MOLECULE

alpha-Guaiene

alpha-Guaiene (α-guaiene) belongs to the class of organic compounds known as guaianes. These are sesquiterpenoids with a structure based on the guaiane skeleton. Guaiane is a bicyclic compound consisting of a decahydroazulene moiety, substituted with two methyl groups and a 1-methylethyl group at the 1-, 4-, and 7-position, respectively. Sesquiterpenes are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496, 17710406). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. α-Guaiene is one of three isomers of Guaiene (α-Guaiene, β-Guaiene, and δ-Guaiene). α-Guaiene is the most common member of this group and was first isolated from guaiac wood oil from Bulnesia sarmientoi. It has since been detected in several plant species, including Cannabis sativa (PMID: 31816756) The guaienes are used in the fragrance and flavoring industries to impart earthy, spicy aromas and tastes.