The trunk bark of Tabebuia caraiba Bignoniaceae was found to contain four novel iridoids, 6-O-E-p-coumaroyljioglutin D (2), 6-O-E-p-coumaroyl-3-demethyl-3-O-ethyljioglutin D (3), 6-O-E-p-coumaroyl-1-demethyl-1-O-ethyljioglutin D (4), 7-O-E-p-coumaroyljiofuranaldehyde (5), three known iridoids, including one iridoid glucoside, jioglutin D (1), rehmaglutin D (6), 6-O-E-p-coumaroylcatalpol (7). From the flowers were obtained six triterpenes, betulinic acid (8), olean-12-en-3-one (9), β-amyrin (10), oleanolic acid (11), ursolic acid (12), 3-O-E-p-coumaroylursolic acid (13), 2α-hydroxyursolic acid (14), 6β,19α-dihydroxyursolic acid (15), and one phenylethanoid, tyrosol (16), in addition to β-sitosterol, β-sitosterol-3-O-β-D-glucopyranoside and β-sitosterol-3-O-β-D-(6´-O-acyl)-glucopyranoside and E-p-coumaric acid. The structures of the isolated compounds were established on the basis of 1D and 2D NMR spectroscopic techniques. The chemical profile of the trunk bark of the plant was determined by HPLC/DAD/HRESIMS and did not present a good correlation with the phytochemical study. It did not detect most of the isolated substances and allowed to propose the presence of some non-isolated compounds.

O alcalóide azafluorenona 5,8-dimetóxi-7-hidróxi-1-metil-4-azafluoren-9-ona e o megastigmano (-)-(5R*, 6S*)-megastigman-3-ona-10,7-olidio foram isolados das partes aéreas de Unonopsis lindmanii (Annonaceae), juntamente com os compostos conhecidos (3S*, 5S*, 8R*)-3,5-di-hidróxi-megastigma-6,7-dien-9-ona (grasshopper ketone), N-trans-feruloiltiramina, (-)-anonaína, (-)-asimilobina, liriodenina e (-)-siringaresinol. Este é o primeiro relato da presença de megastigmanos em Annonaceae. As estruturas dos compostos foram elucidadas com base em dados espectroscópicos.

The azafluorenone alkaloid 5,8-dimethoxy-7-hydroxy-1-methyl-4-azafluoren-9-one and the megastigman (-)-(5R*, 6S*)-megastigman-3-one-10,7-olide were isolated from aerial parts of Unonopsis lindmanii (Annonaceae), along with the known compounds (3S*, 5S*, 8R*)-3,5-dihydroxy-megastigma-6,7-dien-9-one (grasshopper ketone), N-trans-feruloyltyramine, (-)-anonaine, (-)-asimilobine, liriodenine and (-)-syringaresinol. This is the first description of the presence of megastigmanes in Annonaceae. The structures of the compounds were elucidated based on spectroscopic data.

Four eudesmane-type sesquiterpenes, costic acid (1), 12-carboxyeudesman-3,11(13)-diene (2), viscic acid (3), 3-oxo-γ-costic acid (4) and two rearranged eudesmane derivatives, 3α-hydroxyisoiphion-11(13)-en-12-oic acid (5) and 5β-hydroxy-4-oxo-11(13)-dehydroiphionan-12-oic acid (6), in addition to (-)-epicatechin, have been isolated from the trunk bark of Nectandra cissiflora. This is the first reported occurrence in the Lauraceae of 3-6. The structures of the isolated compounds have been established on the basis of 1D and 2D NMR spectroscopic techniques. The 13C NMR assignments of 3, 5 and 6 are given here for the first time, as well as some corrections to the previously reported chemical shift assignments of 4.

Dois novos e incomuns derivados de epicatequina e epiafzelequina contendo unidades feniloctanóides glicosiladas e denominados mascagninas A e B foram isolados, juntamente com quercetina-3-O-±-L-ramnopiranosil-(1→6)-²-D-glucopiranosídeo, das partes aéreas de Mascagnia pubiflora(Malpighiaceae), uma planta tóxica para o gado. Suas estruturas foram determinadas pela combinação de espectroscopia de ressonância magnética nuclear (RMN) uni e bidimensionais e dados de espectroscopia de massas (MS).

