Search

Species from the Ocotea genus have shown scientific evidence of anti-inflammatory activity through a promising mechanism of action. This study is the first in vivo evaluation of the anti-inflammatory potential and mechanism of action of extracts and essential oils from the leaves and bark of O. diospyrifolia. We isolated and identified compounds from the leaf and bark extracts and chemically characterized these extracts by ultra high-performance liquid chromatography–high-resolution mass spectrometry (UPLC-HRMS). Additionally, the essential oils were characterized by gas chromatography–mass spectrometry (GC–MS). Nine compounds (1-9) were isolated; among them, a new compound (9) was elucidated as 6aS,7S-(-)-11-hydroxy-7-methoxy-1,2-methylenedioxy-aporphine, named as diospirifoline. The aporphine substitution pattern found in diospirifoline, with substitution at C-7, was identified for first time in the Ocotea genus. Mururin A(1) and salsoline (5) were also isolated for the first time in this genus. The biosynthetically linked alkaloids coclaurine (7), reticuline (6), and isoboldine (8) were found to be 6aR-(-) isomers, which is different from the 6aS-(+) isomers that are most often found in other Ocotea spp. UPLC-HRMS analysis detected various classes of compounds in the leaf and bark extracts, such as flavonolignans, flavonoids, chlorogenic acids, alkaloids, and many other unidentified compounds. The GC–MS analysis revealed that both leaf and bark essential oils contained α-phellandrene as the major compound and that the chemotaxonomic marker of the Lauraceae family, the phenylpropanoid safrole, was not detected. Furthermore, some of the compounds identified in the extracts and essential oils have known anti-inflammatory activities, such as 5-caffeoylquinic acid, quercitrin, α-humulene, and (E)-caryophyllene. Indeed, the leaf extract, its ethyl acetate fraction, and the essential oils showed in vivo anti-inflammatory activity through the dual inhibition of edema and neutrophil recruitment, suggesting the inhibition of main inflammatory pathways. This mechanism of action is associated with a better efficacy and safety profile than that of the currently available anti-inflammatory drugs. The extract and essential oils of O. diospyrifolia showed high chemical diversity and a promising anti-inflammatory mechanism of action; thus, clearly indicating that this species should be further investigated.

Endophytes are microorganisms that live inside vegetal tissues without causing any loss to the host plant. They display wide biosynthetic capacity when producing several bioactive secondary metabolites, whose induction could be related to activation of genes, which might be silent or expressed depending on the geographic characteristics from where the endophytic was isolated. The extraordinary richness of the Brazilian biodiversity has encouraged several research groups in the endophytic bioprospecting. This review covers natural products reported by studies on from the Brazilian endophytic fungi cultures and classified them into three chemical classes (terpenes, phenolic, and nitrogen-containing compounds). For discussion purposes, Principal Component Analysis (PCA) was used as an unsupervised explorative method to evaluate the chemical variation in the Brazilian endophyte dataset. In addition, the dendrogram from the Hierarchical Clustering Analysis (HCA) confirmed the PCA results, and HCA could identify some main endophytic clusters. Our analysis clarified how the secondary metabolites were distributed in the different Brazilian endophyte strains, and this information will be a reliable guide that will support researchers to design microbial culture strategies.

This work describes the chemical and biological investigations of leaves and stems of Macrolobium latifolium (Vogel). The DCM, EtOAc soluble fractions obtained by liquid-liquid partition the crude methanolic extract of this species were submitted to usual chromatographic techniques which permitted to isolate an unusual 5,7-dihydroxychromone-3α- d -C-glucoside, named macrolobin, along with the known compounds identified as β-taraxerol, friedelin, stigmasterol, β-sitosterol, campesterol, and apigenin. The structures of all compounds were elucidated by 1H, 13C, HSQC and HMBC NMR spectra, IR spectra data analysis, and MS. Furthermore, the chemical profile from fatty acids and/or triglycerides fraction was also determined after transesterification. The reaction products were subjected to GC-FID and GC–MS permitted to detected methyl palmitate as the main fatty acid derivate present in the oil and, lauric (7.52 %), octadecanoic (17.15 %), docosanoic (5.36 %), tricosanoic (11.83 %) and tetracosanoic as minor methyl esters. Concerning the biological activities, the organic soluble fractions and macrolobin displayed antimicrobial activity against Salmonella enterica, Staphylococcus aureus, Pseudomonas aeruginosa and Escherichia coli (MIC values 125−1000 μg.mL−1) and, macrolobin exhibited significant acetylcholinesterase inhibition (IC50 0.8 μM). These findings indicate M. latifolium can contribute with the development of new bioactive compounds, especially the AChE inhibition.

