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Triterpenes
Triterpenes are a class of terpenes composed of six isoprene units with the molecular formula C30H48; they may also be thought of as consisting of three terpene units. Animals, plants and fungi all produce triterpenes, including squalene, the precursor to all steroids. Structures Triterpenes exist in a great variety of structures. Nearly 200 different skeletons have been identified. These skeletons may be broadly divided according to the number of rings present. In general pentacyclic structures (5 rings) tend to dominate. Squalene is biosynthesized through the head-to-head condensation of two farnesyl pyrophosphate units. This coupling converts a pair of C15 components into a C30 product. Squalene serves as precursor for the formation of many triterpenoids, including bacterial hopanoids and eukaryotic sterols. Triterpenoids By definition triterpenoids are triterpenes that possess heteroatoms, usually oxygen. The terms ''triterpene'' and ''triterpenoid'' often are used in ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Malabaricane
The molecule malabaricane and its derivatives, the malabaricanes, are triterpene and triterpenoid compounds found in various organisms. They are named after the rain forest tree '' Ailanthus malabarica'' (''Ailanthus triphysa''), from which they were first isolated in 1967 by scientists at the National Chemical Laboratory in Pune, India. Later, great varieties of malabaricanes were discovered in other organisms, mostly in marine sponges such as '' Rhabdastrella globostellata''. Isomalabaricanes are malabaricanes in which the three carbon rings of the molecule are connected in '' trans−syn−trans'' conformation, as opposed to other malabaricanes, where the rings are connected in ''trans−anti−trans'' conformation. They are of particular research interest because many of them have been reported to show anti-tumour activity in cell culture Cell culture or tissue culture is the process by which cell (biology), cells are grown under controlled conditions, generally outsi ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Squalene
Squalene is an organic compound. It is a triterpene with the formula C30H50. It is a colourless oil, although impure samples appear yellow. It was originally obtained from shark liver oil (hence its name, as '' Squalus'' is a genus of sharks). An estimated 12% of bodily squalene in humans is found in sebum. Squalene has a role in topical skin lubrication and protection. Most plants, fungi, and animals produce squalene as biochemical precursor in sterol biosynthesis, including cholesterol and steroid hormones in the human body. It is also an intermediate in the biosynthesis of hopanoids in many bacteria. Squalene is an important ingredient in some vaccine adjuvants: The Novartis and GlaxoSmithKline adjuvants are called MF59 and AS03, respectively. Role in triterpenoid synthesis Squalene is a biochemical precursor to both steroids and hopanoids. For sterols, the squalene conversion begins with oxidation (via squalene monooxygenase) of one of its terminal double bonds, ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cucurbitane
Cucurbitane is a tetracyclic chemical compound with formula . It is a polycyclic hydrocarbon, specifically triterpene. It is also an isomer of lanostane (specifically 19(10→9β)-abeolanostane), from which it differs by the formal shift of a methyl group (carbon number 19) from the 10 to the 9β position in the standard steroid numbering scheme.Satish Kumar and Raj Kumar (1991), ''Dictionary of Biochemistry''. Anmol Publications, India The name is applied to two stereoisomers, distinguished by the prefixes 5α- and 5β-, which differ by the handedness of the bonds at a particular carbon atom (number 5 in the standard steroid numbering scheme). File:5alpha-cucurbitane.svg, 5α-Cucurbitane File:5beta-cucurbitane.svg, 5β-Cucurbitane Cucurbitane is the core chemical structure of a class of derivatives known as cucurbitane-type triterpenoids or simply as cucurbitanes. Derivatives Natural compounds Compounds with the basic cucurbitane skeleton are found in many plants, an ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Squalene
Squalene is an organic compound. It is a triterpene with the formula C30H50. It is a colourless oil, although impure samples appear yellow. It was originally obtained from shark liver oil (hence its name, as '' Squalus'' is a genus of sharks). An estimated 12% of bodily squalene in humans is found in sebum. Squalene has a role in topical skin lubrication and protection. Most plants, fungi, and animals produce squalene as biochemical precursor in sterol biosynthesis, including cholesterol and steroid hormones in the human body. It is also an intermediate in the biosynthesis of hopanoids in many bacteria. Squalene is an important ingredient in some vaccine adjuvants: The Novartis and GlaxoSmithKline adjuvants are called MF59 and AS03, respectively. Role in triterpenoid synthesis Squalene is a biochemical precursor to both steroids and hopanoids. For sterols, the squalene conversion begins with oxidation (via squalene monooxygenase) of one of its terminal double bonds, ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Terpene
Terpenes () are a class of natural products consisting of compounds with the formula (C5H8)n for n ≥ 2. Terpenes are major biosynthetic building blocks. Comprising more than 30,000 compounds, these unsaturated hydrocarbons are produced predominantly by plants, particularly Pinophyta, conifers. In plants, terpenes and terpenoids are important mediators of ecological biological interaction, interactions, while some insects use some terpenes as a form of defense. Other functions of terpenoids include cell growth modulation and plant elongation, light harvesting and photoprotection, and membrane permeability and fluidity control. Terpenes are classified by the number of carbons: monoterpenes (C10), sesquiterpenes (C15), diterpenes (C20), as examples. The terpene alpha-pinene is a major component of the common solvent, turpentine. The one terpene that has major applications is natural rubber (i.e., polyisoprene). The possibility that other terpenes could be used as precursors to pr ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Chamaecydin
