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The hydroethanolic extract obtained from the dry leaves of Fridericia chica (HEFc) underwent several fractionations by different chromatographic techniques. The ethyl acetate and dichloromethane fraction were subjected to phytochemical analysis, resulting in the identification and isolation of scutellarein (1) and in a fraction rich in carajurone (2). They were tested for cytotoxicity in CHO-K1 and the antibacterial activity and mode of action by in vitro assays. The HEFc and scutellarein (1) presented no cytotoxicity. The results showed good antibacterial effect of HEFc against Streptococcus pyogenes and Staphylococcus aureus and moderate activity for Staphylococcus epidermidis, Pseudomonas aeruginosa and Salmonella typhimurium. The fraction containing the compound carajurone (2) showed good activity against Staphylococcus aureus and Staphylococcus epidermidis and moderate activity against Streptococcus pyogenes. Scutellarein (1) showed no activity against the bacteria tested. HEFc antibacterial mode of action appeared to be associated with changes in the permeability of bacterial membranes and nucleotide leakage.

In a search for new antitrypanosomal agents in the Brazilian flora, the ethanol extract of the xylopodium from Aiouea trinervis (Lauraceae) exhibited in vitro activity against the epimastigote forms of Trypanosoma cruzi, the etiological agent of Chagas disease. Bioassay-guided chromatographic fractionation of the ethanol extract afforded three butanolides, isoobtusilactone A (1), epilitsenolide C2 (2), and epilitsenolide C1 (3). Butanolides 1 and 3 were more active against T. cruzi epimastigotes than the reference drug benznidazole (by 8.9-fold and 3.2-fold, respectively), while 2 proved inactive. Compounds 1 and 3 showed low cytotoxicity in mammalian Vero cells (CC50> 156 μmol L-1) and high selectivity index (SI) values for epimastigotes (SI = 56.8 and 28.6, respectively), and 1 was more selective than benznidazole (SI = 46.5). Butanolide 1 at 24 μmol L-1 also led to cell cycle alterations in epimastigote forms, and inhibited the growth of amastigote cells in more than 70 %. In silico ADMET properties of 1 were also analyzed and predicted favorable drug-like characteristics. This butanolide also complied with Lipinski’s rule of five and was not predicted as interference compound (PAINS). This is the first report on the isolation of these bioactive butanolides under the guidance of in vitro trypanocidal activity against T. cruzi., EXCLI Journal;Vol. 19 2020

Six new eremophilane sesquiterpenes, (rel)-4β,5β,7β-eremophil-9-en-12-oic acid (1), (rel)-4β,5β,7β-eremophil-1(10)-en-12-oic acid (2), (rel)-4β,5β,7β-eremophil-1(10)-en-2-oxo-12-oic acid (3), (rel)-4β,5β,7β-eremophil-9-en-12,8α-olide (4), (rel)-4β,5β,7β-eremophil-9-en-12,8β-olide (5) and (rel)-4β,5β,7β-eremophil-9α,10α-epoxy-12-oic acid (6), were isolated from the leaves of a specimen of Ocotea lancifolia (Lauraceae). Two other known sesquiterpenes, 4β,5β,7β-eremophil-11-en- 10α-ol (7) reported for the first time in the genus Ocotea, and the aromadendrene sesquiterpene, spathulenol (8), were also isolated. Their structures were determined on the basis of spectral data (MS, IR, UV and NMR-1D and 2D) and subsequent comparisons with the literature.

Ocotea are commonly used by population as a medicine, however there are few research is on the genotoxic activity of extracts and compounds obtained from plants of this genus. The present study examined the genotoxic potential (mutagenic and recombinogenic) of ethanol extracts obtained from the leaves of Ocotea acutifolia, Ocotea lancifolia and Ocotea minarum from in Mato Grosso do Sul state. Genotoxic activity of the plants was investigated by the Somatic mutation and Recombination Test (SMART) in wing cells of Drosophila melanogaster. Extracts of O. lancifolia and O. minarum showed no genotoxic activity, at the concentrations used. Otherside, the extract of O. acutifolia showed higher genotoxic potential and induced high frequencies of mitotic recombination. This difference in activity seems to be related to the presence of different classes of secondary metabolites and their concentrations in each extract. The pronounced genotoxic potential presented by O. acutifolia showed that, despite the frequent use of plants of the genus Ocotea pharmacological studies of these and other plant species are essential in order to characterize the possible adverse effects., Plantas do gênero Ocotea são comumente utilizadas pela população como medicamento, porém são escassas as pesquisas sobre a atividade genotóxica de extratos e compostos químicos obtidos de plantas desse gênero. No presente trabalho foi avaliado o potencial genotóxico (mutagênico e recombinogênico) de extratos etanólicos obtidos das folhas de Ocotea acutifolia, Ocotea lancifolia e Ocotea minarum, que ocorrem no estado de Mato Grosso do Sul. A atividade genotóxica destas plantas foi investigada por meio do SMART (Somatic Mutation And Recombination Test) em células de asas de Drosophila melanogaster. Nas concentrações testadas os extratos de O. lancifolia e O. minarum não apresentaram atividade genotóxica, por outro lado o extrato de O. acutifolia demonstrou elevado potencial genotóxico e induziu altas frequencias de recombinação mitótica. Esta diferença de atividade parece estar relacionada à concentração e as distintas classes de metabólitos secundários encontradas em cada extrato. O pronunciado potencial genotóxico apresentado por O. acutifolia demonstra que, apesar do uso freqüente de plantas do gênero Ocotea, são imprescindíveis estudos farmacológicos destas e outras espécies de plantas, a fim de caracterizar os possíveis efeitos adversos.

