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Pimarane-Type Diterpenes with Anti-Inflammatory Activity from Arctic-Derived Fungus Eutypella sp. D-1
The Arctic-derived fungus Eutypella sp. D-1 can produce numerous secondary metabolites, and some compounds exhibit excellent biological activity. Seven pimarane-type diterpenes, including three new compounds eutypellenone F (1), libertellenone Y (2), and libertellenone Z (3), and four known compound...
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Published in: | Marine drugs 2023-10, Vol.21 (10), p.541 |
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description | The Arctic-derived fungus Eutypella sp. D-1 can produce numerous secondary metabolites, and some compounds exhibit excellent biological activity. Seven pimarane-type diterpenes, including three new compounds eutypellenone F (1), libertellenone Y (2), and libertellenone Z (3), and four known compounds (4–7), were isolated from fermentation broth of Eutypella sp. D-1 by the OSMAC strategy of adding ethanol as a promoter in the culture medium. Compound 2 has a rare tetrahydrofuran-fused pimarane diterpene skeleton. The anti-inflammatory activity of all compounds was evaluated. Compounds 3–6 showed a significant inhibitory effect on cell NO release at 10 μmol/L by in vitro experiments, of which 3–5 had inhibitory rates over 60% on nitric oxide (NO) release. Subsequently, the anti-inflammatory activity of 3–5 was evaluated based on a zebrafish model, and the results showed that 3 had a significant inhibitory effect on inflammatory cells migration at 40 μmol/L, while 4 and 5 had a significant inhibitory effect at 20 μmol/L. Moreover, compounds 3–5 have the same conjugated double bond structure, which may be an important group for these compounds to exert anti-inflammatory activity. |
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D-1</title><source>Publicly Available Content Database</source><source>PubMed Central</source><creator>Ning, Yaodong ; Zhang, Shi ; Zheng, Te ; Xu, Yao ; Li, Song ; Zhang, Jianpeng ; Jiao, Binghua ; Zhang, Yun ; Ma, Zengling ; Lu, Xiaoling</creator><creatorcontrib>Ning, Yaodong ; Zhang, Shi ; Zheng, Te ; Xu, Yao ; Li, Song ; Zhang, Jianpeng ; Jiao, Binghua ; Zhang, Yun ; Ma, Zengling ; Lu, Xiaoling</creatorcontrib><description>The Arctic-derived fungus Eutypella sp. D-1 can produce numerous secondary metabolites, and some compounds exhibit excellent biological activity. Seven pimarane-type diterpenes, including three new compounds eutypellenone F (1), libertellenone Y (2), and libertellenone Z (3), and four known compounds (4–7), were isolated from fermentation broth of Eutypella sp. D-1 by the OSMAC strategy of adding ethanol as a promoter in the culture medium. Compound 2 has a rare tetrahydrofuran-fused pimarane diterpene skeleton. The anti-inflammatory activity of all compounds was evaluated. Compounds 3–6 showed a significant inhibitory effect on cell NO release at 10 μmol/L by in vitro experiments, of which 3–5 had inhibitory rates over 60% on nitric oxide (NO) release. Subsequently, the anti-inflammatory activity of 3–5 was evaluated based on a zebrafish model, and the results showed that 3 had a significant inhibitory effect on inflammatory cells migration at 40 μmol/L, while 4 and 5 had a significant inhibitory effect at 20 μmol/L. Moreover, compounds 3–5 have the same conjugated double bond structure, which may be an important group for these compounds to exert anti-inflammatory activity.</description><identifier>ISSN: 1660-3397</identifier><identifier>EISSN: 1660-3397</identifier><identifier>DOI: 10.3390/md21100541</identifier><identifier>PMID: 37888476</identifier><language>eng</language><publisher>Basel: MDPI AG</publisher><subject>anti-inflammatory ; Anti-inflammatory agents ; Biological activity ; Carbon ; Cell culture ; Cell migration ; Culture media ; diterpene ; Diterpenes ; Ethanol ; Eutypella sp. D-1 ; Fermentation ; Fungi ; Inflammation ; Metabolites ; Migrations ; Nitric oxide ; Polar environments ; Secondary metabolites ; Spectrum analysis ; Tetrahydrofuran ; Zebrafish ; zebrafish model</subject><ispartof>Marine drugs, 2023-10, Vol.21 (10), p.541</ispartof><rights>2023 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). 