Biotransformation has been successfully employed to conduct uncommon reactions, which would hardly be carried out by chemical synthesis. A wide diversity of compounds may be metabolized by fungi, leading to chemical derivatives through selective reactions that work under ecofriendly conditions. Endophytic fungi live inside vegetal tissues without causing damage to the host plant, making available unique enzymes for interesting chemical derivatization. Biotransformation of steroids by endophytic fungi may provide new derivatives as these microorganisms came from uncommon and underexplored habitats. In this study, endophytic strains isolated from Handroanthus impetiginosus leaves were assayed for biotransformation of progesterone, and its derivatives were identified through GC-EI-MS analysis. The endophyte Talaromyces sp. H4 was capable of transforming the steroidal nucleus selectively into four products through selective ene-reduction of the C4-C5 double bond and C-17 oxidation. The best conversion rate of progesterone (90 %) was reached with Penicillium citrinum H7 endophytic strain that transformed the substrate into one derivative. The results highlight endophytic fungi's potential to obtain new and interesting steroidal derivatizations.

Hundreds of millions of people worldwide are affected by Chagas' disease caused by Trypanosoma cruzi. Since the current treatment lack efficacy, specificity, and suffers from several side-effects, novel therapeutics are mandatory. Natural products from endophytic fungi have been useful sources of lead compounds. In this study, three lactones isolated from an endophytic strain culture were in silico evaluated for rational guidance of their bioassay screening. All lactones displayed in vitro activity against T. cruzi epimastigote and trypomastigote forms. Notably, the IC50 values of (+)-phomolactone were lower than benznidazole (0.86 vs. 30.78 μM against epimastigotes and 0.41 vs. 4.88 μM against trypomastigotes). Target-based studies suggested that lactones displayed their trypanocidal activities due to T. cruzi glyceraldehyde-3-phosphate dehydrogenase (TcGAPDH) inhibition, and the binding free energy for all three TcGAPDH-lactone complexes suggested that (+)-phomolactone has a lower score value (-3.38), corroborating with IC50 assays. These results highlight the potential of these lactones for further anti-T. cruzi drug development.

Coumarins are natural 1,2-benzopyrones, present in remarkable amounts as secondary metabolites in edible and medicinal plants. The low yield in the coumarins isolation from natural sources, along with the difficulties faced by the total synthesis, make them attractive for biotechnological studies. The current literature contains several reports on the biotransformation of coumarins by fungi, which can generate chemical analogs with high selectivity, using mild and eco-friendly conditions. Prompted by the enormous pharmacological interest in the coumarin-related compounds, their alimentary and chemical applications, this review covers the biotransformation of coumarins by filamentous fungi. The chemical structures of the analogs were presented and compared with those from the pattern structures. The main chemical reactions catalyzed the insertion of functional groups, and the impact on the biological activities caused by the chemical transformations were discussed. Several chemical reactions can be catalyzed by filamentous fungi in the coumarin scores, mainly lactone ring opening, C3-C4 reduction and hydroxylation. Chunninghamella sp. and Aspergillus sp. are the most common fungi used in these transformations. Concerning the substrates, the biotransformation of pyranocoumarins is a rarer process. Sometimes, the bioactivities were improved by the chemical modifications and coincidences with the mammalian metabolism were pointed out.

Among the various types of industry-generated effluents, those containing phenolic compounds are serious recalcitrant. There is therefore a need to develop new technologies that emphasize the depletion of these pollutants from the environment, and that work as a viable alternative to traditional physical and chemical remediation methods. Filamentous fungi are capable of producing a great number of enzymes that efficiently transform several organic compounds. Despite the use of fungi as first-choice agents for bioremediation of hazardous contaminants, the definitions of the chemical reactions and products that are included in the fungal transformation processes still are poorly reported. In this work, Aspergillus brasiliensis efficiently transformed methyl p-coumarate under an unexpected way into two new compounds, 5-(oxiran-2-yl)benzene-1,2,3-triol (23.03%) and 4-(3-hydroxyoxiran-2-yl)benzene-1,2-diol (4.90%), along with acetophenone (72.07%). The chemical structures of derivatives were determined by gas chromatography coupled to mass spectrometry (GC-MS) analysis and a plausible bioremediation pathway for phenolic recalcitrant was proposed. Interestingly, the uncommon phenyloxirane moiety has been formed as part of the transformation from 4-vinylphenol intermediate through double bond oxidation. Certainly, our results will open new insights in the bioremediation of phenolic compounds and they will be useful guidance for future planning of other similar processes.

