572-76-9

Usage

Uses

Used in Pharmaceutical Industry:
Nandinine is used as a pharmaceutical compound for its unique chemical properties and potential applications in drug development. Nandinine's ability to change color in different solutions and its interaction with other substances make it a promising candidate for further research and development in the pharmaceutical field.
Used in Chemical Research:
Nandinine is used as a research compound for studying its chemical properties, interactions with other substances, and potential applications in various industries. Its unique characteristics, such as color changes in different solutions, make it an interesting subject for chemical research and analysis.
Used in Plant Biology and Ethnobotany:
Nandinine is used as a subject of study in plant biology and ethnobotany, as it is derived from the Nandina domestica L. plant. Researchers can explore the plant's traditional uses, its role in the ecosystem, and its potential for future applications in various fields.

References

Eijkman., Rec. trav. Chim., 3, 197 (1884)Iwakawa.,Mitt. Med. Ges. Tokyo, 24, 15 (1910)Kitasato., J. Pharm. Soc., Japan, No. 522, 1 (1925)Kitasato., Acta Phytochem., 3, 177 (1927)

InChI:InChI=1/C19H19NO4/c1-22-16-3-2-11-6-15-13-8-18-17(23-10-24-18)7-12(13)4-5-20(15)9-14(11)19(16)21/h2-3,7-8,15,21H,4-6,9-10H2,1H3

Upstream product

• 15401-69-1 berberrubine chloride 
• 1380506-36-4 C₁₉H₁₉NO₇S 
• 633-65-8 berberine chloride 
• 17388-17-9 (+/-)-nandinine 
• 1429118-98-8 14-(R)-9-benzyloxy-2,3-methylenedioxy-10-methoxytetrahyrdooxyprotoberberine 
• 1484-85-1 3,4-methylenedioxyphenylethylamine 
• 14199-15-6 Methyl 4-hydroxyphenylacetate 
• 34918-57-5 methyl 3-bromo-4-hydroxyphenylacetate 
• 19626-36-9 methyl 2-(3-bromo-4-methoxyphenyl)acetate 
• 605-34-5 (S)-scoulerine 
• 485-19-8 (+)-(S)-reticuline 
• 1380506-34-2 C₂₅H₂₉NO₉ 
• 1422431-64-8 14-(S)-9-benzyloxy-2,3-methylenedioxy-10-methoxytetrahyrdooxyprotoberberine 
• 1485-00-3 5-(2-nitrovinyl)benzo[1,3]dioxole 

Relevant academic research and scientific papers

Significantly different effects of tetrahydroberberrubine enantiomers on dopamine D1/D2 receptors revealed by experimental study and integrated in silico simulation

Tetrahydroberberrubine (TU), an active tetrahydroprotoberberines (THPBs), is gaining increasing popularity as a potential candidate for treatment of anxiety and depression. One of its two enantiomers, l-TU, has been reported to be an antagonist of both D1 and D2 receptors, but the functional activity of the other enantiomer, d-TU, is still unknown. In this study, experiments were combined with in silico molecular simulations to (1) confirm and discover the functional activities of l-TU and d-TU, and (2) systematically evaluate the molecular mechanisms beyond the experimental observations. l-TU proved to be an antagonist of both D1 and D2 receptors (IC50 = 385?nM and 985?nM, respectively), while d-TU shows no affinity against either D1 or D2 receptor, based on the cAMP assay (D1 receptor) and calcium flux assay (D2 receptor). Results from both flexible-ligand docking studies and molecular dynamic (MD) simulations provided insights at the atomic level. The l-TU-bound structures predicted by MD (1) undergo an outward rotation of the extracellular helical bundles; (2) have an enlarged orthosteric binding pocket; and (3) have a central toggle switch that is prevented from rotating freely. These features are unique to the l-TU enantiomer and provide an explanation for its antagonistic behavior toward both D1 and D2 receptors. The present study provides new sight on the structural and functional relationships of l-TU and d-TU binding to dopamine receptors, and provides guidance to the rational design of novel molecules targeting these two dopamine receptors in the future.

Asymmetric total synthesis and identification of tetrahydroprotoberberine derivatives as new antipsychotic agents possessing a dopamine D1, D2 and serotonin 5-HT1A multi-action profile

An effective and rapid method for the microwave-assisted preparation of the key intermediate for the total synthesis of tetrahydroprotoberberines (THPBs) including l-stepholidine (l-SPD) was developed. Thirty-one THPB derivatives with diverse substituents on A and D ring were synthesized, and their binding affinity to dopamine D1, D2 and serotonin 5-HT 1A and 5-HT2A receptors were determined. Compounds 18k and 18m were identified as partial agonists at the D1 receptor with Ki values of 50 and 6.3 nM, while both compounds act as D2 receptor antagonists (Ki = 305 and 145 nM, respectively) and 5-HT1A receptor full agonists (Ki = 149 and 908 nM, respectively). These two THPBs compounds exerted antipsychotic actions in animal models. Further electrophysiological studies employing single-unit recording in intact animals demonstrated that 18k-excited dopaminergic (DA) neurons are associated with its 5-HT1A receptor agonistic activity. These results suggest that these two compounds targeted to multiple neurotransmitter receptors may present novel lead drugs with new pharmacological profiles for the treatment of schizophrenia.

