Aspergillus fumigatus CY018, an endophytic fungus in Cynodon dactylon as a versatile producer of new and bioactive metabolites
Aspergillus fumigatus CY018 was recognized as an endophytic fungus for the first time in the leaf of Cynodon dactylon. By bioassay-guided fractionation, the EtOAc extract of a solid-matrix steady culture of this fungus afforded two new metabolites, named asperfumoid ( 1) and asperfumin ( 2), togethe...
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| Veröffentlicht in: | Journal of biotechnology 2004-11, Vol.114 (3), p.279-287 |
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| creator | Liu, J.Y. Song, Y.C. Zhang, Z. Wang, L. Guo, Z.J. Zou, W.X. Tan, R.X. |
| description | Aspergillus fumigatus CY018 was recognized as an endophytic fungus for the first time in the leaf of
Cynodon dactylon. By bioassay-guided fractionation, the EtOAc extract of a solid-matrix steady culture of this fungus afforded two new metabolites, named asperfumoid (
1) and asperfumin (
2), together with six known bioactive compounds including monomethylsulochrin, fumigaclavine C, fumitremorgin C, physcion, helvolic acid and 5α,8α-epidioxy-ergosta-6,22-diene-3β-ol as well as other four known compounds ergosta-4,22-diene-3β-ol, ergosterol,
cyclo(Ala-Leu) and
cyclo(Ala-Ile). Through detailed spectroscopic analyses including HRESI-MS, homo- and hetero-nuclear correlation NMR experiments (HMQC, COSY, NOESY and HMBC), the structures of asperfumoid and asperfumin were established to be spiro-(3-hydroxyl-2,6-dimethoxyl-2,5-diene-4-cyclohexone-(1,3′)-5′-methoxyl-7′-methyl-(1′H, 2′H, 4′H)-quinoline-2′,4′-dione) and 5-hydroxyl-2-(6-hydroxyl-2-methoxyl-4-methylbenzoyl)-3,6-dimethoxyl-benzoic methyl ester, respectively. All of the 12 isolates were subjected to in vitro bioactive assays against three human pathogenic fungi
Candida albicans, Tricophyton rubrum and
Aspergillus niger. As a result, asperfumoid, fumigaclavine C, fumitremorgin C, physcion and helvolic acid were shown to inhibit
C. albicans with MICs of 75.0, 31.5, 62.5, 125.0 and 31.5
μg/mL, respectively. |
| doi_str_mv | 10.1016/j.jbiotec.2004.07.008 |
| format | Article |
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Cynodon dactylon. By bioassay-guided fractionation, the EtOAc extract of a solid-matrix steady culture of this fungus afforded two new metabolites, named asperfumoid (
1) and asperfumin (
2), together with six known bioactive compounds including monomethylsulochrin, fumigaclavine C, fumitremorgin C, physcion, helvolic acid and 5α,8α-epidioxy-ergosta-6,22-diene-3β-ol as well as other four known compounds ergosta-4,22-diene-3β-ol, ergosterol,
cyclo(Ala-Leu) and
cyclo(Ala-Ile). Through detailed spectroscopic analyses including HRESI-MS, homo- and hetero-nuclear correlation NMR experiments (HMQC, COSY, NOESY and HMBC), the structures of asperfumoid and asperfumin were established to be spiro-(3-hydroxyl-2,6-dimethoxyl-2,5-diene-4-cyclohexone-(1,3′)-5′-methoxyl-7′-methyl-(1′H, 2′H, 4′H)-quinoline-2′,4′-dione) and 5-hydroxyl-2-(6-hydroxyl-2-methoxyl-4-methylbenzoyl)-3,6-dimethoxyl-benzoic methyl ester, respectively. All of the 12 isolates were subjected to in vitro bioactive assays against three human pathogenic fungi
Candida albicans, Tricophyton rubrum and
Aspergillus niger. As a result, asperfumoid, fumigaclavine C, fumitremorgin C, physcion and helvolic acid were shown to inhibit
C. albicans with MICs of 75.0, 31.5, 62.5, 125.0 and 31.5
