'Squalene' is a biologically occurring triterpene compound, naturally produced in humans, animals, and plants, that forms an essential part of the lipid-rich membranes in various tissues, including the skin surface and the liver, and has been studied for its potential benefits in skincare, dietary supplements, and vaccine adjuvant systems.
The second enzyme in the committed pathway for CHOLESTEROL biosynthesis, this enzyme catalyzes the first oxygenation step in the biosynthesis of STEROLS and is thought to be a rate limiting enzyme in this pathway. Specifically, this enzyme catalyzes the conversion of SQUALENE to (S)-squalene-2,3-epoxide.
The first committed enzyme of the biosynthesis pathway that leads to the production of STEROLS. it catalyzes the synthesis of SQUALENE from farnesyl pyrophosphate via the intermediate PRESQUALENE PYROPHOSPHATE. This enzyme is also a critical branch point enzyme in the biosynthesis of ISOPRENOIDS that is thought to regulate the flux of isoprene intermediates through the sterol pathway.
Organic compounds that are acyclic and contain three acid groups. A member of this class is citric acid which is the first product formed by reaction of pyruvate and oxaloacetate. (From Lehninger, Principles of Biochemistry, 1982, p443)
A triterpene that derives from the chair-boat-chair-boat folding of 2,3-oxidosqualene. It is metabolized to CHOLESTEROL and CUCURBITACINS.
Mevalonic acid is a crucial intermediate compound in the HMG-CoA reductase pathway, which is a metabolic route that produces cholesterol, other steroids, and isoprenoids in cells.
Steroids with a hydroxyl group at C-3 and most of the skeleton of cholestane. Additional carbon atoms may be present in the side chain. (IUPAC Steroid Nomenclature, 1987)
The oily substance secreted by SEBACEOUS GLANDS. It is composed of KERATIN, fat, and cellular debris.
Oxidases that specifically introduce DIOXYGEN-derived oxygen atoms into a variety of organic molecules.
Enzymes of the isomerase class that catalyze the transfer of acyl-, phospho-, amino- or other groups from one position within a molecule to another. EC 5.4.
A steroid of interest both because its biosynthesis in FUNGI is a target of ANTIFUNGAL AGENTS, notably AZOLES, and because when it is present in SKIN of animals, ULTRAVIOLET RAYS break a bond to result in ERGOCALCIFEROL.
A colorless liquid extracted from oils of plants such as citronella, neroli, cyclamen, and tuberose. It is an intermediate step in the biological synthesis of cholesterol from mevalonic acid in vertebrates. It has a delicate odor and is used in perfumery. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)
Phosphoric or pyrophosphoric acid esters of polyisoprenoids.
A fungal metabolite isolated from cultures of Aspergillus terreus. The compound is a potent anticholesteremic agent. It inhibits 3-hydroxy-3-methylglutaryl coenzyme A reductase (HYDROXYMETHYLGLUTARYL COA REDUCTASES), which is the rate-limiting enzyme in cholesterol biosynthesis. It also stimulates the production of low-density lipoprotein receptors in the liver.
Enzymes that catalyze the reversible reduction of alpha-carboxyl group of 3-hydroxy-3-methylglutaryl-coenzyme A to yield MEVALONIC ACID.
Triterpenes are a class of naturally occurring compounds consisting of six isoprene units arranged to form a 30-carbon skeleton, often found in plants and some animals, with various bioactivities including anti-inflammatory, antiviral, and cytotoxic properties.
Possesses an unusual and selective cytotoxicity for VASCULAR SMOOTH MUSCLE cells in dogs and rats. Useful for experiments dealing with arterial injury, myocardial fibrosis or cardiac decompensation.
An enzyme that catalyzes the condensation of two molecules of geranylgeranyl diphosphate to give prephytoene diphosphate. The prephytoene diphosphate molecule is a precursor for CAROTENOIDS and other tetraterpenes.
The principal sterol of all higher animals, distributed in body tissues, especially the brain and spinal cord, and in animal fats and oils.
