Biosynthesis of the Cyclooligomer Depsipeptide Beauvericin, a Virulence Factor of the Entomopathogenic Fungus Beauveria bassiana
Beauvericin, a cyclohexadepsipeptide ionophore from the entomopathogen Beauveria bassiana, shows antibiotic, antifungal, insecticidal, and cancer cell antiproliferative and antihaptotactic (cell motility inhibitory) activity in vitro. The bbBeas gene encoding the BbBEAS nonribosomal peptide syntheta...
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| Veröffentlicht in: | Chemistry & biology 2008-09, Vol.15 (9), p.898-907 |
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| creator | Xu, Yuquan Orozco, Rousel Wijeratne, E.M. Kithsiri Gunatilaka, A.A. Leslie Stock, S. Patricia Molnár, István |
| description | Beauvericin, a cyclohexadepsipeptide ionophore from the entomopathogen Beauveria bassiana, shows antibiotic, antifungal, insecticidal, and cancer cell antiproliferative and antihaptotactic (cell motility inhibitory) activity in vitro. The bbBeas gene encoding the BbBEAS nonribosomal peptide synthetase was isolated from B. bassiana and confirmed to be responsible for beauvericin biosynthesis by targeted disruption. BbBEAS utilizes D-2-hydroxyisovalerate (D-Hiv) and L-phenylalanine (Phe) for the iterative synthesis of a predicted N-methyl-dipeptidol intermediate, and forms the cyclic trimeric ester beauvericin from this intermediate in an unusual recursive process. Heterologous expression of the bbBeas gene in Escherichia coli to produce the 3189 amino acid, 351.9 kDa BbBEAS enzyme provided a strain proficient in beauvericin biosynthesis. Comparative infection assays with a BbBEAS knockout B. bassiana strain against three insect hosts revealed that beauvericin plays a highly significant but not indispensable role in virulence. |
| doi_str_mv | 10.1016/j.chembiol.2008.07.011 |
| format | Article |
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Heterologous expression of the bbBeas gene in Escherichia coli to produce the 3189 amino acid, 351.9 kDa BbBEAS enzyme provided a strain proficient in beauvericin biosynthesis. Comparative infection assays with a BbBEAS knockout B. bassiana strain against three insect hosts revealed that beauvericin plays a highly significant but not indispensable role in virulence.</description><identifier>ISSN: 1074-5521</identifier><identifier>EISSN: 1879-1301</identifier><identifier>DOI: 10.1016/j.chembiol.2008.07.011</identifier><identifier>PMID: 18804027</identifier><language>eng</language><publisher>United States: Elsevier Ltd</publisher><subject>Animals ; Beauveria - chemistry ; Beauveria - metabolism ; Beauveria - pathogenicity ; Beauveria bassiana ; CHEMBIO ; Depsipeptides - biosynthesis ; Depsipeptides - chemistry ; Escherichia coli ; Escherichia coli - genetics ; Escherichia coli - metabolism ; Fungal Proteins - genetics ; Fungal Proteins - metabolism ; Insecta - chemistry ; Insecta - genetics ; Insecta - metabolism ; Molecular Sequence Data ; Molecular Structure ; Virulence ; Virulence Factors - biosynthesis ; Virulence Factors - chemistry</subject><ispartof>Chemistry & biology, 2008-09, Vol.15 (9), p.898-907</ispartof><rights>2008 Elsevier Ltd</rights><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c463t-a0e39ba5d106984a0a1c013d42a9d110aac3b154b07ca7dcfc5beb49a65dbdef3</citedby><cites>FETCH-LOGICAL-c463t-a0e39ba5d106984a0a1c013d42a9d110aac3b154b07ca7dcfc5beb49a65dbdef3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.chembiol.2008.07.011$$EHTML$$P50$$Gelsevier$$Hfree_for_read</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18804027$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Xu, Yuquan</creatorcontrib><creatorcontrib>Orozco, Rousel</creatorcontrib><creatorcontrib>Wijeratne, E.M. 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BbBEAS utilizes D-2-hydroxyisovalerate (D-Hiv) and L-phenylalanine (Phe) for the iterative synthesis of a predicted N-methyl-dipeptidol intermediate, and forms the cyclic trimeric ester beauvericin from this intermediate in an unusual recursive process. Heterologous expression of the bbBeas gene in Escherichia coli to produce the 3189 amino acid, 351.9 kDa BbBEAS enzyme provided a strain proficient in beauvericin biosynthesis. Comparative infection assays with a BbBEAS knockout B. bassiana strain against three insect hosts revealed that beauvericin plays a highly significant but not indispensable role in virulence.</description><subject>Animals</subject><subject>Beauveria - chemistry</subject><subject>Beauveria - metabolism</subject><subject>Beauveria - pathogenicity</subject><subject>Beauveria bassiana</subject><subject>CHEMBIO</subject><subject>Depsipeptides - biosynthesis</subject><subject>Depsipeptides - chemistry</subject><subject>Escherichia coli</subject><subject>Escherichia coli - genetics</subject><subject>Escherichia coli - metabolism</subject><subject>Fungal Proteins - genetics</subject><subject>Fungal Proteins - metabolism</subject><subject>Insecta - chemistry</subject><subject>Insecta - genetics</subject><subject>Insecta - metabolism</subject><subject>Molecular Sequence Data</subject><subject>Molecular Structure</subject><subject>Virulence</subject><subject>Virulence Factors - biosynthesis</subject><subject>Virulence Factors - chemistry</subject><issn>1074-5521</issn><issn>1879-1301</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkU1v00AQhi0EoqXwF6o9ccLuTLz-ukFDQ5EqcQGuq9ndcbKR7TW7dqXc-tNxlBSOPc0cnndGep8kuUbIELC82Wdmx712vstWAHUGVQaIr5JLrKsmxRzw9bJDJdOiWOFF8i7GPQBg3ZRvkwusa5Cwqi6Tp1vn42GYdhxdFL4VyybWB9N537mt7zmIrzxGN_I4Ocvilml-5OCMGz4JEr9dmDseDIsNmcmH5wt3w-R7P9K081senBGbedjO8V-chKYYHQ30PnnTUhf5w3leJb82dz_X9-nDj2_f118eUiPLfEoJOG80FRahbGpJQGgAcytX1FhEIDK5xkJqqAxV1rSm0KxlQ2VhteU2v0o-nu6Owf-ZOU6qd9Fw19HAfo6qbIpaLvW8CGJTSVlguYDlCTTBxxi4VWNwPYWDQlBHSWqvniWpoyQFlVokLcHr84dZ92z_x85WFuDzCeClkEfHQUXjji1bF9hMynr30o-_Pr6p1w</recordid><startdate>20080922</startdate><enddate>20080922</enddate><creator>Xu, Yuquan</creator><creator>Orozco, Rousel</creator><creator>Wijeratne, E.M. 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| subjects | Animals Beauveria - chemistry Beauveria - metabolism Beauveria - pathogenicity Beauveria bassiana CHEMBIO Depsipeptides - biosynthesis Depsipeptides - chemistry Escherichia coli Escherichia coli - genetics Escherichia coli - metabolism Fungal Proteins - genetics Fungal Proteins - metabolism Insecta - chemistry Insecta - genetics Insecta - metabolism Molecular Sequence Data Molecular Structure Virulence Virulence Factors - biosynthesis Virulence Factors - chemistry |
| title | Biosynthesis of the Cyclooligomer Depsipeptide Beauvericin, a Virulence Factor of the Entomopathogenic Fungus Beauveria bassiana |
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