5,6-Dihydro-1,2-dimethoxy-6-methyl-4H-dibenzo[de,g]quinoline Chemical Properties

Boiling point:

493.0±45.0 °C(Predicted)

Density 

1.193±0.06 g/cm3(Predicted)

storage temp. 

Store at -20°C

solubility 

Soluble in DMSO

pka

4.04±0.20(Predicted)

form 

Solid

color 

Light yellow to yellow

InChI

InChI=1S/C19H19NO2/c1-20-9-8-13-11-16(21-2)19(22-3)18-14-7-5-4-6-12(14)10-15(20)17(13)18/h4-7,10-11H,8-9H2,1-3H3

InChIKey

JBGSWIBJAGBGOP-UHFFFAOYSA-N

SMILES

N1(C)C2=C3C(C(OC)=C(OC)C=C3CC1)=C1C=CC=CC1=C2

5,6-Dihydro-1,2-dimethoxy-6-methyl-4H-dibenzo[de,g]quinoline Usage And Synthesis

Uses

Dehydronuciferine is isolated from the leaves of Nelumbo nucifera Gaertn, a acetylcholinesterase (AChE) inhibitor with an IC50 of 25 μg/mL[1].

Definition

ChEBI: Dehydronuciferine is an isoquinoline alkaloid.

Synthesis

The preparation process for total alkaloid extracts from lotus leaves generally comprises the following steps: (1) Extraction: The solvent employed may be water or any alcohol, ketone, or ester solvent; a mixed solvent composed of these solvents in specific proportions; or acidic or alkaline solvents formulated by combining these solvents with acids or alkalis. The preferred extraction method involves adding 30?C90% ethanol to lotus leaf material, followed by reflux extraction for 2?C3 cycles, each lasting 1?C2 hours, with a solvent volume of 15?C30 times the material weight (L/kg). (2) Filtration: Includes methods such as centrifugation, vacuum filtration, ultrafiltration, and pressure filtration, with or without the use of any one or a combination of the following clarifying agents: alcohol precipitants, gelatin, kaolin, various resins, polyethylene glycol, polyethylene triol, chitosan, and commercial natural clarifying agents such as 101 Juice Clarifier or ZTC+1 Natural Clarifier. (3) Concentration: Includes thin-film evaporation, rotary evaporation, and decoction concentration under atmospheric or reduced pressure conditions. (4) Drying: Includes vacuum drying, spray drying, and freeze drying. The composition of active alkaloid constituents from lotus leaves is extracted and prepared from the dried leaves of Nelumbonum nectariniflorum Gaertn., containing multiple alkaloid active components. These alkaloids primarily include lotus leaf alkaloid, N-demethyl lotus leaf alkaloid, O-demethyl lotus leaf alkaloid, saponin alkaloid, lotus alkaloid, lotus leaf alkaloid, N-demethylamaphylline, 2-hydroxy-1-methoxyapomorphine, amaphylline, N-methylisohengzhouwuyaoine, N-methylhengzhouwuyaoine, dehydrohepenine, dehydrolotusine, and other derivatives based on their parent nucleus.

References

[1] Yang, et al. Synthesis and structure-activity relationship of nuciferine derivatives as potential acetylcholinesterase inhibitors. Medicinal Chemistry Research June 2014, Volume 23, Issue 6, pp 3178–3186

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