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The dimerization of ⊿~9-tetrahydrocannabinolic acid A(THCA-A)

Acta Pharmaceutica Sinica B 2019年第5期9卷 1078-1083页

作者： Arben Cuadari Federica Pollastro Juan D.Unciti-Broceta Diego Caprioglio Alberto Minassi Annalisa Lopatriello Eduardo Munoz Orazio Taglialatela-Scafati Giovanni Appendino Dipartimento di Scienze del Farmaco Universita del Piemonte OrientaleNovara28100Italy emerald health biotechnology espana Calle Cecilia PayneCordoba14014Spain Dipartimento di Farmacia Universita di Napoli Federico IINapoli80131Italy Maimonides Biomedical Research Institute of Cordoba Cordoba14004Spain Department of Cellular Biology Physiology and ImmunologyUniversity of CordobaCordoba14004Spain University Hospital Reina Sofia Avenida de Menendez Pidal s/nCordoba14004Spain

The renewed interest in dimeric salicylates as broad-spectrum anti-inflammatory and antidiabetic agents provided a rationale to investigate the dimerization of the substituted salicylate D9-tetrahydrocannabinolic acid(THCA-A, 3 a) as a strategy to solve its instability to decarboxylation and to generate analogues and/or pro-drugs of this native pre-cannabinoid. Activation of the carboxylic group with the DCC-HOBt-DMAP protocol afforded a high yield of the OBt ester 4, that was next converted into the highly crystalline di-depsidic dimer 5 upon treatment with DMAP. The mono-depsidic dimer 6 was also formed when the reaction was carried out with partially decarboxylated THCA-A samples. The structure of the depsidic dimers was established by spectroscopic methods and by aminolysis of 5 into the pre-cannabinoid amide 7. Both dimers showed excellent shelf stability and did not generate significant amounts of D9-THC upon heating. However, only the didepsidic dimer 5 activated PPAR-g, the major target of pre-cannabinoids, but strong binding to serum proteins abolished this activity, also shielding it from the action of esterases.

关键词： Phytocannabinoids Dimerization D9-Tetrahydrocannabinolic acid A D9-Tetrahydrocannabinol PPAR-g

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