Chemical characterisation of oxidative degradation products of Δ9-THC

被引：33

作者：

Carbone, Marianna ^{[1
]}

Castelluccio, Francesco ^{[1
]}

Daniele, Antonella ^{[1
]}

Sutton, Alan ^{[2
]}

Ligresti, Alessia ^{[3
]}

Di Marzo, Vincenzo ^{[3
]}

Gavagnin, Margherita ^{[1
]}

机构：

[1] CNR, Ist Chim Biomol, I-80078 Naples, Italy

[2] GW Pharmaceut Plc, GW Pharmaceut, Salisbury SP4 0JQ, Wilts, England

[3] CNR, Ist Chim Biomol, Endocannabinoid Res Grp, I-80078 Naples, Italy

来源：

TETRAHEDRON | 2010年 / 66卷 / 49期

关键词：

Cannabis sativa; Cannabinoids; THC; Oxidative degradation; Chemical characterization; NMR;

D O I：

10.1016/j.tet.2010.10.025

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The chemical analysis of a sample of Delta(9)-THC which had been stored in an ethanol/propylene glycol solution for 5 years resulted in the isolation of several hydroxylated Delta(9)-THC derivatives the main of which were trans-cannabitriol monoethyl ether (4) and trans-propanediol ethers 7 and 8 cis-Cannabitriol monoethyl ether (5) and the oxidised derivatives 3 and 6 were detected in lesser amounts The structure elucidation of the unprecedented cannabinoids 3 5 7 and 8 was achieved mainly by NMR techniques Full NMR assignment of compounds 4 and 6 were also made The detection of cannabitriol (6) and the corresponding solvent-adduct analogues (compounds 4-8) was in agreement with the decomposition mechanisms previously proposed for Delta(9)-THC The isolation of the endoperoxide 3 represents indirect evidence of the existence of unstable precursors that were suspected to be intermediates in the non-enzymatic oxidation pathway of Delta(9)-THC Both isomers of cannabitriol monoethyl ether exhibited weak affinity at either CB1 (K-1=2 25 6 30 mu M) or CB2 cannabmoid receptors (K-1=1 97 3 13 mu M) the trans Isomer always being more potent than the cis isomer (C) 2010 Elsevier Ltd All rights reserved

引用

页码：9497 / 9501

页数：5

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