Metabolism of androst-4-en-3,17-dione by the filamentous fungus Neurospora crassa
Microbial transformation of androst-4-en-3,17-dione (AD; I) using Neurospora crassa afforded six metabolites; 6β,14α-dihydroxyandrost-4-en-3,17-dione ( II), 6β,9α-dihydroxyandrost-4-en-3,17-dione ( III), 7α-hydroxyandrost-4-en-3,17-dione ( IV), 9α-hydroxyandrost-4-en-3,17-dione ( V), 14α-hydroxyandr...
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| Veröffentlicht in: | Steroids 2008, Vol.73 (1), p.13-18 |
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| creator | Faramarzi, Mohammad Ali Aghelnejad, Maryam Tabatabaei Yazdi, Mojtaba Amini, Mohsen Hajarolasvadi, Naghmeh |
| description | Microbial transformation of androst-4-en-3,17-dione (AD;
I) using
Neurospora crassa afforded six metabolites; 6β,14α-dihydroxyandrost-4-en-3,17-dione (
II), 6β,9α-dihydroxyandrost-4-en-3,17-dione (
III), 7α-hydroxyandrost-4-en-3,17-dione (
IV), 9α-hydroxyandrost-4-en-3,17-dione (
V), 14α-hydroxyandrost-4-en-3,17-dione (
VI), and androst-4,6-dien-3,17-dione (
VII). The steroid products were assigned by interpretation of their spectral data such as
1H NMR,
13C NMR, FTIR, and mass spectroscopy. The characteristic transformations observed were C-6β, C-7α, C-9α, C-14α hydroxylations, and C6–C7 dehydrogenation. The best fermentation condition was found to be 6-day incubation at 25
°C and pH value of 5.0–6.5 according to TLC profiles. Time course study showed the accumulation of
V and
VI from the third day and
IV from the fourth day of the fermentation. Optimum concentration of the substrate, which gave maximum bioconversion efficiency, was 3.5
mM in one batch. Biotransformation was completely inhibited in a concentration above 7.0
mM. |
| doi_str_mv | 10.1016/j.steroids.2007.06.008 |
| format | Article |
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I) using
Neurospora crassa afforded six metabolites; 6β,14α-dihydroxyandrost-4-en-3,17-dione (
II), 6β,9α-dihydroxyandrost-4-en-3,17-dione (
III), 7α-hydroxyandrost-4-en-3,17-dione (
IV), 9α-hydroxyandrost-4-en-3,17-dione (
V), 14α-hydroxyandrost-4-en-3,17-dione (
VI), and androst-4,6-dien-3,17-dione (
VII). The steroid products were assigned by interpretation of their spectral data such as
1H NMR,
13C NMR, FTIR, and mass spectroscopy. The characteristic transformations observed were C-6β, C-7α, C-9α, C-14α hydroxylations, and C6–C7 dehydrogenation. The best fermentation condition was found to be 6-day incubation at 25
°C and pH value of 5.0–6.5 according to TLC profiles. Time course study showed the accumulation of
V and
VI from the third day and
IV from the fourth day of the fermentation. Optimum concentration of the substrate, which gave maximum bioconversion efficiency, was 3.5
mM in one batch. Biotransformation was completely inhibited in a concentration above 7.0
mM.</description><identifier>ISSN: 0039-128X</identifier><identifier>EISSN: 1878-5867</identifier><identifier>DOI: 10.1016/j.steroids.2007.06.008</identifier><identifier>PMID: 17981313</identifier><identifier>CODEN: STEDAM</identifier><language>eng</language><publisher>New York, NY: Elsevier Inc</publisher><subject>Androst-4-en-3,17-dione ; Androstenedione - chemistry ; Androstenedione - metabolism ; Biological and medical sciences ; Biotransformation ; Fundamental and applied biological sciences. Psychology ; Hydrogen-Ion Concentration ; Molecular Structure ; Neurospora crassa ; Neurospora crassa - metabolism ; Temperature ; Vertebrates: endocrinology</subject><ispartof>Steroids, 