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Diterpene
Diterpenes are a class of chemical compounds 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. They are known to be antimicrobial and antiinflammatory. 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 geranylg ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Abietane
Abietane is a diterpene that forms the structural basis for a variety of natural chemical compounds such as abietic acid, carnosic acid, and ferruginol which are collectively known as abietanes or abietane diterpenes. Abietanes are found in the tissues and resins of certain higher plants, particularly gymnosperms. Although the functions of terpenes are not fully understood, conifers appear to produce abietane diterpenoids as a form of defense against insect and microbial attack. Some abietane diterpenoids, especially aromatic abietenes, are of interest to the pharmacology and natural products communities for their potential biological activities. In the rock record, abietanes are commonly found in amber as well as in fossil wood, sometimes in the form of the mineral fichtelite. Additionally, abietanes are observed in sediments—both riverine and marine—and in coals, where they are often interpreted as geochemical biomarkers for terrestrial input from conifers. Chemical stru ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Labdane
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. A variety of biological activities have been determined for labdane diterpenes including antibacterial, antifungal, antiprotozoal, and anti-inflammatory activities. Example labdane derivatives * Forskolin * Galanolactone * Isocupressic acid - is an abortifacient component of ''Cupressus macrocarpa''. * Medigenin * Sclareol * Stemodene See also * Abietane Abietane is a diterpene that forms the structural basis for a variety of natural chemical compounds such as abietic acid, carnosic acid, and ferruginol which are collectively known as abietanes or abietane diterpenes. Abietanes are found in the ... References {{reflist Diterpenes Decalins ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Geranylgeranyl Pyrophosphate
Geranylgeranyl pyrophosphate is an intermediate in the biosynthesis of diterpenes and diterpenoids. It is also the precursor to carotenoids, gibberellins, tocopherols, and chlorophylls. It is also a precursor to geranylgeranylated proteins, which is its primary use in human cells. It is formed from farnesyl pyrophosphate by the addition of an isoprene unit from isopentenyl pyrophosphate. In ''Drosophila'', geranylgeranyl pyrophosphate is synthesised by HMG-CoA encoded by the Columbus gene. Geranylgeranyl pyrophosphate is utilised as a chemoattractant for migrating germ cells that have traversed the midgut epithelia. The attractant signal is produced at the gonadal precursors, directing the germ cells to these sites, where they will differentiate into eggs and spermatozoa (sperm). Related compounds * Farnesyl pyrophosphate * Geranylgeraniol * Geranyl pyrophosphate Geranyl pyrophosphate (GPP), also known as geranyl diphosphate (GDP), is the pyrophosphate ester of the terpeno ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Geranylgeranyl Pyrophosphate
Geranylgeranyl pyrophosphate is an intermediate in the biosynthesis of diterpenes and diterpenoids. It is also the precursor to carotenoids, gibberellins, tocopherols, and chlorophylls. It is also a precursor to geranylgeranylated proteins, which is its primary use in human cells. It is formed from farnesyl pyrophosphate by the addition of an isoprene unit from isopentenyl pyrophosphate. In ''Drosophila'', geranylgeranyl pyrophosphate is synthesised by HMG-CoA encoded by the Columbus gene. Geranylgeranyl pyrophosphate is utilised as a chemoattractant for migrating germ cells that have traversed the midgut epithelia. The attractant signal is produced at the gonadal precursors, directing the germ cells to these sites, where they will differentiate into eggs and spermatozoa (sperm). Related compounds * Farnesyl pyrophosphate * Geranylgeraniol * Geranyl pyrophosphate Geranyl pyrophosphate (GPP), also known as geranyl diphosphate (GDP), is the pyrophosphate ester of the terpeno ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Stemodene
Stemodene is a labdane-related diterpene whose corresponding terpene synthase has been discovered in rice and subsequently cloned and functionally characterized. The gene responsible for stemodene production has not been found in the completed rice genome, thus suggesting that perhaps other genes are as yet undiscovered in the "completed" genome. Stemarene synthase demonstrates high sequence homology with stemodene synthase, thus accounting for the latter's discovery by Dana Morrone in 2005. Additionally, the corresponding olefin In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond. Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic, an ... produced by each cyclase shows structural similarities and is derived from the common precursor of ''syn''-copalyl diphosphate. References Diterpenes Cyclopentanes {{Organic-compound-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cembrene A
