Cannabichromene, a new active principle in hashish

Gaoni, Yehiel; Mechoulam, Raphael

doi:10.1039/c19660000020

Cited by 61 publications

(62 citation statements)

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“…This Wnding is in agreement with Shoyama et al (1975), Vogelmann et al (1988) and Morimoto et al (1997). If, as Hillig and Mahlberg (2004) report, CBC is not detected in certain mature Xower samples, it is quite likely that its presence can be conWrmed in earlier leaves of the corresponding plants.…”

Section: Discussionsupporting

confidence: 87%

“…This reaction is catalysed by the enzyme geranylpyrophosphate:olivetolate geranyltransferase (GOT; Fellermeier and Zenk 1998). CBG is the direct precursor for each of the compounds THC (Taura et al 1995), CBD (Taura et al 1996) and CBC (Gaoni and Mechoulam 1966;Morimoto et al 1997Morimoto et al , 1998. The diVerent conversions of CBG are enzymatically catalysed, and for each reaction an enzyme has been identiWed: THC acid synthase (Taura et al 1995), CBD acid synthase (Taura et al 1996) and CBC acid synthase (Morimoto et al 1997(Morimoto et al , 1998.…”

Section: Cannabinoid Biogenesismentioning

confidence: 99%

“…In this paper these compounds will be indicated by the abbreviations for their neutral forms. The most common cannabinoids, those with a pentyl side chain, are cannabidiol (CBD; Adams et al 1940;Mechoulam and Shvo 1963), delta 9-tetrahydrocannabinol (THC; Gaoni and Mechoulam 1964a), cannabichromene (CBC; Gaoni and Mechoulam 1966) and cannabigerol (CBG; Gaoni and Mechoulam 1964b).…”

Section: Cannabinoid Biogenesismentioning

confidence: 99%

“…They found a constant presence of CBC in all plants, occupying a 3-9% proportion of the total cannabinoid fraction. Hillig and Mahlberg (2004) examined the cannabinoid proWle of a representative germplasm collection and classiWed the individual plants into three discrete chemotypes: strongly THC predominant; strongly CBD predominant and intermediate. CBC was detected as a minor compound in each category but not in all plants.…”

Section: The Occurrence Of Cannabichromene In Cannabis Chemotypesmentioning

confidence: 99%

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The inheritance of chemical phenotype in Cannabis sativa L. (III): variation in cannabichromene proportion

2008

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The mechanism that controls the proportion of cannabichromene (CBC), a potential pharmaceutical, in the cannabinoid fraction of Cannabis sativa L. is explored. As with tetrahydrocannabinol (THC) and cannabidiol (CBD), CBC is an enzymatic conversion product of the precursor cannabigerol (CBG). CBC is reported to dominate the cannabinoid fraction of juveniles and to decline with maturation. This ontogeny was conWrmed in inbred lines with diVerent mature chemotypes. A consistent CBC presence was found in early leaves from a diverse clone collection, suggesting that CBC synthase is encoded by a Wxed locus. Morphological variants possessing a 'prolonged juvenile chemotype' (PJC), a substantial proportion of CBC persisting up to maturity, are presented. PJC is associated with a reduced presence of Xoral bracts, bracteoles, and capitate-stalked trichomes. Genetic factors causing these features were independent of the allelic chemotype locus B that was previously postulated and regulates THC and CBD synthesis and CBG accumulation. In contrast to previously described Cannabis chemotypes, the cannabinoid composition of PJCs showed plasticity in that reduced light levels increased the CBC proportion. The ability of PJC plants to enable the production of pharmaceutical raw material with high CBC purity is demonstrated.

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Section: Discussionsupporting

confidence: 87%

Section: Cannabinoid Biogenesismentioning

confidence: 99%

Section: Cannabinoid Biogenesismentioning

confidence: 99%

Section: The Occurrence Of Cannabichromene In Cannabis Chemotypesmentioning

confidence: 99%

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The inheritance of chemical phenotype in Cannabis sativa L. (III): variation in cannabichromene proportion

2008

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“…La première étape consiste en une réaction de condensation du pyrophosphate de géranyle avec l'acide olivétolique pour former le cannabigérol (CBG) lui-même précurseur du cannabichromène (CBC), du cannabidiol (CBD) ou du A-9-tétrahydrocannabinol (A-9-THC) (2)(3)(4)(5)(6)(7)(8)(9)(10)(11). A chaque étape, des enzymes catalysent la réaction (12)(13)(14).…”

Section: Introductionunclassified