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Quassin

Names

[ CAS No. ]:
76-78-8

[ Name ]:
Quassin

[Synonym ]:
Einecs 200-985-9
Picrasa-2,12-diene-1,11,16-trione, 2,12-dimethoxy-
2,12-Dimethoxypicrasa-2,12-diene-1,11,16-trione
Quassin,mixture of isomers w/Neoquassin and Isoquassin
11,16-trione,2,12-dimethoxy-picrasa-12-diene-1
Picrasa-2,12-diene-1,11,16-trione,2,12-dimethoxy
Nigakilactone D
Quassin
(3aR,6aR,7aS,8S,11aS,11bS,11cS)-2,10-Dimethoxy-3,8,11a,11c-tetramethyl-3a,6a,7,7a,8,11a,11b,11c-octahydrodibenzo[de,g]chromene-1,5,11(4H)-trione
3ab,6ab,7,7aa,8,11a,11ba,11c-Octahydro-2,10-dimethoxy-3,8a,11ab,11cb-tetramethylphenanthro[10,1-bc]pyran-1,5,11(4H)-trione

Biological Activity

[Description]:

Quassin (Nigakilactone D) is a bioactive triterpenoid from stem bark extract of Quassia amara. Quassin inhibits P. falciparum with an IC50 of 0.15 μM. Quassin possesses reversible antifertility, anti-estrogenic and anti-plasmodial activity[1][2].

[Related Catalog]:

Research Areas >> Endocrinology
Research Areas >> Infection

[Target]

IC50: 0.15 μM (P. falciparum)[2]


[In Vitro]

Quassin (Compound 1; 5-25 ng/mL) inhibits both the basal and luteinizing hormone-stimulated testosterone secretion of rat Leydig cells in a dose-dependent fashion[3].

[In Vivo]

Quassin (0.1-2.0 mg/kg; oral administration; daily; for 60 days; females albino rats) treatment shows a significant decrease in the weight of the ovary and uterus. And also shows a significant decrease in serum estrogen levels in quassin treated rats. The Quassin treated rats has a significantly decreased mean litter number and weight. Quassin does not adversely affect the weight of the kidney, heart, liver and the body of the rats[1]. Animal Model: 35 females albino rats (150-170 g)[1] Dosage: 0.1 mg/kg, 1.0 mg/kg and 2.0 mg/kg Administration: Oral administration; daily; for 60 days Result: There was a significant decrease in the weight of the ovary and uterus in all the groups relative to the control. There was also a significant decrease in serum estrogen levels in quassin treated rats.

[References]

[1]. Raji Y, et al. Reproductive activities of female albino rats treated with quassin, a bioactive triterpenoid from stem bark extract of Quassia amara. Niger J Physiol Sci. 2010 Nov 24;25(2):95-102.

[2]. Mishra K, et al. Plasmodium falciparum: in vitro interaction of quassin and neo-quassin with artesunate, a hemisuccinate derivative of artemisinin. Exp Parasitol. 2010 Apr;124(4):421-7.

[3]. Njar VC, et al. Antifertility activity of Quassia amara: quassin inhibits the steroidogenesis in rat Leydig cells in vitro. Planta Med. 1995 Apr;61(2):180-2.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
586.3±50.0 °C at 760 mmHg

[ Melting Point ]:
200 - 222ºC

[ Molecular Formula ]:
C22H28O6

[ Molecular Weight ]:
388.454

[ Flash Point ]:
255.4±30.2 °C

[ Exact Mass ]:
388.188599

[ PSA ]:
78.90000

[ LogP ]:
2.22

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

[ Index of Refraction ]:
1.553

[ Storage condition ]:
2-8℃

Safety Information

[ Hazard Codes ]:
Xi

Precursor & DownStream

Precursor

DownStream

Related Compounds