Terpenoids: Higher

Abstract

Terpenoids (or isoprenoids/isopentenoids) are a diverse group of compounds that are found throughout nature and are biosynthesized through the successive condensation of the five‐carbon compound isoprene. Higher terpenoids are complex structures that possess minimally between 20 and 40 carbon atoms. Although higher terpenoids are found in all organisms, plants produce the largest array of higher terpenoids in terms of number, structure and function. These plant‐derived higher terpenoids can be utilized by humans for purposes such as drugs to fight diseases or as feedstocks for biofuel production. The genes responsible for producing these plant of higher terpenoids are just now beginning to be identified and these studies are showing that higher terpenoids are essential for plant growth, development and defence against pathogens.

Key concepts:

  • Higher terpenoids contain at least 20 carbons and comprise many different structures and functions.

  • Triterpenoids originate from C30 squalene which is directly cyclized in bacteria and oxygenated and then cyclized by eukaryotes.

  • Sterols are important regulators of membrane fluidity as well as the production of steroid hormones in both animals and plants.

  • Plants produce more higher terpenoids than any other organisms with many functions including defence against pathogens.

Keywords: diterpene; triterpenoid; tetraterpenoid; sterol

Figure 1.

Head and tail positions of the basic isoprene unit and pathways for producing IPP. (a) Head and tail position for IPP and FPP. (b) The MVA pathway utilizing acetyl–CoA for production of IPP and DMAPP. (c) The MEP pathway utilizing pyruvate and glyceraldehyde‐3‐phosphate to produce IPP and DMAPP. Dashed lines indicate multiple steps.

Figure 2.

Structures of some common higher terpenoids.

Figure 3.

Cyclic triterpenoid production beginning with squalene. (a) The sterol numbering system. (b) The tetracyclic‐pentacyclic isopentenoid bifurcation to sterol and sterol‐like molecules.

Figure 4.

Phytoecdysteroid structure and biosynthesis of squalene and botryococcene. (a) 20‐Hydroxyecdysone, a common phytoecdysteroid. (b) The reaction mechanism of the enzymes squalene synthase (SS) and botryococcene synthase (BS). (c) Botryococcene liquid hydrocarbon expelled from a colony of B. braunii by pressure.

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Devarenne, Timothy P(Sep 2009) Terpenoids: Higher. In: eLS. John Wiley & Sons Ltd, Chichester. http://www.els.net [doi: 10.1002/9780470015902.a0001916.pub2]