Terpene in the context of Isoprenoid


Terpene in the context of Isoprenoid

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⭐ Core Definition: Terpene

Terpenes (/ˈtɜːrpnz/ TUR-peenz) are a large and diverse class of natural products with the general formula (C5H8)n, where n ≥ 2. They serve as crucial biosynthetic building blocks in many organisms, particularly plants. 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 turpentine, a common solvent.

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Terpene in the context of Resin

A resin is a solid or highly viscous liquid that can be converted into a polymer. Resins may be biological or synthetic in origin, but are typically harvested from plants. Resins are mixtures of organic compounds insoluble in water, predominantly terpenes. Technically, resins should not be confused with gums, which consist predominantly of water-soluble polysaccharides, although these two terms are often interchangeable in the less formal context. Common resins include pine oleoresins, amber, hashish, frankincense, myrrh and the animal-derived resin, shellac. Resins are used in varnishes, adhesives, food additives, incenses and perfumes.

Resins protect plants from insects and pathogens, and are secreted in response to injury. Resins repel herbivores, insects, and pathogens, while the volatile phenolic compounds may attract benefactors such as predators of insects that attack the plant.

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Terpene in the context of Medicinal plant

Medicinal plants, also called medicinal herbs, have been discovered and used in traditional medicine practices since prehistoric times. Plants synthesize hundreds of chemical compounds for various functions, including defense and protection against insects, fungi, diseases, against parasites and herbivorous mammals.

The earliest historical records of herbs are found from the Sumerian civilization, where hundreds of medicinal plants including opium are listed on clay tablets, c. 3000 BC. The Ebers Papyrus from ancient Egypt, c. 1550 BC, describes over 850 plant medicines. The Greek physician Dioscorides, who worked in the Roman army, documented over 1000 recipes for medicines using over 600 medicinal plants in De materia medica, c. 60 AD; this formed the basis of pharmacopoeias for some 1500 years. Drug research sometimes makes use of ethnobotany to search for pharmacologically active substances, and this approach has yielded hundreds of useful compounds. These include the common drugs aspirin, digoxin, quinine, and opium. The compounds found in plants are diverse, with most in four biochemical classes: alkaloids, glycosides, polyphenols, and terpenes. Few of these are scientifically confirmed as medicines or used in conventional medicine.

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Terpene in the context of Turpentine

Turpentine (which is also called spirit of turpentine, oil of turpentine, terebenthine, terebenthene, terebinthine and, colloquially, turps) is a fluid obtainable by the distillation of resin harvested from living trees, mainly pines. Principally used as a specialized solvent, it is also a source of material for organic syntheses.

Turpentine is composed of terpenes, primarily the monoterpenes α-pinene and β-pinene, with lesser amounts of carene, camphene, limonene, and terpinolene. Nowadays, turpentine is rarely the product of distillation of pine resin, but is a byproduct of pulping. Pulping is achieved by two processes, the Kraft process and the sulfite process. The turpentines obtained from these two processes differ in their chemical compositions. The sulfite process gives a product that is rich in cymene, whereas the Kraft process gives a pinene-rich product.

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Terpene in the context of Cannabidiol

Cannabidiol (CBD) is a phytocannabinoid, one of 113 identified cannabinoids in Cannabis, along with tetrahydrocannabinol (THC), and accounts for up to 40% of the plant's extract. Medically, it is an anticonvulsant used to treat two rare forms of childhood epilepsy. It was discovered in 1940. Clinical research on CBD has included studies related to the treatment of anxiety, addiction, psychosis, movement disorders, and pain, but there is insufficient high-quality evidence that CBD is effective for these conditions. CBD is sold as an herbal dietary supplement and promoted with unproven claims of particular therapeutic effects.

Cannabidiol can be taken internally in multiple ways, including by inhaling cannabis smoke or vapor, swallowing it by mouth, and through use of an aerosol spray inside the cheek. It may be supplied as CBD oil containing only CBD as the active ingredient (excluding THC or terpenes), CBD-dominant hemp extract oil, capsules, dried cannabis, or prescription liquid solution. CBD does not have the same psychoactivity as THC, and can modulate the psychoactive effects of THC on the body if both are present. Conversion of CBD to THC can occur when CBD is heated to temperatures between 250–300 °C, potentially leading to its partial transformation into THC.

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Terpene in the context of Tetraterpene

Tetraterpenes are terpenes consisting of eight isoprene units and have the molecular formula C40H64. Tetraterpenoids (including many carotenoids) are tetraterpenes that have been chemically modified, as indicated by the presence of oxygen-containing functional groups.

Phytoene is biosynthesized via the head-to-head condensation of two GGPP molecules. One group of tetraterpenes, and possibly the most studied one, is the carotenoids pigments. Carotenoids have important biological functions, with roles in light capture, antioxidative activity and protection against free radicals, synthesis of plant hormones and as structural components of the membranes. Aside their biological relevance, carotenoids are also high-value compounds for the food and pharmaceutical industries. Carotenoids are biosynthesized by photosynthetic and non-photosynthetic organisms; however, in photosynthetic organisms, they are essential components as accessory pigments for the light-harvesting reaction centers. Xanthophylls are another group of tetraterpene pigments distributed widely in nature.

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Terpene in the context of Isoprenoids

The terpenoids, also known as isoprenoids, are a class of naturally occurring organic chemicals derived from the 5-carbon compound isoprene and its derivatives called terpenes, diterpenes, etc. While sometimes used interchangeably with "terpenes", terpenoids contain additional functional groups, usually containing oxygen. When combined with the hydrocarbon terpenes, terpenoids comprise about 80,000 compounds. They are the largest class of plant secondary metabolites, representing about 60% of known natural products. Many terpenoids have substantial pharmacological bioactivity and are therefore of interest to medicinal chemists.

