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

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

Síntesis de moléculas híbridas, inspiradas en la genómica, como antifúngicos contra el hongo fitopatógeno Botrytis cinerea

En esta conferencia se han presentado los últimos resultados en la investigación del grupo que dirige el Prof. Isidro González para el diseño de nuevos agentes antifúngicos frente al hongo Botrytis cinerea que resulta particularmente perjudicial para las plantaciones de diversas frutas y verduras, entre las que se encuentra el de la uva. Así, mediante estudios bioquímicos y genómicos han identificado las toxinas del hongo causantes de su poder destructivo, así como las enzimas implicadas en su biosíntesis. Con ello, han diseñado moléculas capaces de inhibir algunas de estas enzimas y con ello el bloqueo de la producción de tales toxinas, con lo que se consigue frenar el crecimiento del hongo. Estas moléculas se han basado en derivados terpénicos del clovano, realizándose un amplio estudio de relación estructura-actividad con el que han identificado potentes inhibidores que representan prometedores agentes antifúngicos frente a este tipo de hongos.Universidad de Málaga. Campus de Excelencia Internacional Andalucía Tech

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

Comparative genome analysis of Bacillus spp. and its relationship with bioactive nonribosomal peptide production

Bacillus genus comprises an important number of species which produce a wide range of secondary metabolites displaying a broad spectrum of activity and great structural diversity. The genome sequences of an important number of species have been published and a large number of orphan genes reported. This review, covering all the literature in this field up to end of 2011, summarizes and compares the genetic potential of these organisms from the point of view of bioactive nonribosomal peptide production and their application as antibiotics, plant pathogen biocontrol, promotion of plant growth, etc. The biological and structural studies of the peptides isolated from Bacillus species are revised and some aspects of the biosynthesis of these metabolites and related compounds are discussed

Stereoselective Synthesis and Absolute Configuration Determination of Xylariolide A

The asymmetric synthesis of the antibacterial and antitumoral natural compound xylariolide A (1) and five stereoisomers has been achieved. The strategy is based on the onepot epoxidation/lactonisation or dihydroxylation/lactonisation of the hypothetical biosynthetic intermediate xylarioic A acid (8). The absolute configuration of xylariolide A was thus determined to be 3R,4S,5R,1 R,2 R after the synthesis of 1, two epimers, i.e., 1 -epi-xylariolide A (3) and 2 -epi-xylariolide A (4), and three more diastereoisomers 5–7

Degraded limonoids: biologically active limonoid fragments re-enhancing interest in Meliaceae and Rutaceae sources

Phytochemical studies on the roots, twigs and leaves of Meliaceae and Rutaceae family plants have revealed the presence of non-complex terpenes derived from limonoid fragmentation. The occurrence and chemical structure of these degraded limonoids isolated from 1930 to March 2022 are reported in this review. Particular attention is given to the degradation levels in these compounds and their absolute configuration to discover presumable deconstruction pathways from more complex limonoids. Plausible intermediates have been postulated for most of them that would explain their origin from limonoids. The total or semi-synthesis of the most isolated degraded limonoids or analogues remains undescribed. This review focuses on the bioactivity of these fragmented limonoids and their synthesized analogues. Based on pharmacological and agrochemical studies, degraded limonoids appear to be excellent structural leads to consider for the total or semi-synthesis of more potent derivatives with the aim of discovering new hits and clarifying their modes of action

Non-terpenoid biotransformations by Mucor species

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