{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,9]],"date-time":"2026-10-09T12:04:27Z","timestamp":1791547467298,"version":"4.3.4"},"reference-count":33,"publisher":"MDPI AG","issue":"1","license":[{"start":{"date-parts":[[2022,12,22]],"date-time":"2022-12-22T00:00:00Z","timestamp":1671667200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"National Key Research and Development Project","award":["2018YFA0902504"],"award-info":[{"award-number":["2018YFA0902504"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Marine Drugs"],"abstract":"<jats:p>Six new sesquiterpene aminoglycosides, trichaspside F (2) and cyclonerosides A\u2013E (5\u20139), two new diterpene aminoglycosides, harzianosides A and B (10, 11), and three known sesquiterpenes, trichodermoside (1), cycloneran-3,7,10,11-tetraol (3), and cyclonerodiol (4), have been isolated from the n-butanol extract of Trichoderma sp. SCSIOW21 (Hypocreaceae), a deep-sea-sediment-derived fungus. The structures and relative configurations of the new compounds were determined using spectroscopic techniques and comparisons with those reported in the literature. The absolute configurations of the aglycone part of cyclonerosides A\u2013E (5\u20139) were tentatively proposed based on optical rotation and biogenic considerations. Cyclonerosides A\u2013E (5\u20139) represent the first glycosides of cyclonelane-type sesquiterpenes generated from Trichoderma. The NO-production-inhibitory activities were evaluated using macrophage RAW264.7 cells. Among the isolated compounds, trichaspside F (2) and cyclonerosides B\u2013E (6\u20139) exhibited the strongest NO-production-inhibitory activities with IC50 values of 54.8, 50.7, 57.1, 42.0, and 48.0 \u00b5M, respectively, compared to the IC50 value of 30.8 \u00b5M for the positive control (quercetin). When tested for anti-fungal activities against several pathogenic fungi, none of the compounds exhibited significant activities at a concentration of 100 \u00b5M.<\/jats:p>","DOI":"10.3390\/md21010007","type":"journal-article","created":{"date-parts":[[2022,12,23]],"date-time":"2022-12-23T03:26:25Z","timestamp":1671765985000},"page":"7","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Novel Sesquiterpene and Diterpene Aminoglycosides from the Deep-Sea-Sediment Fungus Trichoderma sp. SCSIOW21"],"prefix":"10.3390","volume":"21","author":[{"given":"Hongxu","family":"Li","sequence":"first","affiliation":[{"name":"Shenzhen Key Laboratory of Marine Bioresource and Eco-Environmental Science, College of Life Sciences and Oceanography, Shenzhen University, Shenzhen 518060, China"},{"name":"Key Laboratory of Optoelectronic Engineering, Shenzhen University, Shenzhen 518060, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xinyi","family":"Liu","sequence":"additional","affiliation":[{"name":"Shenzhen Key Laboratory of Marine Bioresource and Eco-Environmental Science, College of Life Sciences and Oceanography, Shenzhen University, Shenzhen 518060, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2596-8515","authenticated-orcid":false,"given":"Zhangli","family":"Hu","sequence":"additional","affiliation":[{"name":"Shenzhen Key Laboratory of Marine Bioresource and Eco-Environmental Science, College of Life Sciences and Oceanography, Shenzhen University, Shenzhen 518060, China"},{"name":"Key Laboratory of Optoelectronic Engineering, Shenzhen University, Shenzhen 518060, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7253-5862","authenticated-orcid":false,"given":"Liyan","family":"Wang","sequence":"additional","affiliation":[{"name":"Shenzhen Key Laboratory of Marine Bioresource and Eco-Environmental Science, College of Life Sciences and Oceanography, Shenzhen University, Shenzhen 518060, China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2022,12,22]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Giddings, L.A., and Newman, D.J. (2022). Extremophilic Fungi from Marine Environments: Underexplored Sources of Antitumor, Anti-Infective and Other Biologically Active Agents. Mar. Drugs, 20.","DOI":"10.3390\/md20010062"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"382","DOI":"10.1039\/C5NP00156K","article-title":"Marine natural products","volume":"33","author":"Blunt","year":"2016","journal-title":"Nat. Prod. Rep."