μg/mL, respectively.</description><identifier>ISSN: 0168-1656</identifier><identifier>EISSN: 1873-4863</identifier><identifier>DOI: 10.1016/j.jbiotec.2004.07.008</identifier><identifier>PMID: 15522437</identifier><identifier>CODEN: JBITD4</identifier><language>eng</language><publisher>Lausanne: Elsevier B.V</publisher><subject>animal pathogenic fungi ; Antifungal ; Antifungal Agents - metabolism ; Antifungal Agents - pharmacology ; antifungal properties ; Asperfumin ; Asperfumoid ; Aspergillus fumigatus ; Aspergillus fumigatus - isolation & purification ; Aspergillus fumigatus - metabolism ; Aspergillus niger ; Benzoates - metabolism ; Benzophenones - chemistry ; Biological and medical sciences ; biosynthesis ; Biotechnology ; Candida albicans ; Candida albicans - drug effects ; Cynodon - microbiology ; Cynodon dactylon ; Emodin - analogs & derivatives ; Emodin - metabolism ; Emodin - pharmacology ; Endophyte ; endophytes ; Ergosterol - analogs & derivatives ; Ergosterol - metabolism ; Ergot Alkaloids ; Fundamental and applied biological sciences. Psychology ; Fusidic Acid - analogs & derivatives ; Fusidic Acid - metabolism ; Fusidic Acid - pharmacology ; Hydroxybenzoate Ethers ; Hydroxybenzoates - chemistry ; Indole Alkaloids - metabolism ; Indole Alkaloids - pharmacology ; Indoles - metabolism ; Indoles - pharmacology ; Industrial Microbiology - methods ; Magnetic Resonance Spectroscopy ; Microbial Sensitivity Tests ; Molecular Structure ; Peptides, Cyclic - metabolism ; Plant Leaves - microbiology ; Pyrones - chemistry ; Pyrones - metabolism ; Quinolones - chemistry ; Quinolones - metabolism ; secondary metabolites</subject><ispartof>Journal of biotechnology, 2004-11, Vol.114 (3), p.279-287</ispartof><rights>2004 Elsevier B.V.</rights><rights>2004 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c483t-96b420694df5200fba4cbcbbb624676db2ada2f98e3f402c3714151570ddc8eb3</citedby><cites>FETCH-LOGICAL-c483t-96b420694df5200fba4cbcbbb624676db2ada2f98e3f402c3714151570ddc8eb3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0168165604004043$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3536,27903,27904,65309</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=16242439$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15522437$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Liu, J.Y.</creatorcontrib><creatorcontrib>Song, Y.C.</creatorcontrib><creatorcontrib>Zhang, Z.</creatorcontrib><creatorcontrib>Wang, L.</creatorcontrib><creatorcontrib>Guo, Z.J.</creatorcontrib><creatorcontrib>Zou, W.X.</creatorcontrib><creatorcontrib>Tan, R.X.</creatorcontrib><title>Aspergillus fumigatus CY018, an endophytic fungus in Cynodon dactylon as a versatile producer of new and bioactive metabolites</title><title>Journal of biotechnology</title><addtitle>J Biotechnol</addtitle><description>Aspergillus fumigatus CY018 was recognized as an endophytic fungus for the first time in the leaf of
Cynodon dactylon. By bioassay-guided fractionation, the EtOAc extract of a solid-matrix steady culture of this fungus afforded two new metabolites, named asperfumoid (
1) and asperfumin (
2), together with six known bioactive compounds including monomethylsulochrin, fumigaclavine C, fumitremorgin C, physcion, helvolic acid and 5α,8α-epidioxy-ergosta-6,22-diene-3β-ol as well as other four known compounds ergosta-4,22-diene-3β-ol, ergosterol,
cyclo(Ala-Leu) and
