6MK2

Crystal structure of Coleus blumei rosmarinic acid synthase (RAS) in complex with 4-coumaroyl-(R)-3-(4-hydroxyphenyl)lactate

Summary for 6MK2

• Entry DOI: 10.2210/pdb6mk2/pdb
• Descriptor: Rosmarinate synthase, (2R)-3-(4-hydroxyphenyl)-2-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}propanoic acid (2 entities in total)
• Functional Keywords: bahd acyltransferase, hydroxycinnamoyltransferase, transferase
• Biological source: Plectranthus scutellarioides (Coleus)
• Total number of polymer chains: 1
• Total formula weight: 48286.42

Authors

Weng, J.K.,Levsh, O.L. (deposition date: 2018-09-24, release date: 2019-09-11, Last modification date: 2024-03-13)

Primary citation

Levsh, O.,Pluskal, T.,Carballo, V.,Mitchell, A.J.,Weng, J.K.
Independent evolution of rosmarinic acid biosynthesis in two sister families under the Lamiids clade of flowering plants.
J.Biol.Chem., 294:15193-15205, 2019

PubMed Abstract: As a means to maintain their sessile lifestyle amid challenging environments, plants produce an enormous diversity of compounds as chemical defenses against biotic and abiotic insults. The underpinning metabolic pathways that support the biosynthesis of these specialized chemicals in divergent plant species provide a rich arena for understanding the molecular evolution of complex metabolic traits. Rosmarinic acid (RA) is a phenolic natural product first discovered in plants of the mint family (Lamiaceae) and is recognized for its wide range of medicinal properties and potential applications in human dietary and medical interventions. Interestingly, the RA chemotype is present sporadically in multiple taxa of flowering plants as well as some hornworts and ferns, prompting the question whether its biosynthesis arose independently across different lineages. Here we report the elucidation of the RA biosynthetic pathway in (desert bells). This species represents the borage family (Boraginaceae), an RA-producing family closely related to the Lamiaceae within the Lamiids clade. Using a multi-omics approach in combination with functional characterization of candidate genes both and , we found that RA biosynthesis in involves specific activities of a BAHD acyltransferase and two cytochrome P450 hydroxylases. Further phylogenetic and comparative structure-function analyses of the RA biosynthetic enzymes clearly indicate that RA biosynthesis has evolved independently at least twice in the Lamiids, an exemplary case of chemotypic convergence through disparate evolutionary trajectories.

PubMed: 31481469
DOI: 10.1074/jbc.RA119.010454

Experimental method

X-RAY DIFFRACTION (3.35 Å)