Labdane Diterpene
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Labdane Diterpene
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 Sclareol is a fragrant chemical compound found in ''Salvia sclarea'', from which it derives its name. It is classified as a bicyclic diterpene alcohol. It is an amber colored solid with a sweet, balsamic scent. Sclareol is also able to kill huma ... * Stemodene See also * Abietane References {{reflist Diterpenes Decalins ...
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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 geranylger ...
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Natural Product
A natural product is a natural compound or substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural products can also be prepared by chemical synthesis (both semisynthesis and total synthesis) and have played a central role in the development of the field of organic chemistry by providing challenging synthetic targets. The term natural product has also been extended for commercial purposes to refer to cosmetics, dietary supplements, and foods produced from natural sources without added artificial ingredients. Within the field of organic chemistry, the definition of natural products is usually restricted to organic compounds isolated from natural sources that are produced by the pathways of primary or secondary metabolism. Within the field of medicinal chemistry, the definition is often further restricted to secondary metabolites. Secondary metabolites (or specialized metabolites ...
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Labdanum
Labdanum, also called ladanum, ladan, or ladanon, is a sticky brown resin obtained from the shrubs ''Cistus ladanifer'' (western Mediterranean) and ''Cistus creticus'' (eastern Mediterranean), species of rockrose. It was historically used in herbal medicine and is still used in the preparation of some perfumes and vermouths. History In ancient times, labdanum was collected by combing the beards and thighs of goats and sheep that had grazed on the cistus shrubs. Wooden instruments used were referred to in 19th-century Crete as ''ergastiri''; a ''lambadistrion'' ("labdanum-gatherer") was a kind of rake to which a double row of leathern thongs were fixed instead of teeth. These were used to sweep the shrubs and collect the resin which was later extracted. It was collected by the shepherds and sold to coastal traders. The resin was used as an ingredient for incense, and medicinally to treat colds, coughs, menstrual problems and rheumatism. as cited in Labdanum was produced on the ...
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Cistus Ladanifer
''Cistus ladanifer'' is a species of flowering plant in the family Cistaceae. It is native to the western Mediterranean region. Common names include gum rockrose, labdanum, common gum cistus, and brown-eyed rockrose. Description It is a shrub growing tall and wide. The leaves are evergreen, lanceolate, 3–10 cm long and 1–2 cm broad, dark green above and paler underneath. The flowers are 5–8 cm diameter, with 5 papery white petals, usually with a red to maroon spot at the base, surrounding the yellow stamens and pistils. The whole plant is covered with the sticky exudate of fragrant resin, the source of labdanum, used in herbal medicine and perfumery. Ecology ''C. ladanifer'' is particularly well suited to the Mediterranean climate, standing both long summer droughts and cold weather. It is an extremely aggressive plant which has taken over much of former farmland and grasslands in the mountain regions of central Spain and much of southern Portugal. In Span ...
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Forskolin
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. Forskolin is commonly used in laboratory research to increase levels of cyclic AMP by stimulation of adenylate cyclase. Mechanism of action Forskolin is commonly used in biochemistry to raise levels of cyclic AMP (cAMP) in the study and research of cell physiology. Forskolin activates the enzyme adenylyl cyclase and increases intracellular levels of cAMP. cAMP is an important second messenger necessary for the proper biological response of cells to hormones and other extracellular signals. It is required for cell communication in the hyp ...
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Galanolactone
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 Receptor may refer to: *Sensory receptor, in physiology, any structure which, on receiving environmental stimuli, produces an informative nerve impulse *Receptor (biochemistry), in biochemistry, a protein molecule that receives and responds to a n .... References {{reflist Furanones Diterpenes Decalins Epoxides Tetrahydrofurans Spiro compounds ...
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Isocupressic Acid
Isocupressic acid is a diterpene acid present in a variety of conifer needles. It induces abortion in cattle. It is found in all parts of the ponderosa pine (''Pinus ponderosa''), especially the needles. This gives its toxic and abortifacient effects. It is also present in the lodgepole pine (''P. contorta''), the jeffrey pine (''P. jeffreyi'') and possibly in the monterey pine ''Pinus radiata'' ( syn. ''Pinus insignis''), the Monterey pine, insignis pine or radiata pine, is a species of pine native to the Central Coast of California and Mexico (Guadalupe Island and Cedros island). It is an evergreen conifer in the fa ... (''P. radiata''). References Pinus Carboxylic acids Diterpenes {{organic-compound-stub ...
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Cupressus Macrocarpa
''Hesperocyparis macrocarpa'' is a coniferous tree. It is commonly known as the Monterey cypress and is one of several species of cypress trees endemic to California. The Monterey cypress is found naturally only on the Central Coast of California. The natural distributional range of the species during modern times is confined to two small relict populations near Carmel, California, at Cypress Point in Pebble Beach and at Point Lobos. Historically during the peak of the last ice age, Monterey cypress would have likely comprised a much larger forest that extended much further north and south.Axelrod, D. I. (1982)AGE AND ORIGIN OF THE MONTEREY ENDEMIC AREA.''Madroño'', ''29''(3), 127–147. Description ''Hesperocyparis macrocarpa'' is a medium-sized coniferous evergreen tree, which often becomes irregular and flat-topped as a result of the strong winds that are typical of its native area. It grows to heights of up to 40 meters (133 feet) in perfect growing conditions, and ...
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Sclareol
Sclareol is a fragrant chemical compound found in ''Salvia sclarea'', from which it derives its name. It is classified as a bicyclic diterpene alcohol. It is an amber colored solid with a sweet, balsamic scent. Sclareol is also able to kill human leukemic cells and colon cancer cells by apoptosis Apoptosis (from grc, ἀπόπτωσις, apóptōsis, 'falling off') is a form of programmed cell death that occurs in multicellular organisms. Biochemical events lead to characteristic cell changes (morphology) and death. These changes incl .... References {{reflist Diols Diterpenes Vinyl compounds Decalins ...
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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 produced by each cyclase A cyclase is an enzyme, almost always a lyase, that catalyzes a chemical reaction to form a cyclic compound. Important cyclase enzymes include: * Adenylyl cyclase, which forms cyclic AMP from adenosine triphosphate (EC 4.6.1.1) ** ADCY1 ** ADCY2 ... shows structural similarities and is derived from the common precursor of ''syn''-copalyl diphosphate. References Diterpenes Cyclopentanes {{Organic-compound-stub ...
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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 str ...
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