Cannabigerolic Acid

Amongst the many phytocannabinoids found in the Cannabis genus, cannabigerolic acid (CBGA) is an acidic form of cannabigerol. It is a precursor to the principal psychoactive constituent of the Cannabis plant, Delta-9-tetrahydrocannabinol (THC).

Background

Among the cannabinoid swarm, cannabigerolic acid is one of the most important molecules in the Sativa. It is the precursor to cannabigerol, a substance that is a precursor to the more infamous D9-tetrahydrocannabinol, or THC for short.

There are numerous cannabinoids in the genus Cannabis sativa, but they are not all created equal. There are over 180 known cannabinoids, the most prominent of which include delta-9 tetrahydrocannabinol, cannabidiol, cannabichromene, and cannabigerolic acid. While the majority of these compounds were identified in the last few decades, there is still a great deal of mystery surrounding the origins of these compounds.

The first known discovery of the cannabis Sativa was the existence of a cannabigerolic acid, a precursor to the more well-known cannabigerol and the precursor to the more elusive D9-tetrahydrocannabinol. The genesis of this compound is a complicated process that involves the sequential condensation of hexanoyl-CoA and malonyl-CoA in an enzyme known as tetraketide synthase.

Biosynthesis

Phytocannabinoids are a structurally diverse class of chemical constituents found in Cannabis spp. The main psychoactive constituent is tetrahydrocannabinol (THC). Other compounds include cannabidioloic acid (CBGA), olivetolic acid (OLA), bisnoryangonin, and cannabigerolic acid.

Biosynthesis of cannabinoids occurs in glandular trichomes on female flowers. The enzymes used to synthesize cannabinoids are prenyltransferases, geranylpyrophosphate:olivetolate geranyltransferase, and tetrahydrocannabinolic acid synthesis (THCA). The enzymes are controlled by a single locus B.

Olivetolic acid is a critical component of cannabinoid biosynthesis. This is synthesized from hexanoyl-CoA by fatty acids, and subsequently reacts with geranyl pyrophosphate. The polyketide nucleus of cannabinoids is formed from this reaction. The enzymes that synthesize olivetol are a type III polyketide synthase and an olivetolic acid cyclase.

Geranylpyrophosphate:olivetolate transferase is the first enzyme in the cannabinoid biosynthetic pathway. It accepts geranylpyrophosphate as a cosubstrate, and then catalyzes the conversion of cannabigerolic acid to cannabibidioloic acid. The enzyme has been isolated from hemp leaves.

Scientific Discoveries

Phytocannabioids, including the mainstay THC, are widely studied and isolated in laboratories worldwide. Despite this scientific activity, however, the biochemical processes that produce them are still largely uncharted territory. It is thus no surprise that research teams have been attempting to optimize the production of cannabinoid precursors and their derivatives.

In the search for the holy grail, scientists have turned to biocatalysts, notably the deoxyribolase. These enzymes have been engineered for stereoselective synthesis of complex carbohydrates. As a result, a variety of biologically-produced cannabinoid precursors and their derived analogs have been synthesized.

The first reported pure cannabigerolic acid was produced in 1955. The aforementioned chemical was a precursor to D9-tetrahydrocannabinolic acid (THCA), which is the primary psychoactive component of cannabis. THCA was then converted to the tetrahedral structure that spawned the THC clone of interest.

Phytocannabinoids Are a Class of Naturally Occurring Chemical Constituents in The Genus Cannabis

Phytocannabinoids are a type of natural chemical constituents of Cannabis. The compounds are synthesized in the glandular trichomes of the plants. They interact with CB2 receptors in the human body. In addition, cannabinoids are found in many plant species other than Cannabis.

There are three main groups of cannabinoids. The group of cannabinoids containing a heptyl side-chain is called the phorol group. The group containing a propyl side-chain is named the varin group. Phytocannabinoids are soluble in alcohols and in lipids, but are virtually insoluble in water.

The term cannabimimetic effects is used to describe the effects of cannabinoids on the body. The effects of cannabinoids are similar to the effects of the alkaloids that are found in plants. The alkaloids were developed as a defense against herbivores.

Medical Applications

Fortunately, scientists have been putting the green stuff to good use. Cannabigerolic acid is the first biogenetic phytocannabinoid to make the cut. It is a triterpenoid compound and is found in high concentrations in prickly pear, hemp and jigsaw. Its therapeutic and medicinal applications are still in the research phase. A recent study suggests the presence of the chemical in adipose tissue and skin. CBG is also present in the urine of cannabis users. CBG has some significant medical applications, as well as some minor drawbacks. The presence of the compound in adipose tissue may pose some risks for transplant recipients. Its use in other parts of the body is also fraught with uncertainties. A recent study in mice suggests that CBG has some unforeseen side effects. This is a concern, as the compound may have an uncanny ability to induce a plethora of inflammatory and anti-inflammatory responses.