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.

In the present work, the crude ethanol extract from wood of G. macrophylla was submitted to liquid/liquid partition between hexane, CH2Cl2, EtOAc and n-BuOH. Each phase was individually chromatographed over silica gel, Sephadex LH-20 or Amberlite XAD-2 to give eight terpene derivatives, such as five sesquiterpenoids (caryophyllene oxide, guai-6-en-10β-ol, spathulenol, aromadendrane-4β,10α-diol and aloaromadendrane-4α,10β-diol) as well as three triterpenoids (cicloart-24-ene-3β,23(R*)-diol, cicloart-24-ene-3β,23(S*)-diol, and cicloart-23E-ene-3β,25-diol). Additionally, were isolated three fatty acids (linolenic, linoleic and stearic), two steroids (sitosterol and stigmasterol) and sacarose. The structures of all these compounds were characterized by spectrometric analysis, mainly mass spectrometry and NMR and comparison of these data described in the literature.

A espécie Poiretia bahiana, popularmente conhecida como arrudinha, arruda da serra ou arruda brava, tem uma ocorrência restrita aos campos rupestres da Chapada Diamantina, BA. Suas partes aéreas apresentam um aroma pungente e é usada pelo povo do local no controle de infestações por pulgas e no tratamento de hemorróidas, dores nas articulações e sinusite. Neste trabalho, relatamos a composição dos óleos voláteis obtidos das partes aéreas de cinco espécimes e do óleo volátil obtido dos frutos de um espécime de P. bahiana, os quais foram coletados em diferentes regiões da Chapada Diamantina. Nos óleos voláteis que foram analisados por CG-FID e CG-EM foram identificados vinte e nove componentes sendo que os dois principais foram a umbelulona, em concentrações entre 55,0% e 75,3%, e sabineno, em concentrações entre 10,3% e 25,2%. O óleo das partes aéreas de um espécime e o óleo dos frutos de outro espécime foram avaliados quanto às suas propriedades antimicrobianas contra seis bactérias, duas leveduras e cinco fungos filamentosos pelos ensaios de difusão em ágar e microdiluição. Os óleos exibiram atividade contra Escherichia coli, Salmonella choleraesuis, Proteus mirabilis, Staphylococcus aureus, Staphylococcus aureus resistente à meticilina (MRSA), Candida albicans, Cryptococcus neoformans, Cladosporium herbarum, Microsporum canis, Trichophyton rubrum e foram inativos contra Pseudomonas aeruginosa, Aspergillus fumigatus e Penicillium notatum. A toxicidade do óleo das partes aéreas foi determinada contra Artemia salina apresentando uma LC50 de 459,03 mg mL-1.

Poiretia bahiana known as "arrudinha", "arruda da serra" or "arruda brava", has its occurrence restricted to the rock fields (campo rupestre) areas in Chapada Diamantina, Bahia, northeastern region of Brazil. Its aerial parts present a pungent smell and have been used by local communities as fumigant for the control of infestation of fleas and in the treatment of hemorrhoids, articulations pain and sinusitis. This work reports the composition of the volatile oils from aerial parts of five specimens and of the essential oil from the fruits of one specimen of Poiretia bahiana that were harvested in four different places of Chapada Diamantina. Twenty nine components were identified from the oils analyzed by GC-FID and GC-MS. Umbellulone, in concentrations between 55.0% and 75.3% and sabinene, in concentrations between 10.3% and 25.2% are the major components. The oil from the aerial parts of one specimen and the oil of fruits of another specimen had their antimicrobial properties evaluated against six bacteria, two yeasts and five filamentous fungi by the agar diffusion method and microdilution assay. The in vitro results demonstrated that these essential oils exhibit antimicrobial activity against Escherichia coli, Salmonella choleraesuis, Proteus mirabilis, Staphylococcus aureus, methicilin resistant Staphylococcus aureus (MRSA), Candida albicans, Cryptococcus neoformans, Cladosporium herbarum, Microsporum canis, Trichophyton rubrum and are inactive against Pseudomonas aeruginosa, Aspergillus fumigatus and Penicillium notatum. The oil obtained from the aerial parts of one specimen displayed moderate toxicity against Artemia salina with a LC50 value of 459.03 mg mL-1.

