Diterpenes

Gibberellins (GAs) are plant hormones that regulate various developmental processes, including stem elongation, germination, dormancy, flowering, flower development, and leaf and fruit senescence. They are one of the longest-known classes of plant hormone. It is thought that the selective breeding (albeit unconscious) of crop strains that were deficient in GA synthesis was one of the key drivers of the "green revolution" in the 1960s, a revolution that is credited to have saved over a billion lives all over the world.

Retinol is a hydrolytic metabolite of retinyl esters belonging to the group of vitamin A1 as a alcohol form. Retinol or other forms of vitamin A are fat-soluble vitamins that are found in food and used as a dietary supplement. Either of them is needed for vision, cellular development, maintenance of skin and mucous membranes, immune function and reproductive development. Dietary sources include fish, dairy products, and meat.

chemical compound

Cafestol is a diterpenoid molecule present in coffee beans. It is one of the compounds that may be responsible for proposed biological and pharmacological effects of coffee.

Phytol (florasol, phytosol) is an acyclic hydrogenated diterpene alcohol that is used as a precursor for the manufacture of synthetic forms of vitamin E and vitamin K1, as well as in the fragrance industry. Its other commercial uses include cosmetics, shampoos, toilet soaps, and detergents, as well as in some cannabis distillates as a diluent or for flavoring. It smells grassy and dominates the aroma of certain green teas.

thumb|right|Geranylgeranyl pyrophosphate, the starting material for the biosynthesis of diterpenes

chemical compound

Phorbol is a natural, plant-derived organic compound. It is a member of the tigliane family of diterpenes. Phorbol was first isolated in 1934 via the hydrolysis of croton oil, which is derived from the seeds of the purging croton, Croton tiglium. The structure of phorbol was determined in 1967. Various esters of phorbol have important biological properties, the most notable of which is the capacity to act as tumor promoters through activation of protein kinase C. They mimic diacylglycerols, glycerol derivatives in which two hydroxyl groups have reacted with fatty acids to form esters. The mos

Pristane is a natural saturated terpenoid alkane obtained primarily from shark liver oil, from which its name is derived (Latin pristis, "shark"). It is also found in the stomach oil of birds in the order Procellariiformes and in mineral oil and some foods. Pristane and phytane are used in the fields of geology and environmental science as biomarkers to characterize origins and evolution of petroleum hydrocarbons and coal.

Steviol is a diterpene first isolated from the plant Stevia rebaudiana in 1931. Its chemical structure was not fully elucidated until 1960.

chemical compound

Sclareol is a fragrant chemical compound found in Salvia sclarea, from which it derives its name. It is classified as a bicyclic diterpene alcohol having roles in plant growth, development, defense, and attraction of pollinators.

Grayanotoxins are a group of closely related neurotoxins named after Leucothoe grayana, a plant native to Japan and named for 19th-century American botanist Asa Gray. Grayanotoxin I (grayanotoxane-3,5,6,10,14,16-hexol 14-acetate) is also known as andromedotoxin, acetylandromedol, rhodotoxin and asebotoxin. Grayanotoxins are produced by Rhododendron species and other plants in the family Ericaceae. Honey made from the nectar and so containing pollen of these plants also contains grayanotoxins and is commonly referred to as mad honey.

Phytane is the isoprenoid alkane formed when phytol, a chemical substituent of chlorophyll, loses its hydroxyl group. When phytol loses one carbon atom, it yields pristane. Other sources of phytane and pristane have also been proposed than phytol.

Forskolin (coleonol) is a labdane diterpene produced by the plant Coleus barbatus (blue spur flower). Other names include pashanabhedi, Indian coleus, makandi, HL-362, mao hou qiao rui hua. As with other members of the large diterpene class of plant metabolites, forskolin is derived from geranylgeranyl pyrophosphate (GGPP). Forskolin contains some unique functional elements, including the presence of a tetrahydropyran-derived heterocyclic ring.

