Diterpene
Encyclopedia
Diterpenes are a type of terpene
s composed of four isoprene
units. They derive from geranylgeranyl pyrophosphate
. Diterpenes form the basis for biologically important compounds such as retinol
, retinal
, and phytol
. They are known to be antimicrobial
and antiinflammatory.
Terpene
Terpenes are a large and diverse class of organic compounds, produced by a variety of plants, particularly conifers, though also by some insects such as termites or swallowtail butterflies, which emit terpenes from their osmeterium. They are often strong smelling and thus may have had a protective...
s composed of four isoprene
Isoprene
Isoprene , or 2-methyl-1,3-butadiene, is a common organic compound with the formula CH2=CCH=CH2. Under standard conditions it is a colorless liquid...
units. They derive from geranylgeranyl pyrophosphate
Geranylgeranyl pyrophosphate
Geranylgeranyl pyrophosphate is an intermediate in the HMG-CoA reductase pathway used by organisms in the biosynthesis of terpenes and terpenoids. In plants it is also the precursor to carotenoids, gibberellins, tocopherols, and chlorophylls....
. Diterpenes form the basis for biologically important compounds such as retinol
Retinol
Retinol is one of the animal forms of vitamin A. It is a diterpenoid and an alcohol. It is convertible to other forms of vitamin A, and the retinyl ester derivative of the alcohol serves as the storage form of the vitamin in animals....
, retinal
Retinal
Retinal, also called retinaldehyde or vitamin A aldehyde, is one of the many forms of vitamin A . Retinal is a polyene chromophore, and bound to proteins called opsins, is the chemical basis of animal vision...
, and phytol
Phytol
Phytol is an acyclic diterpene alcohol that can be used as a precursor for the manufacture of synthetic forms of vitamin E and vitamin K1. In ruminants, the gut fermentation of ingested plant materials liberates phytol, a constituent of chlorophyll, which is then converted to phytanic acid and...
. They are known to be antimicrobial
Antimicrobial
An anti-microbial is a substance that kills or inhibits the growth of microorganisms such as bacteria, fungi, or protozoans. Antimicrobial drugs either kill microbes or prevent the growth of microbes...
and antiinflammatory.
Examples of diterpenes
- Abietic acidAbietic acidAbietic acid , an organic compound that occurs widely in trees. It is the primary component of resin acid, is the primary irritant in pine wood and resin, isolated from rosin and is the most abundant of several closely related organic acids that constitute most of rosin, the solid portion of the...
- AphidicolinAphidicolinAphidicolin is defined as a tetracyclic diterpene antibiotic with antiviral and antimitotical properties. Aphidicolin is a reversible inhibitor of eukaryotic nuclear DNA replication. It blocks the cell cycle at early S phase...
- CafestolCafestolCafestol is a diterpene molecule present in coffee.A typical bean of Coffea arabica contains about 0.6% cafestol by weight. Cafestol is present in highest quantity in unfiltered coffee drinks such as French press coffee or Turkish coffee/Greek coffee...
- CembreneCembreneCembrene A, or sometimes neocembrene, is a natural monocyclic diterpene isolated from corals of the genus Nephthea. It is a colorless oil with a faint wax-like odor....
- FerruginolFerruginolFerruginol is a natural phenol and a meroterpene that has been isolated from the needles of the redwood Sequoia sempervirens...
- ForskolinForskolinForskolin is a labdane diterpene that is produced by the Indian Coleus plant . Forskolin is commonly used to raise levels of cyclic AMP in the study and research of cell physiology. Forskolin resensitizes cell receptors by activating the enzyme adenylyl cyclase and increasing the intracellular...
- Guanacastepene AGuanacastepene AGuanacastepene A is a compound showing promising antibiotic activity. It is a diterpene that was extracted with hexane from a Costa Rican fungus , found on the branches of the Daphnopsis Americana tree and purified by chromatography....
- KahweolKahweolKahweol is a diterpene molecule found in the beans of Coffea arabica. It is structurally related to cafestol....
- LabdaneLabdaneLabdane is a natural bicyclic diterpene. It forms the structural core for a wide variety of natural products collectively known as labdanes or labdane diterpenes...
- Lagochilin
- SclareneSclareneSclarene is a diterpene present in the foliage of Podocarpus hallii....
- StemareneStemareneStemarene is a diterpene hydrocarbon created by the biosynthesis of enzyme extracts from rice....
- SteviolSteviolSteviol is a diterpene first isolated from Stevia rebaudiana in 1931. Its chemical structure was not fully elucidated until 1960.Steviol is found in the form of glycosides including the sweet chemical compound stevioside....
- Taxadiene (precursor of taxol)
- TiamulinTiamulinTiamulin is a pleuromutilin antibiotic drug that is used in veterinary medicine particularly for pigs and poultry.Tiamulin is a diterpene antimicrobial with a pleuromutilin chemical structure similar to that of valnemulin....
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.
- Spirostachys africanaSpirostachys africanaSpirostachys africana is a medium-sized deciduous tree with a straight, clear trunk, occurring in the warmer parts of Southern Africa...
yields excoecarin in its latex, a compound with a purgative effect. - Salvia divinorumSalvia divinorumSalvia divinorum is a psychoactive plant which can induce dissociative effects and is a potent producer of "visions" and other hallucinatory experiences...
yields Salvinorin ASalvinorin ASalvinorin A is the main active psychotropic molecule in Salvia divinorum, a Mexican plant which has a long history of use as an entheogen by indigenous Mazatec shamans...
, an hallucinogen