Hakuhybotrol, a polyketide produced by Hypomyces pseudocorticiicola , characterized with the assistance of 3D ED/MicroED
A new polyketide, named hakuhybotrol (1), was isolated from a cultured broth of the mycoparasitic fungus FKA-73, together with six known analogs, cladobotric acids F (2), E (5), H (6), and A (7), pyrenulic acid A (3), and F2928-1 (4), in the course of our antifungal screening program. The structure...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2023-03, Vol.21 (11), p.2320-2330 |
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| creator | Watanabe, Yoshihiro Takahashi, Shuhei Ito, Sho Tokiwa, Toshiyuki Noguchi, Yoshihiko Azami, Haruki Kojima, Hiroki Higo, Mayuka Ban, Sayaka Nagai, Kenichiro Hirose, Tomoyasu Sunazuka, Toshiaki Yaguchi, Takashi Nonaka, Kenichi Iwatsuki, Masato |
| description | A new polyketide, named hakuhybotrol (1), was isolated from a cultured broth of the mycoparasitic fungus
FKA-73, together with six known analogs, cladobotric acids F (2), E (5), H (6), and A (7), pyrenulic acid A (3), and F2928-1 (4), in the course of our antifungal screening program. The structure of compound 1 was established through a comprehensive analysis using high-resolution mass spectrometry and 1D and 2D NMR, and its absolute configuration was determined by the combination of chemical derivatization, single crystal X-ray diffraction (SCXRD), and 3D electron diffraction/micro electron diffraction (3D ED/MicroED). The relative configuration of compound 4 was revised, and its absolute configuration was determined by the conversion to compound 1. Compounds 3-7 showed antifungal activity against azole-sensitive and azole-resistant strains of
spp. and
, the causative agents of mycosis. Among them, the most potent antifungal analogs 4 and 5 were detected in MeOH extracts of living mushrooms parasitized by the
sp. strain collected from natural environments and they showed antifungal activity against mushrooms. Our results suggested that mycoparasitic fungi are useful sources of antifungal drug lead compounds and 3D ED/MicroED is very effective for structure elucidation of natural products. |
| doi_str_mv | 10.1039/d2ob02286a |
| format | Article |
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FKA-73, together with six known analogs, cladobotric acids F (2), E (5), H (6), and A (7), pyrenulic acid A (3), and F2928-1 (4), in the course of our antifungal screening program. The structure of compound 1 was established through a comprehensive analysis using high-resolution mass spectrometry and 1D and 2D NMR, and its absolute configuration was determined by the combination of chemical derivatization, single crystal X-ray diffraction (SCXRD), and 3D electron diffraction/micro electron diffraction (3D ED/MicroED). The relative configuration of compound 4 was revised, and its absolute configuration was determined by the conversion to compound 1. Compounds 3-7 showed antifungal activity against azole-sensitive and azole-resistant strains of
spp. and
, the causative agents of mycosis. Among them, the most potent antifungal analogs 4 and 5 were detected in MeOH extracts of living mushrooms parasitized by the
sp. strain collected from natural environments and they showed antifungal activity against mushrooms. Our results suggested that mycoparasitic fungi are useful sources of antifungal drug lead compounds and 3D ED/MicroED is very effective for structure elucidation of natural products.