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Names | |
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IUPAC name 3,10-Dimethoxy-8,8a-secoberbine-2,9-diol | |
Systematic IUPAC name (1S)-1-[(3-Hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol | |
Identifiers | |
3D model (JSmol) | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.006.920 |
KEGG | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C19H23NO4 | |
Molar mass | 329.396 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Reticuline is a chemical compound found in a variety of plants including Lindera aggregata , [1] Annona squamosa , [2] and Ocotea fasciculata (also known as Ocotea duckei). [3]
Reticuline is one of the alkaloids found in opium, and experiments in rodents suggest it possesses potent central nervous system depressing effects. [3] It is the precursor of morphine and many other alkaloids. It is also toxic to dopaminergic neurons causing a form of atypical parkinsonism known as Guadeloupean Parkinsonism. [4]
3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase uses S-adenosyl methionine and 3'-hydroxy-N-methyl-(S)-coclaurine to produce S-adenosylhomocysteine and (S)-reticuline.
Reticuline oxidase uses (S)-reticuline and O2 to produce (S)-scoulerine and H2O2.
Salutaridine synthase uses (R)-reticuline, NADPH, H+, and O2 to produce salutaridine, NADP+, and H2O. Salutaridine can then be transformed progressively to thebaine, oripavine, and morphine.
1,2-dehydroreticulinium reductase (NADPH) uses (R)-reticuline and NADP+ to produce 1,2-dehydroreticulinium, NADPH, and H+.
Thebaine (paramorphine), also known as codeine methyl enol ether, is an opiate alkaloid, its name coming from the Greek Θῆβαι, Thēbai (Thebes), an ancient city in Upper Egypt. A minor constituent of opium, thebaine is chemically similar to both morphine and codeine, but has stimulatory rather than depressant effects. At high doses, it causes convulsions similar to strychnine poisoning. The synthetic enantiomer (+)-thebaine does show analgesic effects apparently mediated through opioid receptors, unlike the inactive natural enantiomer (−)-thebaine. While thebaine is not used therapeutically, it is the main alkaloid extracted from Papaver bracteatum and can be converted industrially into a variety of compounds, including hydrocodone, hydromorphone, oxycodone, oxymorphone, nalbuphine, naloxone, naltrexone, buprenorphine, butorphanol and etorphine.
Annona squamosa is a small, well-branched tree or shrub from the family Annonaceae that bears edible fruits called sugar apples or sweetsops. It tolerates a tropical lowland climate better than its relatives Annona reticulata and Annona cherimola helping make it the most widely cultivated of these species. Annona squamosa is a small, semi-(or late) deciduous, much-branched shrub or small tree 3 to 8 metres tall similar to soursop. It is a native of tropical climate in the Americas and West Indies, and Spanish traders aboard the Manila galleons docking in the Philippines brought it to Asia.
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.
In enzymology, a hydroxymethylglutaryl-CoA reductase (NADPH) (EC 1.1.1.34) is an enzyme that catalyzes the chemical reaction
In enzymology, a ketol-acid reductoisomerase (EC 1.1.1.86) is an enzyme that catalyzes the chemical reaction
In enzymology, a 3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase is an enzyme that catalyzes the chemical reaction
In enzymology, a 1,2-dihydrovomilenine reductase (EC 1.3.1.73) is an enzyme that catalyzes the chemical reaction
In enzymology, a 7-deoxyloganin 7-hydroxylase (EC 1.14.13.74) is an enzyme that catalyzes the chemical reaction
In enzymology, a N-methylcoclaurine 3'-monooxygenase (EC 1.14.13.71) is an enzyme that catalyzes the chemical reaction
In enzymology, a salutaridine synthase (EC 1.14.21.4) is an enzyme that catalyzes the chemical reaction
Lindera aggregata is a plant species belonging to the genus Lindera.
Boldine is an alkaloid of the aporphine class that is characteristic of the boldo tree Peumus boldus Molina. It is the most abundant alkaloid found in boldo bark, though not in the widely consumed leaves.Italic text Boldine is also found in Lindera aggregata.
Monocyclic monoterpene ketone monooxygenase (EC 1.14.13.105, 1-hydroxy-2-oxolimonene 1,2-monooxygenase, dihydrocarvone 1,2-monooxygenase, MMKMO) is an enzyme with systematic name (-)-menthone,NADPH:oxygen oxidoreductase. This enzyme catalyses the following chemical reaction
Isoleucine N-monooxygenase (EC 1.14.13.117, CYP79D3, CYP79D4) is an enzyme with systematic name L-isoleucine,NADPH:oxygen oxidoreductase (N-hydroxylating). This enzyme catalyses the following chemical reaction
Valine N-monooxygenase (EC 1.14.13.118, CYP79D1, CYP79D2) is an enzyme with systematic name L-valine,NADPH:oxygen oxidoreductase (N-hydroxylating). This enzyme catalyses the following chemical reaction
Phenylalanine N-monooxygenase (EC 1.14.14.40, phenylalanine N-hydroxylase, CYP79A2) is an enzyme with systematic name L-phenylalanine,NADPH:oxygen oxidoreductase (N-hydroxylating). This enzyme catalyses the following chemical reaction
Tryptophan N-monooxygenase (EC 1.14.13.125, tryptophan N-hydroxylase, CYP79B1, CYP79B2, CYP79B3) is an enzyme with systematic name L-tryptophan,NADPH:oxygen oxidoreductase (N-hydroxylating). This enzyme catalyses the following chemical reaction
Beta-amyrin 11-oxidase (EC 1.14.13.134, CYP88D6) is an enzyme with systematic name beta-amyrin,NADPH:oxygen oxidoreductase (hydroxylating). This enzyme catalyses the following chemical reaction
Anonaine is a bioactive benzylisoquinoline alkaloid, present in members of the plant families Magnoliaceae and Annonaceae It is named after the plant it was first extracted from, Annona reticulata, which is commonly known as Anona.
Coclaurine is a nicotinic acetylcholine receptor antagonist which has been isolated from a variety of plant sources including Nelumbo nucifera, Sarcopetalum harveyanum, Ocotea duckei, and others. It belongs to the class of tetrahydroisoquinoline alkaloids. Dimerization of coclaurine leads to the biscoclaurine alkaloids such as cepharanthine.
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: CS1 maint: location missing publisher (link) CS1 maint: others (link) The dictionary definition of reticuline at Wiktionary