Cannabicitran: Its unexpected racemic nature and potential origins.

Autor: Wood JS; Department of Chemistry and Biochemistry, University of North Carolina Wilmington, Wilmington, North Carolina, USA., Gordon WH; Department of Chemistry and Biochemistry, University of North Carolina Wilmington, Wilmington, North Carolina, USA., Morgan JB; Department of Chemistry and Biochemistry, University of North Carolina Wilmington, Wilmington, North Carolina, USA., Williamson RT; Department of Chemistry and Biochemistry, University of North Carolina Wilmington, Wilmington, North Carolina, USA.
Jazyk: angličtina
Zdroj: Chirality [Chirality] 2023 Sep; Vol. 35 (9), pp. 540-548. Date of Electronic Publication: 2023 May 04.
DOI: 10.1002/chir.23571
Abstrakt: Cannabicitran is a cannabinoid found in levels up to ~10% in commercial "purified" cannabidiol (CBD) extracts. The structure of this natural product was first reported more than 50 years ago. However, few studies have investigated cannabicitran or its origin despite the rapidly increasing interest in the use of cannabinoids for the treatment of a wide range of physiological conditions. Following on a recent detailed NMR and computational characterization of cannabicitran, our group initiated ECD and TDDFT studies aimed at unequivocally determining the absolute configuration of cannabicitran present in Cannabis sativa extracts. To our surprise, we discovered the natural product was racemic, raising questions around its presumed enzymatic origin. Herein, we report the isolation and absolute configuration of (-)-cannabicitran and (+)-cannabicitran. Several possible scenarios for production of the racemate in the plant and/or during extract processing are discussed.
(© 2023 The Authors. Chirality published by Wiley Periodicals LLC.)
Databáze: MEDLINE
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