cyclo(Ala-Ile). Through detailed spectroscopic analyses including HRESI-MS, homo- and hetero-nuclear correlation NMR experiments (HMQC, COSY, NOESY and HMBC), the structures of asperfumoid and asperfumin were established to be spiro-(3-hydroxyl-2,6-dimethoxyl-2,5-diene-4-cyclohexone-(1,3′)-5′-methoxyl-7′-methyl-(1′H, 2′H, 4′H)-quinoline-2′,4′-dione) and 5-hydroxyl-2-(6-hydroxyl-2-methoxyl-4-methylbenzoyl)-3,6-dimethoxyl-benzoic methyl ester, respectively. All of the 12 isolates were subjected to in vitro bioactive assays against three human pathogenic fungi
Candida albicans, Tricophyton rubrum and
Aspergillus niger. As a result, asperfumoid, fumigaclavine C, fumitremorgin C, physcion and helvolic acid were shown to inhibit
C. albicans with MICs of 75.0, 31.5, 62.5, 125.0 and 31.5
μg/mL, respectively.</description><subject>animal pathogenic fungi</subject><subject>Antifungal</subject><subject>Antifungal Agents - metabolism</subject><subject>Antifungal Agents - pharmacology</subject><subject>antifungal properties</subject><subject>Asperfumin</subject><subject>Asperfumoid</subject><subject>Aspergillus fumigatus</subject><subject>Aspergillus fumigatus - isolation & purification</subject><subject>Aspergillus fumigatus - metabolism</subject><subject>Aspergillus niger</subject><subject>Benzoates - metabolism</subject><subject>Benzophenones - chemistry</subject><subject>Biological and medical sciences</subject><subject>biosynthesis</subject><subject>Biotechnology</subject><subject>Candida albicans</subject><subject>Candida albicans - drug effects</subject><subject>Cynodon - microbiology</subject><subject>Cynodon dactylon</subject><subject>Emodin - analogs & derivatives</subject><subject>Emodin - metabolism</subject><subject>Emodin - pharmacology</subject><subject>Endophyte</subject><subject>endophytes</subject><subject>Ergosterol - analogs & derivatives</subject><subject>Ergosterol - metabolism</subject><subject>Ergot Alkaloids</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Fusidic Acid - analogs & derivatives</subject><subject>Fusidic Acid - metabolism</subject><subject>Fusidic Acid - pharmacology</subject><subject>Hydroxybenzoate Ethers</subject><subject>Hydroxybenzoates - chemistry</subject><subject>Indole Alkaloids - metabolism</subject><subject>Indole Alkaloids - pharmacology</subject><subject>Indoles - metabolism</subject><subject>Indoles - pharmacology</subject><subject>Industrial Microbiology - methods</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Microbial Sensitivity Tests</subject><subject>Molecular Structure</subject><subject>Peptides, Cyclic - metabolism</subject><subject>Plant Leaves - microbiology</subject><subject>Pyrones - chemistry</subject><subject>Pyrones - metabolism</subject><subject>Quinolones - chemistry</subject><subject>Quinolones - metabolism</subject><subject>secondary metabolites</subject><issn>0168-1656</issn><issn>1873-4863</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0U1v1DAQBuAIgei28BMAX-BEwjhxnORUVSsKSJU4QA-cLH9MFq-SeLGTRXvhtzPVRuqxJ4_kx-Ox3yx7w6HgwOWnfbE3PsxoixJAFNAUAO2zbMPbpspFK6vn2YZcm3NZy4vsMqU9EOxq_jK74HVdlqJqNtm_m3TAuPPDsCTWL6Pf6Zmq7S_g7UemJ4aTC4ffp9lb2p52tOcntj1NwYWJOW3n00CFTkyzI8akZz8gO8TgFouRhZ5N-Jf6OEbTkvZHZCPO2oTBz5heZS96PSR8va5X2f3t55_br_nd9y_ftjd3uRVtNeedNKIE2QnX1_Tc3mhhjTXGyFLIRjpTaqfLvmux6gWUtmq44DWvG3DOtmiqq-zDuS9N9mfBNKvRJ4vDoCcMS1KygaoDWT0JedNwaEEQrM_QxpBSxF4doh91PCkO6iEhtVdrQuohIQWNooTo3Nv1gsWM6B5PrZEQeL8Cnawe-qgn69OjoyeT68i9O7teB6V3kcz9jxJ4BdBJ6HhN4voskH726DGqZD1OFp2PaGflgn9i2P9OlrwW</recordid><startdate>20041109</startdate><enddate>20041109</enddate><creator>Liu, J.Y.</creator><creator>Song, Y.C.</creator><creator>Zhang, Z.