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. 2018 Feb 1;8:2116. doi: 10.1038/s41598-018-20514-x

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© The Author(s) 2018

Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.

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Biosynthetic molecular steps of terreic acid (TA) that were identified by heterologous pathway assembly. Speculated transition compounds are boxed. The AtX (polyketide synthase) catalyzes formation of polyketide 6-MSA (2); AtA (decarboxylase) catalyzes formation of 3-methylcatechol (5) by decarboxylative hydroxylation of 6-MSA; AtG (cytochrome P450 monooxygenase) helps AtE (cytochrome P450 monooxygenase) to catalyze formation of 3-methyl-1,2,4-benzenetriol (6); AtD (cyclooxygenase) catalyzes formation of terremutin (3) by epoxidation and hydroxyl oxidation of 3-methyl-1,2,4-benzenetriol (6); AtC (GMC oxidoreductase) catalyzes formation of the final product, TA (1), via a reaction of oxidation of the hydroxyl group in terremutin (3).