MOLECULE

Cannabigerovarinic acid

Cannabigerovarinic acid (CBGVA) is the C3 analogue of cannabigerolic acid (CBGA). CBGVA is a phytocannabinoid that belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Cannabigerovarinic acid is a dihydroxybenzoic acid derived from divarinic acid on which the hydrogen at position 3 is substituted by a geranyl group. Cannabigerovarinic acid is a molecule of mixed biosynthetic origin, in which its aromatic moiety (derived from divarinic acid) occurs through the polyketide biosynthetic pathway while the prenylated sidechain derives from the MEP pathway of the terpenoids (DOI: 10.1016/B978-0-12-800756-3.00002-8). As such, cannabigerovarinic acid can be considered a polyketide, a monoterpenoid and a resorcinol, due to the meta arrangement of its two hydroxyl groups substituting the benzene ring. Cannabigerovarinic acid is a key biosynthetic precursor of C3-cannabinoids. Cannabigerovarinic acid is an important cannabinoid found in cannabis and due to its biosynthetic relationship to other compounds efforts have been addressed to find alternative ways of producing it (in yeast; PMID: 30814733). A cell free system was developed to produces cannabinoids, including cannabigerovarinic acid, from glucose by supplying several enzymes that create isoprenylate derivatives and these prenylated cannabinoid intermediates (PMID: 30718485). The yeast and cell free systems produce these important natural products that are difficult to make or purify from living organisms.