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Novel Sesquiterpene and Diterpene Aminoglycosides from the Deep-Sea-Sediment Fungus Trichoderma sp. SCSIOW21

Six new sesquiterpene aminoglycosides, trichaspside F (2) and cyclonerosides A–E (5–9), 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-butan...

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Autores principales: Li, Hongxu, Liu, Xinyi, Hu, Zhangli, Wang, Liyan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9863909/
https://www.ncbi.nlm.nih.gov/pubmed/36662180
http://dx.doi.org/10.3390/md21010007
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author Li, Hongxu
Liu, Xinyi
Hu, Zhangli
Wang, Liyan
author_facet Li, Hongxu
Liu, Xinyi
Hu, Zhangli
Wang, Liyan
author_sort Li, Hongxu
collection PubMed
description Six new sesquiterpene aminoglycosides, trichaspside F (2) and cyclonerosides A–E (5–9), 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–E (5–9) were tentatively proposed based on optical rotation and biogenic considerations. Cyclonerosides A–E (5–9) 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–E (6–9) exhibited the strongest NO-production-inhibitory activities with IC(50) values of 54.8, 50.7, 57.1, 42.0, and 48.0 µM, respectively, compared to the IC(50) value of 30.8 µM 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 µM.
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spelling pubmed-98639092023-01-22 Novel Sesquiterpene and Diterpene Aminoglycosides from the Deep-Sea-Sediment Fungus Trichoderma sp. SCSIOW21 Li, Hongxu Liu, Xinyi Hu, Zhangli Wang, Liyan Mar Drugs Article Six new sesquiterpene aminoglycosides, trichaspside F (2) and cyclonerosides A–E (5–9), 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–E (5–9) were tentatively proposed based on optical rotation and biogenic considerations. Cyclonerosides A–E (5–9) 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–E (6–9) exhibited the strongest NO-production-inhibitory activities with IC(50) values of 54.8, 50.7, 57.1, 42.0, and 48.0 µM, respectively, compared to the IC(50) value of 30.8 µM 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 µM. MDPI 2022-12-22 /pmc/articles/PMC9863909/ /pubmed/36662180 http://dx.doi.org/10.3390/md21010007 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/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/).
spellingShingle Article
Li, Hongxu
Liu, Xinyi
Hu, Zhangli
Wang, Liyan
Novel Sesquiterpene and Diterpene Aminoglycosides from the Deep-Sea-Sediment Fungus Trichoderma sp. SCSIOW21
title Novel Sesquiterpene and Diterpene Aminoglycosides from the Deep-Sea-Sediment Fungus Trichoderma sp. SCSIOW21
title_full Novel Sesquiterpene and Diterpene Aminoglycosides from the Deep-Sea-Sediment Fungus Trichoderma sp. SCSIOW21
title_fullStr Novel Sesquiterpene and Diterpene Aminoglycosides from the Deep-Sea-Sediment Fungus Trichoderma sp. SCSIOW21
title_full_unstemmed Novel Sesquiterpene and Diterpene Aminoglycosides from the Deep-Sea-Sediment Fungus Trichoderma sp. SCSIOW21
title_short Novel Sesquiterpene and Diterpene Aminoglycosides from the Deep-Sea-Sediment Fungus Trichoderma sp. SCSIOW21
title_sort novel sesquiterpene and diterpene aminoglycosides from the deep-sea-sediment fungus trichoderma sp. scsiow21
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9863909/
https://www.ncbi.nlm.nih.gov/pubmed/36662180
http://dx.doi.org/10.3390/md21010007
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