New acorane-sesequiterpenes and anti-retinoblastoma constituents from the marine algicolous fungus Trichoderma harzianum NTU2180 guided by molecular networking strategy
Abstract Background Trichoderma species, known as biocontrol agents against plant diseases, contain diverse compounds, especially terpenoids, with various bioactivities. To facilitate the exploration of bioactive secondary metabolites of Trichoderma harzianum NTU2180, the OSMAC approach MS/MS molecu...
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SpringerOpen
2025-01-01
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| Series: | Botanical Studies |
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| Online Access: | https://doi.org/10.1186/s40529-024-00449-5 |
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| author | Andrea Gu Fan-Li Lin Chung-Kuang Lu Tz-Wei Yeh Yih-Fung Chen Ho-Cheng Wu Tzong-Huei Lee |
| author_facet | Andrea Gu Fan-Li Lin Chung-Kuang Lu Tz-Wei Yeh Yih-Fung Chen Ho-Cheng Wu Tzong-Huei Lee |
| author_sort | Andrea Gu |
| collection | DOAJ |
| description | Abstract Background Trichoderma species, known as biocontrol agents against plant diseases, contain diverse compounds, especially terpenoids, with various bioactivities. To facilitate the exploration of bioactive secondary metabolites of Trichoderma harzianum NTU2180, the OSMAC approach MS/MS molecular networking was applied in the current study. Results The feature-based molecular networking (FBMN) analysis showed that T. harzianum NTU2180 fermented on germinated brown rice (GBR) produced more terpenoids. Here, two new acorane-sesequiterpenes, trichospirols A (1) and B (2), and 12 known compounds (3 − 14) were isolated from the EtOAc layer of T. harzianum NTU2180 fermentation on GBR. Structures of these compounds were determined through NMR, UV, IR, and MS analyses. The absolute configuration of trichospirols A (1) was also elucidated by x-ray with Cu K-α radiation. Among them, six compounds (1, 2, 3, 4, 5, and 11) were annotated as terpenoids by the NPClassifier on FBMN. 5-Hydroxy-3-hydroxmethyl-2-methyl-7-methoxychromone (7) and ergosterol peroxide (11) showed significant anti-angiogenic activity in ex vivo experiments with respective 0.57 ± 0.12- and 0.20 ± 0.12-fold changes. In addition, compound 11 displayed cytotoxicity against Y79 retinoblastoma cells with IC50 value of 35.3 ± 6.9 µM. Conclusions The current study utilizes FBMN concept with OSMAC approach to accelerate the exploration of potential metabolites of the fungus Trichoderma harzianum NTU2180. Through a series of FBMN-guided isolation and purification, two new acorane-sesequiterpenes and 12 known compounds were obtained. The ex vivo and in vitro experiments were evaluated to assess anticancer isolates. It is worth noting that compound 11 was identified as a dual inhibitor targeting both angiogenesis and proliferation of retinoblastomas. Altogether, the results revealed the novel potential of T. harzianum for developing natural therapeutics against retinoblastomas. |
| format | Article |
| id | doaj-art-b4a5a341d7e149b2bfab60c82018122e |
| institution | Kabale University |
| issn | 1999-3110 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | SpringerOpen |
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| series | Botanical Studies |
| spelling | doaj-art-b4a5a341d7e149b2bfab60c82018122e2025-01-19T12:14:44ZengSpringerOpenBotanical Studies1999-31102025-01-0166111310.1186/s40529-024-00449-5New acorane-sesequiterpenes and anti-retinoblastoma constituents from the marine algicolous fungus Trichoderma harzianum NTU2180 guided by molecular networking strategyAndrea Gu0Fan-Li Lin1Chung-Kuang Lu2Tz-Wei Yeh3Yih-Fung Chen4Ho-Cheng Wu5Tzong-Huei Lee6Institute of Fisheries Science, College of Life Science, National Taiwan UniversityDepartment of Pharmacology, School of Post-Baccalaureate Medicine, College of Medicine, Kaohsiung Medical UniversityNational Research Institute of Chinese Medicine, Ministry of Health and WelfareInstitute of Fisheries Science, College of Life Science, National Taiwan UniversityGraduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical UniversitySchool of Pharmacy, College of Pharmacy, Kaohsiung Medical UniversityInstitute of Fisheries Science, College of Life Science, National Taiwan UniversityAbstract Background Trichoderma species, known as biocontrol agents against plant diseases, contain diverse compounds, especially terpenoids, with various bioactivities. To facilitate the exploration of bioactive secondary metabolites of Trichoderma harzianum NTU2180, the OSMAC approach MS/MS molecular networking was applied in the current study. Results The feature-based molecular networking (FBMN) analysis showed that T. harzianum NTU2180 fermented on germinated brown rice (GBR) produced more terpenoids. Here, two new acorane-sesequiterpenes, trichospirols A (1) and B (2), and 12 known compounds (3 − 14) were isolated from the EtOAc layer of T. harzianum NTU2180 fermentation on GBR. Structures of these compounds were determined through NMR, UV, IR, and MS analyses. The absolute configuration of trichospirols A (1) was also elucidated by x-ray with Cu K-α radiation. Among them, six compounds (1, 2, 3, 4, 5, and 11) were annotated as terpenoids by the NPClassifier on FBMN. 5-Hydroxy-3-hydroxmethyl-2-methyl-7-methoxychromone (7) and ergosterol peroxide (11) showed significant anti-angiogenic activity in ex vivo experiments with respective 0.57 ± 0.12- and 0.20 ± 0.12-fold changes. In addition, compound 11 displayed cytotoxicity against Y79 retinoblastoma cells with IC50 value of 35.3 ± 6.9 µM. Conclusions The current study utilizes FBMN concept with OSMAC approach to accelerate the exploration of potential metabolites of the fungus Trichoderma harzianum NTU2180. Through a series of FBMN-guided isolation and purification, two new acorane-sesequiterpenes and 12 known compounds were obtained. The ex vivo and in vitro experiments were evaluated to assess anticancer isolates. It is worth noting that compound 11 was identified as a dual inhibitor targeting both angiogenesis and proliferation of retinoblastomas. Altogether, the results revealed the novel potential of T. harzianum for developing natural therapeutics against retinoblastomas.https://doi.org/10.1186/s40529-024-00449-5Ex vivo anti-angiogenic activityFeature-based molecular networking (FBMN)OSMAC approachRetinoblastomaTrichoderma harzianum NTU2180Triterpenoid |
| spellingShingle | Andrea Gu Fan-Li Lin Chung-Kuang Lu Tz-Wei Yeh Yih-Fung Chen Ho-Cheng Wu Tzong-Huei Lee New acorane-sesequiterpenes and anti-retinoblastoma constituents from the marine algicolous fungus Trichoderma harzianum NTU2180 guided by molecular networking strategy Botanical Studies Ex vivo anti-angiogenic activity Feature-based molecular networking (FBMN) OSMAC approach Retinoblastoma Trichoderma harzianum NTU2180 Triterpenoid |
| title | New acorane-sesequiterpenes and anti-retinoblastoma constituents from the marine algicolous fungus Trichoderma harzianum NTU2180 guided by molecular networking strategy |
| title_full | New acorane-sesequiterpenes and anti-retinoblastoma constituents from the marine algicolous fungus Trichoderma harzianum NTU2180 guided by molecular networking strategy |
| title_fullStr | New acorane-sesequiterpenes and anti-retinoblastoma constituents from the marine algicolous fungus Trichoderma harzianum NTU2180 guided by molecular networking strategy |
| title_full_unstemmed | New acorane-sesequiterpenes and anti-retinoblastoma constituents from the marine algicolous fungus Trichoderma harzianum NTU2180 guided by molecular networking strategy |
| title_short | New acorane-sesequiterpenes and anti-retinoblastoma constituents from the marine algicolous fungus Trichoderma harzianum NTU2180 guided by molecular networking strategy |
| title_sort | new acorane sesequiterpenes and anti retinoblastoma constituents from the marine algicolous fungus trichoderma harzianum ntu2180 guided by molecular networking strategy |
| topic | Ex vivo anti-angiogenic activity Feature-based molecular networking (FBMN) OSMAC approach Retinoblastoma Trichoderma harzianum NTU2180 Triterpenoid |
| url | https://doi.org/10.1186/s40529-024-00449-5 |
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