Ferulic acid (FA) is a natural hydroxycinnamic acid widely found in medicinal and edible plants. Several experts have reported the biological potential of FA, including antioxidant and antimicrobia...

We report the molecular designing of non-symmetrical luminescent liquid crystals based on the 1,2,3-benzotriazole (BTZ), 2,1,3-benzoxadiazole (BOX) and 2,1,3-benzothiadiazole (BTD) heterocycles. The compounds showed stable nematic and smectic mesophases in a wide range of temperatures (between 70 and 170 °C). Translational order parameter investigations based on X-ray diffraction experiments demonstrated high ordered layers, closely dependent of the molecular structure and the smectic organization. The molecules exhibited intense photoluminescence under UV–vis light excitation in solutions. The emission spectrum for BTZ revealed a maximum in the blue region (447 nm), while BOX and BTD emit in the yellow one (around 550 nm). The fluorescence quantum yields of the BTZ-based derivatives solution are up to 64%, significantly higher than BOX and BTD. Moreover, in solid films, the efficiencies remained in the same range of solution. DFT calculations indicate dihedral angles of 24-30° between the benzazole-phenyl rings, which may suppress π-stacking and consequently reduce fluorescence quenching in the solid phase. This work contributes to general knowledge, where asymmetric cores improve mesophase stabilization and photoluminescence preservation in the solid state compared to their symmetric pairs.

The ubiquitous compound 4-hydroxy-3-methoxycinnamic acid, also known as ferulic acid (FA), constitutes a bioactive ingredient of many foods that may offer beneficial effects against disorders related to oxidative stress, including cancer, diabetes, and neurodegenerative diseases. This review discusses the antioxidant properties of FA, establishing relationships to several biological activities already described for this natural product. Next, 387 naturally occurring compounds, all isolated from plants and published between 1990 and 2015, the structures of which bear 1 or more feruloyl moieties, are covered in this review along with their structural formulas, botanical sources, and bioactivities. The compounds' distribution, structural patterns, bioactivities, and perspectives on food research are also succinctly discussed.

This work describes the isolation of pure bergenin from Peltophorum dubium roots with good yields and its further derivatization through Williamson synthesis. The alkyl derivatives of the bergenin were identified by nuclear magnetic resonance and mass spectrometry data analysis. Among them, three derivatives were reported for the first time herein, 8,10-dihexyl-bergenin, 8,10-didecyl-bergenin, and 8,10-ditetradecyl-bergenin, along with three previously reported ones (8,10-dimethylbergenin, 8-methylbergenin, 8,10-dioctyl-bergenin). Most derivatives of the bergenin displayed moderate cytotoxicity against Artemia salina, except the 8,10-dihexyl-bergenin (lethal concentration doses for 50% (LC50) = 70.55 µg mL-1). The antimicrobial assay showed that all derivatives selectively inhibited the Gram-positive bacteria Staphylococcus aureus, and two of them (8,10-dihexyl-bergenin and 8,10-didecyl-bergenin) had promising activities (minimum inhibitory concentration (MIC) = 5.1-6.2 µmol L-1). In addition, bergenin displayed interesting inhibition on acetylcholinesterase (half maximal inhibitory concentration (IC50) = 141.19 ± 0.41 µmol L-1), while its semi-synthetic derivatives displayed modest activity. Our results revealed that the antibacterial activity of bergenin could be greatly improved through its structural modification.

Labdane diterpenes and their derivatives have shown remarkable biological activities and are useful as chiral building blocks for the synthesis of a variety of bioactive compounds. There is great interest in developing biocatalyst technology to achieve regio- and stereoselective hydroxylation of unactivated C-H bonds in complex natural products, since the functionalization of unactivated C-H bonds generally requires hard reaction conditions and highly reactive oxidizing agents, which are limited regarding the control of regio- and stereoselectivity. Filamentous fungi are efficient biocatalysts capable of catalyzing a wide variety of hydroxylation reactions, and the use of whole cell biocatalysts provides advantages regarding cofactor regeneration and is much less expensive. Therefore, the goal of this study was to select biocatalysts to develop biotransformation processes that can be scalable under mild reaction conditions for hydroxylation of a labdane diterpene, 3β-acetoxy-copalic acid, which contains the trans-decalin moiety and a side chain dienic system appropriate for the preparation of a variety of compounds. Biotransformation processes were carried out and five filamentous fungi were selected as capable of producing hydroxylated diterpenes at positions C-3, C-6, C-7 and C-18 of the trans-decalin moiety and C-13 of the side chain dienic system. Hydroxylation reactions occurred with regio- and stereoselectivity by using some fungi that produced only the 6α, 7α and 13α-hydroxyl derivatives. The chemical structures of the hydroxylated diterpenes were determined from spectrometric and spectroscopic data, and the relative stereochemistry of stereogenic centers was established from coupling constants, by NOE-diff experiments and/or by computational calculations.

