Abstract
A biosynthetic pathway for rosmarinic acid is proposed. This pathway is deduced from studies of the enzymes detectable in preparations from suspension cells of Coleus blumei. Phenylalanine is transformed to 4-coumaroyl-CoA by the enzymes of the general phenylpropanoid pathway: phenylalanine ammonia-lyase (EC 4.3.1.5), cinnamic acid 4-hydroxylase (EC 1.14.13.11) and hydroxycinnamic acid:CoA ligase (EC 6.2.1.12). Tyrosine is metabolized to 4-hydroxyphenyllactate by tyrosine aminotransferase (EC 2.6.1.5) and hydroxyphenylpyruvate reductase. The ester can be formed from 4-coumaroyl-CoA and 4-hydroxyphenyllactate by the catalytic activity of rosmarinic acid synthase with concomitant release of CoA. Microsomal hydroxylase activities introduce the hydroxyl groups at positions 3 and 3′ of the aromatic rings of the ester 4-coumaroyl-4′-hydroxyphenyllactate giving rise to rosmarinic acid.
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Abbreviations
- Caf-pHPL:
-
caffeoyl-4′-hydroxyphenyllactate
- DHPL:
-
3,4-dihydroxyphenyllactic acid
- pC-DHPL:
-
4-coumaryl-3′,4′-dihydroxyphenyllactate
- pC-pHPL:
-
4′-coumaryl-4-hydroxyphenyllactate
- pHPL:
-
4-hydroxyphenyllactic acid
- RA:
-
rosmarinic acid
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The financial support of the Deutsche Forschungsgemeinschaft and the Fonds der Chemischen Industrie is gratefully acknowledged.
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Petersen, M., Häusler, E., Karwatzki, B. et al. Proposed biosynthetic pathway for rosmarinic acid in cell cultures of Coleus blumei Benth. Planta 189, 10–14 (1993). https://doi.org/10.1007/BF00201337
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DOI: https://doi.org/10.1007/BF00201337