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D-1</title><title>Marine drugs</title><description>The Arctic-derived fungus Eutypella sp. D-1 can produce numerous secondary metabolites, and some compounds exhibit excellent biological activity. Seven pimarane-type diterpenes, including three new compounds eutypellenone F (1), libertellenone Y (2), and libertellenone Z (3), and four known compounds (4–7), were isolated from fermentation broth of Eutypella sp. D-1 by the OSMAC strategy of adding ethanol as a promoter in the culture medium. Compound 2 has a rare tetrahydrofuran-fused pimarane diterpene skeleton. The anti-inflammatory activity of all compounds was evaluated. Compounds 3–6 showed a significant inhibitory effect on cell NO release at 10 μmol/L by in vitro experiments, of which 3–5 had inhibitory rates over 60% on nitric oxide (NO) release. Subsequently, the anti-inflammatory activity of 3–5 was evaluated based on a zebrafish model, and the results showed that 3 had a significant inhibitory effect on inflammatory cells migration at 40 μmol/L, while 4 and 5 had a significant inhibitory effect at 20 μmol/L. Moreover, compounds 3–5 have the same conjugated double bond structure, which may be an important group for these compounds to exert anti-inflammatory activity.</description><subject>anti-inflammatory</subject><subject>Anti-inflammatory agents</subject><subject>Biological activity</subject><subject>Carbon</subject><subject>Cell culture</subject><subject>Cell migration</subject><subject>Culture media</subject><subject>diterpene</subject><subject>Diterpenes</subject><subject>Ethanol</subject><subject>Eutypella sp. D-1</subject><subject>Fermentation</subject><subject>Fungi</subject><subject>Inflammation</subject><subject>Metabolites</subject><subject>Migrations</subject><subject>Nitric oxide</subject><subject>Polar environments</subject><subject>Secondary metabolites</subject><subject>Spectrum analysis</subject><subject>Tetrahydrofuran</subject><subject>Zebrafish</subject><subject>zebrafish model</subject><issn>1660-3397</issn><issn>1660-3397</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><sourceid>PIMPY</sourceid><sourceid>DOA</sourceid><recordid>eNpdkt-L1DAQgIso3g998S8I-CJCz6RpmuRJltu7c-FAH87nkE0me1napibpyv73pu6hnhBIZubjYzJMVb0j-IpSiT8NtiEEY9aSF9U56TpclzR_-c_7rLpIaY8xZUK2r6szyoUQLe_OK_jmBx31CPXDcQK09hniBCMk9NPnR7Qas683o-v1MOgc4hGtTPYHn4_IxTCgVSyhqdcQ_QEsup3H3ZzQzZyLrO81StMVWtfkTfXK6T7B26f7svp-e_Nw_aW-_3q3uV7d16ZlONeMSAvYdsRB5_SWNwQIZaw1VEtMO8Z01wojOZiGk7ahtJQN5oRIsNxhTS-rzclrg96rKS5_O6qgvfqdCHGndCwN96CaRnDTOLx1cttaS6U2IKnRmgIltnXF9fnkmubtANbAmKPun0mfV0b_qHbhoAjusOCEFcOHJ0MMP2ZIWQ0-mWUuI4Q5qUYIyvhyCvr-P3Qf5jiWWS1UwySnhBfq44kyMaQUwf3phmC1rIL6uwr0F8XvpJM</recordid><startdate>20231018</startdate><enddate>20231018</enddate><creator>Ning, Yaodong</creator><creator>Zhang, Shi</creator><creator>Zheng, Te</creator><creator>Xu, Yao</creator><creator>Li, Song</creator><creator>Zhang, Jianpeng</creator><creator>Jiao, Binghua</creator><creator>Zhang, Yun</creator><creator>Ma, Zengling</creator><creator>Lu, Xiaoling</creator><general>MDPI AG</general><general>MDPI</general><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7T7</scope><scope>7TN</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>8FD</scope><scope>8FE</scope><scope>8FH</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AEUYN</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BBNVY</scope><scope>BENPR</scope><scope>BHPHI</scope><scope>BKSAR</scope><scope>C1K</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>F1W</scope><scope>FR3</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>H95</scope><scope>H99</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>L.F</scope><scope>L.G</scope><scope>LK8</scope><scope>M0S</scope><scope>M1P</scope><scope>M7P</scope><scope>P64</scope><scope>PCBAR</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>7X8</scope><scope>5PM</scope><scope>DOA</scope><orcidid>https://orcid.org/0000-0002-4165-0339</orcidid></search><sort><creationdate>20231018</creationdate><title>Pimarane-Type Diterpenes with Anti-Inflammatory Activity from Arctic-Derived Fungus Eutypella sp. 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subjects | anti-inflammatory Anti-inflammatory agents Biological activity Carbon Cell culture Cell migration Culture media diterpene Diterpenes Ethanol Eutypella sp. D-1 Fermentation Fungi Inflammation Metabolites Migrations Nitric oxide Polar environments Secondary metabolites Spectrum analysis Tetrahydrofuran Zebrafish zebrafish model |
title | Pimarane-Type Diterpenes with Anti-Inflammatory Activity from Arctic-Derived Fungus Eutypella sp. D-1 |
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