Concentricolide, an anti-HIV agent from the ascomycete Daldinia concentrica

A novel benzofuran lactone, named concentricolide (=rel-(6R)-6-ethylbenzo[2.1-b:3,4-c']difuran-8(6H)-one; 1), was isolated along with four known compounds (friedelin, cytochalasin L-696.474, armillaramide, and russulamide) from the fruiting bodies of the

几种森林类型土壤中木栓酮含量的分布及其与土壤的关系

本论文在较大尺度上选择我国温带、暖温带、中亚热带3个不同区带典型林型作为研究地区，探讨各区带不同林型土壤中木栓酮的分布及其与林型、土壤和微生物多样性的相互关系，初步研究木栓酮在森林生态系统中的指示作用。 研究结果表明： ⑴林分中物种数越多，生物多样水平越高，其土壤中木栓酮的含量就越高。木栓酮含量与多样性指数呈正相关 ,但程度较弱。试验中某些阔叶林纯林中的木栓酮的含量高于天然次生林。说明木栓酮在土壤中分布还受到地上植被种类，凋落物的构成及分解过程等许多其他因素影响。是否能用木栓酮表征林地植被的多样性，这一规律的普遍性还有待于进一步证实。 ⑵各林分土壤养分、有机质、微生物及其酶活性均与木栓酮含量呈正相关，其变化趋势大致为：天然次生林>混交林>针叶纯林，均与木栓酮含量呈正相关。表明土壤质量越高木栓酮含量越高。土壤中木栓酮的含量是否能作为评价土壤质量变化的指标，以及这一规律是否具有普遍性还有待证实。 ⑶在室内培养条件下，木栓酮能够促进土壤细菌的生长，而对真菌则有显著的抑制效应，对放线菌无生物活性。通过比较PLFA指纹图谱发现，土壤中添加实际浓度范围的木栓酮后并未对土壤中的微生物群落结构变化产生显著影响。由此可以得知，在自然条件下，木栓酮并不是影响土壤微生物的群落结构的主要因素。

Triterpenoids from the mangrove plant Hibiscus tiliaceus

Three new triterpenoids with the rarely occurring nigrum skeleton, namely (20E)-22-hydroxynigrum-20-en-3-one (1), 21 beta-hydroxynigrum-22(29)-en-3-one (2), and 21 alpha-hydroxynigrum-22(29)-en-3-one (3), were isolated from the mangrove plant Hibiscus tiliaceus. Additionally, five known triterpenoids including friedelin (4),12-oleanen-3 beta-ol (5), 3 beta-hydroxy-12-oleanen-28-oic acid (6),20(29)-lupen-3 beta,28-diol (7). and cucurbita-5,23-dien-3 beta,25-diol (8) were also isolated and identified. The latter structures were elucidated by a detailed NMR and MS analyses, as well as by comparison with reported literature data.

Development of novel brush-type chiral stationary phases based on terpenoid selectors: HPLC evaluation and theoretical investigation of enantioselective binding interactions

The terpenoid chiral selectors dehydroabietic acid, 12,14-dinitrodehydroabietic acid and friedelin have been covalently linked to silica gel yielding three chiral stationary phases CSP 1, CSP 2 and CSP 3, respectively. The enantiodiscriminating capability of each one of these phases was evaluated by HPLC with four families of chiral aromatic compounds composed of alcohols, amines, phenylalanine and tryptophan amino acid derivatives and beta-lactams. The CSP 3 phase, containing a selector with a large friedelane backbone is particularly suitable for resolving free alcohols and their derivatives bearing fluorine substituents, while CSP 2 with a dehydroabietic architecture is the only phase that efficiently discriminates 1, 1'-binaphthol atropisomers. CSP 3 also gives efficient resolution of the free amines. All three phases resolve well the racemates of N-trifluoracetyl and N-3,5-dinitrobenzoyl phenylalanine amino acid ester derivatives. Good enantioseparation of beta-lactams and N-benzoyl tryptophan amino acid derivatives was achieved on CSP 1. In order to understand the structural factors that govern the chiral molecular recognition ability of these phases, molecular dynamics simulations were carried out in the gas phase with binary diastereomeric complexes formed by the selectors of CSP 1 and CSP 2 and several amino acid derivatives. Decomposition of molecular mechanics energies shows that van der Waals interactions dominate the formation of the diastereomeric transient complexes while the electrostatic binding interactions are primarily responsible for the enantioselective binding of the (R)- and (S)-analytes. Analysis of the hydrogen bonds shows that electrostatic interactions are mainly associated with the formation of N-(HO)-O-...=C enantio selective hydrogen bonds between the amide binding sites from the selectors and the carbonyl groups of the analytes. The role of mobile phase polarity, a mixture of n-hexane and propan-2-ol in different ratios, was also evaluated through molecular dynamics simulations in explicit solvent. (c) 2006 Elsevier Ltd. All rights reserved.

Co-cultivation of plant cells as a technique for the elicitation of secondary metabolite production

Cells of Mikania glomerata, Cephaelis ipecacuanha and Maytenus aquifolia were co-cultured in a two-phase system using filter paper as a solid support. The species were co-cultured in all possible paired combinations. Interaction between Mikania and Maytenus cells resulted in increased biomass production of Maytenus cells, but the friedelin content was reduced. Co-cultivation of Cephaelis and Mikania cells enhanced coumarin content, but inhibited the growth of Mikania cells. However, yield of emetine as well as Cephaelis biomass accumulation were positively stimulated by the co-cultivation. Results indicate a possible occurrence of allelopathy in such a system.

