Diterpene

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Geranylgeranyl pyrophosphate, the starting material for the biosynthesis of diterpenes

Diterpenes are a class of chemical compounds composed of two terpene units with the molecular formula C20H32; they may also be thought of as consisting of four isoprene units. They are biosynthesized by plants, animals and fungi via the HMG-CoA reductase pathway, with geranylgeranyl pyrophosphate being a primary intermediate. Diterpenes form the basis for biologically important compounds such as retinol, retinal, and phytol. They are known to be antimicrobial and antiinflammatory.

Structures[edit]

Taxadiene: a tricyclic diterpene

As with most terpenes a huge number of potential structures exists, which may be broadly divided according to the number of rings present.

Number of rings Examples
0 Phytane
1 Cembrene A
2 Sclarene, Labdane
3 Abietane, Taxadiene
4 Stemarene, Stemodene

Diterpenoids[edit]

Retinol: one of the animal forms of vitamin A
Phytol: used in the biosynthesis of vitamin E and vitamin K1

Diterpenes are formally defined as being hydrocarbons and thus contain no heteroatoms. Functionalized structures should instead be called diterpenoids[citation needed], although in scientific literature the two terms are often used interchangeably. Although a wide range of terpene structures exist few of them are biologically significant, by contrast diterpenoids possess a rich pharmacology and include important compounds such as retinol and phytol.

Taxanes[edit]

Taxanes are class of diterpenoids featuring a taxadiene core. They are produced by plants of the genus Taxus (yew trees) and are widely used as chemotherapy agents.[1]

See also[edit]

Other[edit]

References[edit]

  1. ^ Rowinsky, MD, Eric K. (February 1997). "THE DEVELOPMENT AND CLINICAL UTILITY OF THE TAXANE CLASS OF ANTIMICROTUBULE CHEMOTHERAPY AGENTS". Annual Review of Medicine. 48 (1): 353–374. doi:10.1146/annurev.med.48.1.353. 
  2. ^ Jefferies, P. R.; Payne, T. G.; Raston, C. L.; White, A. H. (1981). "The chemistry of Dodonaea spp. VIII. Isolation and crystal structure of a diterpene acid from Dodonaea petiolaris". Australian Journal of Chemistry. 34 (5): 1001–1007. doi:10.1071/CH9811001.