Natural coumarins are present in remarkable amounts as secondary metabolites in edible and medicinal plants, where they display interesting bioactivities. Considering the wide enzymatic arsenal of filamentous fungi, studies on the biotransformation of coumarins using these microorganisms have great importance in green chemical derivatization. Several reports on the biotransformation of coumarins using fungi have highlighted the achievement of chemical analogs with high selectivity by using mild and ecofriendly conditions. Prompted by the enormous pharmacological, alimentary, and chemical interest in coumarin-like compounds, this study evaluated the biotransformation of nine coumarin sca olds using Cunninghamella elegans ATCC 10028b and Aspergillus brasiliensis ATCC 16404. The chemical reactions which were catalyzed by the microorganisms were highly selective. Among the nine studied coumarins, only two of them were biotransformed. One of the coumarins, 7-hydroxy-2,3-dihydrocyclopenta[c]chromen-4(1H)-one, was biotransformed into the new 7,9-dihydroxy-2,3-dihydrocyclopenta[c]chromen-4(1H)-one, which was generated by selective hydroxylation in an unactivated carbon. Our results highlight some chemical features of coumarin cores that are important to biotransformation using filamentous fungi.

The biotransformation reactions are used as a successful alternative to derivatization by the traditional chemistry because they conduct to uncommon reactions, which would hardly be carried out by chemical synthesis. A wide diversity of compounds may be metabolized by fungi, leading to chemical derivatives through selective reactions that work under ecofriendly conditions. Endophytic fungi live in symbiosis with health tissues of plants. The employment of endophytic fungi as enzymatic sources to biotransformation reactions is very promising since these microorganisms came from uncommon and underexplored habitat. The environmental conditions directly influence the composition of the endophytic microbiota and its genetic expression, which could change also the production of the enzymes. The extraordinary richness of the Brazilian biodiversity is a key factor in the diversification of the endophytic community. The present review presents a mapping of the biotransformation reactions catalyzed by Brazilian endophytic fungi. Our findings contribute both to the appreciation of these fungi in the chemical derivatization and for the preservation of the Brazilian species.

The filamentous fungus Trametes versicolor is a rich source of laccase (Tvlac). Laccases catalyze reactions that convert substituted phenol substrates into diverse derivatives through aromatic oxidation. We investigated methyl p-coumarate, methyl ferulate, and methyl caffeate biotransformation by Trametes versicolor ATCC 200801. Despite substrate similarity, the biotransformation reactions varied widely. Only methyl p-coumarate was converted into three derivatives. We isolated and identified the chemical structures of such derivatives by NMR and IR analysis. Hydroxylation, methylation, and hydrolysis were the main reactions resulting from the studied biotransformation. We also analyzed the interactions between Tvlac (PDB ID: 1GYC) and the three phenolic substrates by molecular docking simulations. The substituents in the phenol ring influenced substrate conformation and orientation in the Tvlac site. The biotransformation reaction selectivity correlated with the different binding energies to the Tvlac site. Our results demonstrated that docking studies successfully predict the biotransformation of cinnamic acid analogs by T. versicolor.

There is some evidence in the literature of the photocyclization reaction of Tagitinin C (1) to Tagitinin F (2). Compound 2 has high pharmacological potential, but it is not easy to obtain, while compound 1 is easily obtained from a widespread plant, Tithonia diversifolia. Among different reaction conditions monitored, one was found that allowed the cyclization of 1 into 2 in

This study reports on the chemical composition and antimicrobial activity of the essential oil from Artemisia absinthium L. leaves AA EO collected in Brazil against a representative panel of cariogenic bacteria. The minimum inhibitory concentrations MICs were determined by the broth dilution method in 96-well microplates. AA EO was inactive against most of the investigated oral pathogens, but it displayed moderate activity against Streptococcus mutans MIC = 250 μg/mL and very promising activity against Streptococcus mitis MIC = 62.5 μg/mL. Gas chromatography GC FID and gas chromatography mass spectrometry GC-MS revealed that camphor 1, 19.0 %, E-caryophyllene 2, 9.3 %, eucalyptol 3, 6.8 %, germacrene D 6.7 %, and α-cadinol 6.5 % were the major chemical constituents of AA EO. However, when tested alone, compounds 1, 2, and 3 were inactive MIC > 1000 μg/mL against all the studied microorganisms.