</creator><creator>Wang, L.</creator><creator>Guo, Z.J.</creator><creator>Zou, W.X.</creator><creator>Tan, R.X.</creator><general>Elsevier B.V</general><general>Elsevier</general><scope>FBQ</scope><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>7QO</scope><scope>7T7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>M7N</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20041109</creationdate><title>Aspergillus fumigatus CY018, an endophytic fungus in Cynodon dactylon as a versatile producer of new and bioactive metabolites</title><author>Liu, J.Y. ; Song, Y.C. ; Zhang, Z. ; Wang, L. ; Guo, Z.J. ; Zou, W.X. ; Tan, R.X.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c483t-96b420694df5200fba4cbcbbb624676db2ada2f98e3f402c3714151570ddc8eb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>animal pathogenic fungi</topic><topic>Antifungal</topic><topic>Antifungal Agents - metabolism</topic><topic>Antifungal Agents - pharmacology</topic><topic>antifungal properties</topic><topic>Asperfumin</topic><topic>Asperfumoid</topic><topic>Aspergillus fumigatus</topic><topic>Aspergillus fumigatus - isolation & purification</topic><topic>Aspergillus fumigatus - metabolism</topic><topic>Aspergillus niger</topic><topic>Benzoates - metabolism</topic><topic>Benzophenones - chemistry</topic><topic>Biological and medical sciences</topic><topic>biosynthesis</topic><topic>Biotechnology</topic><topic>Candida albicans</topic><topic>Candida albicans - drug effects</topic><topic>Cynodon - microbiology</topic><topic>Cynodon dactylon</topic><topic>Emodin - analogs & derivatives</topic><topic>Emodin - metabolism</topic><topic>Emodin - pharmacology</topic><topic>Endophyte</topic><topic>endophytes</topic><topic>Ergosterol - analogs & derivatives</topic><topic>Ergosterol - metabolism</topic><topic>Ergot Alkaloids</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Fusidic Acid - analogs & derivatives</topic><topic>Fusidic Acid - metabolism</topic><topic>Fusidic Acid - pharmacology</topic><topic>Hydroxybenzoate Ethers</topic><topic>Hydroxybenzoates - chemistry</topic><topic>Indole Alkaloids - metabolism</topic><topic>Indole Alkaloids - pharmacology</topic><topic>Indoles - metabolism</topic><topic>Indoles - pharmacology</topic><topic>Industrial Microbiology - methods</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Microbial Sensitivity Tests</topic><topic>Molecular Structure</topic><topic>Peptides, Cyclic - metabolism</topic><topic>Plant Leaves - microbiology</topic><topic>Pyrones - chemistry</topic><topic>Pyrones - metabolism</topic><topic>Quinolones - chemistry</topic><topic>Quinolones - metabolism</topic><topic>secondary metabolites</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liu, J.Y.</creatorcontrib><creatorcontrib>Song, Y.C.</creatorcontrib><creatorcontrib>Zhang, Z.</creatorcontrib><creatorcontrib>Wang, L.</creatorcontrib><creatorcontrib>Guo, Z.J.</creatorcontrib><creatorcontrib>Zou, W.X.</creatorcontrib><creatorcontrib>Tan, R.X.</creatorcontrib><collection>AGRIS</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>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of biotechnology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liu, J.Y.</au><au>Song, Y.C.</au><au>Zhang, Z.</au><au>Wang, L.</au><au>Guo, Z.J.</au><au>Zou, W.X.</au><au>Tan, R.X.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Aspergillus fumigatus CY018, an endophytic fungus in Cynodon dactylon as a versatile producer of new and bioactive metabolites</atitle><jtitle>Journal of biotechnology</jtitle><addtitle>J Biotechnol</addtitle><date>2004-11-09</date><risdate>2004</risdate><volume>114</volume><issue>3</issue><spage>279</spage><epage>287</epage><pages>279-287</pages><issn>0168-1656</issn><eissn>1873-4863</eissn><coden>JBITD4</coden><abstract>Aspergillus fumigatus CY018 was recognized as an endophytic fungus for the first time in the leaf of
