# Diterpene

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{{Short description|Organic compound}}
thumb|right|Geranylgeranyl pyrophosphate, the starting material for the biosynthesis of diterpenes

'''Diterpenes''' are a class of [terpenes](/source/terpenes) composed of four [isoprene](/source/isoprene) units, often with the molecular formula C<sub>20</sub>H<sub>32</sub>. They are biosynthesized by plants, animals and fungi via the [HMG-CoA reductase pathway](/source/HMG-CoA_reductase_pathway), with [geranylgeranyl pyrophosphate](/source/geranylgeranyl_pyrophosphate) being a primary intermediate. Diterpenes form the basis for biologically important [compounds](/source/Chemical_compound) such as [retinol](/source/retinol), [retinal](/source/retinal), and [phytol](/source/phytol). Some diterpenes are [antimicrobial](/source/antimicrobial) and [anti-inflammatory](/source/anti-inflammatory).<ref>{{cite book|title=Terpenes: Flavors, Fragrances, Pharmaca, Pheromones|chapter=Diterpenes|author=Eberhard Breitmaier|year= 2006|pages=52–81|isbn=978-3-527-60994-9 |doi=10.1002/9783527609949.ch4}}</ref><ref name=Crot>{{cite journal|title=Cyclization Enzymes in the Biosynthesis of Monoterpenes, Sesquiterpenes, and Diterpenes|author1=Davis, Edward M. |author2=Croteau, Rodney |journal=Topics in Current Chemistry|year=2000|volume=209|pages=53–95|doi=10.1007/3-540-48146-X_2|isbn=978-3-540-66573-1}}</ref>

==Structures==
[[File:Taxadiene.svg|thumbnail|right|[Taxadiene](/source/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.

{| class="wikitable"
|-
! Number of rings !! Examples
|-
| 0 || [Phytane](/source/Phytane) 
|-
| 1 || [Cembrene A](/source/Cembrene_A)
|-
| 2 || [Sclarene](/source/Sclarene), [Labdane](/source/Labdane)
|-
| 3 || [Abietane](/source/Abietane), [Taxadiene](/source/Taxadiene)
|-
| 4 || [Stemarene](/source/Stemarene), [Stemodene](/source/Stemodene)
|}

== Biosynthesis==
Diterpenes are derived from the addition of one [IPP](/source/Isopentenyl_pyrophosphate) unit to [FPP](/source/Farnesyl_pyrophosphate) to form [geranylgeranyl pyrophosphate](/source/geranylgeranyl_pyrophosphate) (GGPP). From GGPP, structural diversity is achieved mainly by two classes of enzymes; the diterpene synthases and [cytochromes P450](/source/Cytochrome_P450). Several diterpenes are produced by plants and [cyanobacteria](/source/cyanobacteria). GGPP is also the precursor for the synthesis of the [phytane](/source/phytane) by the action of the enzyme geranylgeranyl reductase. This compound is used for the biosynthesis of [tocopherol](/source/tocopherol)s and the [phytyl](/source/phytyl) functional group is used in the formation of [chlorophyll ''a''](/source/Chlorophyll_a), [ubiquinone](/source/ubiquinone)s, [plastoquinone](/source/plastoquinone) and [phylloquinone](/source/phylloquinone).<ref>{{cite journal | vauthors = Pattanaik B, Lindberg P | title = Terpenoids and their biosynthesis in cyanobacteria | journal = Life | volume = 5 | issue = 1 | pages = 269–93 | date = January 2015 | pmid = 25615610 | pmc = 4390852 | doi = 10.3390/life5010269 | doi-access = free }}</ref>

==Diterpenoids==
{{multiple image
| direction = vertical
| align     = right
| header    =
| width     = 220
| image1    = All-trans-Retinol2.svg
| alt1      = 
| caption1  = [Retinol](/source/Retinol), a diterpenoid is one of the animal forms of vitamin A 
| image2    = Phytol.svg
| alt2      = 
| caption2  = [Phytol](/source/Phytol), a diterpenoid is used in the biosynthesis of vitamin E and vitamin K1
}}

Diterpenes are formally defined as being [hydrocarbons](/source/hydrocarbons) and thus contain no heteroatoms. Functionalized structures should instead be called diterpenoids,<ref>{{cite web |title=Terpenoid |url=https://goldbook.iupac.org/terms/view/T06279 |website=IUPAC GoldBook}}</ref> 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](/source/retinol), [phytol](/source/phytol) or [taxadiene](/source/taxadiene). 

===Taxanes===
[Taxane](/source/Taxane)s are class of diterpenoids featuring a [taxadiene](/source/taxadiene) core. They are produced by plants of the genus ''[Taxus](/source/Taxus)'' (yew trees) and are widely used as [chemotherapy](/source/chemotherapy) agents.<ref>{{cite journal|last1=Rowinsky, MD|first1=Eric K.|title=The Development and Clinical Utility of the Taxane Class of Antimicrotubule Chemotherapy Agents|journal=Annual Review of Medicine|date=February 1997|volume=48|issue=1|pages=353–374|doi=10.1146/annurev.med.48.1.353|pmid=9046968}}</ref>

==Other==
* ''Dodonaea petiolaris'' yields the diterpene [''ent''-3β-acetoxy-15,16-epoxylabda-8(17),13(16),14-trien-18-oic acid](/source/ent-3%CE%B2-acetoxy-_15%2C16-epoxylabda-8(17)%2C13(16)%2C14-trien-18-oic_acid) (C<sub>22</sub>H<sub>28</sub>O<sub>6</sub>) or its enantiomer.<ref>{{cite journal|title = The chemistry of Dodonaea spp. VIII. Isolation and crystal structure of a diterpene acid from Dodonaea petiolaris|first1 = P. R.|last1 = Jefferies|first2 = T. G.|last2 = Payne|first3 = C. L.|last3 = Raston|authorlink3 = Colin Raston|first4 = A. H.|last4 = White|journal = [Australian Journal of Chemistry](/source/Australian_Journal_of_Chemistry)|volume = 34|issue = 5|pages = 1001–1007|doi = 10.1071/CH9811001 |year = 1981}}</ref>
* ''[Salvia divinorum](/source/Salvia_divinorum)'' yields [Salvinorin A](/source/Salvinorin_A), a psychotropic drug

==See also==
* [Abeotaxane](/source/Abeotaxane)
* [Cafestol](/source/Cafestol)
* [Kahweol](/source/Kahweol)
* [Monoterpene](/source/Monoterpene)
* [Sesquiterpene](/source/Sesquiterpene)
* [Triterpene](/source/Triterpene)

==References==
{{reflist}}

Category:Diterpenes

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Adapted from the Wikipedia article [Diterpene](https://en.wikipedia.org/wiki/Diterpene) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Diterpene?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.