Frederico G. Cruz

Seasonal variation and antimicrobial activity of Myrcia myrtifolia essential oils

This work reports the seasonal variation of the composition of leaf volatile oils and the composition of volatile oils from flowers and fruits of Myrcia myrtifolia DC harvested in the sand dunes of Salvador, Bahia, northeastern region of Brazil between 2002 and 2003. The oils were analyzed by GC-FID and GC-MS so that 28 components were identified. a-Pinene was predominant in a range from 61.5 to 90.9% in all samples analyzed. The leaf oil collected in October 2002 had their antimicrobial properties tested against six bacteria, two yeasts and five filamentous fungi being active against Staphylococcus aureus, methicilin-resistant Staphylococcus aureus, Candida albicans, Cryptococcus neoformans and Aspergillus fumigatus, and showed strongest activity against Microsporum canis and Trichophyton rubrum. The oil displayed moderate toxicity against Artemia salina showing a LC50 of 479.16 µg mL-1.

Leishmanicidal activity of Cecropia pachystachya flavonoids: Arginase inhibition and altered mitochondrial DNA arrangement

The plant Cecropia pachystachya Trécul is widely used in Brazilian ethnomedicine to treat hypertension, asthma, and diabetes. Arginase is an enzyme with levels that are elevated in these disorders, and it is central to Leishmania polyamine biosynthesis. The aims of this study were to evaluate antileishmanial activity and inhibition of the arginase enzyme by C. pachystachya extracts, and to study changes in cellular organization using electron microscopy. The ethanol extract of C. pachystachya was tested on Leishmania (Leishmania) amazonensis promastigote survival/proliferation and arginase activity in vitro. Qualitative ultrastructural analysis was also used to observe changes in cell organization. The major bioactive molecules of the ethanol extract were characterized using liquid chromatography-electrospray ionization-mass spectrometry (LC-ESI-MS). The ethyl acetate fraction of the ethanol extract diminished promastigote axenic growth/survival, inhibited arginase activity, and altered a mitochondrial kinetoplast DNA (K-DNA) array. The bioactive compounds of C. pachystachya were characterized as glucoside flavonoids. Orientin (9) (luteolin-8-C-glucoside) was the main component of the methanol-soluble ethyl acetate fraction obtained from the ethanol extract and is an arginase inhibitor (IC50 15.9 μM). The ethyl acetate fraction was not cytotoxic to splenocytes at a concentration of 200 μg/mL. In conclusion, C. pachystachya contains bioactive compounds that reduce the growth of L. (L.) amazonensis promastigotes, altering mitochondrial K-DNA arrangement and inhibiting arginase.

Flavonoids and triterpene ester derivatives from Erythroxylum leal costae

A methanolic leaf extract of Erythroxylum leal costae yielded quercetin 3-rhamnoside, epicatechin, and the new glycosides, 8-hydroxyluteolin 8-rhamnoside and 6-hydroxyluteolin 6-rhamnoside. Palmitic acid esterified with β-amyrin, lupeol and lupenyl acetate were also identified.

Variação sazonal da composição do óleo essencial de Myrcia salzmannii Berg. (Myrtaceae)

This work report the seasonal variation of composition of the volatile oils from leaves and from flowers of Myrcia salzmannii harvested in the sand dunes of Salvador, Bahia, northeastern region of Brazil in the years 2001 and 2003. The oils were analyzed by GC-FID and GC-MS being identified 49 components. Nine essential oil samples of leaves collected on different months and years and one sample of flowers were analyzed. β-Caryophyllene and α-humulene were the only compounds present in all of the samples being the first the majority compound.

Triterpenos da resina de Protium heptaphyllum March (B0urseraceae): caracterização em misturas binárias

Eight triterpenes, maniladiol, breine, ursa-9(11):12-dien-3b-ol, oleana-9(11):12-dien-3b-ol, 3a-hydroxy-tirucalla-8,24-dien-21-oic acid, 3a-hydroxy-tirucalla-7,24-dien-21-oic, a and b amyrines were isolated as binary mixtures obtained from the chloroform extract of the oil-resin of Protium heptaphyllum March. The identification of the compounds was based mainly in 13C NMR data and mass spectra. The diene and the tetracyclic acid triterpenes were not reported before in the literature as constituents of the studied resin.

