biostudies-literatureIwama RInstitute for Fermentation975https://www.ebi.ac.uk/biostudies/studies/S-EPMC9502257biostudies-literatureUnknown8(9)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-SMJournal of fungi (Basel, Switzerland)Amine-Regulated pri-SMTP Oxidation in SMTP Biosynthesis in <i>Stachybotrys</i>: Possible Implication in Nitrogen Acquisition.PMC9502257G-25-2-10Hasumi KSasano YHiramatsu TIwama RSuzuki EOtake SfalseAmine-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 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-SM2022-01-01T00:00:00Z2022 Sep2025-06-01T00:11:22.957Z2025-02-19T00:41:50.139ZS-EPMC95022573613570010.3390/jof8090975