Mascagnins A and B, two novel and unusual epicatechin and epiafzelechin derivatives bearing glucosylated phenyloctanoid units, along with quercetin-3-O-±-L-rhamnopyranosyl-(1→6)-²-Dglucopyranoside were isolated from the aerial parts of Mascagnia pubiflora(Malpighiaceae), a plant toxic to cattle. Their structures were established by a combination of 1D- and 2D-nuclear magnetic resonance spectroscopic techniques and mass spectrometry data.

From the trunk bark of Nectandra megapotamica (Lauraceae) four phenylpropanoids, elemicin, isoelemicin, (±)-erythro-1-(3,4,5-trimethoxyphenyl)-1,2-propanediol and (±)-threo-1-(3,4,5-trimetoxyphenyl)-1,2-propanediol have been isolated, in addition to 3,4,5-trimethoxybenzoic acid, (-)-epicatechin and trans-1(10)-epoxy-4(15)-caryophyllene. The diastereoisomeric erythro- and threo- phenylpropanoids are being reported for the first time in a plant taxon as well as the occurrence of the other compounds in Nectandra. The structures of the isolated compounds have been established on the basis of 1D and 2D NMR spectroscopic techniques. Their in vitro antifungal activities against standard strains of Candida albicans, C. krusei, C. tropicalis and Cryptococcus neoformans and antioxidant properties were also evaluated in this work.

No presente trabalho foi realizado um estudo fitoquímico com os diferentes extratos obtidos a partir de órgãos subterrâneos de Duguetia furfuracea (Annonaceae), o qual incluiu o teste de toxicidade para Artemia salina. O extrato alcaloídico, obtido das cascas do caule subterrâneo, conduziu ao isolamento de (-)-duguetina beta-N-óxido, de (-)-duguetina, dicentrinona, (-)-N-metiltetraidropalmatina e (+)-N-metilglaucina. Do extrato etanólico do cerne do caule subterrâneo obteve-se alantoína por precipitação. O óleo volátil e o extrato apolar também foram extraídos das cascas do caule subterrâneo. As substâncias 2,4,5-trimetoxiestireno, alfa-gurjuneno, aromadendreno, biciclogermacreno, (E)-metil-isoeugenol e a-asarona foram isoladas a partir do óleo volátil, e as substâncias policarpol, óxido de beta-cariofileno, 2,4,5-trimetóxi-estireno, alfa-asarona e asaraldeído foram obtidas do extrato em éter de petróleo. Este estudo descreve pela primeira vez o alcalóide beta-N-óxido de (-)-duguetina, e a ocorrência das substâncias (-)-N-metiltetraidropalmatina e (+)-N-metilglaucina na família Annonaceae. Todos os extratos se mostraram tóxicos nos testes com Artemia salina.

In the present investigation the underground parts of Duguetia furfuracea (Annonaceae) were used to conduct a phytochemical study that included the brine shrimp (Artemia salina) lethality bioassay. The substances (-)-duguetine beta-N-oxide, (-)-duguetine, dicentrinone, (-)-N-methyltetrahydropalmatine, and (+)-N-methylglaucine were isolated from the alkaloid extract of the bark of the underground stem, and the ureide allantoin was also isolated by precipitation from the ethanol extract of the wood of the underground stem. A fresh volatile oil and a nonpolar extract were also obtained from the underground stem bark. The substances 2,4,5-trimethoxystyrene, a-gurjunene, aromadendrene, bicyclogermacrene, (E)-methylisoeugenol, and alpha-asarone were isolated from the fresh volatile oil and polycarpol, beta-caryophyllene oxide, 2,4,5-trimethoxystyrene, a-asarone, and asaraldehyde were obtained from the petroleum ether extract. The present study describes for the first time the alkaloid (-)-duguetine beta-N-oxide and the occurrence of (-)-N-methyltetrahydropalmatine and (+)-N-methylglaucine in the family Annonaceae. All extracts were active in the brine shrimp lethality bioassay.