2008, Vol.73 (1), p.13-18</ispartof><rights>2007</rights><rights>2008 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c462t-75098ee20ee6593699eb0b4500801f121e053a424d378036ada5168d28c69e0c3</citedby><cites>FETCH-LOGICAL-c462t-75098ee20ee6593699eb0b4500801f121e053a424d378036ada5168d28c69e0c3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.steroids.2007.06.008$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,4024,27923,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=19976968$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17981313$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Faramarzi, Mohammad Ali</creatorcontrib><creatorcontrib>Aghelnejad, Maryam</creatorcontrib><creatorcontrib>Tabatabaei Yazdi, Mojtaba</creatorcontrib><creatorcontrib>Amini, Mohsen</creatorcontrib><creatorcontrib>Hajarolasvadi, Naghmeh</creatorcontrib><title>Metabolism of androst-4-en-3,17-dione by the filamentous fungus Neurospora crassa</title><title>Steroids</title><addtitle>Steroids</addtitle><description>Microbial transformation of androst-4-en-3,17-dione (AD;
I) using
Neurospora crassa afforded six metabolites; 6β,14α-dihydroxyandrost-4-en-3,17-dione (
II), 6β,9α-dihydroxyandrost-4-en-3,17-dione (
III), 7α-hydroxyandrost-4-en-3,17-dione (
IV), 9α-hydroxyandrost-4-en-3,17-dione (
V), 14α-hydroxyandrost-4-en-3,17-dione (
VI), and androst-4,6-dien-3,17-dione (
VII). The steroid products were assigned by interpretation of their spectral data such as
1H NMR,
13C NMR, FTIR, and mass spectroscopy. The characteristic transformations observed were C-6β, C-7α, C-9α, C-14α hydroxylations, and C6–C7 dehydrogenation. The best fermentation condition was found to be 6-day incubation at 25
°C and pH value of 5.0–6.5 according to TLC profiles. Time course study showed the accumulation of
V and
VI from the third day and
IV from the fourth day of the fermentation. Optimum concentration of the substrate, which gave maximum bioconversion efficiency, was 3.5
mM in one batch. Biotransformation was completely inhibited in a concentration above 7.0
mM.</description><subject>Androst-4-en-3,17-dione</subject><subject>Androstenedione - chemistry</subject><subject>Androstenedione - metabolism</subject><subject>Biological and medical sciences</subject><subject>Biotransformation</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Hydrogen-Ion Concentration</subject><subject>Molecular Structure</subject><subject>Neurospora crassa</subject><subject>Neurospora crassa - metabolism</subject><subject>Temperature</subject><subject>Vertebrates: endocrinology</subject><issn>0039-128X</issn><issn>1878-5867</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkE1v1DAQhq0K1G4Lf6HKpZxwGMeJP25FFW2RWhASSNwsx56AV0m82AlS_z1e7aIee5rL88688xByyaBmwMSHbZ0XTDH4XDcAsgZRA6gTsmFKKtopIV-RDQDXlDXq5xk5z3kLAILr5pScMakV44xvyLdHXGwfx5CnKg6VnX2KeaEtxZny90xSH-KMVf9ULb-xGsJoJ5yXuOZqWOdfZXzBtSR2MdnKJZuzfUNeD3bM-PY4L8iP20_fb-7pw9e7zzcfH6hrRbNQ2YFWiA0gik5zoTX20Ldd-QLYwBqG0HHbNq3nUgEX1tuOCeUb5YRGcPyCvDvs3aX4Z8W8mClkh-NoZyz9jATWCSZ4AcUBdKVoTjiYXQqTTU-GgdnLNFvzX6bZyzQgTKlRgpfHC2s_oX-OHe0V4OoI2OzsOCQ7u5CfOa2l0GK_6PrAYfHxN2Ay2QWcHfqQ0C3Gx_BSl38HApTy</recordid><startdate>2008</startdate><enddate>2008</enddate><creator>Faramarzi, Mohammad Ali</creator><creator>Aghelnejad, Maryam</creator><creator>Tabatabaei Yazdi, Mojtaba</creator><creator>Amini, Mohsen</creator><creator>Hajarolasvadi, Naghmeh</creator><general>Elsevier Inc</general><general>Elsevier Science</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>2008</creationdate><title>Metabolism