O extrato hexânico dos frutos de Xylopia emarginata foi particionado entre hexano e MeOH/H2O. A fase hidroalcoólica foi submetida à separação cromatográfica fornecendo quatro sesquiterpenos: óxido de cariofileno, espatulenol, 1beta,6alfa-diidroxi-4(15)-eudesmeno e 4-hidroxi-1,15-peróxieudesmano. A fase hexânica foi fracionada através de cromatografia em coluna fornecendo dois hidrocarbonetos (nonadecano e 1-nonadeceno) e uma cetona alifática (hentriacontan-16-ona). As estruturas dos compostos isolados foram estabelecidas através de análise espectroscópica, principalmente RMN e EM.

The hexane extract from Xylopia emarginata fruits was partitioned between hexane and MeOH/H2O. The hydro-alcoholic phase was submitted to chromatographic separation to afford four sesquiterpenes: caryophyllene oxide, spathulenol, 1beta,6alpha-dihydroxy-4(15)-eudesmene and 4-hydroxy-1,15-peroxy-eudesmane. The hexane phase was fractioned in column chromatography to afford two hydrocarbons (nonadecane and 1-nonadecene) and one aliphatic ketone (hentriacontan-16-one). The structures of the isolated compounds were established by spectral data analysis, mainly NMR and MS.

Os óleos essenciais das folhas, flores e frutos de Myrcia myrtifolia DC foram coletados ao longo dos anos de 2002 e 2003 e foram analisados utilizando CG-DIC e CG-EM. No total foram identificados 28 componentes sendo que o alfa-pineno foi a substância predominante em todas as amostras analisadas apresentando-se em concentrações que variaram entre 61.5 e 90.9%. As propriedades antimicrobianas do óleo essencial das folhas coletadas em outubro de 2002 foram avaliadas contra seis bactérias, duas leveduras e cinco fungos filamentosos sendo mais fortemente ativo contra Microsporum canis e Trichophyton rubrum, ativo contra Staphylococcus aureus, Staphylococcus aureus resistente à meticilina, Candida albicans, Cryptococcus neoformans e Aspergillus fumigatus. O óleo ainda mostrou uma toxicidade moderada, LC50 of 479,16 µg mL-1, contra Artemia salina.

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. alpha-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.

A fase em hexano do extrato etanólico das folhas de Guarea macrophylla (Meliaceae) foi submetida a fracionamento cromatográfico. Esses procedimentos permitiram o isolamento de um novo diterpenóide: 7alfa-hidroperóxido-isopimara-8(14),15-dieno-2alfa ,3beta-diol, um novo nor-diterpenóide: 19-nor-isopimara-7,15,4(18)-trien-3-ona além de sete diterpenóides de estruturas conhecidas. As estruturas dos compostos isolados foram definidas através de análise dos dados espectrométricos e comparação com aqueles descritos na literatura.

The hexane phase from the ethanol extract from leaves of Guarea macrophylla (Meliaceae) was submitted to chromatographic separation. These procedures allowed the isolation of one new diterpenoid: 7alpha-hydroperoxy-isopimara-8(14),15-diene-2alpha,3beta-diol, one new nor-diterpenoid: 19-nor-isopimara-7,15,4(18)-trien-3-one besides seven known diterpenoids. Their structures were deduced by analysis of spectrometric data and comparison of data described in the literature.

Um novo sesquiterpeno, aromadendrano-4b,10a,15-triol, foi isolado das folhas de Xylopia brasiliensis Spreng (Annonaceae), juntamente com quatro derivados de esqueleto aromadendrano e três esteróides. As estruturas dos metabólitos foram definidas por meio da análise dos respectivos espectros de RMN, incluindo experimentos bidimensionais, além de espectrometria de massas. Os sesquiterpenos aromadendranos diidroxilados apresentaram atividade antifúngica frente a Cladosporium cladosporioides.

A new sesquiterpenoid, aromadendrane-4b,10a,15-triol, was isolated from the leaves of Xylopia brasiliensis Spreng (Annonaceae), together with four known aromadendrane derivatives and three steroids. The structures of these compounds were defined by analysis of their NMR spectral data, including bidimensional analysis, and mass spectrometry. The isolated aromadendranediol derivatives showed antifungal activity against Cladosporium cladosporioides.

