Catalytic Potential of Cannabis Prenyltransferase to Expand Cannabinoid Scaffold Diversity

Biologically active cannabinoids are derived from cannabigerolic acid (CBGA), which is biosynthesized by aromatic prenyltransferase CsPT4. We exploit the catalytic versatility of CsPT4 to synthesize various CBGA analogues, including a geranylated bibenzyl acid, the precursor to bibenzyl cannabinoids...

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Bibliographic Details
Published in:Organic letters 2023-12, Vol.25 (48), p.8601-8605
Main Authors: Tanaya, Ryosuke, Kodama, Takeshi, Lee, Yuan-E, Yasuno, Yoko, Shinada, Tetsuro, Takahashi, Hironobu, Ito, Takuya, Morita, Hiroyuki, Awale, Suresh, Taura, Futoshi
Format: Article
Language:English
Subjects:
Bibenzyls
Cannabinoids
Cannabis
Dimethylallyltranstransferase
Humans
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Summary:Biologically active cannabinoids are derived from cannabigerolic acid (CBGA), which is biosynthesized by aromatic prenyltransferase CsPT4. We exploit the catalytic versatility of CsPT4 to synthesize various CBGA analogues, including a geranylated bibenzyl acid, the precursor to bibenzyl cannabinoids of liverwort origin. The synthesized natural and new-to-nature cannabinoids exhibit potent cytotoxicity in human pancreatic cancer cells. CsPT4 can artificially extend the cannabinoid biosynthetic diversity with novel and improved biological activities.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c03410