β-Lapachone is a drug candidate in phase II clinical trials for treatment of solid tumors. The therapeutic efficacy of β-lapachone is closely related to its metabolism, since this o-naphthoquinone produces cytotoxic effect after intracellular bioreduction by reactive oxygen species formation. The aim of this study was to produce β-lapachone human blood phase I metabolites to evaluate their cytotoxic activities. The biotransformation of β-lapachone was performed using Mucor rouxii NRRL 1894 and Papulaspora immersa SS13. The metabolites were isolated and their chemical structures determined from spectrometric and spectroscopic data. Cell cytotoxicity assays were carried out with β-lapachone and its metabolites using the neoplastic cell line SKBR-3 derived from human breast cancer and normal human fibroblast cell line GM07492-A. Microbial transformation of β-lapachone by filamentous fungi resulted in the production of five metabolites identical to those found during human blood metabolism, a novel metabolite and a product stated before only in a synthetic procedure. The analysis of the results showed that β-lapachone metabolites were not cytotoxic for the neoplastic cell line SKBR-3 derived from human breast cancer and the normal human fibroblast cell line GM07492-A. The cytotoxic activity assay against the neoplastic cell line SKBR-3 revealed that the lowest half-maximal inhibitory concentration (IC50) values of these β-lapachone metabolites were 33- to 52-fold greater than IC50 values of β-lapachone. The cytotoxic activity of β-lapachone in vivo may be reduced due to its swift conversion in blood.

Endophytic fungi live inside vegetal tissues without causing damage to the host plant and may provide lead compounds for drug discovery. The co-culture of two or more endophytic fungi can trigger silent gene clusters, which could lead to the isolation of bioactive compounds. In this study, two endophytic strains isolated from Handroanthus impetiginosus leaves, identified as Talaromyces purpurogenus H4 and Phanerochaete sp. H2, were grown in mixed and axenic cultures. The meroterpenoid austin was detected only in the extracts from the mixed culture. Once isolated, austin displayed very interesting trypanocidal activity, with an IC50 value of 36.6 ± 1.2 μg/mL against Trypanosoma cruzi in the epimastigote form. The results obtained highlight the importance of the co-culturing of endophytic fungi to obtain natural bioactive products. The findings also enhance our understanding of the ecological relationships between endophytic fungi. Fil: do Nascimento, Jainara Santos. Universidade Federal da Bahia; Brasil Fil: Silva, Felipe Moura. Universidade Federal da Bahia; Brasil Fil: Magallanes Noguera, Cynthia Alejandra. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; Argentina Fil: Kurina Sanz, Marcela Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; Argentina Fil: dos Santos, Elda Gonçalves. Universidade Federal da Bahia; Brasil Fil: Caldas, Ivo Santana. Universidade Federal da Bahia; Brasil Fil: Luiz, Jaine Honorata Hortolan. Universidade Federal da Bahia; Brasil Fil: Silva, Eliane de Oliveira. Universidade Federal da Bahia; Brasil

Tithonia diversifolia is an invasive shrub found in the tropical regions. The aim of this study was to investigate the chemical composition as well as anti-inflammatory and antibacterial activities...

Made available in DSpace on 2018-11-26T17:52:05Z (GMT). No. of bitstreams: 0 Previous issue date: 2018-06-01 Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) The common bean Phaseolus vulgaris L (Fabaceae) is an important vegetable protein source and constitutes a significant part of the diet in many tropical countries. The Mexican bean weevil Zabrotes subfasciatus (Boheman) (Coleoptera: Bruchidae) is one of the main pests affecting stored beans: it causes extensive qualitative and quantitative grain loss. We investigated the bioactivity of the essential oils extracted from Chenopodium ambrosioides L (CA-EO), Ocimum gratissimum L (OG-EO), and Schinus terebinthifolius Raddi (ST-EO) against Z. subfasciatus. After 12-h treatment, CA-EO and OG-EO at 20.0 mu L/L of air killed 100% Z subfasciatus, whereas ST-EO at 100.0 mu L/L of air afforded 100% 1 subfasciatus mortality after 24 h. CA-EO provided the lowest 24 h LD50 (0.8 mu L/L of air) and displayed efficient repellent activity against Z subfasciatus. Our results demonstrate that CA-EO is a potentially economical and environmentally friendly alternative to manage Z. subfasciatus in stored beans. (C) 2018 Elsevier Ltd. All rights reserved. Univ Estadual Paulista, Fac Ciencias Agron, Dept Protecao Vegetal, BR-18610307 Botucatu, SP, Brazil Univ Fed Bahia, Inst Quim, Dept Quim Organ, BR-40170115 Salvador, BA, Brazil Univ Sao Paulo, Fac Filosofia Ciencias & Letras Ribeirao Preto, Dept Quim, BR-14040900 Ribeirao Preto, SP, Brazil Univ Estadual Paulista, Fac Ciencias Agron, Dept Protecao Vegetal, BR-18610307 Botucatu, SP, Brazil FAPESP: 2007/54241-8 CNPq: 303892/2016-1

