Triterpenes

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.

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. In the eyes of vertebrates, lanosterol is a natural constituent, having a role in maintaining health of the lens. Lanosterol is the precursor to cholesterol.

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.

Betulin is an abundant, naturally occurring triterpene. It is commonly isolated from the bark of birch trees, hence its name, from betula. It forms up to 30% of the dry weight of silver birch bark. It is also found in birch sap. Inonotus obliquus contains betulin.

chemical compound

chemical compound

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.

chemical compound

Ambrein is a triterpene alcohol that is the chief constituent of ambergris, a secretion from the digestive system of the sperm whale. It has been suggested as the possible active component producing the supposed aphrodisiac effects of ambergris. Although ambrein itself is odorless, it serves as the biological precursor for aromatic derivatives such as ambroxide and is thought to possess fixative properties for other odorants.

'(S)-2,3-Oxidosqualene ((S)-2,3-epoxysqualene') is an intermediate in the synthesis of the cell membrane sterol precursors lanosterol and cycloartenol, as well as saponins. It is formed when squalene is oxidized by the enzyme squalene monooxygenase. 2,3-Oxidosqualene is the substrate of various oxidosqualene cyclases, including lanosterol synthase, which produces lanosterol, a precursor to cholesterol.

Absinthin is a naturally produced triterpene lactone from the plant Artemisia absinthium (Wormwood). It constitutes one of the most bitter chemical agents responsible for absinthe's distinct taste. The compound shows biological activity and has shown promise as an anti-inflammatory agent, and should not be confused with thujone, a neurotoxin also found in Artemisia absinthium.

Lupeol is a pharmacologically active pentacyclic triterpenoid. It has several potential medicinal properties, like anticancer and anti-inflammatory activity.

Carbenoxolone (CBX) is a glycyrrhetinic acid derivative with a steroid-like structure, similar to substances found in the root of the licorice plant. Carbenoxolone is used for the treatment of peptic, esophageal and oral ulceration and inflammation. Electrolyte imbalance is a serious side effect of carbenoxolone when used systemically.

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.

Enoxolone (INN, BAN; also known as glycyrrhetinic acid or glycyrrhetic acid) is a pentacyclic triterpenoid derivative of the beta-amyrin type obtained from the hydrolysis of glycyrrhizic acid, which was obtained from the herb liquorice.

alt=|thumb|377x377px|Some representative hopanoids: A. Diploptene, also called 22(29)-hopene B. Diplopterol, also called hopan-22-ol, the hydrated cyclomer of diploptene C. Bacteriohopanetetrol (BHT), a common extended hopanoid D. Hopane, the diagenetic product of A and B that results from reducing conditions during deposition and persists in the rock record. The diagenetic product of C would be an extended C35 hopane.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 hopene

Cholane is a triterpene which can exist as either of two stereoisomers, 5α-cholane and 5β-cholane. Its name is derived from (chole) meaning 'bile' in reference to its original discovery from the bile of the American bullfrog (Rana catesbeiana). The compound itself has no known uses. However, various functionalized analogues are produced by plants and animals, typically in the form of sterols, steroids and bile acids (e.g. cholic acid).

Squalane is the organic compound with the formula . A colorless hydrocarbon, it is the hydrogenated derivative of squalene, although commercial samples are derived from nature. In contrast to squalene, due to the complete saturation of squalane, it is not subject to auto-oxidation. This fact, coupled with its lower costs and desirable physical properties, led to its use as an emollient and moisturizer in cosmetics.

The amyrins are three closely related natural chemical compounds of the triterpene class. They are designated α-amyrin (ursane skeleton), β-amyrin (oleanane skeleton), and δ-amyrin. Each is a pentacyclic triterpenol with the chemical formula C30H50O. They are widely distributed in nature and have been isolated from a variety of plant sources such as epicuticular wax. In plant biosynthesis, α-amyrin is the precursor of ursolic acid and β-amyrin is the precursor of oleanolic acid. All three amyrins occur in the surface wax of tomato fruit. α-Amyrin is found in dandelion coffee.

thumb|right|The chemical structure of yamogenin, a sapogenin found in [[fenugreek]]

Cholestane is a saturated tetracyclic steroid biosynthetically derived from triterpenoids. This 27-carbon biomarker is produced by diagenesis of cholesterol and is one of the most abundant biomarkers in the rock record. Presence of cholestane, its derivatives and related chemical compounds in environmental samples is commonly interpreted as an indicator of animal life and/or traces of O2, as animals are known for exclusively producing cholesterol, and thus has been used to draw evolutionary relationships between ancient organisms of unknown phylogenetic origin and modern metazoan taxa. Cholest

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.

chemical compound

chemical compound

Cycloastragenol is a triterpenoid isolated from various legume species in the genus Astragalus that is purported to have telomerase activation activity. A preliminary in vitro study on human CD4 and CD8 T cells found that cycloastragenol may moderately increase telomerase activity and inhibit the onset of cellular senescence.

chemical compound

Yamogenin is a chemical compound of the class called spirostanol sapogenins. It is found in the herb fenugreek (Trigonella foenum-graecum) and other plants.

