Names | |
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IUPAC name 2-Methoxy-2′H-[1,3]dioxolo[4′,5′:9,10]berbin-3-ol | |
Systematic IUPAC name (6aS)-9-Methoxy-6,6a,11,14-tetrahydro-2H,12H-[1,3]dioxolo[4,5-h]isoquinolino[2,1-b]isoquinolin-8-ol | |
Other names (S)-Cheilanthifoline | |
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3D model (JSmol) |
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ChEBI |
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PubChem CID | |
CompTox Dashboard (EPA) |
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Properties | |
C19H19NO4 | |
Molar mass | 325.364 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
(S)-Cheilanthifoline is a benzylisoquinoline alkaloid (BIA) which has been isolated from Corydalis dubia [1] and Argemone mexicana .[ citation needed ] (S)-Cheilanthifoline is metabolically derived from (S)-reticuline, a pivotal intermediate in the biosynthesis of numerous BIAs. (S)-Cheilanthifoline is the immediate precursor of the BIA (S)-stylopine ((S)-stylopine synthase/CYP719A20), which is the precursor for the alkaloids protopine and sanguinarine. [2]
Noscapine is a benzylisoquinoline alkaloid, of the phthalideisoquinoline structural subgroup, which has been isolated from numerous species of the family Papaveraceae. It lacks significant hypnotic, euphoric, or analgesic effects affording it with very low addictive potential. This agent is primarily used for its antitussive (cough-suppressing) effects.
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.
In enzymology, a (S)-stylopine synthase (EC 1.14.21.1) is an enzyme that catalyzes the chemical reaction
The enzyme (S)-norcoclaurine synthase (EC 4.2.1.78) catalyzes the chemical reaction
Corydalis ambigua is a tuberous early flowering east Asian flowering plant species in the poppy family Papaveraceae. Its exact native range is obscure due to taxonomic confusion. It is one of the sources of the drug tetrahydropalmatine.
Pukateine is an alkaloid found in the bark of the New Zealand tree Laurelia novae-zelandiae ("Pukatea"), as well as some South American plants. An extract from pukatea is used in traditional Māori herbal medicine as an analgesic.
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.
Tetrandrine, a bis-benzylisoquinoline alkaloid, is a calcium channel blocker. It is isolated from the plant Stephania tetrandra, and other Chinese and Japanese herbs.
(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.
Nantenine is an alkaloid found in the plant Nandina domestica as well as some Corydalis species. It is an antagonist of both the α1-adrenergic receptor and the serotonin 5-HT2A receptor, and blocks both the behavioral and physiological effects of MDMA in animals.
Protopine is an alkaloid occurring in opium poppy, Corydalis tubers and other plants of the family papaveraceae, like Fumaria officinalis. Protopine is metabolically derived from the benzylisoquinoline alkaloid (S)-Reticuline through a progressive series of five enzymatic transformations: 1) berberine bridge enzyme to (S)-Scoulerine; 2) (S)-cheilanthifoline synthase/CYP719A25 to (S)-Cheilanthifoline; 3) (S)-stylopine synthase/CYP719A20 to (S)-Stylopine; 4) (S)-tetrahydroprotoberberine N-methyltransferase to (S)-cis-N-Methylstylopine; and ultimately, 5) N-methylstylopine hydroxylase to protopine.
Reticuline is a chemical compound found in a variety of plants including Lindera aggregata, Annona squamosa, and Ocotea fasciculata. It is based on the benzylisoquinoline structure.
Sibiricine is a bioactive isoquinoline alkaloid isolated from Corydalis crispa (Fumariaceae), which is a Bhutanese medicinal plant from the Himalayas.
Tetrahydrocoptisine is an alkaloid isolated from Corydalis impatiens.
Corydaline is an acetylcholinesterase inhibitor isolated from Corydalis yanhusuo.
Chelidonine is an isolate of Papaveraceae with acetylcholinesterase and butyrylcholinesterase inhibitory activity.
(S)-Magnoflorine is a quaternary benzylisoquinoline alkaloid (BIA) of the aporphine structural subgroup which has been isolated from various species of the family Menispermaceae, such as Pachygone ovata,Sinomenium acutum, and Cissampelos pareira.
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.
Corydalis Alkaloids are categorized as natural products of the isoquinoline alkaloid type.