Limonin

Names

[ Name ]:
Limonin

[Synonym ]:
Limonoic acid di-δ-lactone
8-(3-Furyl)decahydro-2,2,4a,8a-tetramethyl-11H,13H-oxireno[d]pyrano[4',3':3,3a]isobenzofuro[5,4-f][2]benzopyran-4,6,13(2H,5aH)-trione
(4aS,6aR,8aR,8bR,9aS,12S,12aS,14aR,14bR)-12-(Furan-3-yl)-6,6,8a,12a-tetramethyldecahydrooxireno[2,3-d]pyrano[4',3':3,3a]isobenzofuro[5,4-f]isochromene-3,8,10(1H,6H,8aH)-trione
Limonoic acid 3,19:16,17 dilactone
1H,3H-Oxireno[c]pyrano[4'',3'':2',3']furo[3',4':5,6]naphtho[1,2-d]pyran-3,8,10(6H,9aH)-trione, 12-(3-furanyl)decahydro-6,6,8a,12a-tetramethyl-, (4aS,6aR,8aR,8bR,9aS,12S,12aS,14aR,14bR)-
LiMone
DICTAMNOLACTONE
CITROLIMONIN
Limonin
Evodine
Limonoic Acid Di-d-lactone
LIMONINE
(4aS,6aR,8aR,8bR,9aS,12R,12aS,14aR,14bR)-12-(furan-3-yl)-6,6,8a,12a-tetramethyldecahydro-3H-oxireno[d]pyrano[4',3':3,3a][2]benzofuro[5,4-f]isochromene-3,8,10(6H,9aH)-trione
EVODIN
OBACULACTONE
(4aS,6aR,8aR,8bR,9aS,12S,12aS,14aR,14bR)-12-(3-Furyl)-6,6,8a,12a-tetramethyldecahydro-3H-oxireno[d]pyrano[4',3':3,3a][2]benzofuro[5,4-f]isochromene-3,8,10(6H,9aH)-trione

Biological Activity

[Description]:

Limonin is a triterpenoid enriched in citrus fruits, which has antivirus and antitumor ability.IC50 Value: Target: HIV; anticancerLimonin is a triterpenoid aglycone that is a bitter principle of citrus fruits. Limonin is chemically induced carcinogenesis inhibitor and HIV-1 replication inhibitor. Limonin has anti-proliferative, proapoptotic activity on several cancer cell lines and inhibits azoxymethane-induced colon cancer in rats. Limonin also inhibits HIV-1 replication in culturedf monocytes, macrophages, and mononuclear cells, perhaps by inhibition of HIV-1 protease activity.

[Related Catalog]:

Signaling Pathways >> Anti-infection >> HIV

Research Areas >> Infection

Natural Products >> Terpenoids and Glycosides

[References]

[1]. Han YL, Yu HL, Li D, et al. Inhibitory effects of limonin on six human cytochrome P450 enzymes and P-glycoprotein in vitro. Toxicol In Vitro. 2011 Dec;25(8):1828-33.

[2]. Kotamballi N. Chidambara Murthy, Jayaprakasha, Vinod Kumar, et al. Citrus Limonin and Its Glucoside Inhibit Colon Adenocarcinoma Cell Proliferation through Apoptosis. J. Agric. Food Chem., 2011, 59 (6):2314-2323.

[3]. Mahmoud Zaki El-Readi, Dalia Hamdana, Nawal Farrag, et al. Inhibition of P-glycoprotein activity by limonin and other secondary metabolites from Citrus species in human colon and leukaemia cell lines. European Journal of Pharmacology. 2010,626 (2-3): 139-145.

[4]. Battinelli L, Mengoni F, Lichtner M, et al. Effect of limonin and nomilin on HIV-1 replication on infected human mononuclear cells. Planta Med. 2003 Oct;69(10):910-3.

[5]. Tanaka T, Kohno H, Tsukio Y, et al. Citrus limonoids obacunone and limonin inhibit azoxymethane-induced colon carcinogenesis in rats. Biofactors. 2000;13(1-4):213-8.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
668.4±55.0 °C at 760 mmHg

[ Melting Point ]:
298ºC

[ Molecular Formula ]:
C₂₆H₃₀O₈

[ Molecular Weight ]:
470.512

[ Flash Point ]:
358.0±31.5 °C

[ Exact Mass ]:
470.194061

[ PSA ]:
104.57000

[ LogP ]:
1.66

[ Vapour Pressure ]:
0.0±2.0 mmHg at 25°C

[ Index of Refraction ]:
1.602

MSDS

Click to get detail MSDS

Safety Information

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R20/21/22

[ Safety Phrases ]:
S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
RR1122000

Precursor & DownStream

Precursor

DownStream

Articles

Grapefruit (Citrus paradisi Macfad) phytochemicals composition is modulated by household processing techniques.

J. Food Sci. 77(9) , C921-6, (2012)

Grapefruits (Citrus paradisi Macfad) contain several phytochemicals known to have health maintaining properties. Due to the consumer's interest in obtaining high levels of these phytochemicals, it is ...

Ethylene degreening modulates health promoting phytochemicals in Rio Red grapefruit.

Food Chem. 188 , 77-83, (2015)

In the current study, we examined the effects of postharvest degreening and storage on phytochemicals in Rio Red grapefruit. Grapefruits were degreened with 3.5 μl/l of ethylene at 21 °C and 80% relat...

Quinine Bitterness and Grapefruit Liking Associate with Allelic Variants in TAS2R31.

Chem. Senses 40 , 437-43, (2015)

Multiple psychophysical gene-association studies suggest a single nucleotide polymorphism (SNP) within the bitter receptor gene TAS2R19 on chromosome 12 may be functional. Previously, the Arg299Cys SN...