Ésteres metílicos dos diterpenos ácido ent-pimara-9(11),15-dien-19-óico (1), ácido ent-pimara-7,15-dien-19-óico (2) e ácido ent-pimara-8,15-dien-19-óico (3) foram submetidos a reações de fotooxigenação via formação sensibilizada de oxigênio singlete. Enquanto os compostos 2 e 3 foram totalmente convertidos nos produtos, o composto 1 reagiu apenas parcialmente sugerindo uma influência do impedimento estéreo sobre a ligação dupla endocíclica deste diterpeno. Os produtos de oxidação obtidos, 7alfa,11beta-diidroxipimara-8,15-dien-19-oato de metila (5), 7alfa-hidroperoxipimara-8(14),15-dien-19-oato de metila (6), 7alfa-hidroxi-14-oxopimara-15-en-19-oato de metila (8), 7alfa,9alfa-diidroxipimara-8(14),15-dien-19-oato de metila (9) e 7alfa,14alfa-diidroxipimara-8,15-dien-19-oato de metila (10) são inéditos e suas estruturas foram determinadas pela análise de seus dados espectrais.

Methyl esters of diterpenoids ent-pimara-9(11),15-dien-19-oic acid (1), ent-pimara-7,15-dien-19-oic acid (2), and ent-pimara-8,15-dien-19-oic acid (3) were submitted to photooxygenation reactions with sensitized singlet oxygen. While compounds 2 and 3 were converted to the products, compound 1 reacted only partially, suggesting an influence of the steric hindrance on the endocyclic double bond of 1. The oxidation products obtained, methyl-7alpha,11beta-dihydroxypimara-8,15-dien-19-oate (5), methyl-7alpha-hydroperoxypimara-8(14),15-dien-19 oate (6), methyl-7alpha-hydroxy-14-oxopimara-15-en-19-oate (8), methyl-7alpha,9alpha-dihydroxypimara-8(14),15-dien-19-oate (9) and methyl-7alpha,14alpha-dihydroxypimara-8,15-dien-19-oate (10), are new and their structures were elucidated by spectral data analysis.

O óleo volátil e o extrato hexânico das folhas de Porcelia macrocarpa (Warm.) R.E. Fries, Annonaceae, foram submetidos a fracionamentos cromatográficos. Nove sesquiterpenos (alfa-cubebeno, alfa-copaeno, germacreno-D, biciclogermacreno, gama-cadineno, delta-cadineno, espatulenol, globulol e cis-cubenol) além de um diterpeno (fitol) foram identificados no óleo volátil, correspondendo a 83.1% (em massa) do total de constituintes. Dois sesquiterpenos (espatulenol e macrocarp-11(15)-en-8-ol), o último apresentando um novo esqueleto estrutural, um diterpeno (fitol), além de dois esteróides (sitosta-5,25-dien-3beta-ol e sitosta-5,22,25-trien-3beta-ol), foram isolados do extrato hexânico. As substâncias foram caracterizadas através de experimentos de RMN de ¹H e 13C, incluindo análise bidimensional, além de espectrometria de massas.

The volatile oil and the hexane extract from the leaves of Porcelia macrocarpa (Warm.) R.E. Fries, Annonaceae, were submitted to chromatographic separations. Nine sesquiterpenes (alpha-cubebene, alpha-copaene, germacrene-D, bicyclogermacrene, gamma-cadinene, delta-cadinene, spathulenol, globulol and cis-cubenol) and one diterpene (phytol) were identified in the volatile oil (83.1 % in weight). Two sesquiterpenes (spathulenol and macrocarp-11(15)-en-8-ol), the latter with a novel skeleton, one diterpene (phytol) and two steroids (sistosta-5,25-dien-3beta-ol and sitosta-5,22,25-trien-3beta-ol) were isolated from the hexane extract. These compounds were characterized by ¹H and 13C NMR spectroscopy, including bidimensional analysis and mass spectrometry.

This paper describes a methodology to separate and identify polar compounds as flavonoid and lignan glucosides, amino acids, salt of quaternary ammonium amino acid and carbohydrates from branches of Porcelia macrocarpa (Annonaceae).

Dois novos flavonóis glicosilados, juntamente com iridóides, triterpenóides, esteróides e tocoferolquinona, foram isolados das folhas de Alibertia sessilis (Rubiaceae). As estruturas dos flavonóides foram determinadas através de métodos espectroscópicos, principalmente da RMN de 13C e de ¹H.

Two novel acylated flavonol glycosides, along with iridoids, triterpenes, steroids and a-tocopherolquinone, were isolated from the leaves of Alibertia sessilis (Rubiaceae). The determination of the structures of the new compounds was based mainly on ¹H- and 13C-NMR.

RESUMO Dos tubérculos de H. ampla (Miers) Baehni (Icacinacea), coletados em Itacoatiara (AM), foram isolados, além de sitosterol, os humiriantenolídeos A, C e D.