Catalytic Potential of Cannabis Prenyltransferase to Expand Cannabinoid Scaffold Diversity

Ryosuke Tanaya; Takeshi Kodama; Yuan E. Lee; Yoko Yasuno; Tetsuro Shinada; Hironobu Takahashi; Takuya Ito; Hiroyuki Morita; Suresh Awale; Futoshi Taura

doi:10.1021/acs.orglett.3c03410

Catalytic Potential of Cannabis Prenyltransferase to Expand Cannabinoid Scaffold Diversity

Ryosuke Tanaya, Takeshi Kodama, Yuan E. Lee, Yoko Yasuno, Tetsuro Shinada, Hironobu Takahashi, Takuya Ito, Hiroyuki Morita, Suresh Awale, Futoshi Taura^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

6 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	8601-8605
Number of pages	5
Journal	Organic Letters
Volume	25
Issue number	48
DOIs	https://doi.org/10.1021/acs.orglett.3c03410
State	Published - 2023/12/08

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.3c03410

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title = "Catalytic Potential of Cannabis Prenyltransferase to Expand Cannabinoid Scaffold Diversity",

abstract = "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.",

author = "Ryosuke Tanaya and Takeshi Kodama and Lee, {Yuan E.} and Yoko Yasuno and Tetsuro Shinada and Hironobu Takahashi and Takuya Ito and Hiroyuki Morita and Suresh Awale and Futoshi Taura",

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year = "2023",

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doi = "10.1021/acs.orglett.3c03410",

language = "英語",

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TY - JOUR

T1 - Catalytic Potential of Cannabis Prenyltransferase to Expand Cannabinoid Scaffold Diversity

AU - Tanaya, Ryosuke

AU - Kodama, Takeshi

AU - Lee, Yuan E.

AU - Yasuno, Yoko

AU - Shinada, Tetsuro

AU - Takahashi, Hironobu

AU - Ito, Takuya

AU - Morita, Hiroyuki

AU - Awale, Suresh

AU - Taura, Futoshi

PY - 2023/12/8

Y1 - 2023/12/8

N2 - 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.

AB - 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.

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U2 - 10.1021/acs.orglett.3c03410

DO - 10.1021/acs.orglett.3c03410

M3 - 学術論文

C2 - 38010421

AN - SCOPUS:85179603011

SN - 1523-7060

VL - 25

SP - 8601

EP - 8605

JO - Organic Letters

JF - Organic Letters

IS - 48

ER -

Catalytic Potential of Cannabis Prenyltransferase to Expand Cannabinoid Scaffold Diversity

Abstract

ASJC Scopus subject areas

UN SDGs

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