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      Use of P450 cytochrome inhibitors in studies of enokipodin biosynthesis

      research-article

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          Abstract

          Enokipodins A, B, C, and D are antimicrobial sesquiterpenes isolated from the mycelial culture medium of Flammulina velutipes, an edible mushroom. The presence of a quaternary carbon stereocenter on the cyclopentane ring makes enokipodins A-D attractive synthetic targets. In this study, nine different cytochrome P450 inhibitors were used to trap the biosynthetic intermediates of highly oxygenated cuparene-type sesquiterpenes of F. velutipes. Of these, 1-aminobenzotriazole produced three less-highly oxygenated biosynthetic intermediates of enokipodins A-D; these were identified as ( S)-(−)-cuparene-1,4-quinone and epimers at C-3 of 6-hydroxy-6-methyl-3-(1,2,2-trimethylcyclopentyl)-2-cyclohexen-1-one. One of the epimers was found to be a new compound.

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          Therapeutic effects of substances occurring in higher Basidiomycetes mushrooms: a modern perspective.

          Jeffrey S Wasser, Jennifer Weis (1998)
          This review highlights some of the recently isolated and identified substances of higher Basidiomycetes mushrooms origin that express promising antitumor, immune modulating, cardiovascular and hypercholesterolemia, antiviral, antibacterial, and antiparasitic effects. Medicinal mushrooms have a long history of use in folk medicine. In particular, mushrooms useful against cancers of the stomach, esophagus, lungs, etc. are known in China, Russia, Japan, Korea, as well as the U.S.A. and Canada. There are about 200 species of mushrooms that have been found to markedly inhibit the growth of different kinds of tumors. Searching for new antitumor and other medicinal substances from mushrooms and to study the medicinal value of these mushrooms have become a matter of great significance. However, most of the mushroom origin antitumor substances have not been clearly defined. Several antitumor polysaccharides such as hetero-beta-glucans and their protein complexes (e.g., xyloglucans and acidic beta-glucan-containing uronic acid), as well as dietary fibers, lectins, and terpenoids have been isolated from medicinal mushrooms. In Japan, Russia, China, and the U.S.A. several different polysaccharide antitumor agents have been developed from the fruiting body, mycelia, and culture medium of various medicinal mushrooms (Lentinus edodes, Ganoderma lucidum, Schizophyllum commune, Trametes versicolor, Inonotus obliquus, and Flammulina velutipes). Both cellular components and secondary metabolites of a large number of mushrooms have been shown to effect the immune system of the host and therefore could be used to treat a variety of disease states.
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            Cytochrome P450 enzyme systems in fungi.

            Hans van den Brink, Robert van Gorcom, Cees van den Hondel … (1998)
            The involvement of cytochrome P450 enzymes in many complex fungal bioconversion processes has been characterized in recent years. Accordingly, there is now considerable scientific interest in fungal cytochrome P450 enzyme systems. In contrast to S. cerevisiae, where surprisingly few P450 genes have been identified, biochemical data suggest that many fungi possess numerous P450 genes. This review summarizes the current information pertaining to these fungal cytochrome P450 systems, with emphasis on the molecular genetics. The use of molecular techniques to improve cytochrome P450 activities in fungi is also discussed.
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              A new fungal immunomodulatory protein, FIP-fve isolated from the edible mushroom, Flammulina velutipes and its complete amino acid sequence.

              Chin Lin, Raymond Kao, Y. Lin … (1995)
              A new fungal immunomodulatory protein (FIP-fve) has been isolated and purified from the edible golden needle mushroom (Flammulina velutipes). The apparent molecular mass of FIP-fve determined by SDS/PAGE agrees well with the value of 12704 Da calculated from its amino acid composition and sequence. The complete amino acid sequence of FIP-fve was elucidated by protein sequencing techniques. FIP-fve consists of 114 amino acid residues with an acetylated amino end, and lacks methionine, half-cystine and histidine residues. FIP-fve was able to hemagglutinate human red blood cells. The immunomodulatory activity of FIP-fve was demonstrated by its stimulatory activity toward human peripheral blood lymphocytes, and its suppression of systemic anaphylaxis reactions and local swelling of mouse footpads. FIP-fve was found to enhance the transcriptional expression of interleukin-2 and interferon-gamma.
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                Author and article information

                Journal
                Journal ID (nlm-ta): Braz J Microbiol
                Journal ID (iso-abbrev): Braz. J. Microbiol
                Title: Brazilian Journal of Microbiology
                Publisher: Brazilian Society of Microbiology
                ISSN (Print): 1517-8382
                ISSN (Electronic): 1678-4405
                Publication date Collection: December 2013
                Publication date (Electronic): 10 March 2014
                Volume: 44
                Issue: 4
                Pages: 1285-1290
                Affiliations
                [1 ]Division of Environmental Resources, Graduate School of Agriculture, Hokkaido University, Sapporo, Japan.
                [2 ]Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University, Sapporo, Japan.
                Author notes
                Send correspondence to N.K. Ishikawa. Coordenação de Biodiversidade, Instituto Nacional de Pesquisas da Amazônia, Av. André Araújo 2936, 69067-375 Manaus, AM, Brazil. E-mail: noemia@ 123456inpa.gov.br .
                Article
                Publisher ID: bmj-44-4-1285
                PMC ID: 3958200
                PubMed ID: 24688524
                SO-VID: 02150a11-5731-42a4-880f-c692c0b3fe19
                Copyright © Copyright © 2013, Sociedade Brasileira de Microbiologia
                License:

                All the content of the journal, except where otherwise noted, is licensed under a Creative Commons License CC BY-NC.

                History
                Date received : 27 November 2011
                Date accepted : 04 April 2013
                Categories
                Subject: Research Paper

                Keywords: antimicrobial compound,cuparene-1,4-quinone,edible mushroom,enokitake,flammulina velutipes
                Data availability:
                Keywords: antimicrobial compound, cuparene-1, 4-quinone, edible mushroom, enokitake, flammulina velutipes

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