Asymmetric microbial conversion of (E)-2-benzylideneindan-1-one by the filamentous fungi Botrytis cinerea, Trichoderma viride, and Eutypa lata

The transformation of (E)-2-benzylideneindan-1-one 1 by the filamentous fungi Botrytis cinerea, Trichoderma viride, and Eutypa lata as biocatalysts was studied. The results showed the catalytic potential of these fungi in affording several hydroxylation and reduction products, three of them reported here for the first time. The absolute configuration of enantiomerically pure 2-benzylindane derivatives was determined

Pollutants Biodegradation by Fungi

Revisión sobre los mecanismos de detoxificación de contaminantes por hongosOne of the major problems facing the industrialized world today is the contamination of soils, ground water, sediments, surfacewater and air with hazardous and toxic chemicals. The application of microorganisms which degrade or transform hazardous organic contaminants to less toxic compounds has become increasingly popular in recent years. This review, with approximately 300 references covering the period 2005-2008, describes the use of fungi as a method of bioremediation to clean up environmental pollutants

Metabolism of antifungal thiochroman-4-ones by Trichoderma viride and Botrytis cinerea

Biotransformation of 6-methylthiochroman-4- one (1) and 6-chlorothiochroman-4-one (2) was performed using Trichoderma viride in order to obtain new derivatives with antifungal properties against the phytopathogen Botrytis cinerea. Two thiochromanone derivatives are described for the first time. Antifungal activity of these compounds was tested against two different strains of Botrytis cinerea; 1 and 2 gave 100% inhibition of Bc2100 at 100−250 μg/mL, and 3 gave a maximal inhibition of 96% of BcUCA992 at 200 μg/mL. The detoxification mechanism of 1 and 2 by B. cinerea was also investigated

Asymmetric preparation of antifungal 1-(4 -chlorophenyl)-1-cyclopropyl methanol and 1-(4 -chlorophenyl)-2-phenylethanol. Study of the detoxification mechanism by Botrytis cinerea

Chiral alcohols are important as bioactive compounds or as precursors to such molecules. On the basis of the different antifungal properties of the enantiopure alcohol derivatives of 4-chlorophenyl cyclopropyl ketone and benzyl 4-chlorophenyl ketone, their enantioselective synthesis by chemical and biocatalytic methods was studied. The detoxification pathways by the phytopathogen fungus Botrytis cinerea are reported

Asymmetric microbial reduction of ketones: absolute configuration of trans-4-ethyl-1-(1S-hydroxyethyl)cyclohexanol

A set of five fungal species, Botrytis cinerea, Trichoderma viride and Eutypa lata, and the endophytic fungi Colletotrichum crassipes and Xylaria sp., was used in screening for microbial biocatalysts to detect monooxygenase and alcohol dehydrogenase activities (for the stereoselective reduction of carbonyl compounds). 4-Ethylcyclohexanone and acetophenone were biotransformed by the fungal set. The main reaction pathways involved reduction and hydroxylations at several positions including tertiary carbons. B. cinerea was very effective in the bioreduction of both substrates leading to the chiral alcohol (S)-1- phenylethanol in up to 90% enantiomeric excess, and the cis–trans ratio for 4-ethylcyclohexanol was 0:100. trans-4-Ethyl-1-(1S-hydroxyethyl)cyclohexanol, obtained from biotransformation by means of an acyloin-type reaction, is reported here for the first time. The absolute configurations of the compounds trans-4-ethyl-1-(1S-hydroxyethyl)cyclohexanol and 4-(1S- and 4-(1R-hydroxyethyl)cyclohexanone were determined by NMR analysis of the corresponding Mosher’s esters

Botrylactone: new interest in an old moleculedreview of its absolute configuration and related compounds

The absolute configuration of botrylactone, a unique compound with an interesting polyketide lactone skeleton with two oxirane bridges previously isolated from Botrytis cinerea and described as a powerful antibiotic, has been reviewed on the basis of sign of the optical rotation, NOE experiments and NMR method. The isolation of 7-deoxybotrylactone and 5-hydroxy-7-(4-hydroxydec-2(3)-enoyl) botrylactone enables us to characterize an intriguing new family of compounds with this interesting polyketide skeleton. A common biosynthetic origin with botcinin derivatives is proposed

Study of the secondary metabolism of phytopathogenic fungi as a source of compounds with antibiotic activity.