Abnormal multiplication of oral bacteria causes dental caries and dental plaque. These diseases continue to be major public health concerns worldwide, mainly in developing countries. In this study, the chemical composition and antimicrobial activity of the essential oil of Vitex agnus-castus leaves (VAC‒EO) collected in the North of Brazil against a representative panel of cariogenic bacteria were investigated. The antimicrobial activity of VAC-EO was evaluated in terms of its minimum inhibitory concentration (MIC) values by using the broth microdilution method in 96-well microplates. The chemical constituents of VAC-EO were identified by gas chromatography (GC‒FID) and gas chromatography‒mass spectrometry (GC‒MS). VAC‒EO displayed some activity against all the investigated oral pathogens; MIC values ranged from 15.6 to 200 μg/mL. VAC-EO had promising activity against Streptococcus mutans (MIC= 15.6 μg/mL), Lactobacillus casei (MIC= 15.6 μg/mL), and Streptococcus mitis (MIC= 31.2 μg/mL). The compounds 1,8-cineole (23.8%), (E)-β-farnesene (14.6%), (E)-caryophyllene (12.5%), sabinene (11.4%), and α-terpinyl acetate (7.7%) were the major chemical constituents of VAC‒EO. VAC-EO displays antimicrobial activity against cariogenic bacteria. The efficacy of VAC-EO against S. mutans is noteworthy and should be further investigated.

Papaya apical curl necrosis (PACN) has frequently been observed in several Brazilian states. Affected plants exhibit foliar chlorosis, curvature of the apex, shortening of the internodes leading to bunching of the crown leaves, necrosis of the young apical parts, leaf drop, and dieback. Naturally infected plants were sampled and subjected to PCR assays, which confirmed that a phytoplasma was associated with the disease. Sequencing of the 16S rRNA gene, conventional and computer-simulated RFLP analyses, and phylogenetic analysis allowed the determination of the PACN phytoplasma as a representative of a new subgroup, designated 16SrXIII-E. The phytoplasmas of various 16Sr groups, including 16SrI, 16SrII, 16SrX, 16SrXII, and 16SrXVII, are known to be involved in anomalies in papaya plants in several countries. However, the present study reports, for the first time, the occurrence of a 16SrXIII phytoplasma in association with a papaya disease.

The ubiquitous compound 4-hydroxy-3-methoxycinnamic acid, also known as ferulic acid (FA), constitutes a bioactive ingredient of many foods that may offer beneficial effects against disorders related to oxidative stress, including cancer, diabetes, and neurodegenerative diseases. This review discusses the antioxidant properties of FA, establishing relationships to several biological activities already described for this natural product. Next, 387 naturally occurring compounds, all isolated from plants and published between 1990 and 2015, the structures of which bear 1 or more feruloyl moieties, are covered in this review along with their structural formulas, botanical sources, and bioactivities. The compounds' distribution, structural patterns, bioactivities, and perspectives on food research are also succinctly discussed.

