Amine-Regulated pri-SMTP Oxidation in SMTP Biosynthesis in <i>Stachybotrys</i>: Possible Implication in Nitrogen Acquisition
SMTP (the name SMTP is derived from <i>Stachybotrys microspora</i> triprenyl phenol) is a family of triprenyl phenol secondary metabolites from a black mold, <i>Stachybotrys microspora</i>. Some SMTP congeners exhibit anti-inflammatory and profibrinolytic activities that, in...
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MDPI AG
2022-09-01
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| Series: | Journal of Fungi |
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| Online Access: | https://www.mdpi.com/2309-608X/8/9/975 |
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| author | Ryota Iwama Yu Sasano Taichi Hiramatsu Shinya Otake Eriko Suzuki Keiji Hasumi |
| author_facet | Ryota Iwama Yu Sasano Taichi Hiramatsu Shinya Otake Eriko Suzuki Keiji Hasumi |
| author_sort | Ryota Iwama |
| collection | DOAJ |
| description | SMTP (the name SMTP is derived from <i>Stachybotrys microspora</i> triprenyl phenol) is a family of triprenyl phenol secondary metabolites from a black mold, <i>Stachybotrys microspora</i>. Some SMTP congeners exhibit anti-inflammatory and profibrinolytic activities that, in combination, contribute to the treatment of ischemic stroke. The final step in the SMTP biosynthesis is a non-enzymatic amine conjugation with an <i>o</i>-phthalaldehyde moiety of the precursor pre-SMTP, which can form adducts with proteins and nucleic acids. Thus, pre-SMTP formation should be a precisely regulated, rate-limiting step in the SMTP biosynthesis. To address the mechanism backing this regulation, we purified a metabolite that rapidly disappeared following amine feeding, identifying a novel compound, pri-SMTP. Furthermore, an enzyme, designated as pri-SMTP oxidase, responsible for pri-SMTP conversion to pre-SMTP, was purified. The formation of pri-SMTP, which is regulated by nitrogen and carbon nutrients, occurred in particular septate mycelia. Although pri-SMTP oxidase was expressed constitutively, the consumption of pri-SMTP was accelerated only when a primary amine was fed. Thus, SMTP biosynthesis is regulated by at least three mechanisms: (i) pri-SMTP formation affected by nutrients, (ii) the compartmentalization of pri-SMTP formation/storage, and (iii) amine-regulated pri-SMTP oxidation. Amine-regulated SMTP formation (i.e., amine-capturing with pre-SMTP) may play a role in the nitrogen acquisition/assimilation strategy in <i>S. microspora</i>, since pri-SMTP synthesis occurs on non-preferred nitrogen. |
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| language | English |
| last_indexed | 2024-03-09T23:30:03Z |
| publishDate | 2022-09-01 |
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| series | Journal of Fungi |
| spelling | doaj.art-44485819419e4d0bac808ef4eebf13412023-11-23T17:10:11ZengMDPI AGJournal of Fungi2309-608X2022-09-018997510.3390/jof8090975Amine-Regulated pri-SMTP Oxidation in SMTP Biosynthesis in <i>Stachybotrys</i>: Possible Implication in Nitrogen AcquisitionRyota Iwama0Yu Sasano1Taichi Hiramatsu2Shinya Otake3Eriko Suzuki4Keiji Hasumi5Department of Applied Biological Science, Tokyo University of Agriculture and Technology, Fuchu, Tokyo 183-8509, JapanDepartment of Applied Biological Science, Tokyo University of Agriculture and Technology, Fuchu, Tokyo 183-8509, JapanDepartment of Applied Biological Science, Tokyo University of Agriculture and Technology, Fuchu, Tokyo 183-8509, JapanDepartment of Applied Biological Science, Tokyo University of Agriculture and Technology, Fuchu, Tokyo 183-8509, JapanDepartment of Applied Biological Science, Tokyo University of Agriculture and Technology, Fuchu, Tokyo 183-8509, JapanDepartment of Applied Biological Science, Tokyo University of Agriculture and Technology, Fuchu, Tokyo 183-8509, JapanSMTP (the name SMTP is derived from <i>Stachybotrys microspora</i> triprenyl phenol) is a family of triprenyl phenol secondary metabolites from a black mold, <i>Stachybotrys microspora</i>. Some SMTP congeners exhibit anti-inflammatory and profibrinolytic activities that, in combination, contribute to the treatment of ischemic stroke. The final step in the SMTP biosynthesis is a non-enzymatic amine conjugation with an <i>o</i>-phthalaldehyde moiety of the precursor pre-SMTP, which can form adducts with proteins and nucleic acids. Thus, pre-SMTP formation should be a precisely regulated, rate-limiting step in the SMTP biosynthesis. To address the mechanism backing this regulation, we purified a metabolite that rapidly disappeared following amine feeding, identifying a novel compound, pri-SMTP. Furthermore, an enzyme, designated as pri-SMTP oxidase, responsible for pri-SMTP conversion to pre-SMTP, was purified. The formation of pri-SMTP, which is regulated by nitrogen and carbon nutrients, occurred in particular septate mycelia. Although pri-SMTP oxidase was expressed constitutively, the consumption of pri-SMTP was accelerated only when a primary amine was fed. Thus, SMTP biosynthesis is regulated by at least three mechanisms: (i) pri-SMTP formation affected by nutrients, (ii) the compartmentalization of pri-SMTP formation/storage, and (iii) amine-regulated pri-SMTP oxidation. Amine-regulated SMTP formation (i.e., amine-capturing with pre-SMTP) may play a role in the nitrogen acquisition/assimilation strategy in <i>S. microspora</i>, since pri-SMTP synthesis occurs on non-preferred nitrogen.https://www.mdpi.com/2309-608X/8/9/975nitrogen acquisitionsecondary metabolismoxidaseSMTPcompartmentalizationbiosynthesis |
| spellingShingle | Ryota Iwama Yu Sasano Taichi Hiramatsu Shinya Otake Eriko Suzuki Keiji Hasumi Amine-Regulated pri-SMTP Oxidation in SMTP Biosynthesis in <i>Stachybotrys</i>: Possible Implication in Nitrogen Acquisition Journal of Fungi nitrogen acquisition secondary metabolism oxidase SMTP compartmentalization biosynthesis |
| title | Amine-Regulated pri-SMTP Oxidation in SMTP Biosynthesis in <i>Stachybotrys</i>: Possible Implication in Nitrogen Acquisition |
| title_full | Amine-Regulated pri-SMTP Oxidation in SMTP Biosynthesis in <i>Stachybotrys</i>: Possible Implication in Nitrogen Acquisition |
| title_fullStr | Amine-Regulated pri-SMTP Oxidation in SMTP Biosynthesis in <i>Stachybotrys</i>: Possible Implication in Nitrogen Acquisition |
| title_full_unstemmed | Amine-Regulated pri-SMTP Oxidation in SMTP Biosynthesis in <i>Stachybotrys</i>: Possible Implication in Nitrogen Acquisition |
| title_short | Amine-Regulated pri-SMTP Oxidation in SMTP Biosynthesis in <i>Stachybotrys</i>: Possible Implication in Nitrogen Acquisition |
| title_sort | amine regulated pri smtp oxidation in smtp biosynthesis in i stachybotrys i possible implication in nitrogen acquisition |
| topic | nitrogen acquisition secondary metabolism oxidase SMTP compartmentalization biosynthesis |
| url | https://www.mdpi.com/2309-608X/8/9/975 |
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