Diterpenes are a class of terpenes composed of four isoprene units, often with the molecular formula C20H32. 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. Some diterpenes are known to be antimicrobial and anti-inflammatory.
Structures
As with most terpenes a huge number of potential structures exists, which may be broadly divided according to the number of rings present.
Biosynthesis
Diterpenes are derived from the addition of one IPP unit to FPP to form geranylgeranyl pyrophosphate (GGPP). From GGPP, structural diversity is achieved mainly by two classes of enzymes; the diterpene synthases and cytochromes P450. Several diterpenes are produced by plants and
cyanobacteria. GGPP is also the precursor for the synthesis of the
phytane by the action of the enzyme geranylgeranyl reductase. This compound is used for the biosynthesis of
and the
phytyl functional group is used in the formation of
Chlorophyll a,
,
plastoquinone and
phylloquinone.
Diterpenoids
Diterpenes are formally defined as being
hydrocarbons and thus contain no heteroatoms. Functionalized structures should instead be called diterpenoids,
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,
phytol or
taxadiene.
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.
Other
-
Dodonaea petiolaris yields the diterpene ent-3β-acetoxy-15,16-epoxylabda-8(17),13(16),14-trien-18-oic acid (C22H28O6) or its enantiomer.
-
Salvia divinorum yields Salvinorin A, a psychotropic drug
See also