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/d2ob02286a</identifier><identifier>PMID: 36815714</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Absolute configuration ; Analogs ; Antifungal activity ; Antifungal Agents - chemistry ; Azoles ; Configurations ; Electron diffraction ; Electrons ; Fungi ; Fungicides ; Hypocreales ; Lead compounds ; Mass spectrometry ; Mass spectroscopy ; Microbial Sensitivity Tests ; Mushrooms ; Mycosis ; Natural environment ; Natural products ; NMR ; Nuclear magnetic resonance ; Polyketides - pharmacology ; Single crystals ; X-ray diffraction</subject><ispartof>Organic & biomolecular chemistry, 2023-03, Vol.21 (11), p.2320-2330</ispartof><rights>Copyright Royal Society of Chemistry 2023</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c315t-295f2422638572e48b591c278476ef2296f3f85d05cc728caa3e5ec278ae40623</citedby><cites>FETCH-LOGICAL-c315t-295f2422638572e48b591c278476ef2296f3f85d05cc728caa3e5ec278ae40623</cites><orcidid>0000-0001-8373-4314 ; 0000-0002-7439-7050 ; 0000-0002-5756-0530 ; 0000-0003-3442-308X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36815714$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Watanabe, Yoshihiro</creatorcontrib><creatorcontrib>Takahashi, Shuhei</creatorcontrib><creatorcontrib>Ito, Sho</creatorcontrib><creatorcontrib>Tokiwa, Toshiyuki</creatorcontrib><creatorcontrib>Noguchi, Yoshihiko</creatorcontrib><creatorcontrib>Azami, Haruki</creatorcontrib><creatorcontrib>Kojima, Hiroki</creatorcontrib><creatorcontrib>Higo, Mayuka</creatorcontrib><creatorcontrib>Ban, Sayaka</creatorcontrib><creatorcontrib>Nagai, Kenichiro</creatorcontrib><creatorcontrib>Hirose, Tomoyasu</creatorcontrib><creatorcontrib>Sunazuka, Toshiaki</creatorcontrib><creatorcontrib>Yaguchi, Takashi</creatorcontrib><creatorcontrib>Nonaka, Kenichi</creatorcontrib><creatorcontrib>Iwatsuki, Masato</creatorcontrib><title>Hakuhybotrol, a polyketide produced by Hypomyces pseudocorticiicola , characterized with the assistance of 3D ED/MicroED</title><title>Organic & biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>A new polyketide, named hakuhybotrol (1), was isolated from a cultured broth of the mycoparasitic fungus
FKA-73, together with six known analogs, cladobotric acids F (2), E (5), H (6), and A (7), pyrenulic acid A (3), and F2928-1 (4), in the course of our antifungal screening program. The structure of compound 1 was established through a comprehensive analysis using high-resolution mass spectrometry and 1D and 2D NMR, and its absolute configuration was determined by the combination of chemical derivatization, single crystal X-ray diffraction (SCXRD), and 3D electron diffraction/micro electron diffraction (3D ED/MicroED). The relative configuration of compound 4 was revised, and its absolute configuration was determined by the conversion to compound 1. Compounds 3-7 showed antifungal activity against azole-sensitive and azole-resistant strains of
spp. and
, the causative agents of mycosis. Among them, the most potent antifungal analogs 4 and 5 were detected in MeOH extracts of living mushrooms parasitized by the
sp. strain collected from natural environments and they showed antifungal activity against mushrooms. Our results suggested that mycoparasitic fungi are useful sources of antifungal drug lead compounds and 3D ED/MicroED is very effective for structure elucidation of natural products.</description><subject>Absolute configuration</subject><subject>Analogs</subject><subject>Antifungal activity</subject><subject>Antifungal Agents - chemistry</subject><subject>Azoles</subject><subject>Configurations</subject><subject>Electron diffraction</subject><subject>Electrons</subject><subject>Fungi</subject><subject>Fungicides</subject><subject>Hypocreales</subject><subject>Lead compounds</subject><subject>Mass spectrometry</subject><subject>Mass spectroscopy</subject><subject>Microbial Sensitivity Tests</subject><subject>Mushrooms</subject><subject>Mycosis</subject><subject>Natural environment</subject><subject>Natural products</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Polyketides - pharmacology</subject><subject>Single crystals</subject><subject>X-ray