick response of mice in immersion test, but previous administration of EE (0.5 g/kg, p.o.) reduced writhings induced by 0.8% acetic acid (0.1 ml/10 g, i.p.) in mice by 47%. EE (0.5 and 1 g/kg, p.o.) inhibited the paw edema induced by carrageenan in rats by respectively 46% and 58% after 2 h, being ineffective on the paw edema induced by dextran. No significant analgesic or anti-edema effects were detected in animals pretreated with WE (1 g/kg, p.o.). Administration of Glutinol (30 mg/kg, p.o.) reduced writhing induced by acetic acid in mice by 40% and the carrageenan induced paw edema in rats by 73%. The results indicate that the analgesic activity of S. dulcis L. may be explained by an anti-inflammatory activity probably related to the triterpene Glutinol.

Alkaloids from Porcelia macrocarpa.

Three new azaanthracene alkaloids, 6,7-dimethoxycleistopholine (3), 5-hydroxy-6-methoxycleistopholine (4), and 5-hydroxy-6,7-dimethoxycleistopholine (5), along with 14 known alkaloids, including the new natural product 6-methoxycleistopholine (2), were isolated from a CH2Cl2 extract of the branches of Porcelia macrocarpa.

Sesquiterpenes, limonoid and coumarin from the wood bark of Guarea guidonia.

Investigation of the wood bark of Guarea guidonia (Meliaceae) led to the isolation of a limonoid (mombasol), a coumarin (scopoletin), and six sesquiterpenes [trans-1(10)-epoxy-4(15)-caryophyllene, 1(10)-epoxy-4,7-humuladiene, viridiflorol, 1(10),4-diepoxy-7-humulene, 3-oxo-10-alloaromadendranol, 1beta-6alpha-dihydroxyeudesm-4(15)ene]. The occurrence of these metabolites in the Guarea genus is reported for the first time. Stigmasterol, sitosterol and its oleate and palmitate esters were also obtained. Some corrections to the previously reported chemical shift assignments of 3-oxo-10-alloaromadendranol ( (13)C-NMR) were made.

Antimicrobial activity pf kaurenoic acid derivatives substituted on carbon-15

The antibacterial and antifungic activities of two kaurenic acids, ent kaurenoic acid and cinnamoylgrandifloric acid isolated from a hexane extract of aerial parts of Mikania laevigata, were investigated and compared with the activities of other kaurenic acid-derivatives substituted on carbon-15. Only acetylgrandifloric acid (en-kaur-16-en-15 alfa-acetyloxy-19-oic) and its epimer xylopic acid (ent-kaur-16-4n-15 beta-acetyloxy-19-oic) displayed significant antibacterial activity at concentrations >=250 microng/ml., the 15 alfa epimer being the most active

Antimitotic action of extracts of Petiveria alliacea on sea urchin egg development

The hydroethanol extract of the roots of Petiveria alliacea L. (Phytolaccaceae) has been investigated previously as an antitumor agent against mouse Ehrlich ascites. The extract and its methanol, butanol and ether fractions exhibited an antimitotic effect on sea urchin egg development. The aqueous fraction did not produce inhibition of cell cleavage. At the first cleavage the inhibition, at the lowest concentration (10 micrograms/ml), produced by the ether fraction was 42 per cent , whereas the inhibition produced by the total extract and by the other fractions was only 5 to 10 per cent showing that the ether fraction was the most active. Even at higher concentrations the butanol and methanol fractions inhibit the cleavage about 30 per cent . At the first cleavage, the ED50 of the hydroethanol extract and of the ether fraction were 45.02 and 12.40 micrograms/ml, respectively. Furthermore, in the second cleavage, the hydroethanol extract was about twice as potent as the methanol or butanol fractions (ED50 of 22.40, 44.80 and 54.10 micrograms/ml, respectively)