Two new sesquiterpenes 6α-ethoxyeudesm-4(15)-en-1β-ol (1) and (7R*)-5-epi-opposit-4(15)-ene-1β,7-diol (7) were isolated from the seeds of a specimen of Guarea guidonia (Meliaceae). Five other known sesquiterpenes, eudesm-4(15)-ene-1β,6α-diol (2), 5-epi-eudesm-4(15)-ene-1β,6β-diol (3), eudesm-4(15)-ene-1β,5α-diol (4), eudesm-4(15),7-dien-1β-ol (5) and (7R*)-opposit-4(15)-ene-1β,7-diol (6), were also isolated in this work. Their structures were determined on the basis of spectral data (MS, IR, and NMR-1D and 2D) and subsequent comparisons with the literature. The substances 3, 4 and 6 are reported for the first time in Meliaceae and 5 for the first time in the genus Guarea.

A new triterpene, 3beta,6beta,21beta-trihydroxyolean-12-ene and a new iridoid, 8alpha-methyl-8beta-hydroxy-6beta-(3',4'-dimethoxy)benzoyloxy-1 alpha,3alpha-dimethoxy-octahydro-cyclopenta[c]pyran were isolated from the trunk bark of a specimen of Tabebuia heptaphylla (Bignoniaceae) collected in the "Pantanal" of Mato Grosso do Sul, Brazil. Twelve known compounds were also obtained in this work, comprising four iridoids, 6-O-p-hydroxybenzoylajugol, 6-O-p-methoxybenzoylajugol, 6-O-3",4"-dimethoxybenzoylajugol, 8alpha-methyl-8beta-hydroxy-6beta-(4'-hydroxy)benzoyloxy-1alpha,3 alpha-dimethoxy-octahydro-cyclopenta[c]pyran, a cyclopentene dialdehyde, 2-formyl-5-(3',4'-dimethoxybenzoyloxy)-3-methyl-2-cyclopentene-1-acetaldehyde, a phenylethanoid glycoside, verbascoside and three benzoic acid derivatives, p-hydroxybenzoic, p-methoxybenzoic and 3,4-dimethoxybenzoic acids, in addition to squalene, sitostenone and sitosterol. The antioxidant properties of the isolated compounds were also evaluated in this work.

Da madeira e das cascas do caule de Terminalia fagifolia foram isolados dois 1,3-diarilpropanos, 1-(4'-hidróxi-2'-metóxifenil)-3-(3"-metóxi-4"-hidróxifenil)-propano e 1-(2'-hidróxi-4',6'-dimetóxifenil)-3-(3"-metóxi-4"-hidróxifenil)-propano, sete flavanonas, naringenina, 5-hidróxi-4',7-dimetóxiflavanona, sakuranetina, isosakuranetina, 7,4'-dimetóxiflavanona, 7-hidróxi-4'-metóxiflavanona, 7-metóxi-4'-hidróxiflavanona, duas chalconas, 2',4'-diidroxi-4-metóxichalcona e 2'-4-diidroxi-4'-metóxichalcona, uma flavana, 7,4'-diidróxi-3'-metóxiflavana e nove triterpenos pentacíclicos, ácido arjúnico, arjunetina, arjungenina, arjunglucosídeo I, ácido arjunólico, arjunglucosídeo II, 23-galoilarjunglucosídeo (isolado como seus derivados mono-, di- e trimetilados após metilação com diazometano), ácido betulínico e acetato do ácido ursólico, além de ácido gálico e sitosterol. Os diarilpropanos representam os primeiros membros desta classe em Combretaceae e as flavanonas e chalconas estão sendo descritas pela primeira vez na família. As substâncias isoladas foram avaliadas quanto às atividades citotóxica in vitro (células Hep2 e H292, carcinomas de laringe e mucoepidermóide de pulmão humanos, respectivamente) e antioxidante. As chalconas, o diarilpropano 1-(2'-hidróxi-4',6'-dimetóxifenil)-3-(3"-metóxi-4"-hidróxifenil) -propano e os derivados di- e tri-metilados de 23-galoilarjunglucosídeo foram os mais ativos quanto à atividade citotóxica. ABSTRACT - Two 1,3-diarylpropanes, 1-(4'-hydroxy-2'-methoxyphenyl)-3-(3"-methoxy-4" -hydroxyphenyl)-propane and 1-(2'-hydroxy-4',6'-dimethoxyphenyl)-3-(3"-methoxy-4" -hydroxyphenyl)-propane, seven flavanones, naringenin, naringenin-4',7-dimethyl-ether, sakuranetin, isosakuranetin, liquiritigenin-4',7-dimethyl-ether, liquiritigenin-7-methyl-ether and liquiritigenin-4'-methyl-ether, two chalcones, isoliquiritigenin-4-methyl-ether and isoliquiritigenin-4'-methyl-ether, one flavan, 7,4'-dihydroxy-3'-methoxyflavan, nine triterpenes, arjunic acid, arjunetin, arjungenin, arjunglucoside I, arjunolic acid, arjunglucoside II, 23-galloylarjunglucoside II (isolated as its mono-, di- and tri-O-methyl derivatives after methylation with diazomethane), betulinic acid and ursolic acid acetate, along with gallic acid and sitosterol were isolated from the heartwood and trunk bark of of Terminalia fagifolia. The flavanones and chalcones obtained in the present work are new in the Combretaceae and this is the first report of the occurrence of 1,3-diarylpropanes in this family. The isolated compounds were evaluated for their in vitro cytotoxic activity against two human cancer cell lines (Hep2 larynx carcinoma and H292 lung mucoepidermoid carcinoma) and antioxidant properties. Isoliquiritigenin-4-methyl-ether, isoliquiritigenin-4'-methyl-ether, 1-(2'-hydroxy-4',6'-dimethoxyphenyl)-3-(3"-methoxy -4"-hydroxyphenyl)-propane and the di- and tri-O-methyl derivatives of 23-galloylarjunglucoside II were the most active in the cytotoxic assay.