Chemical and microbial semi-synthesis of tetrahydroprotoberberines as inhibitors on tissue factor procoagulant activity

To discover new inhibitors on tissue factor procoagulant activity, 21 tetrahydroprotoberberines were screened on the model of human THP-1 cells stimulated by lipopolysaccharide. Among these tetrahydroprotoberberines, several unique compounds were synthesized through microbial transformation: compound 6 (l-corydalmine) was obtained through regio-selective demethylation by Streptomyces griseus ATCC 13273, whereas compounds 4a, 4b, 5h, and 5i were microbial glycosylation products by Gliocladium deliquescens NRRL1086. The bioassay results showed that compounds 3 (tetrahydroberberine), 10 (tetrahydroberberrubine), and 5f (cinnamyl ester of 5) and 5i (glycosidic product of 5), exhibited the most potential effects, with IC50 values of 8.35, 6.75, 3.75, and 8.79 nM, respectively. The preliminary structure and activity relationship analysis revealed that the 2,3-methylenedioxy group of the A ring was essential for the strong inhibitory effects, and the R configuration of the chiral center C-14 showed higher activity than S-form products. The formation of fatty acid or aromatic acid esters of compound 5, except the cinnamyl esters, would weaken its effects. It is also interesting to note that the glycosylation of tetrahydroprotoberberines will maintain and even enhance the inhibitory effects. Because of the importance of glycochemistry in new drug discovery and development, this deserves further exploration and may provide some guide on the semi-synthesis of tetrahydroprotoberberines as tissue factor pathway inhibitors. Our findings also provide some potential leading compounds for tissue factor-related diseases, such as cancer and cardiovascular diseases.

Unique biocatalytic resolution of racemic tetrahydroberberrubine via kinetic glycosylation and enantio-selective sulfation

In this communication, we document a facile kinetic glycosylation resolution of racemic tetrahydroberberrubine. We also demonstrate that the enantiomeric excess of the resolved products is increased via a second resolution of the minor product of the first glycosylation resolution. This provides a rare example of tandem kinetic resolution of racemates.

Characterization of two methylenedioxy bridge-forming cytochrome P450-dependent enzymes of alkaloid formation in the Mexican prickly poppy Argemone mexicana

Formation of the methylenedioxy bridge is an integral step in the biosynthesis of benzo[c]phenanthridine and protoberberine alkaloids in the Papaveraceae family of plants. This reaction in plants is catalyzed by cytochrome P450-dependent enzymes. Two cDNAs that encode cytochrome P450 enzymes belonging to the CYP719 family were identified upon interrogation of an EST dataset prepared from 2-month-old plantlets of the Mexican prickly poppy Argemone mexicana that accumulated the benzo[c]phenanthridine alkaloid sanguinarine and the protoberberine alkaloid berberine. CYP719A13 and CYP719A14 are 58% identical to each other and 77% and 60% identical, respectively, to stylopine synthase CYP719A2 of benzo[c]phenanthridine biosynthesis in Eschscholzia californica. Functional heterologous expression of CYP719A14 and CYP719A13 in Spodoptera frugiperda Sf9 cells produced recombinant enzymes that catalyzed the formation of the methylenedioxy bridge of (S)-cheilanthifoline from (S)-scoulerine and of (S)-stylopine from (S)-cheilanthifoline, respectively. Twenty-seven potential substrates were tested with each enzyme. Whereas CYP719A14 transformed only (S)-scoulerine to (S)-cheilanthifoline (Km 1.9 ± 0.3; kcat/Km 1.7), CYP719A13 converted (S)-tetrahydrocolumbamine to (S)-canadine (Km 2.7 ± 1.3; kcat/Km 12.8), (S)-cheilanthifoline to (S)-stylopine (Km 5.2 ± 3.0; kcat/Km 2.6) and (S)-scoulerine to (S)-nandinine (Km 8.1 ± 1.9; k cat/Km 0.7). These results indicate that although CYP719A14 participates in only sanguinarine biosynthesis, CYP719A13 can be involved in both sanguinarine and berberine formation in A. mexicana.

CORYDALINE DERIVATIVES USEFUL FOR REDUCING LIPID LEVELS

The present technology relates to compounds of Formulas (V) and (VI) and methods of making and using such compounds. Methods of use include prevention and treatment of hyperlipidemia, hypercholesterolemia, hypertriglyceridemia, hepatic steatosis, and metabolic syndrome. Compounds disclosed herein also lower total cholesterol, LDL- cholesterol, and triglycerides and increase hepatic LDL receptor expression, inhibit PCSK9 expression, and activate AMP-activated potein kinase.