Eutypa lata is a phytopathogenic fungus responsible for a "Grapevine Trunk Disease" commonly called "eutypiosis" or "eutypa dieback" which affects several agricultural crops. Its secondary metabolism has been studied in order to find the main toxins that cause the symptoms of the disease, and to learn how to control its production. One of the most phytophatogenic toxins is Eutypine, a hydroxybenzaldehyde, among several acetylenic derivatives related with it. Syccaine is one of them and exhibits antimicrobial activity against Aerobacter aerogenes and a variety of Gram-positive bacteria, and few fungi. That is why, in this study, we enviosioned the study of the secondary metabolism of E. lata as a producer of natural acetylenic compounds with antimicrobial activity to give response to the worlwide problem posed by the shortage of new antibiotics development.Throught OSMAC (One Strain Many Compounds) approach, two strains of the fungus, E. lata 355 y E. lata 311, were grown using different cultivation conditions like culture media composition, aeration, type of culture flask or incubation time. The extract obtained from the extraction with ethyl acetate of the culture media, was tested against Escherichia coli, Staphylococcus aureus and Klebsiella pneumoniae using the broth dilution method. Then, the extracts with antibiotical activity were purified in order to obtain pure compounds to find which compound are responsible for the antibiotical activity.The preliminary results of the research have indicated that OSMAC approach estimulates the production of compounds with antibiotic activity in some of the culture conditions tested

Biocatalytic Preparation of Chloroindanol Derivatives. Antifungal Activity and Detoxification by the Phytopathogenic Fungus Botrytis cinerea

Indanols are a family of chemical compounds that have been widely studied due to their broad range of biological activity. They are also important intermediates used as synthetic precursors to other products with important applications in pharmacology. Enantiomerically pure chloroindanol derivatives exhibiting antifungal activity against the phytopathogenic fungus Botrytis cinerea were prepared using biocatalytic methods. As a result of the biotransformation of racemic 6-chloroindanol (1) and 5-chloroindanol (2) by the fungus B. cinerea, the compounds anti-(+)-6-chloroindan-1,2-diol (anti-(+)-7), anti-(+)-5-chloroindan-1,3-diol (anti-(+)-8), syn-(+)-5-chloroindan-1,3-diol (syn-(+)-8), syn-(-)-5-chloroindan-1,3-diol (syn-(-)-8), and anti-(+)-5-chloroindan-1,2-diol (anti-(+)-9) were isolated for the first time. These products were characterized by spectroscopic techniques and their enantiomeric excesses studied by chromatographic techniques. The results obtained in the biotransformation seem to suggest that the fungus B. cinerea uses oxidation reactions as a detoxification mechanism

Biocatalytic preparation and absolute configuration of enantiomerically pure fungistatic anti-2-benzylindane derivatives. Study of the detoxification mechanism by Botrytis cinerea

Enantiomerically pure 2-benzylindane derivatives were prepared using biocatalytic methods and their absolute configuration determined. (1R,2S)-2-Benzylindan-1-ol ((1R,2S)-2) and (S)-2-benzylindan-1-one ((S)-3) were produced by fermenting baker’s yeast. Lipase-mediated esterifications and hydrolysis of the corresponding racemic substrates gave rise to the enantiopure compounds (1S,2R)-2-benzylindan-1-ol ((1S,2R)-2) and (1R,2S)-2-benzylindan-1-ol ((1R,2S)-2), respectively. The antifungal activity of these products against two strains of the plant pathogen Botrytis cinerea was tested. The metabolism of anti-(±)-2-benzylindan-1-ol (anti-(±)-2) by B. cinerea as part of the fungal detoxification mechanism is also described and revealed interesting differences in the genome of both strains

Optimization of ultrasound-assisted extraction of bioactive compounds from jabuticaba (Myrciaria cauliflora) fruit through a Box-Behnken experimental design

Jabuticaba is a very popular fruit in Brazil being a great source of compounds with considerable biological activities. Novel optimized ultrasound-assisted extraction (UAE) methods have been proposed for anthocyanins and total phenolic compounds from jabuticaba. A Box–Behnken experimental design (BBD) with a response surface methodology (RSM) was used to investigate the effect of six independent variables (solvent composition, solvent-to-sample ratio, ultrasound amplitude and cycle, pH, and temperature) on the UAE. Solvent composition was found to be the most significant variable for the extraction of both anthocyanins (51%) and total phenolic compounds (72%). The other optimum conditions for anthocyanins were as follows: pH 7.00, 39.8 ºC, 20:1.5 mL:g solvent-to-sample ratio, 34% ultrasound amplitude and cycle of 0.47 seconds. The optimum conditions for the extraction of phenolic compounds were: pH 7.00, 26.0 ºC, 20:1.5 (mL:g) solvent-to-sample ratio, 68.5% ultrasound amplitude and cycle of 0.5 seconds. The extraction kinetic was also evaluated. The developed methods showed a high precision, with coefficients of variation of less than 5% for both repeatability and intermediate precision (within-lab reproducibility). The applicability of the new methods was successfully evaluated on several fruits and jams from jabuticaba