O interesse na obtenção de novos fármacos a partir de micro-organismos endofíticos vem crescendo, uma vez que esta é uma fonte ainda pouco explorada. Além disso, o estudo das interações entre plantas e micro-organismos tem sido amplamente discutido ao longo dos últimos anos. No presente trabalho, o fungo endofítico Drechslera ravenelii (SS33), isolado das folhas de Smallanthus sonchifolius (yacon), foi cultivado sob diferentes condições fermentativas, objetivando a determinação das melhores condições para produzir metabólitos secundários com atividades antimicrobiana e/ou citotóxica. Para tal avaliaram-se dois parâmetros: meio fermentativo e tempo de incubação. Os meios fermentativos líquidos utilizados foram Czapek e caldo de batata (PDB), sob agitação (120 RPM), cultivados por 216 e 480 horas. Também foi desenvolvida cultura por fermentação em substrato sólido, meio de arroz-aveia, durante 720 horas. Todos os cultivos foram realizados em temperatura de 30 ºC e precedidos por pré-fermentação. Dos cultivos em meio líquido foram obtidas frações em diclorometano e em acetato de etila. Já dos cultivos provenientes do meio fermentativo sólido foram obtidas frações em n-hexano, diclorometano, acetato de etila e n-butanol. Dessa forma, obtiveram-se 12 frações que foram concentradas em rotaevaporador até a secura, pesadas e identificadas. As frações tiveram sua atividade antimicrobiana avaliada através de duas técnicas: técnica da bioautografia e técnica da microdiluição em microplaca (determinação da Concentração Inibitória Mínima), utilizando-se como indicadores biológicos as cepas Kocuria rhizophila, Staphylococcus aureus, Escherichia coli e Pseudomonas aeruginosa. A avaliação da atividade citotóxica foi realizada pela técnica do MTT, utilizando-se três linhagens de células tumorais MB435 (melanoma humano), HCT-8 (cólon humano) e SF-295 (glioblastoma humano). As frações tiveram também seus perfis químicos avaliados por Cromatografia Líquida de Alta Eficiência. Após observação dos resultados obtidos, concluiu-se que a fração diclorometânica, proveniente do meio fermentativo sólido, foi a que apresentou maior rendimento, manejo mais simples e perfil cromatográfico mais interessante, quando comparada às outras frações obtidas dos meios sólido e líquido. Desse modo, foi realizada ampliação da escala fermentativa em meio sólido e a fração diclorometânica obtida foi submetida a processos cromatográficos visando o isolamento das substâncias majoritárias. Assim, foram isoladas a substância 1 (não identificada) e a substância 2, identificada como terpestacina, um sesterpeno incomum com conhecida atividade na inibição da formação de sincícios pelo vírus HIV. A terpestacina foi isolada pela primeira vez do fungo Drechslera ravenelii no presente estudo. A substância 2 não apresentou atividade antimicrobiana quando submetida ao ensaio da microdiluição em microplaca e apresentou atividade citotóxica discreta, frente a três linhagens de células cancerígenas humanas. The interest in obtaining new drugs from endophytic microorganisms is growing, since this is a source still little exploited. In addition, the study of the interactions between plants and microorganisms has been widely discussed over the past few years. In this work, the endophytic fungus Drechslera ravenelii (SS33), isolated from the leaves of Smallanthus sonchifolius (yacon), was grown under different conditions, targeting the determination of the best conditions to produce secondary metabolites with antimicrobial and/or cytotoxic activities. For that, two parameters were evaluated: culture medium type and incubation time. The liquid media used were Czapek and Potato Dextrose Broth (PDB), swirling (120 RPM), cultivated for 216 and 480 hours, respectively. The fungus has also been culture by fermentation in solid substrate, rice-oats medium, during 720 hours. All crops were conducted in temperature of 30 °C and preceded by pre-fermentation. The obtained liquid mediums were submitted to liquid partition to furnish dichloromethane and ethyl acetate fractions. The solid medium was submitted to extraction to furnish the fractions in n-hexane, dichloromethane, ethyl acetate and n-butanol, in sequence. |Then, the 12 fractions obtained were dried, cumbersome and identified. The antimicrobial activity of the fractions was evaluated through two techniques: bioautography and Microdiluition method (Minimum Inhibitory Concentration-MIC), and for that, the biological indicators used were Kocuria rhizophila, Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa. The cytotoxic activity evaluation was performed by MTT test, using three tumor cell lines: MB435 (human melanoma), HCT-8 (human colon) and SF-295 (human glioblastoma). The chromatographic profiles of the fractions were evaluated by High Performance Liquid Chromatography. Analysis of the results allowed to conclude that the dichloromethane fraction from the solid medium gave greater yield, was easier to manager and more displayed an interesting chromatographic profile when compared to other fractions obtained from both solid and liquid media. Thus, the fungus was cultivated in a larger scale in solid medium and the dichloromethane fraction obtained was subjected to chromatographic processes aiming the isolation of the major compounds. Thus, two compounds were isolated the substance 1 (unidentified) and the substance 2, witch was identified as terpestacin, an uncommon sesterpene, which inhibits the formation of syncytia in the course of HIV infection. The terpestacin was isolated for the first time from the fungus Drechslera ravenelii in this study. The compound 2 did not presented antimicrobial activity when subjected to the microdilution test and it displayed discreet cytotoxic activity in three human cancer cell lines.