Geranylgeraniol is a diterpenoid alcohol. It is a colorless waxy solid. It is an important intermediate in the biosynthesis of other diterpenes, of vitamins E, and of K. It is a derivative of geranylgeraniol pyrophosphate, which is a precursor to carotenoids.

chemical compound

group of stereoisomers

chemical compound

Abietane is an organic compound with the formula C20H36. It is a tricyclic, saturated hydrocarbon with an elaborate stereochemistry. It is a colorless solid. It is of little biochemical interest except as a reference structure of the abietanes.

'12-O-Tetradecanoylphorbol-13-acetate (TPA), also commonly known as tetradecanoylphorbol acetate, tetradecanoyl phorbol acetate, and phorbol 12-myristate 13-acetate (PMA') is a diester of phorbol. It is a potent tumor promoter often employed in biomedical research to activate the signal transduction enzyme protein kinase C (PKC). The effects of TPA on PKC result from its similarity to one of the natural activators of classic PKC isoforms, diacylglycerol. TPA is a small molecule drug.

chemical compound

Salvinorins are a group of natural chemical compounds and their structural analogs. Several salvinorins have been isolated from Salvia divinorum. They are classified as diterpenoid furanolactones. Salvinorin A is a hallucinogen with dissociative effects.

Ferruginol is a natural phenol with a terpenoid substructure. Specifically, it is a diterpene of the abietane chemical class, meaning it is characterized by three fused six-membered rings and alkyl functional groups. Ferruginol was first identified in 1939 by Brandt and Neubauer as the main component in the resin of the miro tree (Podocarpus ferrugneus) and has since been isolated from other conifer species in the families Cupressaceae and Podocarpaceae. As a biomarker, the presence of ferruginol in fossils, mainly resin, is used to describe the density of these conifers in that particular bio

Labdane is a natural bicyclic diterpene. It forms the structural core for a wide variety of natural products collectively known as labdanes or labdane diterpenes. The labdanes were so named because the first members of the class were originally obtained from labdanum, a resin derived from the gum rockrose.

Kahweol is a diterpenoid molecule found in the beans of Coffea arabica and is structurally related to cafestol. It was named after the Arabic meaning "coffee".

thumb|Chemical structure of gingkolide B

Aphidicolin is a tetracyclic diterpene antibiotic isolated from the fungus Cephalosporum aphidicola with antiviral and antimitotic properties. Aphidicolin is a reversible inhibitor of eukaryotic nuclear DNA replication. It blocks the cell cycle at early S phase. It is a specific inhibitor of DNA polymerase Alpha and Delta in eukaryotic cells and in some viruses (vaccinia and herpesviruses) and an apoptosis inducer in HeLa cells. Natural aphidicolin is a secondary metabolite of the fungus Nigrospora oryzae.

Prostratin is a protein kinase C activator found in the bark of the mamala tree of Samoa, Homalanthus nutans (Euphorbiaceae). While prostratin was originally isolated and identified as a new phorbol ester from species of the genus Pimelea (Thymelaceae) in Australia, the antiviral activity of prostratin was discovered during research on the traditional knowledge of Samoan healers in Falealupo village by ethnobotanist Paul Alan Cox and a team at the U.S. National Cancer Institute. Samoan healers use the mamala tree to treat hepatitis. Research indicated that prostratin has potential to be useful

Carnosol is a phenolic diterpene found in the herbs rosemary (Rosmarinus officinalis) and Mountain desert sage (Salvia pachyphylla).

Andrographolide is a labdane diterpenoid that has been isolated from the stem and leaves of Andrographis paniculata. Andrographolide is an extremely bitter substance.

thumb|New Zealand scientist Sir Thomas Hill Easterfield was the first person to discover totarol. Photo 1920. thumb|Totarol powder Totarol is a naturally produced diterpene that is bioactive. It was first isolated by McDowell and Easterfield from the heartwood of Podocarpus totara, an endemic conifer species found in New Zealand. Podocarpus totara was investigated for unique molecules due to the tree's increased resistance to rotting. Recent studies have confirmed totarol's unique antimicrobial and therapeutic properties. Consequently, totarol is a candidate for a new source of drugs and has b

10-Deacetylbaccatins are a series of closely related natural organic compounds isolated from the yew tree (Genera Taxus). 10-Deacetylbaccatin III is a precursor to the anti-cancer drug docetaxel (Taxotere).