A class of saturated compounds consisting of two rings only, having two or more atoms in common, containing at least one hetero atom, and that take the name of an open chain hydrocarbon containing the same total number of atoms. (From Riguady et al., Nomenclature of Organic Chemistry, 1979, p31)
Oxazepines are a class of benzodiazepine-like drugs that have a oxazepine ring in their chemical structure, and are used as anticonvulsants and anxiolytics due to their ability to modulate GABAergic neurotransmission.
Chromatography on thin layers of adsorbents rather than in columns. The adsorbent can be alumina, silica gel, silicates, charcoals, or cellulose. (McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)
A class of organic compounds known as STEROLS or STEROIDS derived from plants.
Benzophenones are synthetic organic compounds characterized as aromatic ketones, often used in chemical synthesis for various applications including sunscreen formulations due to their UV-absorbing properties.
Stigmasterol is a plant-derived steroidal sapogenin, structurally similar to cholesterol, found in various plants and some animal sources, which exhibits weak estrogenic activity and has potential uses in the pharmaceutical industry.
Changing an open-chain hydrocarbon to a closed ring. (McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)
Derivatives of the saturated steroid cholestane with methyl groups at C-18 and C-19 and an iso-octyl side chain at C-17.
'Bicyclo compounds' in medicinal chemistry refer to organic molecules containing two fused rings, where each ring shares two common atoms, creating a topological structure that resembles two overlapping circles or bicycle tires.
An enzyme involved in the MEVALONATE pathway, it catalyses the synthesis of farnesyl diphosphate from isopentenyl diphosphate and dimethylallyl diphosphate.
A family of sterols commonly found in plants and plant oils. Alpha-, beta-, and gamma-isomers have been characterized.
Derivatives of ACETIC ACID. Included under this heading are a broad variety of acid forms, salts, esters, and amides that contain the carboxymethane structure.
Quinuclidines are organic compounds consisting of a tricyclic structure with a three-membered ring fused to a piperidine ring, often used as building blocks in the synthesis of pharmaceuticals and bioactive molecules.
Two-ring crystalline hydrocarbons isolated from coal tar. They are used as intermediates in chemical synthesis, as insect repellents, fungicides, lubricants, preservatives, and, formerly, as topical antiseptics.
A common name (but used formally) for a group of organisms that are mostly kinds of algae including BACILLARIOPHYTA; OOMYCETES; PHAEOPHYCEAE; and CHRYSOPHYCEAE. They all contain CHLOROPLASTS that are thought to have been derived from the endosymbiosis of ancient RED ALGAE.
Vaccines or candidate vaccines used to prevent ANTHRAX.
An acute infection caused by the spore-forming bacteria BACILLUS ANTHRACIS. It commonly affects hoofed animals such as sheep and goats. Infection in humans often involves the skin (cutaneous anthrax), the lungs (inhalation anthrax), or the gastrointestinal tract. Anthrax is not contagious and can be treated with antibiotics.
Vaccines or candidate vaccines used to prevent PAPILLOMAVIRUS INFECTIONS. Human vaccines are intended to reduce the incidence of UTERINE CERVICAL NEOPLASMS, so they are sometimes considered a type of CANCER VACCINES. They are often composed of CAPSID PROTEINS, especially L1 protein, from various types of ALPHAPAPILLOMAVIRUS.
Suspensions of killed or attenuated microorganisms (bacteria, viruses, fungi, protozoa), antigenic proteins, synthetic constructs, or other bio-molecular derivatives, administered for the prevention, amelioration, or treatment of infectious and other diseases.
A species of bacteria that causes ANTHRAX in humans and animals.
Vaccines in which the infectious microbial nucleic acid components have been destroyed by chemical or physical treatment (e.g., formalin, beta-propiolactone, gamma radiation) without affecting the antigenicity or immunogenicity of the viral coat or bacterial outer membrane proteins.
Suspensions of attenuated or killed viruses administered for the prevention or treatment of infectious viral disease.