Microbial O-Demethylation, Hydroxylation, Sulfation, and Ribosylation of a Xanthone Derivative from Halenia elliptica
1-Hydroxy-2,3,5-trimethoxyxanthone (1), one of the major xanthone derivatives isolated from Halenia elliptica, was biotransformed by two fungi, Trichothecium roseum and Paecilomyces marquandii. Transformation of 1 by T. roseumgave 1,5-dihydroxy-2,3-dimethoxyxanthone (2), 5-O-sulfate-1-hydroxy-2,3-di...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2006-05, Vol.69 (5), p.811-814 |
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| creator | Yuan, W Zhang, L.P Cheng, K.D Zhu, P Wang, Q He, H.X Zhu, H.X |
| description | 1-Hydroxy-2,3,5-trimethoxyxanthone (1), one of the major xanthone derivatives isolated from Halenia elliptica, was biotransformed by two fungi, Trichothecium roseum and Paecilomyces marquandii. Transformation of 1 by T. roseumgave 1,5-dihydroxy-2,3-dimethoxyxanthone (2), 5-O-sulfate-1-hydroxy-2,3-dimethoxyxanthone (3), 5-O-sulfate-1-hydroxy-2,3,7-trimethoxyxanthone (4), 5-O-beta-ribofuranosyl-1-hydroxy-2,3-dimethoxyxanthone (5), and 1,5,6-trihydroxy-2,3-dimethoxyxanthone (6). Compound 2 was also formed by P. marquandii. The structures of the isolated compounds were elucidated by spectroscopic analyses. Among the five microbial-converted compounds, 3, 4, 5, and 6 are new compounds. |
| doi_str_mv | 10.1021/np050472x |
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Transformation of 1 by T. roseumgave 1,5-dihydroxy-2,3-dimethoxyxanthone (2), 5-O-sulfate-1-hydroxy-2,3-dimethoxyxanthone (3), 5-O-sulfate-1-hydroxy-2,3,7-trimethoxyxanthone (4), 5-O-beta-ribofuranosyl-1-hydroxy-2,3-dimethoxyxanthone (5), and 1,5,6-trihydroxy-2,3-dimethoxyxanthone (6). Compound 2 was also formed by P. marquandii. The structures of the isolated compounds were elucidated by spectroscopic analyses. Among the five microbial-converted compounds, 3, 4, 5, and 6 are new compounds.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np050472x</identifier><identifier>PMID: 16724847</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>1-hydroxy-2,3,5-trimethoxyxanthone ; Ascomycota - metabolism ; Bioconversions. Hemisynthesis ; Biological and medical sciences ; Biotechnology ; Biotransformation ; chemical structure ; demethylation ; Fundamental and applied biological sciences. Psychology ; General pharmacology ; Gentianaceae - chemistry ; Gentianales ; Halenia elliptica ; Hydroxylation ; Medical sciences ; medicinal plants ; Methods. Procedures. Technologies ; microbial physiology ; Molecular Structure ; Oriental traditional medicine ; Paecilomyces ; Paecilomyces - metabolism ; Paecilomyces marquandii ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; plant pathogenic fungi ; Plants, Medicinal - chemistry ; spectral analysis ; sulfation ; Trichothecium roseum ; xanthones ; Xanthones - chemistry ; Xanthones - isolation & purification ; Xanthones - metabolism</subject><ispartof>Journal of natural products (Washington, D.C.), 2006-05, Vol.69 (5), p.811-814</ispartof><rights>2006 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27923,27924</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=17815604$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16724847$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yuan, W</creatorcontrib><creatorcontrib>Zhang, L.P</creatorcontrib><creatorcontrib>Cheng, K.D</creatorcontrib><creatorcontrib>Zhu, P</creatorcontrib><creatorcontrib>Wang, Q</creatorcontrib><creatorcontrib>He, H.X</creatorcontrib><creatorcontrib>Zhu, H.X</creatorcontrib><title>Microbial O-Demethylation, Hydroxylation, Sulfation, and Ribosylation of a Xanthone Derivative from Halenia