|
Triterpenes
Triterpenes are a class of chemical compounds composed of three terpene units with the molecular formula C30H48; they may also be thought of as consisting of six isoprene 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'' oft ... [...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 ring In organic chemistry, an alicyclic compound contains one or more all-carbon rings which may be either saturated or unsaturated, but do not have aromatic character. Alicyclic compounds may have one or more aliphatic side chains attached. The ...s 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 p ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cucurbitane
Cucurbitane is a class of chemical compounds with formula ( CAS number 65441-59-0). 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 Derivatives Natural compounds Compounds with the basic cucurbitane skeleton are found in many plants, and some are important phytopharmaceuticals. Natural cucurbitane-related compounds include: Named * Balsaminapentaol, ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Squalene
Squalene is an organic compound. It is a triterpenoid 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). All plants and animals produce squalene as a biochemical intermediate to sterol biosynthesis. An estimated 12% of bodily squalene in humans is found in Sebaceous gland, sebum. Squalene has a role in topical skin lubrication and protection. Squalene is a precursor (chemistry), precursor for synthesis of all plant and animal sterols, including cholesterol and steroid hormones in the human body. Squalene is an important ingredient in some vaccine adjuvants: The Novartis and GlaxoSmithKline adjuvants are called MF59 and AS03, respectively. Role in steroid synthesis Squalene is the biochemical precursor to steroids. The squalene conversion begins with oxidation (via squalene monooxygenase) of one of its terminal double bonds, resulting in 2,3- ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Lanosterol
Lanosterol is a tetracyclic triterpenoid and is the compound from which all animal and fungal steroids are derived. By contrast plant steroids are produced via cycloartenol. Role in biosynthesis of other steroids Elaboration of lanosterol under enzyme catalysis leads to the core structure of steroids. 14-Demethylation of lanosterol by CYP51 eventually yields cholesterol. Biosynthesis Research Lanosterol has been identified as a key component in maintaining eye lens clarity. Pre-clinical research has identified Lanosterol as a possible agent for the reversal and prevention of cataracts. In vivo experiments on dogs showed significant reversal of cataracts within 6 weeks of lanosterol injection. In 2018, Lanosterol was shown to improve lens clarity in cells with lens clouding due to aging or physical stressors. A subsequent study found positive results on the optics of the lens in mice with cataracts (Wang, Hoshino,Uesugi, Yagi, Pierscionek and Andley (2022). Use Lanosterol is a ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cycloartenol
Cycloartenol is an important triterpenoid of the sterol class which is found in plants. 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 process used by plants and other organisms to convert light energy into chemical energy that, through cellular respiration, can later be released to fuel the organism's activities. Some of this chemical energy is stored in c ... organisms and plants. The identities and distribution of phytostanols and phytosterols is characteristic of a plant species. References Sterols Triterpenes Cyclopropanes {{Alcohol-stub ... [...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 Bacteriohopanepolyols (BHPs), bacteriohopanoids, or bacterial pentacyclic triterpenoids are commonly found in the lipid cell membranes of many bacteria. BHPs are frequently used as biomarkers in sedimentary rocks and can provide paleoecological inf ... References Triterpenes Hydrocarbons Cyclopentanes Isopropyl compounds {{organic-compound-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hopanoids
Hopanoids are a diverse subclass of triterpenoids with the same hydrocarbon skeleton as the compound hopane. This group of 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, the first Regius Keeper of the Royal Botanic Garden, Edinburgh. Since their initial discovery in an angiosperm, hopanoids have been found in plasma membranes of bacteria, lichens, bryophytes, ferns, tropical trees and fungi. Hopanoids have ... [...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 The molecule has a mass of 448.298 Daltons, and consists of two carbonyl groups and three double bonds. It is a hexacarboxylic triterpene. The 2d structure is shown in Figure 1. The physical properties are not well known; the melting point of chamaecydin is 197-198 C. Its crystal structure is orthorhombic. Chamaecydin shows significant antifeedant activity against the larvae of '' Spodoptera Iitura'' and has an antifeedant index (AFI) of 0.44. The index ranges from 1 to -1, with one being the most powerful antifeedant. It is calcula ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Ursolic Acid
Ursolic acid (sometimes referred to as urson, prunol, malol, or 3β-hydroxyurs-12-en-28-oic acid), is a pentacyclic triterpenoid identified in the epicuticular waxes of apples as early as 1920 and widely found in the peels of fruits, as well as in herbs and spices like rosemary and thyme. Natural occurrence Ursolic acid is present in many plants, such as ''Mirabilis jalapa'', as well as in many fruits and herbs used in daily life (e.g. apples, basil and holy basil, bilberries, cranberries, elder flower, peppermint, rosemary, lavender, oregano, thyme, hawthorn, and prunes). Apple peels contain large quantities of ursolic acid and related compounds. Potential biochemical effects A number of potential biochemical effects of ursolic acid have been investigated, but there has been no clinical study demonstrating benefits to human health. ''In vitro'', ursolic acid inhibits the proliferation of various cancer cell types by inhibiting the STAT3 activation pathway, and may also d ... [...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 taxerol) 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 steroids. 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 oleananes. For example, in 18-alpha-oleanane contains a downward facing methyl group for the 18th carbon atom, while 18-beta-oleanane contains an upward facing methyl group at the same position. Of note is that fact that the A and B rings of the oleanane st ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Squalene
Squalene is an organic compound. It is a triterpenoid 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). All plants and animals produce squalene as a biochemical intermediate to sterol biosynthesis. An estimated 12% of bodily squalene in humans is found in Sebaceous gland, sebum. Squalene has a role in topical skin lubrication and protection. Squalene is a precursor (chemistry), precursor for synthesis of all plant and animal sterols, including cholesterol and steroid hormones in the human body. Squalene is an important ingredient in some vaccine adjuvants: The Novartis and GlaxoSmithKline adjuvants are called MF59 and AS03, respectively. Role in steroid synthesis Squalene is the biochemical precursor to steroids. The squalene conversion begins with oxidation (via squalene monooxygenase) of one of its terminal double bonds, resulting in 2,3- ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Lanostane
Lanostane or 4,4,14α-trimethylcholestane is a chemical compound with formula . It is a polycyclic hydrocarbon, specifically a triterpene. It is an isomer of cucurbitane. 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-lanostane.svg, 5α-Lanostane File:5beta-lanostane.svg, 5β-Lanostane Replacement of a hydrogen atom attached to carbon number 3 in the 5α isomer with a hydroxyl group results in lanosterol, the biogenetic precursor of the steroid A steroid is a biologically active organic compound with four rings arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes that alter membrane fluidity; and a ...s in animals. References {{Saponins Lanostanes Triterpenes ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
