Humulene (Hum)

Humulene is a naturally occurring monocyclic sesquiterpene (C15H24), which is an 11-membered ring,consisting of 3 isoprene units containing three nonconjugated C═C double bonds, two of them being triply substituted and one being doubly substitutedterpenoid. It was first found in the essential oils of Humulus lupulus (hops), from which it derives its name. Humulene is an isomer of β-caryophyllene, and the two are often found together as a mixture in many aromatic plants. Humulene is one of many sesquiterpenoids that are derived from farnesyl diphosphate (FPP). The biosynthesis begins with the loss of diphosphate from FPP under the action of sesquiterpene synthesis enzymes, generating an allylic cation that is highly susceptible to intramolecular attacks. Humulene has been found to produce anti-inflammatory effects in mammals, and has potential to be a tool in the management of inflammatory diseases.