MOLECULE

(-)-Aristolene

Aristolene belongs to the class of organic compounds known as aristolane sesquiterpenoids. These are sesquiterpenoids with a structure based on the aristolane skeleton. Sesquiterpenoids 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. Aristolanes arise from the C6,C11 cyclization of the bicyclic eremophilane skeleton. Aristolene is possibly neutral. It has been identified in cannabis (PMID: 26657499), the essential oil from Pelargonium graveolens (rose geranium) (13.19% relative to total oil constituents) (PMID: 26854645), the essential oil from Ferula communis (giant fennel) leaf (8.5% relative to total oil constituents) (DOI: 10.1002/ffj.1405), and the dry fruit essential oil from Vitex negundo (Chinese chaste tree) (8% relative to total oil constituents) (PMID: 20046787).