The marine environment is a promising source of natural products with possible pharmacological applications. In this sense, marine microorganisms, especially marine fungi, can produce bioactive compounds with various therapeutic... more
The marine environment is a promising source of natural products with possible pharmacological applications. In this sense, marine microorganisms, especially marine fungi, can produce bioactive compounds with various therapeutic properties. Colorectal cancer (CRC) represents a major health problem worldwide, since the treatments used to date are not capable of improving patient survival; that is why natural compounds from marine fungi offer a promising alternative. This study focused on evaluating the antitumor and antioxidant activity of fractions derived from the marine fungi E. maritima and P. lilacinum in two CRC cell lines T84 and SW480. Fractions Fr-EM6, Fr-EM7, Fr-EM8 and Fr-PLMOH-3 demonstrated potent cytotoxic activity in tested CRC cell lines with no activity in the non-tumor line. In particular, the Fr-PLMOH-3 fraction from P. lilacinum showed significant antiproliferative effects on T84 and SW480 cell lines and exhibited a greater cytotoxic effect on cancer stem cells co...
The biotransformation of botrydienediol (6) labelled with deuterium on carbons C-10 and C-15 has been studied. This has led to modification of some previous assumptions about the biodegradative route of botrydial. The... more
The biotransformation of botrydienediol (6) labelled with deuterium on carbons C-10 and C-15 has been studied. This has led to modification of some previous assumptions about the biodegradative route of botrydial. The [10-2H,15-2H]-botry-1(9)-4-diendiol (12) was transformed into dehydrobotrydienediol derivatives 13–15 but it was not incorporated into secobotryane skeleton (7). In addition, three new sesquiterpenoids have been isolated, which shed further
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ABSTRACT
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The labelling and coupling patterns of secobotrytrienediol, biosynthesised from [1-13C] and [1,2-13C2]-acetate by the fungus Botrytis cinerea, have been used to define the mode of formation and the biogenetic origin of... more
The labelling and coupling patterns of secobotrytrienediol, biosynthesised from [1-13C] and [1,2-13C2]-acetate by the fungus Botrytis cinerea, have been used to define the mode of formation and the biogenetic origin of secobotrytrienediol. [10-2H]-Botrydiol was not incorporated into the secobotryane skeleton. In addition, this feeding experiment led to the isolation of three new unlabelled derivatives possessing a secobotryane skeleton, secobotrydiene-3,10,15-triol, secobotrydiene-3,4,10,15-tetraol,
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Isotopic labelling experiments have been carried out in Datura stramonium root cultures with the following isotopically labelled precursors; [2H3]- [2-13C, 2H3]-, [1-13C, 18O2]-acetates, 2H2O, [2H3-methyl]-methionine,... more
Isotopic labelling experiments have been carried out in Datura stramonium root cultures with the following isotopically labelled precursors; [2H3]- [2-13C, 2H3]-, [1-13C, 18O2]-acetates, 2H2O, [2H3-methyl]-methionine, [2-13C]-phenyllactate, [3-2H]-tropine and [2'-13C, 3-2H]-littorine. The study explored the incorporation of isotope into the tropane ring system of littorine 1 and hyoscyamine 2 and revealed that deuterium from acetate is incorporated only into C-6 and C-7, and not into C-2 and C-4 as previously reported. Oxygen-18 was not retained at a detectable level into the C(3)-O bond from [1-13C, 18O2]-acetate. The intramolecular nature of the rearrangement of littorine 1 to hyoscyamine 2 is revealed again by a labelling study using [2'-13C, 3-2H]-littorine, [2-13C]-phenyllactate and [3-2H]-tropine.
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Research Interests: Chemistry, Natural Products, Medicine, Biological Sciences, Botrytis, and 14 moreStereochemistry, Sesquiterpenes, CHEMICAL SCIENCES, Diterpene, Spectrum analysis, Natural, Botrytis cinerea, Biotransformation, Isomerization, Hydroxylation, Molecular Structure, Thallophyta, Terpenoid, and Medical and Health Sciences
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Research Interests: Natural Products, Biology, Medicine, Biological Sciences, Botrytis, and 13 moreUlva lactuca, Lettuce, Sesquiterpenes, CHEMICAL SCIENCES, Botrytis cinerea, Biotransformation, Biological activity, Structure activity Relationship, Metabolite, Molecular Structure, Aldehydes, Medical and Health Sciences, and stereoisomerism
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Research Interests: Biology, Fungi, Medicine, Ulva lactuca, Antifungal, and 4 moreGermination, Fungus, Botrytis cinerea, and Phytotoxicity
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Eighteen compounds with a botryane skeleton have been obtained through chemical transformations of various toxins from the fungus Botrytis cinerea. During the course of these transformations, the C-10 carbon of the botryane skeleton was... more
Eighteen compounds with a botryane skeleton have been obtained through chemical transformations of various toxins from the fungus Botrytis cinerea. During the course of these transformations, the C-10 carbon of the botryane skeleton was found to exhibit an interesting high regioselectivity to oxidizing and reducing agents. In addition, the cytotoxicity of 27 botryane derivatives was determined in vitro against Hs578T, MDA-MB-231, HT-1080, U87-MG, IMR-90, and HUVEC cell lines. The results of this study confirm that the cytotoxicity of botrydial (1) and its derivatives is related to the presence of a 1,5-dialdehyde functionality.
