The benzylisoquinoline alkaloids are natural products that can be classified as isoquinoline alkaloids and are derived from benzylisoquinoline. They also include the benzyl(tetrahydro)isoquinoline alkaloids.
The benzylisoquinoline alkaloids are natural products that can be classified as isoquinoline alkaloids and are derived from benzylisoquinoline. They also include the benzyl(tetrahydro)isoquinoline alkaloids.
Benzylisoquinoline alkaloids are found in several plant families, including the poppy family (Papaveraceae), the annonaceae family, and the laurel family. [1] Well-known representatives are primarily found in poppy plants, specifically those from which opium is derived, as well as in actaea. [2] For instance, reticuline has been isolated from Annona reticulata. [3]
Over 2500 biologically active derivatives are known from the benzylisoquinoline alkaloids. [4] Based on their structure, the compounds can be divided into numerous subgroups: the aporphines, the phthalideisoquinoline alkaloids, the morphinans, the protoberberine alkaloids, and the pavins. [5]
Among the known individual substances in this group are papaverine. Additional examples of compounds in this group are the benzyltetrahydroisoquinoline alkaloids reticuline and laudanosine. [1]
Papaverine has vasodilator and muscle relaxant properties. [3] Laudanosine acts as a tetanic poison. [1]
The biosynthesis of benzylisoquinoline alkaloids has been intensively studied. It begins with the amino acid tyrosine, which is converted to dopamine by hydroxylation and decarboxylation and to 4-hydroxyphenylacetaldehyde by oxidative deamination, respectively. These two compounds are converted into dopamine by enzyme Norcoclaurine synthase catalyzed condensation reaction to form the benzylisoquinoline backbone. [6]
The benzylisoquinoline from this reaction may have different substituents, [6] reticuline is an important intermediate. [5]
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.
Papaver somniferum, commonly known as the opium poppy or breadseed poppy, is a species of flowering plant in the family Papaveraceae. It is the species of plant from which both opium and poppy seeds are derived and is also a valuable ornamental plant grown in gardens. Its native range was east of the Mediterranean Sea, but has since been obscured and vastly expanded by introduction and cultivation from ancient times to the present day, being naturalized across much of Europe and Asia.
Isoquinoline is an individual chemical specimen - a heterocyclic aromatic organic compound - as well as the name of a family of many thousands of natural plant alkaloids, any one of which might be referred to as "an isoquinoline". It is a structural isomer of quinoline. Isoquinoline and quinoline are benzopyridines, which are composed of a benzene ring fused to a pyridine ring. In a broader sense, the term isoquinoline is used to make reference to isoquinoline derivatives. 1-Benzylisoquinoline is the structural backbone in many naturally occurring alkaloids such as papaverine. The isoquinoline ring in these natural compound derives from the aromatic amino acid tyrosine.
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.
Sanguinarine is a polycyclic quaternary alkaloid. It is extracted from some plants, including the bloodroot plant, from whose scientific name, Sanguinaria canadensis, its name is derived; the Mexican prickly poppy ; Chelidonium majus; and Macleaya cordata.
Berberine is a quaternary ammonium salt from the protoberberine group of benzylisoquinoline alkaloids, occurring naturally as a secondary metabolite in some plants including species of Berberis, from which its name is derived.
The enzyme (S)-norcoclaurine synthase (EC 4.2.1.78) catalyzes the chemical reaction
Higenamine (norcoclaurine) is a chemical compound found in a variety of plants including Nandina domestica (fruit), Aconitum carmichaelii (root), Asarum heterotropioides, Galium divaricatum, Annona squamosa, and Nelumbo nucifera.
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.
Steroidal alkaloids have the basic steroidal skeleton with nitrogen-based functional groups attached to the skeleton. More specifically, they are distinguished by their tetracyclic cyclopentanoperhydrophenanthrene skeleton that marks their close relationship with sterols. They fall in two major categories: Solanum alkaloids and Veratrum alkaloids. A Steroidal alkaloid has also been found in Chonemorpha fragrans, 'chonemorphine' was used to treat intestinal infections in Wistar rats..
Chelidonine is an isolate of Papaveraceae with acetylcholinesterase and butyrylcholinesterase inhibitory activity.
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.
Aporphine alkaloids are naturally occurring chemical compounds from the group of alkaloids. After the benzylisoquinoline alkaloids they are the second largest group of isoquinoline alkaloids.
Isoquinoline alkaloids are natural products of the group of alkaloids, which are chemically derived from isoquinoline. They form the largest group among the alkaloids.
Bisbenzylisoquinoline alkaloids are natural products found primarily in the plant families of the barberry family, the Menispermaceae, the Monimiaceae, and the buttercup family.
Indolizidine alkaloids are natural products from various alkaloid groups whose structure can be derived from indolizidine.
Corydalis Alkaloids are categorized as natural products of the isoquinoline alkaloid type.
Diterpene alkaloids are natural products of the terpene alkaloid type.
The pyrrolidine alkaloids are natural products chemically derived from pyrrolidine.