Molecular networking assisted discovery and biosynthesis elucidation of the antimicrobial spiroketals epicospirocins
Two pairs of dibenzospiroketal racemates, (±)-epicospirocin A ( 1a/1b ) and (±)-1- epi -epicospirocin A ( 2a/2b ), and two (+)-enantiomers of aspermicrones, ent -aspermicrone B ( 3b ) and ent -aspermicrone C ( 4b ), together with two hemiacetal epimeric mixtures, epicospirocin B/1- epi -epicospiroci...
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| Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2020-09, Vol.56 (7), p.1171-1174 |
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| creator | Zhu, Guoliang Hou, Chengjian Yuan, Weize Wang, Zhenzhen Zhang, Jingyu Jiang, Lan Karthik, Loganathan Li, Bixiao Ren, Biao Lv, Kangjie Lu, Wanying Cong, Zhanren Dai, Huanqin Hsiang, Tom Zhang, Lixin Liu, Xueting |
| description | Two pairs of dibenzospiroketal racemates, (±)-epicospirocin A (
1a/1b
) and (±)-1-
epi
-epicospirocin A (
2a/2b
), and two (+)-enantiomers of aspermicrones,
ent
-aspermicrone B (
3b
) and
ent
-aspermicrone C (
4b
), together with two hemiacetal epimeric mixtures, epicospirocin B/1-
epi
-epicospirocin B (
5/6
) and epicospirocin C/1-
epi
-epicospirocin C (
7/8
), were investigated from the phytopathogenic fungus
Epicoccum nigrum
09116
via
MS/MS molecular networking guided isolation and chiral separation for the first time. A plausible epicospirocin biosynthetic pathway was elucidated through
in silico
gene function annotation together with knock-out experiments. This is the first report that has applied MS/MS molecular networking to identify intermediates correlated with a biosynthetic pathway.
A series of new antimicrobial dibenzospiroketals epicospirocins, and their biosynthetic pathway, were investigated
via
molecular networking from phytopathogenic fungi EN09116 for the first time. |
| doi_str_mv | 10.1039/d0cc03990j |
| format | Article |
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1a/1b
) and (±)-1-
epi
-epicospirocin A (
2a/2b
), and two (+)-enantiomers of aspermicrones,
ent
-aspermicrone B (
3b
) and
ent
-aspermicrone C (
4b
), together with two hemiacetal epimeric mixtures, epicospirocin B/1-
epi
-epicospirocin B (
5/6
) and epicospirocin C/1-
epi
-epicospirocin C (
7/8
), were investigated from the phytopathogenic fungus
Epicoccum nigrum
09116
via
MS/MS molecular networking guided isolation and chiral separation for the first time. A plausible epicospirocin biosynthetic pathway was elucidated through
in silico
gene function annotation together with knock-out experiments. This is the first report that has applied MS/MS molecular networking to identify intermediates correlated with a biosynthetic pathway.
A series of new antimicrobial dibenzospiroketals epicospirocins, and their biosynthetic pathway, were investigated
via
molecular networking from phytopathogenic fungi EN09116 for the first time.</description><identifier>ISSN: 1359-7345</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/d0cc03990j</identifier><identifier>PMID: 32748904</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Annotations ; Antiinfectives and antibacterials ; Ascomycota - genetics ; Ascomycota - metabolism ; Biosynthesis ; Computer Simulation ; Enantiomers ; Furans - chemistry ; Furans - metabolism ; Spiro Compounds - chemistry ; Spiro Compounds - metabolism ; Stereoisomerism</subject><ispartof>Chemical communications (Cambridge, England), 2020-09, Vol.56 (7), p.1171-1174</ispartof><rights>Copyright Royal Society of Chemistry 2020</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c363t-879fe39f12ba9accf6d741013d9f02db25eb5261046dd045e7f4761020e7b56f3</citedby><cites>FETCH-LOGICAL-c363t-879fe39f12ba9accf6d741013d9f02db25eb5261046dd045e7f4761020e7b56f3</cites><orcidid>0000-0002-2557-2086 ; 