572-76-9

Basic information

• Product Name: nandinine
• Synonyms: nandinine;(13aS)-5,8,13,13a-Tetrahydro-10-methoxy-6H-benzo[g]-1,3-benzodioxolo[5,6-a]quinolizin-9-ol
• CAS NO: 572-76-9
• Molecular Formula: C19H19NO4
• Molecular Weight: 325.3585
• Mol File: 572-76-9.mol
• Article Data: 6

Chemical Properties

• Melting Point: 195-196°
• Boiling Point: 477.7°Cat760mmHg
• Flash Point: 242.7°C
• Appearance: /
• Density: 1.42g/cm³
• Vapor Pressure: 9.49E-10mmHg at 25°C
• Refractive Index: 1.699
• CAS DataBase Reference: nandinine(CAS DataBase Reference)
• NIST Chemistry Reference: nandinine(572-76-9)
• EPA Substance Registry System: nandinine(572-76-9)

Safety Data

• Hazardous Substances Data: 572-76-9(Hazardous Substances Data)

Usage

Description

Eijkman obtained an amorphous compound from the root bark of Nandina domestica L. to which this name was given. It was subsequently obtained crystal_x0002_line by Iwakawa who was also able to separate it into three well-defined phenolic substances, Nandinine, Domesticine and Isodomesticine (q.v.). This alkaloid may be crystallized from EtOH as colourless leaflets which develop a pink colour on exposure to air. With CH2N2 the base yields (+)-Canadine (q.v.). The solution in H2S04 is initially yellow, changing through green to blue.

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

• 17388-17-9 (+/-)-nandinine 
• 1485-00-3 5-(2-nitrovinyl)benzo[1,3]dioxole 
• 1429118-89-7 (S)-(2-(benzyloxy)-3-methoxy-6-((5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)methyl)phenyl)methanol 
• 1422431-44-4 2-(benzyloxy)-6-((7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)methyl)-3-methoxybenzyl acetate 
• 1422431-37-5 6-(2-(2-(benzo[d][1,3]dioxol-5-yl)ethylamino)-2-oxoethyl)-2-(benzyloxy)-3-methoxybenzyl acetate 
• 1422431-30-8 N-(2-(benzo[d][1,3]dioxol-5-yl)ethyl)-2-(3-(benzyloxy)-2-(hydroxymethyl)-4-methoxyphenyl)acetamide 
• 120-57-0 piperonal 
• 56201-87-7 8-hydroxy-7-methoxyisobenzofuranyltetrahydropyran-3-one 
• 1131-94-8 homoisovanillic acid 
• 19626-36-9 methyl 2-(3-bromo-4-methoxyphenyl)acetate 
• 34918-57-5 methyl 3-bromo-4-hydroxyphenylacetate 
• 14199-15-6 Methyl 4-hydroxyphenylacetate 
• 1422431-52-4 C₂₈H₂₉NO₆ 
• 1484-85-1 3,4-methylenedioxyphenylethylamine 

Relevant articles and documents

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.

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.

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.