3968-19-2
3968-19-2
Chemical Structure
(R)-Reticuline
- CAS No.: 3968-19-2
- Formula:C19H23NO4
- Molecular Weight:329.39
IUPAC Name: (R)-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol
InChIKey: BHLYRWXGMIUIHG-OAHLLOKOSA-N
SMILES: OC1=CC2=C(C=C1OC)CCN(C)[C@@H]2CC3=CC=C(OC)C(O)=C3
Biological Activity: (R)-Reticuline is a key intermediate and precursor in the biosynthetic pathway of morphinan alkaloids. (R)-Reticuline plays a central role in the metabolism of opium poppy (Papaver somniferum). (R)-Reticuline can either undergo O-methylation catalyzed by PSOMT1, or be converted to (+)-Salutaridine via regioselective and stereoselective oxidative coupling under the action of salutaridine synthase (CYP719B1). (R)-Reticuline serves as a direct precursor for the synthesis of important alkaloids such as morphine, codeine and thebaine[1][2][3].
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(R)-Reticuline | (R)-Reticuline is a key intermediate and precursor in the biosynthetic pathway of morphinan alkaloids. (R)-Reticuline plays a central role in the metabolism of opium poppy (Papaver somniferum). (R)-Reticuline can either undergo O-methylation catalyzed by PSOMT1, or be converted to (+)-Salutaridine via regioselective and stereoselective oxidative coupling under the action of salutaridine synthase (CYP719B1). (R)-Reticuline serves as a direct precursor for the synthesis of important alkaloids such as morphine, codeine and thebaine. | |||||||||||||||||||||
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(±)-Reticuline | 99.79% | (±)-Reticuline (compound 3f) is a natural product obtained from Peumus boldus Molina. (±)-Reticuline can be used to synthesize S-Reticuline. | ||||||||||||||||||||
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(±)-N-Methylcoclaurine | 98.27% | (±)-N-Methylcoclaurine is a selective α2-adrenoceptor antagonist. | ||||||||||||||||||||
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Reticuline | 98.89% | Reticuline shows anti-inflammatory effects through JAK2/STAT3 and NF-κB signaling pathways. Reticuline inhibits mRNA expressions of TNF-α, and IL-6 and reduces the phosphorylation levels of JAK2 and STAT3. Reticuline exhibits cardiovascular effects. | ||||||||||||||||||||
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Armepavine | 99.19% | Armepavine, found in Nelumbo nucifera, is an orally active NF-κB inhibitor. Armepavine attenuates expression of p-p65, α-SMA, p-JNK1/2, p-ERK1/2, p-p38α stimulated by TNF-α and LPS. Armepavine suppresses NF-κB nuclear translocation, IκBα phosphorylation, and collagen deposition. Armepavine can be used for the research of hepatic fibrosis and leukemia. | ||||||||||||||||||||
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(+)-Armepavine | (+)-Armepavine is a bioactive compound with pharmacological activity. As an alkaloid, (+)-Armepavine belongs to the tetrahydrobenzylisoquinoline class of compounds and may play a role in inhibiting certain diseases. The chemical structure and properties of (+)-Armepavine make it an important chemical classification in phytochemistry. | |||||||||||||||||||||
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(±)-Armepavine hydrochloride | (±)-Armepavine hydrochloride is a compound that has demonstrated immunosuppressive effects on T lymphocytes and in lupus nephritic mice. | |||||||||||||||||||||
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(-)-N-methylcoclaurine | (-)-N-methylcoclaurine ((-)-(1R)-N-methylcoclaurine) is a benzylisoquinoline alkaloid and melanogenesis inhibitor with an IC50 of 6.5 μM that can be found in the flower buds of Nelumbo nucifera. (-)-N-methylcoclaurine inhibits theophylline-stimulated melanogenesis in melanoma cells. (-)-N-methylcoclaurine can be used for the research of skin hyperpigmentation disorders. | |||||||||||||||||||||
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N-Methyl-3'-hydroxycoclaurine hydrochloride | N-Methyl-3'-hydroxycoclaurine (3'-Hydroxy-N-methylcoclaurine) hydrochloride is a Coclaurine (HY-N3610) impurity. | |||||||||||||||||||||
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(+)-Laudanidine | (+)-Laudanidine ((S)-Tritopin) is a benzyltetrahydroisoquinoline alkaloid found in Stephania species. |
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N-Methylcoclaurine | N-Methylcoclaurine is an orally active anticancer agent and PDI inhibitor with an IC50 of 3.91 μM for the bovine-derived target. N-Methylcoclaurine selectively binds to κ opioid receptors with a Ki value of 0.9 μM. N-Methylcoclaurine inhibits tumor cell proliferation, migration, and invasion, and suppresses tumor growth in vivo. N-Methylcoclaurine inhibits iNOS expression and scavenges NO and DPPH radicals. N-Methylcoclaurine is a substrate of CyNMCH and an important branch intermediate in the biosynthesis of benzylisoquinoline alkaloids. N-Methylcoclaurine can be used in research related to hepatocellular carcinoma and neurological diseases. | |||||||||||||||||||||
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References
- [1]. Ounaroon A, et al. (R, S)‐Reticuline 7‐O‐methyltransferase and (R, S)‐norcoclaurine 6‐O‐methyltransferase of Papaver somniferum–cDNA cloning and characterization of methyl transfer enzymes of alkaloid biosynthesis in opium poppy[J]. The plant journal, 2003, 36(6): 808-819.
- [2]. Gerardy R, et al. Formation of salutaridine from (R)-reticuline by a membrane-bound cytochrome P-450 enzyme from Papaver somniferum[J]. Phytochemistry, 1992, 32(1): 79-86.
- [3]. Cigan E, et al. Concise synthesis of (R)-reticuline and (+)-salutaridine by combining early-stage organic synthesis and late-stage biocatalysis. Chem Sci. 2023;14(36):9863-9871. Published 2023 Aug 24. [Content Brief]
