Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar structure may also be termed alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen or sulfur. Rarer still, they may contain elements such as phosphorus, chlorine, and bromine.
L-Tyrosine or tyrosine or 4-hydroxyphenylalanine is one of the 20 standard amino acids that are used by cells to synthesize proteins. It is a conditionally essential amino acid with a polar side group. The word "tyrosine" is from the Greek tyrós, meaning cheese, as it was first discovered in 1846 by German chemist Justus von Liebig in the protein casein from cheese. It is called tyrosyl when referred to as a functional group or side chain. While tyrosine is generally classified as a hydrophobic amino acid, it is more hydrophilic than phenylalanine. It is encoded by the codons UAC and UAU in messenger RNA.
Eschscholzia californica, the California poppy, golden poppy, California sunlight or cup of gold, is a species of flowering plant in the family Papaveraceae, native to the United States and Mexico. It is cultivated as an ornamental plant flowering in summer, with showy cup-shaped flowers in brilliant shades of red, orange and yellow. It is also used as food or a garnish. It became the official state flower of California in 1903.
A natural product is a natural compound or substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural products can also be prepared by chemical synthesis and have played a central role in the development of the field of organic chemistry by providing challenging synthetic targets. The term natural product has also been extended for commercial purposes to refer to cosmetics, dietary supplements, and foods produced from natural sources without added artificial ingredients.
Phytochemistry is the study of phytochemicals, which are chemicals derived from plants. Phytochemists strive to describe the structures of the large number of secondary metabolites found in plants, the functions of these compounds in human and plant biology, and the biosynthesis of these compounds. Plants synthesize phytochemicals for many reasons, including to protect themselves against insect attacks and plant diseases. The compounds found in plants are of many kinds, but most can be grouped into four major biosynthetic classes: alkaloids, phenylpropanoids, polyketides, and terpenoids.
Noscapine, also known as narcotine, nectodon, nospen, anarcotine and (archaic) opiane, is a benzylisoquinoline alkaloid of the phthalideisoquinoline structural subgroup, which has been isolated from numerous species of the family Papaveraceae. It lacks effects associated with opioids such as sedation, euphoria, or analgesia (pain-relief) and lacks addictive potential. Noscapine is primarily used for its antitussive (cough-suppressing) effects.
Dihydrobenzophenanthridine oxidase is an enzyme. In the IUBMB Enzyme Nomenclature, dihydrobenzophenanthridine oxidase is EC 1.5.3.12.
β-arbutin, also known by its International Nomenclature of Cosmetic Ingredients (INCI) name, arbutin, is a glycosylated derivative of hydroquinone. β-Arbutin is naturally present in the leaves and bark of a variety of plants, notably the bearberry plant, Arctostaphylos uva-ursi. Utilized as a biosynthetic active ingredient in topical treatments for skin lightening, β-arbutin is aimed at addressing hyperpigmentation issues. Its mechanism of action involves inhibiting the activity of tyrosinase, an essential enzyme for melanin synthesis in the human skin, thereby leading to a reduction in hyperpigmentation. It is important to distinguish β-arbutin from its structurally similar stereoisomer, α-arbutin, which exhibits similar effects in clinical applications.
Scoulerine, also known as discretamine and aequaline, is a benzylisoquinoline alkaloid (BIA) that is derived directly from (S)-reticuline through the action of berberine bridge enzyme. It is a precursor of other BIAs, notably berberine, noscapine, (S)-tetrahydropalmatine, and (S)-stylopine, as well as the alkaloids protopine, and sanguinarine. It is found in many plants, including opium poppy, Croton flavens, and certain plants in the genus Erythrina.
Sparteine is a class 1a antiarrhythmic agent and sodium channel blocker. It is an alkaloid and can be extracted from scotch broom. It is the predominant alkaloid in Lupinus mutabilis, and is thought to chelate the bivalent metals calcium and magnesium. It is not FDA approved for human use as an antiarrhythmic agent, and it is not included in the Vaughan Williams classification of antiarrhythmic drugs.
(S)-Tetrahydroberberine oxidase is an enzyme that catalyzes the final transformation in the biosynthesis of berberine, a quaternary benzylisoquinoline alkaloid of the protoberberine structural subgroup. This reaction pathway catalyzes the four-electron oxidation of (S)-tetrahydroberberine in the presence of oxygen to produce berberine and hydrogen peroxide as products.
Substitution of the heterocycle isoquinoline at the C1 position by a benzyl group provides 1‑benzylisoquinoline, the most widely examined of the numerous benzylisoquinoline structural isomers. The 1-benzylisoquinoline moiety can be identified within numerous compounds of pharmaceutical interest, such as moxaverine; but most notably it is found within the structures of a wide variety of plant natural products, collectively referred to as benzylisoquinoline alkaloids. This class is exemplified in part by the following compounds: papaverine, noscapine, codeine, morphine, apomorphine, berberine, tubocurarine.
(S)-Canadine, also known as (S)-tetrahydroberberine and xanthopuccine, is a benzylisoquinoline alkaloid (BIA), of the protoberberine structural subgroup, and is present in many plants from the family Papaveraceae, such as Corydalis yanhusuo and C. turtschaninovii.
Castanospermine is an indolizidine alkaloid first isolated from the seeds of Castanospermum australe. It is a potent inhibitor of some glucosidase enzymes and has antiviral activity in vitro and in mouse models.
Berberis koreana, the Korean barberry, is deciduous shrub that can grow up to 5 feet (1.5 m) in height. The species is endemic to Korea. It is widely planted as an ornamental tree in North America, South America and Europe.
Californidine is an alkaloid with the molecular formula C20H20NO4+. It has been isolated from extracts of the California poppy (Eschscholzia californica), from which it gets its name, and from other plants of the genus Eschscholzia.
Chelidonine is an isolate of Papaveraceae with acetylcholinesterase and butyrylcholinesterase inhibitory activity.
Salutaridinol is a modified benzyltetrahydroisoquinoline alkaloid with the formula C19H23NO4. It is produced in the secondary metabolism of the opium poppy Papaver somniferum (Papaveraceae) as an intermediate in the biosynthetic pathway that generates morphine. As an isoquinoline alkaloid, it is fundamentally derived from tyrosine as part of the shikimate pathway of secondary metabolism. Salutaridinol is a product of the enzyme salutaridine: NADPH 7-oxidoreductase and the substrate for the enzyme salutaridinol 7-O-acetyltransferase, which are two of the four enzymes in the morphine biosynthesis pathway that generates morphine from (R)-reticuline. Salutaridinol's unique position adjacent to two of the four enzymes in the morphine biosynthesis pathway gives it an important role in enzymatic, genetic, and synthetic biology studies of morphine biosynthesis. Salutaridinol levels are indicative of the flux through the morphine biosynthesis pathway and the efficacy of both salutaridine: NADPH 7-oxidoreductase and salutaridinol 7-O-acetyltransferase.
Berberine bridge enzyme-like form a subgroup of the superfamily of FAD-linked oxidases, structurally characterized by a typical fold observed initially for vanillyl-alcohol oxidase (VAO). This proteins are part of a multigene family (PF08031) that can be found in plants, fungi and bacteria.
Isoquinoline alkaloids are natural products of the group of alkaloids, which are chemically derived from isoquinoline. They form the largest group among the alkaloids.
