Cannabis Ruderalis

Cannabigerolic acid
CBGA molecule.svg
Names
Preferred IUPAC name
3-[(2E)-3,7-Dimethylocta-2,6-dien-1-yl]-2,4-dihydroxy-6-pentylbenzoic acid
Identifiers
ChEBI
ChEMBL
ChemSpider
KEGG
UNII
Properties
C22H32O4
Molar mass 360.494 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Biosynthesis of tetrahydrocannabinolic acid (THCA). In the first step, geranyl pyrophosphate and olivetolic acid form cannabigerolic acid, which is then enzymatically rearranged to THCA in the second step.

Cannabigerolic acid (CBGA) is the acidic form of cannabigerol (CBG). It is a dihydroxybenzoic acid and olivetolic acid in which the hydrogen at position 3 is substituted by a geranyl group. It is a biosynthetic precursor to Delta-9-tetrahydrocannabinol, which is the principal psychoactive constituent of the Cannabis plant. It is also a diterpenoid, a polyketide, a member of resorcinols and a phytocannabinoid. It derives from an olivetolic acid. It is a conjugate acid of a cannabigerolate.[1]

In the Cannabis plant, olivetolic acid and geranyl diphosphate are synthesized into CBGA.[2][3] CBGA is converted in the plant by CBCA synthase, CBDA synthase and THCA synthase into CBCA, CBDA and THCA respectively.[4] Afterwards, THCA and CBDA can be decarboxylated into THC and CBD by drying and heating plant material. CBGA has emerging pharmacological properties; for example, it had anticonvulsant effects in a mouse model of Dravet syndrome.[5]

References[edit]

  1. ^ PubChem 2020.
  2. ^ Thomas & ElSohly 2015, p. 6.
  3. ^ Degenhardt, Stehle & Kayser 2016, p. 17.
  4. ^ Thomas & ElSohly 2015, pp. 6–7.
  5. ^ Anderson, LL; Heblinski, M; Absalom, NL; Hawkins, NA; Bowen, MT; Benson, MJ; Zhang, F; Bahceci, D; Doohan, PT; Chebib, M; McGregor, IS; Kearney, JA; Arnold, JC (December 2021). "Cannabigerolic acid, a major biosynthetic precursor molecule in cannabis, exhibits divergent effects on seizures in mouse models of epilepsy". British Journal of Pharmacology. 178 (24): 4826–4841. doi:10.1111/bph.15661. ISSN 0007-1188. PMID 34384142. S2CID 236997090.

Sources[edit]

Further reading[edit]

Public Domain This article incorporates public domain material from websites or documents of the National Institutes of Health.

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