Cembrene 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. Cembrene A itself has little importance as a chemical entity, being a trail pheromone for termites; however, the chemical structure of cembrene is central to a very wide variety of other natural products found both in plants and in animals.''Terpenes: Flavors, Fragrances, Pharmaca, Pheromones'', Eberhard Breitmaier, page 7. Cembrenes are biosynthesized by macrocyclization of geranylgeranyl pyrophosphate Geranylgeranyl pyrophosphate is an intermediate in the biosynthesis of diterpenes and diterpenoids. It is also the precursor to carotenoids, gibberellins, tocopherols, and chlorophylls. It is also a precursor to geranylgeranylated proteins, whi .... References {{reflist Diterpenes Alkene derivatives Insect ecology Insect pheromones Cycloalkenes ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Phytol
Phytol (florasol, phytosol) is an acyclic hydrogenated 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 stored in fats. In shark liver it yields pristane. Human pathology Refsum disease (also known as adult Refsum disease) is an autosomal recessive disorder that results in the accumulation of toxic stores of phytanic acid in tissues and frequently manifests as a variable combination of peripheral polyneuropathy, cerebellar ataxia, retinitis pigmentosa, anosmia, and hearing loss. Although humans cannot derive phytanic acid from chlorophyll, they can convert free phytol into phytanic acid. Thus, patients with Refsum disease should limit their intake of phytanic acid and free phytol. The amount of free phytol in numerous food products has been reporte ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Farnesyl Pyrophosphate
Farnesyl pyrophosphate (FPP), also known as farnesyl diphosphate (FDP), is an intermediate in the biosynthesis of terpenes and terpenoids such as sterols and carotenoids. It is also used in the synthesis of CoQ (part of the electron transport chain), as well as dehydrodolichol diphosphate (a precursor of dolichol, which transports proteins to the ER lumen for ''N''-glycosylation). Biosynthesis Farnesyl pyrophosphate synthase (a prenyl transferase) catalyzes sequential condensation reactions of dimethylallyl pyrophosphate with 2 units of 3-isopentenyl pyrophosphate to form farnesyl pyrophosphate, as is shown in the following two steps: * Dimethylallyl pyrophosphate reacts with 3-isopentenyl pyrophosphate to form geranyl pyrophosphate: * Geranyl pyrophosphate then reacts with another molecule of 3-isopentenyl pyrophosphate to form farnesyl pyrophosphate Pharmacology The above reactions are inhibited by bisphosphonates (used for osteoporosis). Farnesyl pyrophosphate is a sele ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Sclarene
Sclarene is a diterpene Diterpenes are a class of chemical compounds 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 ... present in the foliage of '' Podocarpus hallii''. References Diterpenes Decalins Polyenes Vinylidene compounds {{organic-compound-stub ...[...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Stemarene
Stemarene is a diterpene hydrocarbon can be produced biosynthetically through enzyme Enzymes () are proteins that act as biological catalysts by accelerating chemical reactions. The molecules upon which enzymes may act are called substrate (chemistry), substrates, and the enzyme converts the substrates into different molecule ... extracts from rice. References Diterpenes Cyclopentanes {{Organic-compound-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Taxadiene
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. Enzymatically, taxadiene is produced from geranylgeranyl pyrophosphate by taxadiene synthase. A biochemical gram-scale production of taxadiene has been reported in 2010 using genetically engineered ''Escherichia coli ''Escherichia coli'' (),Wells, J. C. (2000) Longman Pronunciation Dictionary. Harlow ngland Pearson Education Ltd. also known as ''E. coli'' (), is a Gram-negative, facultative anaerobic, rod-shaped, coliform bacterium of the genus '' Esc ...''. References Dienes Taxanes Diterpenes {{organic-compound-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Phytol
Phytol (florasol, phytosol) is an acyclic hydrogenated 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 stored in fats. In shark liver it yields pristane. Human pathology Refsum disease (also known as adult Refsum disease) is an autosomal recessive disorder that results in the accumulation of toxic stores of phytanic acid in tissues and frequently manifests as a variable combination of peripheral polyneuropathy, cerebellar ataxia, retinitis pigmentosa, anosmia, and hearing loss. Although humans cannot derive phytanic acid from chlorophyll, they can convert free phytol into phytanic acid. Thus, patients with Refsum disease should limit their intake of phytanic acid and free phytol. The amount of free phytol in numerous food products has been reporte ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