Dammarane is a tetracyclic triterpene found in sapogenins (forming triterpenoid saponins) like those of ginseng (ginsenosides: panaxatriol and protopanaxadiol). Compounds of the series were first isolated from and named after dammar resin, a natural resin from the tropical trees of the dipterocarp family.

Celastrol (tripterine) is a bioactive chemical compound isolated from the roots of Tripterygium wilfordii (Thunder duke vine) and Tripterygium regelii (Regel's threewingnut). Celastrol is a pentacyclic and belongs to the family of quinone methides. It has been used for centuries as a traditional Chinese medicine. In recent years, celastrol has been widely studied for its anti-inflammatory, anticancer, antioxidant, and antibacterial properties.

Protopanaxadiol (PPD) is an organic compound that is an aglycone of ginsenosides, a group of steroid glycosides. It is a dammarane-type tetracyclic terpene sapogenin found in ginseng (Panax ginseng) and in notoginseng (Panax pseudoginseng).

Omaveloxolone, sold under the brand name Skyclarys, is a medication used for the treatment of Friedreich's ataxia. It is taken by mouth.

Ergostane is a tetracyclic triterpene, also known as 24S-methylcholestane. The compound itself has no known uses; however various functionalized analogues are produced by plants and animals. The most important of these are the heavily derivatised withanolides. However simpler forms do exist, such as the sterane campestane (24R-methylcholestane). Along with cholestane and stigmastane, this sterane is used as a biomarker for early eukaryotes.

chemical compound

Hederagenin is a triterpenoid which is a chemical constituent of the Hedera helix plant.

Protopanaxatriol (PPT) is an organic compound that is an aglycone of ginsenosides, a group of steroid glycosides. It is a dammarane-type tetracyclic triterpene sapogenins found in ginseng (Panax ginseng) and in notoginseng (Panax pseudoginseng).

Acetoxolone (also known as acetylglycyrrhetic acid, acetylglycyrrhetinic acid, glycyrrhetinyl acetate and glycyrrhetic acid acetate) is a drug used for peptic ulcer and gastroesophageal reflux disease. It is an acetyl derivative of glycyrrhetinic acid. It is found in Echinopora lamellosa.

Panaxatriol is an organic compound that is an aglycone of ginsenosides, a group of steroid glycosides. It is a dammarane-type tetracyclic triterpene sapogenin found in ginseng (Panax ginseng) and in notoginseng (Panax pseudoginseng). It is formed by the dehydration of protopanaxatriol.

Friedelin is a triterpenoid chemical compound found in Azima tetracantha, Orostachys japonica, and Quercus stenophylla. Friedelin is also found in the roots of the Cannabis plant. It is noted as having antimicrobial properties and has been recovered from the byproducts of corkboard manufacturing. The compound is also a biological precursor of celastrol. It is considered a friedelane-type compound, appearing structurally similar with the addition of a ketone group.

Lanostane or 4,4,14α-trimethylcholestane is a tetracyclic chemical compound with formula . It is a polycyclic hydrocarbon, specifically a triterpene. It is an isomer of cucurbitane.

chemical compound

chemical compound

chemical compound

Bevirimat (research code MPC-4326) is an anti-HIV drug derived from a betulinic acid-like compound, first isolated from Syzygium claviflorum, a Chinese herb. It is believed to inhibit HIV by a novel mechanism, so-called maturation inhibition. It is not currently U.S. Food and Drug Administration (FDA) approved. It was originally developed by the pharmaceutical company Panacos and reached Phase IIb clinical trials. Myriad Genetics announced on January 21, 2009 the acquisition of all rights to bevirimat for $7M USD. On June 8, 2010 Myriad Genetics announced that it was abandoning their HIV portf

Stigmastane or '24R-ethylcholestane' is a tetracyclic triterpene, along with cholestane and ergostane, this sterane is used as a biomarker for early eukaryotes.

chemical compound

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.

Lepidolide is a chemical compound with formula — specifically, a terpenoid with the cucurbitane skeleton — isolated from the fruiting bodies of the mushroom Russula lepida (23 mg/7 kg). It is a pale yellow oil, soluble in chloroform.

Balsaminapentaol or cucurbita-5,25-diene-3β,7β,23(R),24(R),29-pentaol, is a chemical compound with formula , found in the Balsam apple vine (Momordica balsamina). It is a cucurbitane-type triterpenoid, related to cucurbitacin, isolated by C. Ramalhete and others in 2009.