![THC-COOH biosynthesis v2](https://upload.wikimedia.org/wikipedia/commons/c/c5/THC-COOH_biosynthesis_v2.svg)
Cannabigerolic acid (CBGA) is the acidic form of
cannabigerol
Cannabigerol (CBG) is one of more than 120 identified cannabinoid compounds found in the plant genus ''Cannabis''. Cannabigerol is the decarboxylated form of cannabigerolic acid, the parent molecule from which other cannabinoids are synthesized ...
(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
''Cannabis'' () is a genus of flowering plants in the family Cannabaceae. The number of species within the genus is disputed. Three species may be recognized: '' Cannabis sativa'', '' C. indica'', and '' C. ruderalis''. Alternative ...
'' plant. It is also a
diterpenoid
Diterpenes are a class of chemical compounds composed of four isoprene units, often with the molecular formula C20H32. They are biosynthesized by plants, animals and fungi via the HMG-CoA reductase pathway, with geranylgeranyl pyrophosphate being ...
, a polyketide, a member of resorcinols and a
phytocannabinoid
Cannabinoids () are several structural classes of compounds found in the cannabis plant primarily and most animal organisms (although insects lack such receptors) or as synthetic compounds. The most notable cannabinoid is the phytocannabinoid tet ...
. It derives from an olivetolic acid. It is a conjugate acid of a cannabigerolate.
In the ''Cannabis'' plant, olivetolic acid and
geranyl diphosphate
Geranyl pyrophosphate (GPP), also known as geranyl diphosphate (GDP), is the pyrophosphate ester of the terpenoid geraniol. Its salts are colorless. It is a precursor to many natural products.
Occurrence
GPP is an intermediate in the isoprenoid ...
are synthesized into CBGA.
CBGA is converted in the plant by CBCA synthase,
CBDA synthase and
THCA synthase into
CBCA,
CBDA and
THCA respectively.
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
Dravet syndrome, previously known as severe myoclonic epilepsy of infancy (SMEI), is an autosomal dominant genetic disorder which causes a catastrophic form of epilepsy, with prolonged seizures that are often triggered by hot temperatures or feve ...
, a form of epilepsy.
Pharmacology
In an analysis by the
University of Rhode Island
The University of Rhode Island (URI) is a public land-grant research university with its main campus in Kingston, Rhode Island, United States. It is the flagship public research as well as the land-grant university of the state of Rhode Isla ...
on
phytocannabinoids
Cannabinoids () are several structural classes of compounds found in the cannabis plant primarily and most animal organisms (although insects lack such receptors) or as synthetic compounds. The most notable cannabinoid is the phytocannabinoid tet ...
it was found that CBGA had the 2nd highest
3C-like protease
The 3C-like protease (3CLpro) or main protease (Mpro), formally known as C30 endopeptidase or 3-chymotrypsin-like protease, is the main protease found in coronaviruses. It cleaves the coronavirus polyprotein at eleven conserved sites. It is a c ...
inhibitor activity against
COVID-19
Coronavirus disease 2019 (COVID-19) is a contagious disease caused by a virus, the severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2). The first known case was identified in Wuhan, China, in December 2019. The disease quickly ...
out of all the phytocannabinoids tested within that study but not as high as the
antiviral drug GC376
GC376 is a broad-spectrum antiviral medication under development by the biopharmaceutical company Anivive Lifesciences for therapeutic uses in humans and animals. Anivive licensed the exclusive worldwide patent rights to GC376 from Kansas State ...
(72% CBGA vs 24% CBG vs 100% GC376).
References
Further reading
*
{{Transient receptor potential channel modulators
Cannabinoids
Diterpenes