Dihydrochelerythrine

Names

[ Name ]:
Dihydrochelerythrine

[Synonym ]:
bocconoline
[1,3]Benzodioxolo[5,6-c]phenanthridine, 12,13-dihydro-1,2-dimethoxy-12-methyl-
Dihydrochelerythrine
(1,3)Benzodioxolo(5,6-c)phenanthridine, 12,13-dihydro-1,2-dimethoxy-12-methyl-
5,6-dihydrochelerythrine
12,13-dihydrochelerythrine
1,2-Dimethoxy-12-methyl-12,13-dihydro[1,3]benzodioxolo[5,6-c]phenanthridine

Biological Activity

[Description]:

Dihydrochelerythrine is a natural compound isolated from the leaves of Macleaya microcarpa; has antifungal activity.IC50 value:Target: in vitro: Dihydrochelerythrine showed the highest antifungal activity against B. cinerea Pers, with 98.32% mycelial growth inhibition at 50 μg/mL. Dihydrochelerythrine inhibited spore germination in vitro in a concentration-dependent manner [1]. Dihydrochelerythrine appeared to be less cytotoxic since the viability of cells exposed to 20 microM dihydrochelerythrine for 24h was reduced only to 53%. A dose-dependent induction of apoptosis and necrosis by chelerythrine and dihydrochelerythrine was confirmed by annexin V/propidium iodide dual staining flow cytometry [2]. Dihydrochelerythrine (4) exhibited strong activity against methicillin-resistant Staphylococcus aureus SK1 and moderate activity against Escherichia coli TISTR 780 with MIC values of 8 and 16 μg/mL, respectively [3].

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Fungal

Natural Products >> Alkaloid

Research Areas >> Infection

[References]

[1]. Feng G, et al. Inhibitory activity of dihydrosanguinarine and dihydrochelerythrine against phytopathogenic fungi. Nat Prod Res. 2011 Jul;25(11):1082-9.

[2]. Vrba J, et al. Chelerythrine and dihydrochelerythrine induce G1 phase arrest and bimodal cell death in human leukemia HL-60 cells. Toxicol In Vitro. 2008 Jun;22(4):1008-17.

[3]. Tantapakul C, et al. Antibacterial compounds from Zanthoxylum rhetsa. Arch Pharm Res. 2012 Jul;35(7):1139-42.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
565.9±50.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₁H₁₉NO₄

[ Molecular Weight ]:
349.380

[ Flash Point ]:
171.6±27.3 °C

[ Exact Mass ]:
349.131409

[ PSA ]:
40.16000

[ LogP ]:
4.56

[ Vapour Pressure ]:
0.0±1.5 mmHg at 25°C

[ Index of Refraction ]:
1.657

[ Storage condition ]:
2-8℃

Safety Information

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%