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dihydrosanguinarine

Names

[ CAS No. ]:
3606-45-9

[ Name ]:
dihydrosanguinarine

[Synonym ]:
(1,3)Benzodioxolo(5,6-c)-1,3-dioxolo(4,5-i)phenanthridine, 13,14-dihydro-13-methyl-
dihydrosanguinarine
13-Methyl-13,14-dihydro[1,3]benzodioxolo[5,6-c][1,3]dioxolo[4,5-i]phenanthridine
[1,3]Benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridine, 13,14-dihydro-13-methyl-
dihydroavicine
Dihydro Sanguinarine
3lle
Hydrosanguinarine

Biological Activity

[Description]:

Dihydrosanguinarine is a natural compound isolated from the leaves of Macleaya microcarpa; has antifungal and anticancer activity.IC50 value:Target:in vitro: Dihydrosanguinarine showed much less cytotoxicity than sanguinarine: at the highest concentration tested (20 microM) and 24h exposure, dihydrosanguinarine decreased viability only to 52% [1]. Dihydrosanguinarine showed the highest antifungal activity against B. cinerea Pers, with 95.16% mycelial growth inhibition at 50 μg/ml [2]. dihydrosanguinarine showed the most potent leishmanicidal activities (IC(50) value: 0.014 microg/ml, respectively) [4].in vivo: Repeated dosing of DHSG for 90 days at up to 500 ppm in the diet (i.e. approximately 58 mg/kg/day) showed no evidence of toxicity in contrast to results published in the literature [3].

[Related Catalog]:

Signaling Pathways >> Others >> Others
Natural Products >> Alkaloid
Research Areas >> Infection

[References]

[1]. Vrba J, et al. Cytotoxic activity of sanguinarine and dihydrosanguinarine in human promyelocytic leukemia HL-60 cells. Toxicol In Vitro. 2009 Jun;23(4):580-8.

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

[3]. Vrublova E, et al. The toxicity and pharmacokinetics of dihydrosanguinarine in rat: a pilot study. Food Chem Toxicol. 2008 Jul;46(7):2546-53.

[4]. Fuchino H, et al. In vitro leishmanicidal activity of benzophenanthridine alkaloids from Bocconia pearcei and related compounds. Chem Pharm Bull (Tokyo). 2010 Aug;58(8):1047-50.


[Related Small Molecules]

Captisol | Cyclosporin A | H2DCFDA | 0MPTP hydrochloride | GW4869 | Etomoxir | TD139 | Mitoquinone mesylate | GSK2795039 | JC-1 | BAPTA-AM | AP 20187 | Setanaxib (GKT137831) | D-Luciferin | Crotaline

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
566.9±29.0 °C at 760 mmHg

[ Molecular Formula ]:
C20H15NO4

[ Molecular Weight ]:
333.337

[ Flash Point ]:
176.8±21.5 °C

[ Exact Mass ]:
333.100098

[ PSA ]:
40.16000

[ LogP ]:
4.68

[ Vapour Pressure ]:
0.0±1.6 mmHg at 25°C

[ Index of Refraction ]:
1.720

[ Storage condition ]:
2-8℃

Precursor & DownStream

Precursor

DownStream

Related Compounds