Polyprenylated benzophenones with a tricyclo [4.3.1.1(3,8)]undecane skeleton from Clusia obdeltifolia

The hexane extract of Clusia obdeltifolia trunk yielded three new polyprenylated benzophenones 7b-H-11-benzoyl-5a-hydroxy-6,6,10,10-tetramethyl-1-(3-methyl-2-butenyl)tetracyclo [7.3.1.13,1103,7]tetradecane-2,12,14-trione, 8-benzoyl-4a-(1-hydroxy-1-methylethyl)-7,7-dimethyl -1,3-di(3-methyl-2-butenyl)tricyclo[4.3.1.13,8 ]undecane-2,9,11-trione and 7a-H-1-benzoyl-4-hydroxy-3-(3-hydroxy-3methylbutyl)-6,6,13,13-tetramethyl-11- (3-methyl-2-butenyl)-5 -oxatetracyclo[7.3.1.03,704,11 ]tridecane-2,12-dione along with two known polyprenylated benzophenones, sampsonione B and sampsonione G. These benzophenones exhibited a complex tricyclo [4.3.1.13,8]undecane skeleton and their structures were determined from spectral data and comparison with those of previously reported compounds.

A new biphenyl from Clusia melchiorii and a new tocotrienol from C. obdeltifolia

Chromatographic purification of the dichloromethane extract of Clusia melchiorii trunk leading to the isolation of a new biphenyl, 2,2-dimethyl-5-hydroxi-7-phenylchromene, along with the known compounds 2,2-dimethyl-5,10-dihydro-2H-benzo[g]chromene-5,10-dione (xyloidone), betulinic acid, friedelin, friedelinol, euphol, sitostenone, stigmastenone and a mixture of b-sitosterol and stigmasterol. The hexane extract of Clusia obdeltifolia trunk yielded, after chromatographic fractionation, a new d-tocotrienilic alcohol 2Z, 6E, 10E-13-(6-hydroxy-2,8-dimethyl-3,4-dihydro-2H,2-chromenyl)-2,6,10-trimethyl-2,6, 10-tridecatrien-1-ol, along with 2Z and 2E-d-tocotrienoloic acids, betulinic acid, betulonic acid, betunilic aldehyde, glutinol, friedelin, sitostenone and a mixture of b-sitosterol and stigmasterol. Their structures were determined from spectral data and comparison with data from previously reported compounds.

A new biphenyl and antimicrobial activity of extracts and compounds from Clusia burlemarxii

Phytochemical investigation on Clusia burlemarxii (Clusiaceae) led to isolation and identification of nine compounds. Were isolated from leaves 3-O-α-L- rhamnopyranosylquercetin, 3-O-α-L-rhamnopyranosylkaempferol, 4-hydroxy-5,5-dimethyldihydrofuran-2-one, 2Z-δ-tocotrienoloic acid and friedelin and were isolated from trunk betulinic acid, protocatechuic acid, lyoniresinol, and a new biphenyl 2,2-dimethyl-3,5-dihydroxy-7-(4-hydroxyphenyl)chromane. The structures were determined by ¹H, ¹³C-NMR, DEPT, HMBC, HMQC, HRESIMS. The Minimal Inhibitory Concentration against Streptococcus mutans, Staphylococcus aureus, Bacillus subtilis, Micrococcus luteus, Escherichia coli, Salmonella choleraesuis, Pseudomonas aeruginosa, Aspergillus niger and Cladosporium cladosporioides was also determined. Extracts and compounds showed significant activity against tested Gram-positive bacteria, none activity against tested Gram-negative bacteria and fungi.

A quinoline alkaloid from Acanthosyris paulo-alvinii

Abstract Leaves of Acanthosyris paulo-alvinii afforded the new alkaloid 2,3-methylenedioxy-4,7,8-trimethoxy-quinoline (1), as well as the known compounds loliolide (2) and 3-hydroxy-5,6-epoxy-β-ionone (3). 13 C NMR spectroscopic assignments are reported.

Coumarins from Kielmeyera argentea

Abstract Two new prenylated 4- n -propylcoumarins, 7-hydroxy-8-(4-cinnamoyl-3-methyl-1-oxobutyl)-4- n -propyl-2′,2′-dimethyl 2 H ,6 H -benzol[1,2-b:3,4-b′]-dipyran-2-one and 5-hydroxy-6-(4-cinnamoyl-3-methyl-1-oxobutyl)-4- n -propyl-2′,2′-dimethyl-2H,6H-benzo [1,2-b:3,4-b′]-dipyran-2-one, besides two known prenylated 4-phenylcoumarins, 7-hydroxy-8-(4-cinnamoyl-3-methyl-1-oxobutyl)-4-phenyl-2′,2′-dimethyl 2H,6H-benzo[1,2-b:3,4-b′]-dipyran-2-one and 5-hydroxy-6-(4-cinnamoyl-3-methyl-1-oxobutyl)-4-phenyl-2′,2′-dimethyl-2H,6H-benzo [1,2-b:3,4-b′]-dipyran-2-one, were isolated from the hexane extract of stems of Kielmeyera argentea . These compounds were identified by comparison with literature data, and their spectroscopic properties.