Chamaecydin is a chemical compound with the molecular formula C30H40O3. It is made up of three six-membered rings and two five-membered rings and has one polar hydroxyl functional group. It is well preserved in the rock record and is only found in a specific family of conifers, the swamp cypress subfamily. The presence and abundance of chamaecydin in the rock record can reveal environmental changes in ancient biomes. Background Notable properties Chamaecydin is a hexacarboxylic triterpene with a highly conjugated core. Its melting point is 197–198 °C. Its crystal structure is orthorhombic. Chamaecydin shows significant antifeedant activity against the larvae of '' Spodoptera litura'' and has an antifeedant index (AFI) of +0.44 Preservation Chamaecydin is a biomarker for certain species of Conifer trees. Once living organism die, the organic molecules they biosynthesized often undergo various chemical transformations in the soil and thus usually retain only basic ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Terpenes
Terpenes () are a class of natural products consisting of compounds with the formula (C5H8)n for n ≥ 2. Terpenes are major biosynthetic building blocks. Comprising more than 30,000 compounds, these unsaturated hydrocarbons are produced predominantly by plants, particularly conifers. In plants, terpenes and terpenoids are important mediators of ecological interactions, while some insects use some terpenes as a form of defense. Other functions of terpenoids include cell growth modulation and plant elongation, light harvesting and photoprotection, and membrane permeability and fluidity control. Terpenes are classified by the number of carbons: monoterpenes (C10), sesquiterpenes (C15), diterpenes (C20), as examples. The terpene alpha-pinene is a major component of the common solvent, turpentine. The one terpene that has major applications is natural rubber (i.e., polyisoprene). The possibility that other terpenes could be used as precursors to produce synthetic polymers has be ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Oleanane
Oleanane is a natural triterpenoid. It is commonly found in woody angiosperms and as a result is often used as an indicator of these plants in the fossil record. It is a member of the oleanoid series, which consists of pentacyclic triterpenoids (such as beta-amyrin and taraxerol) where all rings are six-membered. Structure Oleanane is a pentacyclic triterpenoid, a class of molecules made up of six connected isoprene units. The naming of both the ring structures and individual carbon atoms in oleanane is the same as in steroid A steroid is an organic compound with four fused compound, fused rings (designated A, B, C, and D) arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes t ...s. As such, it consists of a A, B, C, D, and E ring, all of which are six-membered rings. The structure of oleanane contains a number of different methyl groups, that vary in orientation between different o ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hopane
Hopane is a natural chemical compound classified as a triterpene. It forms the central core of a variety of other chemical compounds which are collectively known as hopanoids. The first compound of the hopane family to be isolated and characterised was hydroxyhopanone, found in dammar resin. The name derives from '' Hopea'', a tree genus from which dammar is obtained. See also * Bacteriohopanepolyol References Triterpenes Hydrocarbons Cyclopentanes Isopropyl compounds {{alkanederivative-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hopanoids
Hopanoids are a diverse subclass of Triterpene, triterpenoids with the same hydrocarbon skeleton as the compound hopane. This group of Pentacyclic compound, pentacyclic molecules therefore refers to simple hopenes, hopanols and hopanes, but also to extensively functionalized derivatives such as bacteriohopanepolyols (BHPs) and hopanoids covalently attached to lipid A. The first known hopanoid, hydroxyhopanone, was isolated by two chemists at The National Gallery, London working on the chemistry of dammar gum, a natural resin used as a varnish for paintings. While hopanoids are often assumed to be made only in bacteria, their name actually comes from the abundance of hopanoid compounds in the resin of plants from the genus ''Hopea''. In turn, this genus is named after John Hope (botanist), John Hope, the first Regius Keeper of the Royal Botanic Garden Edinburgh, Regius Keeper of the Royal Botanic Garden, Edinburgh. Since their initial discovery in an angiosperm, hopanoids have been ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cycloartenol
Cycloartenol is an important triterpenoid often found in plants. It belongs to the sterol class of steroids. It is the starting point for the synthesis of almost all plant steroids, making them chemically distinct from the steroids of fungi and animals, which are, instead, produced from lanosterol. Synthesis The biosynthesis of cycloartenol starts from the triterpenoid squalene. It is the first precursor in the biosynthesis of other stanols and sterols, referred to as phytostanols and phytosterols in photosynthetic Photosynthesis ( ) is a Biological system, system of biological processes by which Photoautotrophism, photosynthetic organisms, such as most plants, algae, and cyanobacteria, convert light energy, typically from sunlight, into the chemical ener ... organisms and plants. The identities and distribution of phytostanols and phytosterols is characteristic of a plant species. References Sterols Triterpenes Cyclopropanes Pentacyclic compounds {{Alcohol- ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