0000-0002-1322-8253</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27903,27904</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32748904$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhu, Guoliang</creatorcontrib><creatorcontrib>Hou, Chengjian</creatorcontrib><creatorcontrib>Yuan, Weize</creatorcontrib><creatorcontrib>Wang, Zhenzhen</creatorcontrib><creatorcontrib>Zhang, Jingyu</creatorcontrib><creatorcontrib>Jiang, Lan</creatorcontrib><creatorcontrib>Karthik, Loganathan</creatorcontrib><creatorcontrib>Li, Bixiao</creatorcontrib><creatorcontrib>Ren, Biao</creatorcontrib><creatorcontrib>Lv, Kangjie</creatorcontrib><creatorcontrib>Lu, Wanying</creatorcontrib><creatorcontrib>Cong, Zhanren</creatorcontrib><creatorcontrib>Dai, Huanqin</creatorcontrib><creatorcontrib>Hsiang, Tom</creatorcontrib><creatorcontrib>Zhang, Lixin</creatorcontrib><creatorcontrib>Liu, Xueting</creatorcontrib><title>Molecular networking assisted discovery and biosynthesis elucidation of the antimicrobial spiroketals epicospirocins</title><title>Chemical communications (Cambridge, England)</title><addtitle>Chem Commun (Camb)</addtitle><description>Two pairs of dibenzospiroketal racemates, (±)-epicospirocin A (
1a/1b
) and (±)-1-
epi
-epicospirocin A (
2a/2b
), and two (+)-enantiomers of aspermicrones,
ent
-aspermicrone B (
3b
) and
ent
-aspermicrone C (
4b
), together with two hemiacetal epimeric mixtures, epicospirocin B/1-
epi
-epicospirocin B (
5/6
) and epicospirocin C/1-
epi
-epicospirocin C (
7/8
), were investigated from the phytopathogenic fungus
Epicoccum nigrum
09116
via
MS/MS molecular networking guided isolation and chiral separation for the first time. A plausible epicospirocin biosynthetic pathway was elucidated through
in silico
gene function annotation together with knock-out experiments. This is the first report that has applied MS/MS molecular networking to identify intermediates correlated with a biosynthetic pathway.
A series of new antimicrobial dibenzospiroketals epicospirocins, and their biosynthetic pathway, were investigated
via
molecular networking from phytopathogenic fungi EN09116 for the first time.</description><subject>Annotations</subject><subject>Antiinfectives and antibacterials</subject><subject>Ascomycota - genetics</subject><subject>Ascomycota - metabolism</subject><subject>Biosynthesis</subject><subject>Computer Simulation</subject><subject>Enantiomers</subject><subject>Furans - chemistry</subject><subject>Furans - metabolism</subject><subject>Spiro Compounds - chemistry</subject><subject>Spiro Compounds - metabolism</subject><subject>Stereoisomerism</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kc1v1DAQxS1ERUvhwh1k1AtCCvgzjo9oC21REReQuEWOPQZvs3FqO0X73-PttkXigC9jv_fTaMYPoReUvKOE6_eOWFurJutH6IjyVjRSdD8e7-5SN4oLeYie5rwm9VDZPUGHnCnRaSKOUPkSR7DLaBKeoPyO6SpMP7HJOeQCDruQbbyBtMVmcngIMW-n8guqi2FcbHCmhDjh6HFVK1PCJtgUh2BGnOeQ4hUUM1Z4DjbeCjZM-Rk68FWF53f1GH3_9PHb6ry5_Hp2sfpw2Vje8tJ0Snvg2lM2GG2s9a1TghLKnfaEuYFJGCRrKRGtc0RIUF6o-mQE1CBbz4_Rm33fOcXrBXLpN3UfGEczQVxyzwQnXDFOWEVP_kHXcUlTnW5HdVp2SuhKvd1TdcecE_h-TmFj0ranpN9l0Z-S1eo2i88VfnXXchk24B7Q-8-vwMs9kLJ9cP-GWf3X__P72Xn-B0BTm_c</recordid><startdate>20200911</startdate><enddate>20200911</enddate><creator>Zhu, Guoliang</creator><creator>Hou, Chengjian</creator><creator>Yuan, Weize</creator><creator>Wang, Zhenzhen</creator><creator>Zhang, Jingyu</creator><creator>Jiang, Lan</creator><creator>Karthik, Loganathan</creator><creator>Li, Bixiao</creator><creator>Ren, Biao</creator><creator>Lv, Kangjie</creator><creator>Lu, Wanying</creator><creator>Cong, Zhanren</creator><creator>Dai, Huanqin</creator><creator>Hsiang, Tom</creator><creator>Zhang, Lixin</creator><creator>Liu, Xueting</creator><general>Royal Society of Chemistry</general><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>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-2557-2086</orcidid><orcidid>https://orcid.org/0000-0002-1322-8253</orcidid></search><sort><creationdate>20200911</creationdate><title>Molecular networking assisted discovery and biosynthesis elucidation of the antimicrobial spiroketals epicospirocins</title><author>Zhu, Guoliang ; Hou, Chengjian ; Yuan, Weize ; Wang, Zhenzhen ; Zhang, Jingyu ; Jiang, Lan ; Karthik, Loganathan ; Li, Bixiao ; Ren, Biao ; Lv, Kangjie ; Lu, Wanying ; Cong, Zhanren ; Dai, Huanqin ; Hsiang, Tom ; Zhang, Lixin ; Liu, Xueting</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c363t-879fe39f12ba9accf6d741013d9f02db25eb5261046dd045e7f4761020e7b56f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Annotations</topic><topic>Antiinfectives and antibacterials</topic><topic>Ascomycota - genetics</topic><topic>Ascomycota - metabolism</topic><topic>Biosynthesis</topic><topic>Computer Simulation</topic><topic>Enantiomers</topic><topic>Furans - chemistry</topic><topic>Furans - metabolism</topic><topic>Spiro Compounds - chemistry</topic><topic>Spiro Compounds - metabolism</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhu, Guoliang</creatorcontrib><creatorcontrib>Hou, Chengjian</creatorcontrib><creatorcontrib>Yuan, Weize</creatorcontrib><creatorcontrib>Wang, Zhenzhen</creatorcontrib><creatorcontrib>Zhang, Jingyu</creatorcontrib><creatorcontrib>Jiang, Lan</creatorcontrib><creatorcontrib>Karthik, Loganathan</creatorcontrib><creatorcontrib>Li, Bixiao</creatorcontrib><creatorcontrib>Ren, Biao</creatorcontrib><creatorcontrib>Lv, Kangjie</creatorcontrib><creatorcontrib>Lu, Wanying</creatorcontrib><creatorcontrib>Cong, Zhanren</creatorcontrib><creatorcontrib>Dai, Huanqin</creatorcontrib><creatorcontrib>Hsiang, Tom</creatorcontrib><creatorcontrib>Zhang, Lixin</creatorcontrib><creatorcontrib>Liu, Xueting</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhu, Guoliang</au><au>Hou, Chengjian</au><au>Yuan, Weize</au><au>Wang, Zhenzhen</au><au>Zhang, Jingyu</au><au>Jiang, Lan</au><au>Karthik, Loganathan</au><au>Li, Bixiao</au><au>Ren, Biao</au><au>Lv, Kangjie</au><au>Lu, Wanying</au><au>Cong, Zhanren</au><au>Dai, Huanqin</au><au>Hsiang, Tom</au><au>Zhang, Lixin</au><au>Liu, Xueting</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Molecular networking assisted discovery and biosynthesis elucidation of the antimicrobial spiroketals epicospirocins</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><addtitle>Chem Commun (Camb)</addtitle><date>2020-09-11</date><risdate>2020</risdate><volume>56</volume><issue>7</issue><spage>1171</spage><epage>1174</epage><pages>1171-1174</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>Two pairs of dibenzospiroketal racemates, (±)-epicospirocin A (
1a/1b
) and (±)-1-
epi
-epicospirocin A (
2a/2b
), and two (+)-enantiomers of aspermicrones,
ent
-aspermicrone B (
3b
) and
ent
-aspermicrone C (
4b
), together with two hemiacetal epimeric mixtures, epicospirocin B/1-
epi
-epicospirocin B (
5/6
) and epicospirocin C/1-
epi
-epicospirocin C (
7/8
), were investigated from the phytopathogenic fungus
Epicoccum nigrum
09116
via
MS/MS molecular networking guided isolation and chiral separation for the first time. A plausible epicospirocin biosynthetic pathway was elucidated through
in silico
gene function annotation together with knock-out experiments. This is the first report that has applied MS/MS molecular networking to identify intermediates correlated with a biosynthetic pathway.
A series of new antimicrobial dibenzospiroketals epicospirocins, and their biosynthetic pathway, were investigated
via
molecular networking from phytopathogenic fungi EN09116 for the first time.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>32748904</pmid><doi>10.1039/d0cc03990j</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0002-2557-2086</orcidid><orcidid>https://orcid.org/0000-0002-1322-8253</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1359-7345 |
| ispartof | Chemical communications (Cambridge, England), 2020-09, Vol.56 (7), p.1171-1174 |
| issn | 1359-7345 1364-548X |
| language | eng |
| recordid | cdi_proquest_miscellaneous_2430372302 |
| source | MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Annotations Antiinfectives and antibacterials Ascomycota - genetics Ascomycota - metabolism Biosynthesis Computer Simulation Enantiomers Furans - chemistry Furans - metabolism Spiro Compounds - chemistry Spiro Compounds - metabolism Stereoisomerism |
| title | Molecular networking assisted discovery and biosynthesis elucidation of the antimicrobial spiroketals epicospirocins |
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