Extraction and Analysis of Terpenes/Terpenoids

Abstract Terpenes/terpenoids constitute one of the largest classes of natural products, due to the incredible chemical diversity that can arise from the biochemical transformations of relatively simple prenyl diphosphate starter units. All terpenes/terpenoids comprise a hydrocarbon backbone generated from various length prenyl diphosphates (a polymer chain of prenyl units). Upon ionization (removal) of the diphosphate group, the remaining allylic carbocation intermediates can be coaxed down complex chemical cascades leading to diverse linear and cyclized hydrocarbon backbones that can be further modified with a wide range of functional groups (e.g., alcohols or ketones) and substituent additions (e.g., sugars or fatty acids). Because of this chemical diversity, terpenes/terpenoids have great industrial uses as flavors, fragrances, high grade lubricants, biofuels, agricultural chemicals, and medicines. The protocols presented here focus on the extraction of terpenes/terpenoids from various plant sources and have been divided into extraction methods for terpenes/terpenoids with various levels of chemical decoration—from relatively small, nonpolar, volatile hydrocarbons to substantially large molecules with greater physical complexity due to chemical modifications. © 2016 by John Wiley & Sons, Inc.