},{"key":"ref_3","doi-asserted-by":"crossref","unstructured":"Jin, L., Quan, C., Hou, X., and Fan, S. (2016). Potential Pharmacological Resources: Natural Bioactive Compounds from Marine-Derived Fungi. Mar. Drugs, 14.","DOI":"10.3390\/md14040076"},{"key":"ref_4","doi-asserted-by":"crossref","unstructured":"Yurchenko, A.N., Girich, E.V., and Yurchenko, E.A. (2021). Metabolites of Marine Sediment-Derived Fungi: Actual Trends of Biological Activity Studies. Mar. Drugs, 19.","DOI":"10.3390\/md19020088"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1007\/s13225-020-00464-4","article-title":"In honor of John Bissett: Authoritative guidelines on molecular identification of Trichoderma","volume":"107","author":"Cai","year":"2021","journal-title":"Fungal. Divers."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"89","DOI":"10.1007\/s11101-006-9032-2","article-title":"Secondary metabolites from species of the biocontrol agent Trichoderma","volume":"7","author":"Reino","year":"2008","journal-title":"Phytochem. Rev."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"723828","DOI":"10.3389\/fmicb.2021.723828","article-title":"Trichoderma: A Treasure House of Structurally Diverse Secondary Metabolites with Medicinal Importance","volume":"12","author":"Zhang","year":"2021","journal-title":"Front. Microbiol."},{"key":"ref_8","doi-asserted-by":"crossref","unstructured":"Jiang, M., Wu, Z., Guo, H., Liu, L., and Chen, S. (2020). A Review of Terpenes from Marine-Derived Fungi: 2015\u20132019. Mar. Drugs, 18.","DOI":"10.3390\/md18060321"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"15440","DOI":"10.1021\/acs.jafc.0c05586","article-title":"Antifungal and Antimicroalgal Trichothecene Sesquiterpenes from the Marine Algicolous Fungus Trichoderma brevicompactum A-DL-9-2","volume":"68","author":"Shi","year":"2020","journal-title":"J. Agric. Food Chem."},{"key":"ref_10","first-page":"544","article-title":"A novel sesquiterpene glucoside from Trichoderma sp. PT2","volume":"22","author":"Du","year":"2010","journal-title":"Nat. Prod. Res. Dev."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"107","DOI":"10.1016\/j.fitote.2019.04.014","article-title":"Seven chromanoid norbisabolane derivatives from the marine-alga-endophytic fungus Trichoderma asperellum A-YMD-9-2","volume":"135","author":"Song","year":"2019","journal-title":"Fitoterapia"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"2037","DOI":"10.1080\/14786419.2019.1574782","article-title":"Trichosordarin A, a norditerpene glycoside from the marine-derived fungus Trichoderma harzianum R5","volume":"34","author":"Liang","year":"2020","journal-title":"Nat. Prod. Res."},{"key":"ref_13","doi-asserted-by":"crossref","unstructured":"Du, F.Y., Ju, G.L., Xiao, L., Zhou, Y.M., and Wu, X. (2020). Sesquiterpenes and Cyclodepsipeptides from Marine-Derived Fungus Trichoderma longibrachiatum and Their Antagonistic Activities against Soil-borne Pathogens. Mar. Drugs, 18.","DOI":"10.3390\/md18030165"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"45","DOI":"10.1016\/j.phytochem.2018.04.017","article-title":"Bisabolane, cyclonerane, and harziane derivatives from the marine-alga-endophytic fungus Trichoderma asperellum cf44-2","volume":"152","author":"Song","year":"2018","journal-title":"Phytochemistry"},{"key":"ref_15","doi-asserted-by":"crossref","unstructured":"Lu, X., He, J., Wu, Y., Du, N., Li, X., Ju, J., Hu, Z., Umezawa, K., and Wang, L. (2020). Isolation and Characterization of New Anti-Inflammatory and Antioxidant Components from Deep Marine-Derived Fungus Myrothecium SP. Bzo-l062. Mar. Drugs, 18.","DOI":"10.3390\/md18120597"},{"key":"ref_16","doi-asserted-by":"crossref","unstructured":"Li, H., Liu, X., Li, X., Hu, Z., and Wang, L. (2021). Novel Harziane Diterpenes from Deep-Sea Sediment Fungus Trichoderma sp. SCSIOW21 and Their Potential Anti-Inflammatory Effects. Mar. Drugs, 19.","DOI":"10.3390\/md19120689"},{"key":"ref_17","doi-asserted-by":"crossref","unstructured":"Wang, L., and Umezawa, K. (2021). Cellular Signal Transductions and Their Inhibitors Derived from Deep-Sea Organisms. Mar. Drugs, 19.","DOI":"10.3390\/md19040205"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"622","DOI":"10.1038\/s41429-020-0302-9","article-title":"Inhibition of cellular inflammatory mediator production and amelioration of learning deficit in flies by deep sea Aspergillus-derived cyclopenin","volume":"73","author":"Wang","year":"2020","journal-title":"J. Antibiot."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"105223","DOI":"10.1016\/j.bioorg.2021.105223","article-title":"Bisabolane, cadinane, and cyclonerane sesquiterpenes from an algicolous strain of Trichoderma asperelloides","volume":"115","author":"Zou","year":"2021","journal-title":"Bioorganic Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"607","DOI":"10.5012\/bkcs.2004.25.5.607","article-title":"Polyketide and Sesquiterpenediol Metabolites from a Marine-Derived Fungus","volume":"25","author":"Li","year":"2004","journal-title":"Bull. Korean Chem. Soc."