Research Interests: Chemistry, Cytotoxicity, Medicine, Biological Sciences, Cell line, and 15 moreIn Vitro, Humans, Botrytis, Female, Fibrosarcoma, CHEMICAL SCIENCES, Cytotoxic Activity, Fungus, Botrytis cinerea, Chemical Synthesis, Molecular Structure, Aldol, Aldehydes, Breast Neoplasms, and Medical and Health Sciences
Marine microorganisms account for over 90% of ocean biomass and their diversity is believed to be the result of their ability to adapt to extreme conditions of the marine environment. Biotransformations are used to produce a wide range of... more
Marine microorganisms account for over 90% of ocean biomass and their diversity is believed to be the result of their ability to adapt to extreme conditions of the marine environment. Biotransformations are used to produce a wide range of high-added value materials, and marine-derived fungi have proven to be a source of new enzymes, even for activities not previously discovered. This review focuses on biotransformations by fungi from marine environments, including bioremediation, from the standpoint of the chemical structure of the substrate, and covers up to September 2022.
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Phytotoxic assays, performed both in vitro and in vivo on leaves of Phaseolus vulgaris, with metabolites excreted by the fungus B. cinerea are evaluated. Exogenous application of the phytotoxin botrydial has been found to produce severe... more
Phytotoxic assays, performed both in vitro and in vivo on leaves of Phaseolus vulgaris, with metabolites excreted by the fungus B. cinerea are evaluated. Exogenous application of the phytotoxin botrydial has been found to produce severe chlorosis and cell collapse and facilitated fungal penetration and colonization of plant tissue. The results also show a light-dependent action mechanism for the phytotoxin and seem to indicate that botrydial is a non-host-specific toxin involved in fungal infection of B. cinerea.
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Isotopic labelling experiments have been carried out in Datura stramonium root cultures with the following isotopically labelled precursors; [2H3]- [2-13C, 2H3]-, [1-13C, 18O2]-acetates, 2H2O, [2H3-methyl]-methionine,... more
Isotopic labelling experiments have been carried out in Datura stramonium root cultures with the following isotopically labelled precursors; [2H3]- [2-13C, 2H3]-, [1-13C, 18O2]-acetates, 2H2O, [2H3-methyl]-methionine, [2-13C]-phenyllactate, [3-2H]-tropine and [2'-13C, 3-2H]-littorine. The study explored the incorporation of isotope into the tropane ring system of littorine 1 and hyoscyamine 2 and revealed that deuterium from acetate is incorporated only into C-6 and C-7, and not into C-2 and C-4 as previously reported. Oxygen-18 was not retained at a detectable level into the C(3)-O bond from [1-13C, 18O2]-acetate. The intramolecular nature of the rearrangement of littorine 1 to hyoscyamine 2 is revealed again by a labelling study using [2'-13C, 3-2H]-littorine, [2-13C]-phenyllactate and [3-2H]-tropine.
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Patulin is a mycotoxin that contaminates pome fruits and derived products worldwide. Basidiomycete yeasts belonging to the subphylum Pucciniomycotina have been identified to have the ability to degrade this molecule efficiently and have... more
Patulin is a mycotoxin that contaminates pome fruits and derived products worldwide. Basidiomycete yeasts belonging to the subphylum Pucciniomycotina have been identified to have the ability to degrade this molecule efficiently and have been explored through different approaches to understand this degradation process. In this study, Sporobolomyces sp. strain IAM 13481 was found to be able to degrade patulin to form two different breakdown products, desoxypatulinic acid and ( Z ) - ascladiol. To gain insight into the genetic basis of tolerance and degradation of patulin, more than 3,000 transfer DNA (T-DNA) insertional mutants were generated in strain IAM 13481 and screened for the inability to degrade patulin using a bioassay based on the sensitivity of Escherichia coli to patulin. Thirteen mutants showing reduced growth in the presence of patulin were isolated and further characterized. Genes disrupted in patulin-sensitive mutants included homologs of Saccharomyces cerevisiae YCK2 ...
