Cannabinoids with a Propyl Side Chain in Cannabis: Occurrence and Chromatographic Behavior

Zeeuw, Rokus A. de; Wijsbeek, J.; Breimer, D.D.; Vree, T. B.; Ginneken, C A van; Rossum, J. M. van

doi:10.1126/science.175.4023.778

Cited by 40 publications

(18 citation statements)

References 9 publications

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“…However, the decline of CBC in the B 0 /B 0 inbred line, where CBC synthase is only competing with a weak CBD synthase (de Meijer and Hammond 2005), cannot be explained by this proposition. Perhaps, during the maturation of these plants, the rate at which CBG is produced by the enzyme GOT (Fellermeier and Zenk 1998) exceeds the combined turnover of CBC synthase and the weak CBD synthase, resulting in CBG accumulation.…”

Section: Cumulative Proportions (%)mentioning

confidence: 98%

“…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. Cannabinoids with propyl side chains, as identiWed by Vree et al (1971) and de Zeeuw et al (1972), result if GPP condenses with divarinic acid instead of OA, into cannabigerovarin (CBGV). The three cannabinoid synthase enzymes are not selective for the length of the alkyl side chain and convert CBGV into the propyl homologues of CBD, THC and CBC, which are indicated as cannabidivarin (CBDV), delta 9-tetrahydrocannabivarin (THCV) and cannabichromevarin (CBCV), respectively (Shoyama et al 1984).…”

Section: Cannabinoid Biogenesismentioning

confidence: 99%

“…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.…”

Section: Cannabinoid Biogenesismentioning

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: Cumulative Proportions (%)mentioning

confidence: 98%

Section: Cannabinoid Biogenesismentioning

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 mentioned cannabinoids have a pentyl side chain, but propyl homologues do occur (Vree et al, 1971;de Zeeuw et al, 1972). The propyl homologues of CBD, THC, CBC and CBG are indicated as cannabidivarin (CBDV), delta 9-tetrahydrocannabivarin (THCV), cannabichromevarin (CBCV) and cannabigerovarin (CBGV), respectively.…”

Section: The Biosynthetic Relationship Of Cbg With Other Cannabinoidsmentioning

confidence: 99%

The inheritance of chemical phenotype in Cannabis sativa L. (II): Cannabigerol predominant plants

2005

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This paper aims to clarify the genetic mechanism that is responsible for the accumulation of cannabigerol (CBG) in certain phenotypes of Cannabis sativa L. CBG is the direct precursor of the cannabinoids CBD, THC and CBC. Plants strongly predominant in CBG have been found in different fibre hemp accessions. Inbred offspring derived from one such individual were crossed with true breeding THC predominant-and CBD predominant plants, respectively. The segregations in the cross progenies indicate that CBG accumulation is due to the homozygous presence of a minimally functional allele, tentatively called B 0 , at the single locus B that normally controls the conversion of CBG into THC (allele B T ) and/or CBD (allele B D ). The fact that CBG accumulating plants have so far been found in European fibre hemp populations that are generally composed of B D /B D plants, and the observation that the here investigated B 0 allele possesses a residual ability to convert small amounts of CBG into CBD, make it plausible that this B 0 is a mutation of normally functional B D . Therefore, B 0 is considered as a member of the B D allelic series encoding a CBD synthase isoform with greatly weakened substrate affinity and/or catalytic capacity.

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“…The phytocannabinoid, (-)-cannabidiol (CBD), was isolated from Cannabis sativa in 1940 (Adams et al, 1940;Jacob and Todd, 1940). CBD is stored as its carboxylic acid precursor, cannabidiolic acid (CBDA), which undergoes spontaneous decarboxylation to produce the neutral CBD (de Zeeuw et al, 1972). The non-psychoactive compound, CBDA, was first isolated from Cannabis sativa in 1955 (Krejci and Santavy, 1955), and the structure of CBDA was elucidated some years later in 1965 (Mechoulam and Gaoni, 1965).…”

Section: Introductionmentioning

confidence: 99%

The effects of cannabidiolic acid and cannabidiol on contractility of the gastrointestinal tract of Suncus murinus

et al. 2011

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Cannabidiol (CBD) has been shown to inhibit gastrointestinal (GI) transit in pathophysiologic in vivo models, while having no effect in physiologic controls. The actions of the precursor of CBD, cannabidiolic acid (CBDA), have not been investigated in the GI tract. The actions of these phytocannabinoids on the contractility of the GI tract of Suncus murinus were investigated in the current study. The effects of CBDA and CBD in resting state and pre-contracted isolated intestinal segments, and on the contractile effects of carbachol and electrical field stimulation (EFS) on the intestines of S. murinus were examined. CBDA and CBD induced a reduction in resting tissue tension of isolated intestinal segments which was not blocked by the cannabinoid CB1 receptor antagonist, AM251, the CB(2) receptor antagonist AM630, or tetrodotoxin. CBDA and CBD reduced the magnitude of contractions induced by carbachol and the tension of intestinal segments that were pre-contracted with potassium chloride. In tissues stimulated by EFS, CBDA inhibited contractions induced by lower frequencies (0.1-4.0 Hz) of EFS, while CBD inhibited contractions induced by higher frequencies (4.0-20.0 Hz) of EFS. The data suggest that CBDA and CBD have inhibitory actions on the intestines of S. murinus that are not neuronallymediated or mediated via CB(1) or CB(2) receptors.

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Cannabinoids with a Propyl Side Chain in Cannabis: Occurrence and Chromatographic Behavior

Cited by 40 publications

References 9 publications

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

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

The inheritance of chemical phenotype in Cannabis sativa L. (II): Cannabigerol predominant plants

The effects of cannabidiolic acid and cannabidiol on contractility of the gastrointestinal tract of Suncus murinus

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