CYP76 Oxidation Network of Abietane Diterpenes in Lamiaceae Reconstituted in Yeast

Ulschan Bathe, Andrej Frolov, Andrea Porzel, Alain Tissier

Research output

3 Citations (Scopus)

Abstract

Rosemary and sage species from Lamiaceae contain high amounts of structurally related but diverse abietane diterpenes. A number of substances from this compound family have potential pharmacological activities and are used in the food and cosmetic industry. This has raised interest in their biosynthesis. Investigations in Rosmarinus officinalis and some sage species have uncovered two main groups of cytochrome P450 oxygenases that are involved in the oxidation of the precursor abietatriene. CYP76AHs produce ferruginol and 11-hydroxyferruginol, while CYP76AKs catalyze oxidations at the C20 position. Using a modular Golden-Gate-compatible assembly system for yeast expression, these enzymes were systematically tested either alone or in combination. A total of 14 abietane diterpenes could be detected, 8 of which have not been reported thus far. We demonstrate here that yeast is a valid system for engineering and reconstituting the abietane diterpene network, allowing for the discovery of novel compounds with potential bioactivity.

Original languageEnglish
JournalJournal of Agricultural and Food Chemistry
DOIs
Publication statusAccepted/In press - 1 Jan 2019

Fingerprint

Abietane Diterpenes
Lamiaceae
diterpenoids
Yeast
Yeasts
oxidation
yeasts
Oxidation
Rosmarinus
Oxygenases
Rosmarinus officinalis
Cosmetics
rosemary
Food Industry
Biosynthesis
oxygenases
cosmetics
Bioactivity
cytochrome P-450
Cytochrome P-450 Enzyme System

Scopus subject areas

  • Chemistry(all)
  • Agricultural and Biological Sciences(all)

Cite this

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title = "CYP76 Oxidation Network of Abietane Diterpenes in Lamiaceae Reconstituted in Yeast",
abstract = "Rosemary and sage species from Lamiaceae contain high amounts of structurally related but diverse abietane diterpenes. A number of substances from this compound family have potential pharmacological activities and are used in the food and cosmetic industry. This has raised interest in their biosynthesis. Investigations in Rosmarinus officinalis and some sage species have uncovered two main groups of cytochrome P450 oxygenases that are involved in the oxidation of the precursor abietatriene. CYP76AHs produce ferruginol and 11-hydroxyferruginol, while CYP76AKs catalyze oxidations at the C20 position. Using a modular Golden-Gate-compatible assembly system for yeast expression, these enzymes were systematically tested either alone or in combination. A total of 14 abietane diterpenes could be detected, 8 of which have not been reported thus far. We demonstrate here that yeast is a valid system for engineering and reconstituting the abietane diterpene network, allowing for the discovery of novel compounds with potential bioactivity.",
keywords = "abietane diterpene, CYP plasticity, CYP76AH, CYP76AK, Lamiaceae, yeast expression",
author = "Ulschan Bathe and Andrej Frolov and Andrea Porzel and Alain Tissier",
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T1 - CYP76 Oxidation Network of Abietane Diterpenes in Lamiaceae Reconstituted in Yeast

AU - Bathe, Ulschan

AU - Frolov, Andrej

AU - Porzel, Andrea

AU - Tissier, Alain

PY - 2019/1/1

Y1 - 2019/1/1

N2 - Rosemary and sage species from Lamiaceae contain high amounts of structurally related but diverse abietane diterpenes. A number of substances from this compound family have potential pharmacological activities and are used in the food and cosmetic industry. This has raised interest in their biosynthesis. Investigations in Rosmarinus officinalis and some sage species have uncovered two main groups of cytochrome P450 oxygenases that are involved in the oxidation of the precursor abietatriene. CYP76AHs produce ferruginol and 11-hydroxyferruginol, while CYP76AKs catalyze oxidations at the C20 position. Using a modular Golden-Gate-compatible assembly system for yeast expression, these enzymes were systematically tested either alone or in combination. A total of 14 abietane diterpenes could be detected, 8 of which have not been reported thus far. We demonstrate here that yeast is a valid system for engineering and reconstituting the abietane diterpene network, allowing for the discovery of novel compounds with potential bioactivity.

AB - Rosemary and sage species from Lamiaceae contain high amounts of structurally related but diverse abietane diterpenes. A number of substances from this compound family have potential pharmacological activities and are used in the food and cosmetic industry. This has raised interest in their biosynthesis. Investigations in Rosmarinus officinalis and some sage species have uncovered two main groups of cytochrome P450 oxygenases that are involved in the oxidation of the precursor abietatriene. CYP76AHs produce ferruginol and 11-hydroxyferruginol, while CYP76AKs catalyze oxidations at the C20 position. Using a modular Golden-Gate-compatible assembly system for yeast expression, these enzymes were systematically tested either alone or in combination. A total of 14 abietane diterpenes could be detected, 8 of which have not been reported thus far. We demonstrate here that yeast is a valid system for engineering and reconstituting the abietane diterpene network, allowing for the discovery of novel compounds with potential bioactivity.

KW - abietane diterpene

KW - CYP plasticity

KW - CYP76AH

KW - CYP76AK

KW - Lamiaceae

KW - yeast expression

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