of androst-4-en-3,17-dione by the filamentous fungus Neurospora crassa</title><author>Faramarzi, Mohammad Ali ; Aghelnejad, Maryam ; Tabatabaei Yazdi, Mojtaba ; Amini, Mohsen ; Hajarolasvadi, Naghmeh</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c462t-75098ee20ee6593699eb0b4500801f121e053a424d378036ada5168d28c69e0c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Androst-4-en-3,17-dione</topic><topic>Androstenedione - chemistry</topic><topic>Androstenedione - metabolism</topic><topic>Biological and medical sciences</topic><topic>Biotransformation</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Hydrogen-Ion Concentration</topic><topic>Molecular Structure</topic><topic>Neurospora crassa</topic><topic>Neurospora crassa - metabolism</topic><topic>Temperature</topic><topic>Vertebrates: endocrinology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Faramarzi, Mohammad Ali</creatorcontrib><creatorcontrib>Aghelnejad, Maryam</creatorcontrib><creatorcontrib>Tabatabaei Yazdi, Mojtaba</creatorcontrib><creatorcontrib>Amini, Mohsen</creatorcontrib><creatorcontrib>Hajarolasvadi, Naghmeh</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Steroids</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Faramarzi, Mohammad Ali</au><au>Aghelnejad, Maryam</au><au>Tabatabaei Yazdi, Mojtaba</au><au>Amini, Mohsen</au><au>Hajarolasvadi, Naghmeh</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Metabolism of androst-4-en-3,17-dione by the filamentous fungus Neurospora crassa</atitle><jtitle>Steroids</jtitle><addtitle>Steroids</addtitle><date>2008</date><risdate>2008</risdate><volume>73</volume><issue>1</issue><spage>13</spage><epage>18</epage><pages>13-18</pages><issn>0039-128X</issn><eissn>1878-5867</eissn><coden>STEDAM</coden><abstract>Microbial transformation of androst-4-en-3,17-dione (AD;
I) using
Neurospora crassa afforded six metabolites; 6β,14α-dihydroxyandrost-4-en-3,17-dione (
II), 6β,9α-dihydroxyandrost-4-en-3,17-dione (
III), 7α-hydroxyandrost-4-en-3,17-dione (
IV), 9α-hydroxyandrost-4-en-3,17-dione (
V), 14α-hydroxyandrost-4-en-3,17-dione (
VI), and androst-4,6-dien-3,17-dione (
VII). The steroid products were assigned by interpretation of their spectral data such as
1H NMR,
13C NMR, FTIR, and mass spectroscopy. The characteristic transformations observed were C-6β, C-7α, C-9α, C-14α hydroxylations, and C6–C7 dehydrogenation. The best fermentation condition was found to be 6-day incubation at 25
°C and pH value of 5.0–6.5 according to TLC profiles. Time course study showed the accumulation of
V and
VI from the third day and
IV from the fourth day of the fermentation. Optimum concentration of the substrate, which gave maximum bioconversion efficiency, was 3.5
mM in one batch. Biotransformation was completely inhibited in a concentration above 7.0
mM.</abstract><cop>New York, NY</cop><pub>Elsevier Inc</pub><pmid>17981313</pmid><doi>10.1016/j.steroids.2007.06.008</doi><tpages>6</tpages></addata></record> |
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| subjects | Androst-4-en-3,17-dione Androstenedione - chemistry Androstenedione - metabolism Biological and medical sciences Biotransformation Fundamental and applied biological sciences. Psychology Hydrogen-Ion Concentration Molecular Structure Neurospora crassa Neurospora crassa - metabolism Temperature Vertebrates: endocrinology |
| title | Metabolism of androst-4-en-3,17-dione by the filamentous fungus Neurospora crassa |
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