Cynodon dactylon. By bioassay-guided fractionation, the EtOAc extract of a solid-matrix steady culture of this fungus afforded two new metabolites, named asperfumoid (
1) and asperfumin (
2), together with six known bioactive compounds including monomethylsulochrin, fumigaclavine C, fumitremorgin C, physcion, helvolic acid and 5α,8α-epidioxy-ergosta-6,22-diene-3β-ol as well as other four known compounds ergosta-4,22-diene-3β-ol, ergosterol,
cyclo(Ala-Leu) and
cyclo(Ala-Ile). Through detailed spectroscopic analyses including HRESI-MS, homo- and hetero-nuclear correlation NMR experiments (HMQC, COSY, NOESY and HMBC), the structures of asperfumoid and asperfumin were established to be spiro-(3-hydroxyl-2,6-dimethoxyl-2,5-diene-4-cyclohexone-(1,3′)-5′-methoxyl-7′-methyl-(1′H, 2′H, 4′H)-quinoline-2′,4′-dione) and 5-hydroxyl-2-(6-hydroxyl-2-methoxyl-4-methylbenzoyl)-3,6-dimethoxyl-benzoic methyl ester, respectively. All of the 12 isolates were subjected to in vitro bioactive assays against three human pathogenic fungi
Candida albicans, Tricophyton rubrum and
Aspergillus niger. As a result, asperfumoid, fumigaclavine C, fumitremorgin C, physcion and helvolic acid were shown to inhibit
C. albicans with MICs of 75.0, 31.5, 62.5, 125.0 and 31.5
μg/mL, respectively.</abstract><cop>Lausanne</cop><cop>Amsterdam</cop><cop>New York, NY</cop><pub>Elsevier B.V</pub><pmid>15522437</pmid><doi>10.1016/j.jbiotec.2004.07.008</doi><tpages>9</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0168-1656 |
| ispartof | Journal of biotechnology, 2004-11, Vol.114 (3), p.279-287 |
| issn | 0168-1656 1873-4863 |
| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals Complete |
| subjects | animal pathogenic fungi Antifungal Antifungal Agents - metabolism Antifungal Agents - pharmacology antifungal properties Asperfumin Asperfumoid Aspergillus fumigatus Aspergillus fumigatus - isolation & purification Aspergillus fumigatus - metabolism Aspergillus niger Benzoates - metabolism Benzophenones - chemistry Biological and medical sciences biosynthesis Biotechnology Candida albicans Candida albicans - drug effects Cynodon - microbiology Cynodon dactylon Emodin - analogs & derivatives Emodin - metabolism Emodin - pharmacology Endophyte endophytes Ergosterol - analogs & derivatives Ergosterol - metabolism Ergot Alkaloids Fundamental and applied biological sciences. Psychology Fusidic Acid - analogs & derivatives Fusidic Acid - metabolism Fusidic Acid - pharmacology Hydroxybenzoate Ethers Hydroxybenzoates - chemistry Indole Alkaloids - metabolism Indole Alkaloids - pharmacology Indoles - metabolism Indoles - pharmacology Industrial Microbiology - methods Magnetic Resonance Spectroscopy Microbial Sensitivity Tests Molecular Structure Peptides, Cyclic - metabolism Plant Leaves - microbiology Pyrones - chemistry Pyrones - metabolism Quinolones - chemistry Quinolones - metabolism secondary metabolites |
| title | Aspergillus fumigatus CY018, an endophytic fungus in Cynodon dactylon as a versatile producer of new and bioactive metabolites |
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