Studies on anti-allergic constituents in the leaves and stems of Anchietia salutaris var. martiana (Violaceae)

The anti-allergic active fractionation of hexane extracts of the leaves and stems of Anchietia salutaris,ar. martiana (family Violaceae) nas performed by monitoring their activities with an in vitro bioassay system measuring the inhibitory effects on induced histamine release from guinea pig lung cells. Three known pentacyclic triterpenes (friedelin, alpha-amyrin, beta-amyrin) were isolated, but these compounds were inactive. Aliphatic hydrocarbons and methyl esters of fatty acids (palmitic, oleic, linoleic, linolenic acids) were detected in active fractions. All compounds isolated were detected for the first time in this medicinal plant.

Triterpenes and antitubercular activity of Byrsonima crassa

Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)

Biosynthesis of friedelane and quinonemethide triterpenoids is compartmentalized in Maytenus aquifolium and Salacia campestris

Maytenus aquifolium (Celastraceae) and Salacia campestris (Hippocrateaceae) species accumulate friedelane and quinonemethide triterpenoids in their leaves and root bark, respectively. Enzymatic extracts obtained from leaves displayed cyclase activity with conversion of the substrate oxidosqualene to the triterpenes, 3 beta -friedelanol and friedelin. In addition, administration of (+/-)5-H-3 mevalonolactone in leaves of M. aquifolium seedlings produced radio labelled friedelin in the leaves, twigs and stems, while the root bark accumulated labelled maytenin and pristimerin. These experiments indicated that the triterpenes once biosynthesized in the leaves are translocated to the root bark and further transformed to the antitumoral quinonemethide triterpenoids. (C) 2000 Elsevier B.V. Ltd. All rights reserved.

Chemistry and bioactivity of Raulinoa echinata Cowan, an endemic Brazilian rutaceae species

The hexane extract of the stems of Raulinoa echinata afforded the sesquiterpenes germacrene D (6), 1β,6α-dihydroxy-4-(15)-eudesmene (4) and oplopanone (5); the triterpenes squalene, isomultiflorenol (7), isobauerenol (8) and friedelin (9); the protolimonoids melianone (2) and melianodiol (3); and the pyranocoumarin 3-(1′-1′-dimethylallyl)-lomatin (1), which has not been reported previously as a natural product; together with β-sitosterol. The hexane extract and some of these compounds were assayed in vitro against trypomastigote forms of Trypanosoma cruzi. Brine shrimp lethality and antimicrobial activities of the crude extract and pure compounds were also evaluated.

Clonagem de oxidoesqualeno ciclases de Maytenus ilicifolia Mart. ex Reissek (CELASTRACEAE)

Pós-graduação em Biotecnologia - IQ

Detecção in silico, isolamento e caracterização estrutural dos constitutintes micromoleculares antimaláricos e antioxidantes em galhosmdemGarcina gardneriana (Clusiaceae)

Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)

Estudo químico e atividade biológica de Garcinia xanthochymus (Clusiaceae)

Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)

Biflavones and triterpenoids isolated from Ouratea castaneifolia (DC.) Engl., Ochnaceae

Trata da investigação química das folhas e caule da espécie Ouratea castaneifolia (DC.) Engl., sobre a qual não há registros de estudos químicos ou farmacológicos anteriores. O estudo fitoquímico clássico dos extratos orgânicos do caule e das folhas de O. castaneifolia foi aliado à técnica da cromatografia líquida de alta eficiência (CLAE) e resultou na identificação de dezessete metabólitos: sete triperpenos (friedelina, 3β-friedelinol, α-amirina, β-amirina, lupeol, taraxerol e germanicol), quatro esteróides (sitosterol, estigmasterol e os glucosídeos sitosteril 3-O-β-D-glicopiranosídeo e estigmasteril 3-O-β-D-glicopiranosídeo), uma isoflavona (5,7,4´-trimetoxiisoflavona), uma flavona (5,4´-diidroxi-7,3´,5´-trimetoxiflavona), quatro biflavonas (amentoflavona, 7,7”-O-dimetil-amentoflavona, heveaflavona e tetrametilamentoflavona). A identificação das substâncias foi feita com base na análise de espectros de RMN de 1H, 13C e técnicas bidimensionais. As classes dos metabólitos identificados estão de acordo com aquelas citadas em estudos químicos do gênero Ouratea.

Efeito dos componentes obtidos de qualea multiflora sobre modelo tumoral mamário murino e sua influência no sistema imunológico

Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)

Atividade alelopática de substâncias químicas isoladas do Capim-Marandu e suas variações em função do pH

Este trabalho teve por objetivos isolar, identificar e caracterizar a atividade alelopática de substâncias químicas produzidas pela Brachiaria brizantha cv. Marandu e determinar as variações na atividade dessas substâncias em função da variação do pH da solução. A atividade alelopática foi realizada em bioensaios de germinação e desenvolvimento da radícula e do hipocótilo, utilizando as plantas daninhas malícia (Mimosa pudica) e mata-pasto (Senna obtusifolia) como receptoras. Os efeitos do pH foram analisados na faixa de 3,0 a 9,0. Os triterpenos pentacíclicos friedelina e epifriedelinol isolados da parte aérea de B. brizantha apresentaram baixa atividade inibitória na germinação de sementes e no desenvolvimento da radícula e do hipocótilo das duas plantas daninhas. As duas substâncias apresentaram comportamento diferenciado em relação à variação do pH da solução, com inibições mais marcantes em relação à planta daninha mata-pasto.