Scalable preparation of furanosteroidal viridin, β-viridin and viridiol from Trichoderma virens
Abstract Viridin and viridiol, along with wortmannin, metabolized by filamentous fungus Trichoderma virens, are identical furanosteroids with high-potent inhibitory activity towards phosphatidylinositol 3-kinase (PI3K) that associates the growth of tumor cells. Therefore, structure–activity relation...
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Nature Portfolio
2025-01-01
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| Online Access: | https://doi.org/10.1038/s41598-025-87070-z |
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| author | Wen Zhang Kazu Sunami Shuo Liu Desita Triana Zetryana Puteri Tachrim Rikuto Kikuchi Tohru Taniguchi Kenji Monde Tsunayoshi Takehara Da-Yang Zhou Takeyuki Suzuki Yasuyuki Hashidoko Makoto Hashimoto Yuta Murai |
| author_facet | Wen Zhang Kazu Sunami Shuo Liu Desita Triana Zetryana Puteri Tachrim Rikuto Kikuchi Tohru Taniguchi Kenji Monde Tsunayoshi Takehara Da-Yang Zhou Takeyuki Suzuki Yasuyuki Hashidoko Makoto Hashimoto Yuta Murai |
| author_sort | Wen Zhang |
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| description | Abstract Viridin and viridiol, along with wortmannin, metabolized by filamentous fungus Trichoderma virens, are identical furanosteroids with high-potent inhibitory activity towards phosphatidylinositol 3-kinase (PI3K) that associates the growth of tumor cells. Therefore, structure–activity relationship study (SAR) of these furanosteroids contributes to the development of novel drugs. However, rational supply methods have not been established yet. In this study, we generated an efficient method to produce both viridin and viridiol by using a unique pH regulated T. virens culture manner. Besides, we successfully obtained β-viridin (epimer of viridin) crystal and X-ray structure, of which the CAS number was registered without stereochemistry. Furthermore, applying the original method to stable isotope study, we also obtained [U-13C]-viridn and [U-13C]-viridol by using [U-13C6]-glucose as a carbon source replacing normal glucose which can be used to elucidate the biosynthesis pathway of furanosteroids. |
| format | Article |
| id | doaj-art-a556867114db44b89d9776f477da6a49 |
| institution | Kabale University |
| issn | 2045-2322 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Scientific Reports |
| spelling | doaj-art-a556867114db44b89d9776f477da6a492025-01-26T12:29:33ZengNature PortfolioScientific Reports2045-23222025-01-011511810.1038/s41598-025-87070-zScalable preparation of furanosteroidal viridin, β-viridin and viridiol from Trichoderma virensWen Zhang0Kazu Sunami1Shuo Liu2Desita Triana3Zetryana Puteri Tachrim4Rikuto Kikuchi5Tohru Taniguchi6Kenji Monde7Tsunayoshi Takehara8Da-Yang Zhou9Takeyuki Suzuki10Yasuyuki Hashidoko11Makoto Hashimoto12Yuta Murai13Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido UniversityDivision of Applied Bioscience, Graduate School of Agriculture, Hokkaido UniversityDivision of Applied Bioscience, Graduate School of Agriculture, Hokkaido UniversityDivision of Applied Bioscience, Graduate School of Agriculture, Hokkaido UniversityDivision of Applied Bioscience, Graduate School of Agriculture, Hokkaido UniversityGraduate School of Life Science, Hokkaido UniversityGraduate School of Life Science, Hokkaido UniversityGraduate School of Life Science, Hokkaido UniversityThe Institute of Scientific and Industrial Research, Osaka UniversityThe Institute of Scientific and Industrial Research, Osaka UniversityThe Institute of Scientific and Industrial Research, Osaka UniversityDivision of Applied Bioscience, Graduate School of Agriculture, Hokkaido UniversityDivision of Applied Bioscience, Graduate School of Agriculture, Hokkaido UniversityDivision of Applied Bioscience, Graduate School of Agriculture, Hokkaido UniversityAbstract Viridin and viridiol, along with wortmannin, metabolized by filamentous fungus Trichoderma virens, are identical furanosteroids with high-potent inhibitory activity towards phosphatidylinositol 3-kinase (PI3K) that associates the growth of tumor cells. Therefore, structure–activity relationship study (SAR) of these furanosteroids contributes to the development of novel drugs. However, rational supply methods have not been established yet. In this study, we generated an efficient method to produce both viridin and viridiol by using a unique pH regulated T. virens culture manner. Besides, we successfully obtained β-viridin (epimer of viridin) crystal and X-ray structure, of which the CAS number was registered without stereochemistry. Furthermore, applying the original method to stable isotope study, we also obtained [U-13C]-viridn and [U-13C]-viridol by using [U-13C6]-glucose as a carbon source replacing normal glucose which can be used to elucidate the biosynthesis pathway of furanosteroids.https://doi.org/10.1038/s41598-025-87070-zTrichoderma virensViridinΒ-viridinViridiol[U-13C]-viridin[U-13C]-viridol |
| spellingShingle | Wen Zhang Kazu Sunami Shuo Liu Desita Triana Zetryana Puteri Tachrim Rikuto Kikuchi Tohru Taniguchi Kenji Monde Tsunayoshi Takehara Da-Yang Zhou Takeyuki Suzuki Yasuyuki Hashidoko Makoto Hashimoto Yuta Murai Scalable preparation of furanosteroidal viridin, β-viridin and viridiol from Trichoderma virens Scientific Reports Trichoderma virens Viridin Β-viridin Viridiol [U-13C]-viridin [U-13C]-viridol |
| title | Scalable preparation of furanosteroidal viridin, β-viridin and viridiol from Trichoderma virens |
| title_full | Scalable preparation of furanosteroidal viridin, β-viridin and viridiol from Trichoderma virens |
| title_fullStr | Scalable preparation of furanosteroidal viridin, β-viridin and viridiol from Trichoderma virens |
| title_full_unstemmed | Scalable preparation of furanosteroidal viridin, β-viridin and viridiol from Trichoderma virens |
| title_short | Scalable preparation of furanosteroidal viridin, β-viridin and viridiol from Trichoderma virens |
| title_sort | scalable preparation of furanosteroidal viridin β viridin and viridiol from trichoderma virens |
| topic | Trichoderma virens Viridin Β-viridin Viridiol [U-13C]-viridin [U-13C]-viridol |
| url | https://doi.org/10.1038/s41598-025-87070-z |
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