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.

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-beta-D-glicopiranosídeo, a cumarina escopoletina e os flavonóides taxifolina, quercetina-7-O-beta-D-glicopiranosídeo, eriodictiol-3'-O-beta-D-glicopiranosídeo e naringenina-7-O-beta-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-beta-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 beta-sitosterol. O ácido lanceólico e 5-propilresorcinol estão sendo relatados pela primeira vez como produtos naturais.

From the fruits of Ocotea minarum a new indole alkaloid, tryptophol-5-O-beta-D-glucopyranoside, was isolated in addition to the coumarin scopoletin and the flavonoids taxifolin, quercetin-7-O-beta-D-glucopyranoside, eriodictyol-3'-O-beta-D-glucopyranoside and naringenin-7-O-beta-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-beta-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 beta-sitosterol were isolated. 5-propylresorcinol and lanceolic acid are reported for the first time as natural products.

Das folhas de Guarea kunthiana foram obtidos um novo diterpeno com esqueleto do tipo caurano (ent-caur-16-eno-2-ona), além de oito diterpenos (ent-caur-16-eno, ent-3alfa- e 3beta-hidroxicaur-16-eno, kolavelool, kolavenol, kolavenal, ent-13-epi-óxido de manoíla e (-)-neftenol), quatro sesquiterpenos (alismol, alismóxido, espatulenol e 4beta,10alfa-aromadendranodiol), poliprenol-12 e alfa- e delta-tocoferóis. Kolavenal está sendo relatado pela primeira vez como produto natural, assim como a ocorrência de diterpenos do tipo cembrano e ent-caurano na família Meliaceae.

From leaves of Guarea kunthiana one new kaurene diterpene (ent-kaur-16-en-2-one) was isolated along with eight known diterpenes (ent-kaur-16-ene, ent-3alpha- and 3beta-hydroxykaur-16-ene, kolavelool, kolavenol, kolavenal, ent-13-epi-manoyloxide and (-)-nephthenol), four sesquiterpenes (alismol, alismoxide, spathulenol and 4beta,10alpha-aromadendranediol), polyprenol-12 and alpha- and delta-tocopherols. Kolavenal is reported for the first time as a natural product, as well as the occurrence of cembrane- and ent-kaurane-type diterpenes in the Meliaceae.

Das folhas de Terminalia glabrescens foram obtidos um novo triterpeno pentacíclico (3beta,6beta,23,28-tetraidroxiolean-12-eno), além dos ácidos ursólico, 2alfa-hidroxiursólico, oleanólico, maslínico, arjunólico, sumaresinólico e asiático, esqualeno, fitol, sitosterol-3-O-beta-D-glucopiranosídeo e n-alcanos. Da casca do caule foram obtidos friedelina, taraxerol, lupeol, lupenona, betulina, betulona, ácido betulínico, arjunglucosídeo I, estigmastano-3beta,6alfa-diol, beta-sitosterol, (-) catequina, beta-D-piranotagatose, beta-D-furanofrutose e alfa-D-furanofrutose.

A new oleanane-type triterpene (3beta,6beta,23,28-tetrahydroxyolean-12-ene) was isolated from the leaves of Terminalia glabrescens, together with ursolic, 2alpha-hydroxyursolic, oleanolic, maslinic, arjunolic, sumaresinolic and asiatic acids, squalene, phytol, sitosterol-3-O-beta-D-glucopyranoside and n-alkanes. Friedelin, taraxerol, lupeol, lupenone, betulin, betulone, betulinic acid, arjunglucoside I, stigmastane-3beta,6alpha-diol, beta-sitosterol, (-) catechin,beta-D-pyranotagatose, beta-D-furanofructose and alpha-D-furanofructose were obtained from the trunk bark.