elliptica</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>1-Hydroxy-2,3,5-trimethoxyxanthone (1), one of the major xanthone derivatives isolated from Halenia elliptica, was biotransformed by two fungi, Trichothecium roseum and Paecilomyces marquandii. Transformation of 1 by T. roseumgave 1,5-dihydroxy-2,3-dimethoxyxanthone (2), 5-O-sulfate-1-hydroxy-2,3-dimethoxyxanthone (3), 5-O-sulfate-1-hydroxy-2,3,7-trimethoxyxanthone (4), 5-O-beta-ribofuranosyl-1-hydroxy-2,3-dimethoxyxanthone (5), and 1,5,6-trihydroxy-2,3-dimethoxyxanthone (6). Compound 2 was also formed by P. marquandii. The structures of the isolated compounds were elucidated by spectroscopic analyses. Among the five microbial-converted compounds, 3, 4, 5, and 6 are new compounds.</description><subject>1-hydroxy-2,3,5-trimethoxyxanthone</subject><subject>Ascomycota - metabolism</subject><subject>Bioconversions. Hemisynthesis</subject><subject>Biological and medical sciences</subject><subject>Biotechnology</subject><subject>Biotransformation</subject><subject>chemical structure</subject><subject>demethylation</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>General pharmacology</subject><subject>Gentianaceae - chemistry</subject><subject>Gentianales</subject><subject>Halenia elliptica</subject><subject>Hydroxylation</subject><subject>Medical sciences</subject><subject>medicinal plants</subject><subject>Methods. Procedures. Technologies</subject><subject>microbial physiology</subject><subject>Molecular Structure</subject><subject>Oriental traditional medicine</subject><subject>Paecilomyces</subject><subject>Paecilomyces - metabolism</subject><subject>Paecilomyces marquandii</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>plant pathogenic fungi</subject><subject>Plants, Medicinal - chemistry</subject><subject>spectral analysis</subject><subject>sulfation</subject><subject>Trichothecium roseum</subject><subject>xanthones</subject><subject>Xanthones - chemistry</subject><subject>Xanthones - isolation & purification</subject><subject>Xanthones - metabolism</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpF0MFu1DAQBmALgehSOPAC4AucCIzt2E6OpQssqFUR20q9WRPHpoYkXuyk2n17Im0op_Ho_zSaMSEvGbxnwNmHYQcSSs33j8iKSQ6FAi4fkxUwJQpRqfKEPMv5FwAIqOVTcsKU5mVV6hWZLoNNsQnY0ati7Xo33h06HEMc3tHNoU1x_9Bup84vTxxa-iM0MS8hjZ4ivcVhvIuDo2uXwv0c3DvqU-zpBjs3BKSu68JuDBafkyceu-xeLPWU3Hz-dH2-KS6uvnw9P7sovAA2FhWC9E6gt22pmXPz2qVumrpsAevKlbVQtmWqsSClFJqzygkLdetbzazkjTglb49zdyn-mVweTR-yndfAwcUpG1UBaCH5DF8tcGp615pdCj2mg_n3UTN4swDMFjufcLAh_3e6YlJBObvi6EIe3f4hx_TbKC20NNfft-bb7cf6ci202cz-9dF7jAZ_pnnmzZYDm--HWrGKib8RUZAC</recordid><startdate>200605</startdate><enddate>200605</enddate><creator>Yuan, W</creator><creator>Zhang, L.P</creator><creator>Cheng, K.D</creator><creator>Zhu, P</creator><creator>Wang, Q</creator><creator>He, H.X</creator><creator>Zhu, H.X</creator><general>American Chemical Society</general><general>American Society of Pharmacognosy</general><scope>FBQ</scope><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>200605</creationdate><title>Microbial O-Demethylation, Hydroxylation, Sulfation, and Ribosylation of a Xanthone Derivative from Halenia elliptica</title><author>Yuan, W ; Zhang, L.P ; Cheng, K.D ; Zhu, P ; Wang, Q ; He, H.X ; Zhu, H.X</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-f301t-8a05fe3afcd471ee16747bb94d0a98e4936cd16bc055537218e3c09dfd71c52b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>1-hydroxy-2,3,5-trimethoxyxanthone</topic><topic>Ascomycota - metabolism</topic><topic>Bioconversions. Hemisynthesis</topic><topic>Biological and medical sciences</topic><topic>Biotechnology</topic><topic>Biotransformation</topic><topic>chemical