Plant terpenoids are used for their aromatic qualities and play a role in traditional herbal remedies. Terpenoids contribute to the scent of eucalyptus, the flavors of cinnamon, cloves, and ginger, the yellow color in sunflowers, and the red color in tomatoes. Well-known terpenoids include citral, menthol, camphor, salvinorin A in the plant Salvia divinorum, ginkgolide and bilobalide found in Ginkgo biloba and the cannabinoids found in cannabis. The provitamin beta carotene is a terpene derivative called a carotenoid.

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Terpene in the context of Polycyclic compound

In the field of organic chemistry, a polycyclic compound is an organic compound featuring several closed rings of atoms, primarily carbon. These ring substructures include cycloalkanes, aromatics, and other ring types. They come in sizes of three atoms and upward, and in combinations of linkages that include tethering (such as in biaryls), fusing (edge-to-edge, such as in anthracene and steroids), links via a single atom (such as in spiro compounds), bridged compounds, and longifolene. Though poly- literally means "many", there is some latitude in determining how many rings are required to be considered polycyclic; many smaller rings are described by specific prefixes (e.g., bicyclic, tricyclic, tetracyclic, etc.), and so while it can refer to these, the title term is used with most specificity when these alternative names and prefixes are unavailable.

In general, the term polycyclic includes polycyclic aromatic compounds, including polycyclic aromatic hydrocarbons, as well as heterocyclic aromatic compounds with multiple rings (where heteroaromatic compounds are aromatic compounds that contain sulfur, nitrogen, oxygen, or another non-carbon atoms in their rings in addition to carbon).

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Terpene in the context of Cyclic compound

A cyclic compound (or ring compound) is a term for a compound in the field of chemistry in which one or more series of atoms in the compound is connected to form a ring. Rings may vary in size from three to many atoms, and include examples where all the atoms are carbon (i.e., are carbocycles), none of the atoms are carbon (inorganic cyclic compounds), or where both carbon and non-carbon atoms are present (heterocyclic compounds with rings containing both carbon and non-carbon). Depending on the ring size, the bond order of the individual links between ring atoms, and their arrangements within the rings, carbocyclic and heterocyclic compounds may be aromatic or non-aromatic; in the latter case, they may vary from being fully saturated to having varying numbers of multiple bonds between the ring atoms. Because of the tremendous diversity allowed, in combination, by the valences of common atoms and their ability to form rings, the number of possible cyclic structures, even of small size (e.g., < 17 total atoms) numbers in the many billions.

Adding to their complexity and number, closing of atoms into rings may lock particular atoms with distinct substitution (by functional groups) such that stereochemistry and chirality of the compound results, including some manifestations that are unique to rings (e.g., configurational isomers). As well, depending on ring size, the three-dimensional shapes of particular cyclic structures – typically rings of five atoms and larger – can vary and interconvert such that conformational isomerism is displayed. Indeed, the development of this important chemical concept arose historically in reference to cyclic compounds. Finally, cyclic compounds, because of the unique shapes, reactivities, properties, and bioactivities that they engender, are the majority of all molecules involved in the biochemistry, structure, and function of living organisms, and in man-made molecules such as drugs, pesticides, etc.

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Terpene in the context of Kappa-opioid receptor

The κ-opioid receptor or kappa opioid receptor, abbreviated KOR or KOP for its ligand ketazocine, is a G protein-coupled receptor that in humans is encoded by the OPRK1 gene. The KOR is coupled to the G protein Gi/G0 and is among related receptors that bind opioid-like compounds in the brain and are responsible for mediating the effects of these compounds. These include altering nociception, mood, reward system, and motor control.

KOR is one of the two opioid receptors that bind dynorphin opioid peptides as the primary endogenous ligands, the other being newly deorphanized GPR139 receptor. In addition, oxytocin was found to be a positive allosteric modulator of KOR, and a variety of natural alkaloids, terpenes and synthetic ligands bind to the receptor.

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Terpene in the context of Α-pinene

α-Pinene is an organic compound of the terpene class. It is one of the two isomers of pinene, the other being β-pinene. An alkene, it contains a strained four-membered ring. It is found in the oils of many species of coniferous trees, notably Pinus and Picea species. It is also found in the essential oil of rosemary (Rosmarinus officinalis) and Satureja myrtifolia (also known as Zoufa in some regions). Both enantiomers are known in nature; (1S,5S)- or (−)-α-pinene is more common in European pines, whereas the (1R,5R)- or (+)-α-isomer is more common in North America. The enantiomers' racemic mixture is present in some oils such as eucalyptus oil and orange peel oil.

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Terpene in the context of Monoterpene

Monoterpenes are a class of terpenes that consist of two isoprene units and have the molecular formula C10H16. Monoterpenes may be linear (acyclic) or contain rings (monocyclic and bicyclic). Modified terpenes, such as those containing oxygen functionality or missing a methyl group, are called monoterpenoids. Monoterpenes and monoterpenoids are diverse. They have relevance to the pharmaceutical, cosmetic, agricultural, and food industries.

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Terpene in the context of Sesquiterpenes

Sesquiterpenes are a class of terpenes that consist of three isoprene units and often have the molecular formula C15H24. Like monoterpenes, sesquiterpenes may be cyclic or contain rings, including many combinations. Biochemical modifications such as oxidation or rearrangement produce the related sesquiterpenoids. It is estimated (2006) that 3000 sesquiterpenes have been identified.

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