Fichtelite is a rare white mineral found in fossilized wood from Bavaria. It crystallizes in the monoclinic crystal system. It is a cyclic hydrocarbon: (dimethyl)(isopropyl)perhydrophenanthrene, C19H34. It is very soft with a Mohs hardness of 1, the same as talc. Its specific gravity is very low at 1.032, just slightly denser than water.

Lagochilin is a bitter diterpene that forms a grey crystalline solid. It is found in various plants from the genus Lagochilus, most notably Lagochilus inebrians, and is thought to be responsible for the sedative, hypotensive and hemostatic effects of these plant species.

Ailanthone is a quassinoid allelochemical produced by the tree Ailanthus altissima (commonly known as tree of heaven). It is a key agent behind the tree's strong allelopathic effects, which inhibit the growth of competing plants by suppressing seed germination and disrupting root elongation. Native to China, Ailanthus altissima has become one of the worst invasive species in North America and Europe, where ailanthone is known to contribute significantly to its competitive spread.

Triptolide is a diterpenoid epoxide which is produced by the thunder god vine, Tripterygium wilfordii. It has in vitro and in vivo activities against mouse models of polycystic kidney disease and pancreatic cancer, but its physical properties and severe toxicity limit its therapeutic potential. Consequently, a synthetic water-soluble prodrug, minnelide, is being studied clinically instead.

chemical compound

Galanolactone is a diterpenoid lactone first isolated from ginger. It is present in acetone extracts of ginger, and appears to be an antagonist at 5-HT3 receptors.

chemical compound

18-Norabietane is a diterpene perhydrogenated phenanthrene derivative. It occurs in the mineral fichtelite. Like many "fossil compounds", it is saturated and devoid of oxygen-containing functional groups. Its presence is usually analyzed by gas chromatography–mass spectrometry.

Paxilline is a toxic, tremorgenic diterpene indole polycyclic alkaloid molecule produced by Penicillium paxilli which was first characterized in 1975. Paxilline is one of a class of tremorigenic mycotoxins, is a potassium channel blocker, and is potentially genotoxic.

Mezerein is a toxic diterpene ester found in the sap of Daphne mezereum and related plants. Plants of the genera Euphorbiaceae and Thymelaeaceae possess a wide variety of different phorbol esters, which share the capacity of mimicking diacylglycerol (DAG) and thus activating different isoforms of protein kinase C. Mezerein was first isolated in 1975. It has antileukemic properties in mice, but it is also defined as a weak promoter of skin cancers in the same species. All parts of the plants contain an acrid and irritant sap that contains mezerein, thought to be the principal poison. The sap is

Isophytol is a terpenoid alcohol that is used as a fragrance and as an intermediate in the production of vitamin E and K1.

chemical compound

Taxodone is a naturally occurring diterpenoid found in Taxodium distichum (bald cypress), Rosmarinus officinalis (rosemary), several salvia species and other plants, along with its oxidized rearrangement product, taxodione. Taxodone and taxodione exhibit anticancer, antibacterial, antioxidant, antifungal, insecticide, and antifeedant activities.

Simonellite (1,1-dimethyl-1,2,3,4-tetrahydro-7-isopropyl phenanthrene) is a polycyclic aromatic hydrocarbon with a chemical formula C19H24. It is similar to retene.

Menatetrenone (INN), also known as menaquinone-4 (MK-4), is one of the nine forms of vitamin K2.

chemical compound

Taxadiene (taxa-4,11-diene) is a diterpene. Taxadiene is the first committed intermediate in the synthesis of taxol. Six hydroxylation reactions, and a few others, are needed to convert taxadiene to baccatin III.

chemical compound

Stemarene is a diterpene hydrocarbon can be produced biosynthetically through enzyme extracts from rice.

chemical compound