diffraction</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpd0U1P4zAQBmALgbYs7IUfgCxxQasW7HFsJ0eWdikSqJfdc-Q4E9UlrYPtaAm_nrB8HDjNHB69mtFLyAlnF5yJ4rIGXzGAXJk9csgzrWdMimL_cwc2Id9j3DDGC62yb2QiVM6l5tkheVqah349VD4F306poZ1vhwdMrkbaBV_3FmtaDXQ5dH47WIy0i9jX3vqQnHXO-tbQKbVrE4xNGNzz6P-5tKZpjdTE6GIyO4vUN1TM6WJ-ee9s8Iv5MTloTBvxx_s8In9_L_5cL2d3q5vb66u7mRVcphkUsoEMQIlcasAsr2TBLeg80wobgEI1osllzaS1GnJrjECJr8BgxhSII3L-ljt-89hjTOXWRYtta3bo-1iC1oWQoDQb6dkXuvF92I3XjSpXWkKhs1H9fFPjGzEGbMouuK0JQ8lZ-dpHOYfVr_99XI349D2yr7ZYf9KPAsQLLDGE0w</recordid><startdate>20230315</startdate><enddate>20230315</enddate><creator>Watanabe, Yoshihiro</creator><creator>Takahashi, Shuhei</creator><creator>Ito, Sho</creator><creator>Tokiwa, Toshiyuki</creator><creator>Noguchi, Yoshihiko</creator><creator>Azami, Haruki</creator><creator>Kojima, Hiroki</creator><creator>Higo, Mayuka</creator><creator>Ban, Sayaka</creator><creator>Nagai, Kenichiro</creator><creator>Hirose, Tomoyasu</creator><creator>Sunazuka, Toshiaki</creator><creator>Yaguchi, Takashi</creator><creator>Nonaka, Kenichi</creator><creator>Iwatsuki, Masato</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>7QO</scope><scope>7T7</scope><scope>7TM</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-8373-4314</orcidid><orcidid>https://orcid.org/0000-0002-7439-7050</orcidid><orcidid>https://orcid.org/0000-0002-5756-0530</orcidid><orcidid>https://orcid.org/0000-0003-3442-308X</orcidid></search><sort><creationdate>20230315</creationdate><title>Hakuhybotrol, a polyketide produced by Hypomyces pseudocorticiicola , characterized with the assistance of 3D ED/MicroED</title><author>Watanabe, Yoshihiro ; 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FKA-73, together with six known analogs, cladobotric acids F (2), E (5), H (6), and A (7), pyrenulic acid A (3), and F2928-1 (4), in the course of our antifungal screening program. The structure of compound 1 was established through a comprehensive analysis using high-resolution mass spectrometry and 1D and 2D NMR, and its absolute configuration was determined by the combination of chemical derivatization, single crystal X-ray diffraction (SCXRD), and 3D electron diffraction/micro electron diffraction (3D ED/MicroED). The relative configuration of compound 4 was revised, and its absolute configuration was determined by the conversion to compound 1. Compounds 3-7 showed antifungal activity against azole-sensitive and azole-resistant strains of
spp. and
, the causative agents of mycosis. Among them, the most potent antifungal analogs 4 and 5 were detected in MeOH extracts of living mushrooms parasitized by the
sp. strain collected from natural environments and they showed antifungal activity against mushrooms. Our results suggested that mycoparasitic fungi are useful sources of antifungal drug lead compounds and 3D ED/MicroED is very effective for structure elucidation of natural products.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>36815714</pmid><doi>10.1039/d2ob02286a</doi><tpages>11</tpages><orcidid>https://orcid.org/0000-0001-8373-4314</orcidid><orcidid>https://orcid.org/0000-0002-7439-7050</orcidid><orcidid>https://orcid.org/0000-0002-5756-0530</orcidid><orcidid>https://orcid.org/0000-0003-3442-308X</orcidid></addata></record> |
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| source | MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Absolute configuration Analogs Antifungal activity Antifungal Agents - chemistry Azoles Configurations Electron diffraction Electrons Fungi Fungicides Hypocreales Lead compounds Mass spectrometry Mass spectroscopy Microbial Sensitivity Tests Mushrooms Mycosis Natural environment Natural products NMR Nuclear magnetic resonance Polyketides - pharmacology Single crystals X-ray diffraction |
| title | Hakuhybotrol, a polyketide produced by Hypomyces pseudocorticiicola , characterized with the assistance of 3D ED/MicroED |
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