structure</topic><topic>demethylation</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>General pharmacology</topic><topic>Gentianaceae - chemistry</topic><topic>Gentianales</topic><topic>Halenia elliptica</topic><topic>Hydroxylation</topic><topic>Medical sciences</topic><topic>medicinal plants</topic><topic>Methods. Procedures. Technologies</topic><topic>microbial physiology</topic><topic>Molecular Structure</topic><topic>Oriental traditional medicine</topic><topic>Paecilomyces</topic><topic>Paecilomyces - metabolism</topic><topic>Paecilomyces marquandii</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>plant pathogenic fungi</topic><topic>Plants, Medicinal - chemistry</topic><topic>spectral analysis</topic><topic>sulfation</topic><topic>Trichothecium roseum</topic><topic>xanthones</topic><topic>Xanthones - chemistry</topic><topic>Xanthones - isolation & purification</topic><topic>Xanthones - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yuan, W</creatorcontrib><creatorcontrib>Zhang, L.P</creatorcontrib><creatorcontrib>Cheng, K.D</creatorcontrib><creatorcontrib>Zhu, P</creatorcontrib><creatorcontrib>Wang, Q</creatorcontrib><creatorcontrib>He, H.X</creatorcontrib><creatorcontrib>Zhu, H.X</creatorcontrib><collection>AGRIS</collection><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yuan, W</au><au>Zhang, L.P</au><au>Cheng, K.D</au><au>Zhu, P</au><au>Wang, Q</au><au>He, H.X</au><au>Zhu, H.X</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Microbial O-Demethylation, Hydroxylation, Sulfation, and Ribosylation of a Xanthone Derivative from Halenia elliptica</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2006-05</date><risdate>2006</risdate><volume>69</volume><issue>5</issue><spage>811</spage><epage>814</epage><pages>811-814</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>1-Hydroxy-2,3,5-trimethoxyxanthone (1), one of the major xanthone derivatives isolated from Halenia elliptica, was biotransformed by two fungi, Trichothecium roseum and Paecilomyces marquandii. Transformation of 1 by T. roseumgave 1,5-dihydroxy-2,3-dimethoxyxanthone (2), 5-O-sulfate-1-hydroxy-2,3-dimethoxyxanthone (3), 5-O-sulfate-1-hydroxy-2,3,7-trimethoxyxanthone (4), 5-O-beta-ribofuranosyl-1-hydroxy-2,3-dimethoxyxanthone (5), and 1,5,6-trihydroxy-2,3-dimethoxyxanthone (6). Compound 2 was also formed by P. marquandii. The structures of the isolated compounds were elucidated by spectroscopic analyses. Among the five microbial-converted compounds, 3, 4, 5, and 6 are new compounds.</abstract><cop>Washington, DC</cop><cop>Glendale, AZ</cop><pub>American Chemical Society</pub><pmid>16724847</pmid><doi>10.1021/np050472x</doi><tpages>4</tpages></addata></record> |
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| subjects | 1-hydroxy-2,3,5-trimethoxyxanthone Ascomycota - metabolism Bioconversions. Hemisynthesis Biological and medical sciences Biotechnology Biotransformation chemical structure demethylation Fundamental and applied biological sciences. Psychology General pharmacology Gentianaceae - chemistry Gentianales Halenia elliptica Hydroxylation Medical sciences medicinal plants Methods. Procedures. Technologies microbial physiology Molecular Structure Oriental traditional medicine Paecilomyces Paecilomyces - metabolism Paecilomyces marquandii Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments plant pathogenic fungi Plants, Medicinal - chemistry spectral analysis sulfation Trichothecium roseum xanthones Xanthones - chemistry Xanthones - isolation & purification Xanthones - metabolism |
| title | Microbial O-Demethylation, Hydroxylation, Sulfation, and Ribosylation of a Xanthone Derivative from Halenia elliptica |
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