The biosynthesis of thymol, carvacrol, and thymohydroquinone in Lamiaceae proceeds via cytochrome P450s and a short-chain dehydrogenase | Proceedings of the National Academy of Sciences thumbnail
The biosynthesis of thymol, carvacrol, and thymohydroquinone in Lamiaceae proceeds via cytochrome P450s and a short-chain dehydrogenase | Proceedings of the National Academy of Sciences
www.pnas.org
biosynthetic pathway to these compounds begins with the cyclization of GDP to γ-terpinene by a terpene synthase, and γ-terpinene synthases we show that thymol and carvacrol formation proceeds via hydroxylation of γ-terpinene at either the 3- (to thymol) or 6- (to carvacrol) position catalyzed by CYP
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  • biosynthetic pathway to these compounds begins with the cyclization of GDP to γ-terpinene by a terpene synthase, and γ-terpinene synthases
  • we show that thymol and carvacrol formation proceeds via hydroxylation of γ-terpinene at either the 3- (to thymol) or 6- (to carvacrol) position catalyzed by CYPs of the 71D subfamily to give unstable products that are likely to be cyclohexadienols.
  • These intermediates are next converted by an SDR, TvSDR1, to their corresponding ketones, which can then aromatize via keto–enol tautomerism, forming thymol and carvacrol
  • Thymol and carvacrol biosynthesis has been proposed to proceed by the cyclization of geranyl diphosphate to γ-terpinene, followed by a series of oxidations via p-cymene.

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