Dos frutos de Ocotea minarum foram isolados um novo alcalóide indólico, triptofol-5-O-b-D-glicopiranosídeo, a cumarina escopoletina e os flavonóides taxifolina, quercetina-7-O-b-D-glicopiranosídeo, eriodictiol-3'-O-b-D-glicopiranosídeo e naringenina-7-O-b-D-glicopiranosídeo. Do cerne foi isolado um novo alquil fenol, 3-(1,4-diidroxipentil)-5-metoxifenol, além de 5-propilresorcinol, trans-asarona, lioniresinol, 3-O-b-D-glicopiranosil estigmasterol e estigmasta-4,22-dien-3-ona. Da casca do caule foram obtidos o sesquiterpeno ácido lanceólico (como seu derivado éster metílico após metilação com diazometano) e b-sitosterol. O ácido lanceólico e 5-propilresorcinol estão sendo relatados pela primeira vez como produtos naturais. ABSTRACT - From the fruits of Ocotea minarum a new indole alkaloid, tryptophol-5-O-b-D-glucopyranoside, was isolated in addition to the coumarin scopoletin and the flavonoids taxifolin, quercetin-7-O-b-D-glucopyranoside, eriodictyol-3'-O-b-D-glucopyranoside and naringenin-7-O-b-D-glucopyranoside. A new alkyl phenol, 3-(1,4-dihydroxypentyl)-5-methoxyphenol, was obtained from the heartwood in addition to 5-propylresorcinol, trans-asarone, lyonyresinol, 3-O-b-D-glucopyranosyl stigmasterol and stigmasta-4,22-dien-3-one, whereas from the trunk bark the sesquiterpene lanceolic acid (as its methyl ester derivative after methylation procedures) and b-sitosterol were isolated. 5-propylresorcinol and lanceolic acid are reported for the first time as natural products.

Das folhas de Terminalia glabrescens foram obtidos um novo triterpeno pentacíclico (3b,6b,23,28-tetraidroxiolean-12-eno), além dos ácidos ursólico, 2a-hidroxiursólico, oleanólico, maslínico, arjunólico, sumaresinólico e asiático, esqualeno, fitol, sitosterol-3-O-b-D-glucopiranosídeo e n-alcanos. Da casca do caule foram obtidos friedelina, taraxerol, lupeol, lupenona, betulina, betulona, ácido betulínico, arjunglucosídeo I, estigmastano-3b,6a-diol, b-sitosterol, (-) catequina, b-D-piranotagatose, b-D-furanofrutose e a-D-furanofrutose. A new oleanane-type triterpene (3b,6b,23,28-tetrahydroxyolean-12-ene) was isolated from the leaves of Terminalia glabrescens, together with ursolic, 2a-hydroxyursolic, oleanolic, maslinic, arjunolic, sumaresinolic and asiatic acids, squalene, phytol, sitosterol-3-O-b-D-glucopyranoside and n-alkanes. Friedelin, taraxerol, lupeol, lupenone, betulin, betulone, betulinic acid, arjunglucoside I, stigmastane-3b,6a-diol, b-sitosterol, (-) catechin, b-D-pyranotagatose, b-D-furanofructose and a-D-furanofructose were obtained from the trunk bark.

Extracts obtained from leaves, seeds and bark of Unonopsis lindmanii were evaluated by means of Brine Shrimp Lethality test (BSL). Through bioassay-guided chromatographic fractionation, liriodenine, an oxoaporphine alkaloid, was isolated from the bark extracts as the bioactive compound. Two additional inactive known alkaloids, unonopsine and lysicamine were also isolated from the bark extracts.