In this work we present a complete proton (1H) and carbon 13 (13C) nuclear magnetic resonance (NMR) spectral analysis of two synthetic dihydrofuran neolignans (±)-trans-dehydrodicoumarate dimethyl ester and (±)-trans-dehydrodiferulate dimethyl ester. Unequivocal assignments were achieved by 1H NMR, proton decoupled 13C (13C{1H}) NMR spectra, gradient-selected correlation spectroscopy (gCOSY), J-resolved, gradient-selected heteronuclear multiple quantum coherence (gHMQC), gradient-selected heteronuclear multiple bond coherence (gHMBC) and nuclear Overhauser effect spectroscopy (NOESY) experiments. All hydrogen coupling constants were measured, clarifying all the hydrogen signals multiplicities. Computational methods were also used to simulate the 1H and 13C chemical shifts and showed good agreement with the trans configuration of the substituents at C7 and C8.

The saturated nitrogen-containing heterocyclic compounds include many drugs and compounds that may be used as synthons for the synthesis of other pharmacologically active substances. The need for new derivatives of saturated nitrogen-containing heterocycles for organic synthesis, biotechnology and the pharmaceutical industry, including optically active derivatives, has increased interest in microbial synthesis. This review provides an overview of microbial technologies that can be valuable to produce new derivatives of saturated nitrogen-containing heterocycles, including hydroxylated derivatives. The chemo-, regio- and enantioselectivity of microbial processes can be indispensable for the synthesis of new compounds. Microbial processes carried out with fungi, including Beauveria bassiana, Cunninghamella verticillata, Penicillium simplicissimum, Aspergillus niger and Saccharomyces cerevisiae, and bacteria, including Pseudomonas sp., Sphingomonas sp. and Rhodococcus erythropolis, biotransform many substrates efficiently. Among the biological activities of saturated nitrogen-containing heterocyclic compounds are antimicrobial, antitumor, antihypertensive and anti-HIV activities; some derivatives are effective for the treatment and prevention of malaria and trypanosomiasis, and others are potent glycosidase inhibitors.

Biotransformation is an important tool for the structural modification of organic compounds, especially natural products with complex structures, which are difficult to achieve using ordinary methods. It is also useful as a model for mammalian metabolism due to similarities between mammalian and microbial enzyme systems. The development of novel biocatalytic methods is a continuously growing area of chemistry, microbiology, and genetic engineering, and novel microorganisms and/or their enzymes are being screened intensively. This review covers the transformation of non-terpenoid compounds such as steroids, coumarins, flavonoids, drugs, pesticides and others by Mucor spp. up to the end of 2012.

In the screening for biological active compounds, the biotransformation processes catalyzed by filamentous fungi are useful because they can provide information about the possible appearance of toxic metabolites after oral administration and also generate new leads. In this paper, biotransformation of lapachol (1) by three fungal strains, Mucor circinelloides NRRL3631, Botrytis cinerea UCA992 and Botrytis cinerea 2100, has been investigated for the first time. Lapachol (1) was biotransformed into avicequinone-A (2) by M. circinelloides, 3′-hydroxylapachol (3) by B. cinerea, and into dehydro-α-lapachone (4) by both fungi. All these compounds were evaluated for their cytotoxic activities. The metabolite 2 displayed non-selective cytotoxicity against tumor and normal cell lines, 3 did not show cytotoxicity against the same cells, while 4 showed higher cytotoxicity against cancer cell lines than lapachol (1). The transformation of 1 into harmless and reactive metabolites evidences the importance of the evaluation of drug metabolism in the drug discovery process. Antifungal potential of lapachol (1) and its metabolites 2 and 4 against B. cinerea has also been evaluated. Dehydro-α-lapachone (4) has been shown to be less toxic to fungal growth than lapachol (1), which indicates a detoxification mechanism of the phytopathogen.

In the natural products research, a valuable approach is the prospection of uncommon sources and unexplored habitat. Special attention has been given to endophytic fungi because of their ability to produce new and interesting secondary metabolites, which have several biological applications. The endophytes establish exclusive symbiotic relationships with plants and the metabolic interactions may support the synthesis of some similar valuables compounds. Among secondary metabolites, phenol-derived structures are responsible for several bioactivities such as antioxidant, cytotoxic, antimicrobial, among others. Phenolic compounds might be biosynthesized from the shikimate pathway. Although shikimic acid is a common precursor in plants, it is described as rare in microorganisms. To the best of our knowledge, this is the first review about phenolic compounds produced by endophytic fungi and a comparison has been made with those produced by the plant host. This review covers 124 phenolic secondary metabolites produced by endophytic fungi. Considering the data analyzed by us, only seven of such compounds were isolated from fungi and from their hosts. These observations claim for more attention to phenolic compounds produced by endophytic fungi with a view to understand the real importance of these compounds to endophytes survival.