Research Interests: Microbiology, Biology, Oxidative Stress, Medicine, Multidisciplinary, and 15 moreSaccharomyces cerevisiae, Sequence alignment, Reactive Oxygen Species, Escherichia coli, Applied Environmental Microbiology, Biocontrol, Yeast, Membrane transport proteins, Mycotoxin, Base Sequence, Furans, Patulin, BASIDIOMYCOTA, Molecular Sequence Data, and Stress Physiological
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Marine microorganisms have proven to be a source of new natural products with a wide spectrum of biological activities relevant in different industrial sectors. The ever-increasing number of sequenced microbial genomes has highlighted a... more
Marine microorganisms have proven to be a source of new natural products with a wide spectrum of biological activities relevant in different industrial sectors. The ever-increasing number of sequenced microbial genomes has highlighted a discrepancy between the number of gene clusters potentially encoding the production of natural products and the actual number of chemically characterized metabolites for a given microorganism. Homologous and heterologous expression of these biosynthetic genes, which are often silent under experimental laboratory culture conditions, may lead to the discovery of new cryptic natural products of medical and biotechnological interest. Several new genetic and cultivation-based strategies have been developed to meet this challenge. The OSMAC approach (one strain—many compounds), based on modification of growth conditions, has proven to be a powerful strategy for the discovery of new cryptic natural products. As a direct extension of this approach, the addit...
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A small library of phorbol 12,13-diesters bearing low lipophilicity ester chains was prepared as potential neurogenic agents in the adult brain. They were also used in a targeted UHPLC-HRMS screening of the latex of Euphorbia resinifera.... more
A small library of phorbol 12,13-diesters bearing low lipophilicity ester chains was prepared as potential neurogenic agents in the adult brain. They were also used in a targeted UHPLC-HRMS screening of the latex of Euphorbia resinifera. Two new 12-deoxy-16-hydroxyphorbol 13,16-diesters were isolated, and their structures were deduced using two-dimensional NMR spectroscopy and NOE experiments. The ability of natural and synthetic compounds to stimulate transforming growth factor alpha (TFGα) release, to increase neural progenitor cell proliferation, and to stimulate neurogenesis was evaluated. All compounds that facilitated TGFα release promoted neural progenitor cell proliferation. The presence of two acyloxy moieties on the tigliane skeleton led to higher levels of activity, which decreased when a free hydroxyl group was at C-12. Remarkably, the compound bearing isobutyryloxy groups was the most potent on the TGFα assay and at inducing neural progenitor cell proliferation in vitro...
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Research Interests: Phytochemistry, Fungi, Biological Sciences, Colletotrichum, Fusarium, and 11 moreAsteraceae, Endophytic Fungi, CHEMICAL SCIENCES, Penicillium, Conformational Analysis, Colletotrichum gloeosporioides, Molecular Conformation, Chemical Structure, Molecular Structure, Fusarium Spp, and Medical and Health Sciences
The labelling and coupling patterns of secobotrytrienediol, biosynthesised from [1-13C] and [1,2-13C2]-acetate by the fungus Botrytis cinerea, have been used to define the mode of formation and the biogenetic origin of... more
The labelling and coupling patterns of secobotrytrienediol, biosynthesised from [1-13C] and [1,2-13C2]-acetate by the fungus Botrytis cinerea, have been used to define the mode of formation and the biogenetic origin of secobotrytrienediol. [10-2H]-Botrydiol was not incorporated into the secobotryane skeleton. In addition, this feeding experiment led to the isolation of three new unlabelled derivatives possessing a secobotryane skeleton, secobotrydiene-3,10,15-triol, secobotrydiene-3,4,10,15-tetraol,
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The development of novel biocatalytic methods is a continuously growing area of chemistry, microbiology, and genetic engineering due to the fact that biocatalysts are selective, easy-to-handle, and environmentally friendly. A wide range... more
The development of novel biocatalytic methods is a continuously growing area of chemistry, microbiology, and genetic engineering due to the fact that biocatalysts are selective, easy-to-handle, and environmentally friendly. A wide range of reactions are catalyzed by microorganisms. Fungi can be considered as a promising source of new biocatalysts, mainly for chiral reactions. Chemo-, regio-, and stereoselective processes are very
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The biotransformation of botrydienediol (6) labelled with deuterium on carbons C-10 and C-15 has been studied. This has led to modification of some previous assumptions about the biodegradative route of botrydial. The... more
The biotransformation of botrydienediol (6) labelled with deuterium on carbons C-10 and C-15 has been studied. This has led to modification of some previous assumptions about the biodegradative route of botrydial. The [10-2H,15-2H]-botry-1(9)-4-diendiol (12) was transformed into dehydrobotrydienediol derivatives 13–15 but it was not incorporated into secobotryane skeleton (7). In addition, three new sesquiterpenoids have been isolated, which shed further