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"1293","DOI":"10.1016\/S0040-4039(01)91612-0","article-title":"Structure of cyclonerodiol","volume":"11","author":"Nozoe","year":"1970","journal-title":"Tetrahedron Lett."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"914","DOI":"10.1021\/ja00394a032","article-title":"Cyclonerodiol Biosynthesis and the Enzymatic Conversion of Farnesyl to Nerolidyl pyrophosphate","volume":"103","author":"David","year":"1981","journal-title":"J. Am. Chem. Soc."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"79","DOI":"10.1021\/acs.jnatprod.9b00710","article-title":"l-Phenylalanine Alters the Privileged Secondary Metabolite Production in the Marine-Derived Fungus Trichoderma erinaceum F1-1","volume":"83","author":"Guo","year":"2020","journal-title":"J. Nat. Prod."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"8572","DOI":"10.1021\/acsomega.9b04421","article-title":"DFT-Calculated IR Spectrum Amide I, II, and III Band Contributions of N-Methylacetamide Fine Components","volume":"5","author":"Ji","year":"2020","journal-title":"ACS Omega"},{"key":"ref_25","doi-asserted-by":"crossref","unstructured":"Song, Y.P., Miao, F.P., Liu, X.H., Yin, X.L., and Ji, N.Y. (2019). Cyclonerane Derivatives from the Algicolous Endophytic Fungus Trichoderma asperellum A-YMD-9-2. Mar. Drugs, 17.","DOI":"10.3390\/md17050252"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"38","DOI":"10.1016\/j.phytol.2019.05.001","article-title":"Harziane and cadinane terpenoids from the alga-endophytic fungus Trichoderma asperellum A-YMD-9-2","volume":"32","author":"Song","year":"2019","journal-title":"Phytochem. Lett."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"2553","DOI":"10.1021\/acs.jnatprod.8b00714","article-title":"Diterpenes and Sesquiterpenes from the Marine Algicolous Fungus Trichoderma harzianum X-5","volume":"81","author":"Song","year":"2018","journal-title":"J. Nat. Prod."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"55","DOI":"10.1016\/j.phytochem.2013.10.016","article-title":"Bicyclic and tetracyclic diterpenes from a Trichoderma symbiont of Taxus baccata","volume":"97","author":"Adelin","year":"2014","journal-title":"Phytochemistry"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"3487","DOI":"10.1038\/s41467-021-23589-9","article-title":"Structural insight on assembly-line catalysis in terpene biosynthesis","volume":"12","author":"Faylo","year":"2021","journal-title":"Nat. Commun."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"7999","DOI":"10.1021\/ja9005332","article-title":"Consequences of conformational preorganization in sesquiterpene biosynthesis: Theoretical studies on the formation of the bisabolene, curcumene, acoradiene, zizaene, cedrene, duprezianene, and sesquithuriferol sesquiterpenes","volume":"131","author":"Hong","year":"2009","journal-title":"J. Am. Chem. Soc."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"4076","DOI":"10.1021\/acs.jafc.2c01029","article-title":"Protein Engineering of PhUGT, a Donor Promiscuous Glycosyltransferase, for the Improved Enzymatic Synthesis of Antioxidant Quercetin 3-O-N-Acetylgalactosamine","volume":"70","author":"Xu","year":"2022","journal-title":"J. Agric. Food Chem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"10082","DOI":"10.1021\/ja0735857","article-title":"Kinetic analysis of teicoplanin glycosyltransferases and acyltransferase reveal ordered tailoring of aglycone scaffold to reconstitute mature teicoplanin","volume":"129","author":"Kruger","year":"2007","journal-title":"J. Am. Chem. Soc."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"113792","DOI":"10.1016\/j.bcp.2020.113792","article-title":"Small molecule inhibitors and stimulators of inducible nitric oxide synthase in cancer cells from natural origin (phytochemicals, marine compounds, antibiotics)","volume":"176","author":"Ozenver","year":"2020","journal-title":"Biochem. Pharmacol."}],"container-title":["Marine Drugs"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1660-3397\/21\/1\/7\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T01:48:09Z","timestamp":1760147289000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1660-3397\/21\/1\/7"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,12,22]]},"references-count":33,"journal-issue":{"issue":"1","published-online":{"date-parts":[[2023,1]]}},"alternative-id":["md21010007"],"URL":"https:\/\/doi.org\/10.3390\/md21010007","relation":{},"ISSN":["1660-3397"],"issn-type":[{"value":"1660-3397","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,12,22]]}}}