Cytochrome P450-Catalyzed Biosynthesis of a Dihydrofuran Neoclerodane in Magic Mint (Salvia divinorum)
- Kwon, Moonhyuk; Utomo, Joseph C.; Park, Keunwan; Pascoe, Cameron A.; Chiorean, Sorina; Ngo, Iris; Pelot, Kyle A.; Pan, Cheol-Ho; Kim, Seon-Won; Zerbe, Philipp; Vederas, John C.; Ro, Dae-Kyun
- Issue Date
- AMER CHEMICAL SOC
- biocatalyst; cytochrome P450; diterpenoid; salvinorin; Salvia divinorum
- ACS CATALYSIS, v.12, no.1, pp.777 - 782
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- ACS CATALYSIS
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- The hallucinogenic plant, Salvia divinorum, synthesizes neoclerodane diterpenes, such as salvinorins, salvidivins, and salvinicins, which are agonistic or antagonistic to mu- or kappa-opioid receptors. From S. divinorum trichomes, crotonolide G synthase (SdCS; CYP76AH39) was identified. It catalyzes the conversion of kolavenol to a dihydrofuran neoclerodane, crotonolide G. O-18(2)-feeding studies confirmed that SdCS incorporates an aerobic oxygen into crotonolide G, rather than forming a cation at C16 that is trapped by the alcohol at C15. Structural modeling of SdCS accompanied by site-directed mutagenesis established the importance of V367 and F479 residues in substrate-binding. The dihydrofuran neoclerodane can serve as a unique lead structure for drug development.
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