Limonin

Carcinogenesis inhibitor and HIV-1 replication inhibitor CAS# 1180-71-8

Limonin

Catalog No. BCN6057----Order now to get a substantial discount!

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Quality Control of Limonin

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Chemical structure

Limonin

3D structure

Chemical Properties of Limonin

Cas No. 1180-71-8 SDF Download SDF
PubChem ID 179651 Appearance White powder
Formula C26H30O8 M.Wt 470.5
Type of Compound Triterpenoids Storage Desiccate at -20°C
Synonyms Limonoic acid 3,19:16,17 dilactone
Solubility DMSO : ≥ 110 mg/mL (233.79 mM)
*"≥" means soluble, but saturation unknown.
SMILES CC1(C2CC(=O)C3(C(C24COC(=O)CC4O1)CCC5(C36C(O6)C(=O)OC5C7=COC=C7)C)C)C
Standard InChIKey KBDSLGBFQAGHBE-MSGMIQHVSA-N
Standard InChI InChI=1S/C26H30O8/c1-22(2)15-9-16(27)24(4)14(25(15)12-31-18(28)10-17(25)33-22)5-7-23(3)19(13-6-8-30-11-13)32-21(29)20-26(23,24)34-20/h6,8,11,14-15,17,19-20H,5,7,9-10,12H2,1-4H3/t14-,15-,17-,19-,20+,23-,24-,25+,26+/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Limonin

1 Dictamnus sp.

Biological Activity of Limonin

DescriptionLimonin is a widely used dietary supplement, one of the most prevalent citrus limonoids, which has antioxidant, anti-inflammatory, anticancer and anti-human immunodeficiency virus(HIV)activity. It induced a down regulation of TLR-2 ,TLR-4,TNF-α, TNF-α/IL-10,NF-κB and caspase. It showed the potent inhibition of CYP3A4, with IC50 values of 6.20 μM (CYP3A4/testosterone) and 19.10 μM (CYP3A4/midazolam).
TargetsHIV | P450 (e.g. CYP17) | TLR
In vitro

Influence of limonin on Wnt signalling molecule in HepG2 cell lines.[Pubmed: 23633848]

J Nat Sci Biol Med. 2013 Jan;4(1):126-33.

The role of Limonin as potent anti carcinogenic, apoptosis and chemotherapeutic agents has been supported by limited studies.
METHODS AND RESULTS:
In this study, Limonin is identified as a potent anti proliferative agent against human hepatoma HepG2 cells based on the cell viability study, LDH leakage assay. Induction of apoptosis in HepG2 cells by Limonin was evidenced by western blot analysis of Bax, Cyclin D1, Caspase 3 and Caspase9. Since Wnt signalling is involved in the initiation and sustaining of hepatocellular carcinoma we studied differential expression of LRP5, LRP6 and DKK wnt players.
CONCLUSIONS:
Limonin found to down regulate these players which forms a rationale for further investigation on effect on Limonin in cancer therapy.

Effect of limonin and nomilin on HIV-1 replication on infected human mononuclear cells.[Pubmed: 14648393]

Planta Med. 2003 Oct;69(10):910-3.

In the last years several plant-derived natural compounds have been screened for their anti-HIV activity in order to find lead compounds with novel structures or mechanisms of action. Among these, several triterpenoids have been found to exhibit an antiretroviral activity with different mechanisms of action.
METHODS AND RESULTS:
In this study the effect of two limonoids, Limonin and nomilin, on the growth of human immunodeficiency virus-1 (HIV-1) in culture of human peripheral blood mononuclear cells (PBMC) and on monocytes/macrophages (M/M) is described. Limonin and nomilin were found to inhibit the HIV-1 replication in all cellular systems used. A dose-dependent inhibition of viral replication was observed in PBMC isolated from healthy donors and infected with HIV-1 strain after incubation with Limonin and nomilin (EC (50) values: 60.0 microM and 52.2 microM, respectively). The two terpenoids inhibited at all concentrations studied the production of HIV-p24 antigen even when the PBMC employed were chronically infected (EC (50) values of 61.0 microM for Limonin and 76.2 microM for nomilin). Moreover, these compounds inhibited the HIV-1 replication even in infected M/M. In this cellular system the inhibitory effect was significant at the concentrations of 20 microM, 40 microM and 80 microM starting from day 14 and reached the maximum effect after 18 days of incubation. As regards the mechanism of action, Limonin and nomilin inhibit in vitro HIV-1 protease activity.
CONCLUSIONS:
In general, the results obtained point out a similar anti-HIV activity of Limonin and nomilin indicating that this activity is not drastically influenced by the structural difference between the two compounds.

In vivo

Limonin attenuates hepatocellular injury following liver ischemia and reperfusion in rats via toll-like receptor dependent pathway.[Pubmed: 24967531]

Eur J Pharmacol. 2014 Oct 5;740:676-82.

Limonin has been shown to exhibit anti-inflammatory and antioxidant properties in the settings of chemically induced hepatic injury.
METHODS AND RESULTS:
The current study aimed to investigate the protective effects of Limonin on experimentally-induced hepatic ischemia reperfusion (I/R) injury in rats. Rats were injected IP with either DMSO or Limonin (100 mg/kg BW), 30 min before submission to 45 min of ischemia, followed by 1 h of reperfusion. Limonin ameliorated the deleterious effects of I/R as indicated by improvement in liver function tests, reduction of lactate dehydrogenase, reduction of oxidative stress, decrease in hepatocyte degeneration, and pyknosis. Furthermore, pretreatment of I/R rats with Limonin, induced a significant down regulation in the various elements of the toll like receptor (TLR)pathway including TLR-2 and TLR-4, myeloid differentiation factor 88 (MYD88) and toll/IR-1(TIR)-domain-containing adaptor protein inducing interferon-beta (TRIF) and the downstream effectors TNF-α, TNF-α/IL-10 ratio and nuclear factor-κB (NF-κB). It also increased the anti-inflammatory cytokine IL-10 and decreased the activity of the apoptotic marker, caspase-3.
CONCLUSIONS:
These data indicate that Limonin exerts antioxidant and anti-inflammatory effects in ischemic liver, thus, protecting hepatocytes against I/R injury in rats. The mechanism of these hepatoprotective effects appears to be related to the antioxidant and anti-inflammatory potential of Limonin mediated by the down regulation of TLR- signaling pathway.

Protocol of Limonin

Kinase Assay

Inhibitory effects of limonin on six human cytochrome P450 enzymes and P-glycoprotein in vitro.[Pubmed: 22001672]

Toxicol In Vitro. 2011 Dec;25(8):1828-33.

Among the various possible causes for drug interactions, pharmacokinetic factors such as inhibition of drug-metabolizing enzymes and transporters, especially cytochrome P450 (CYP) isoenzymes and P-glycoprotein (P-gp), are regarded as the most frequent and clinically important. Limonin is a widely used dietary supplement and one of the most prevalent citrus limonoids, which are known to have inhibitory effects on CYPs and P-gp.
METHODS AND RESULTS:
In this study, the in vitro inhibitory effects of Limonin on the major human CYP isoenzymes (CYP1A2, CYP2C8, CYP2C9, CYP2C19, CYP2D6, and CYP3A4) activities in human liver microsomes were examined using liquid chromatography-tandem mass spectrometry. The inhibitory effects of Limonin on P-gp activity in a human metastatic malignant melanoma cell line WM-266-4 were examined using a calcein-AM fluorometry screening assay. It demonstrates that Limonin has negligible inhibitory effects on human CYP1A2, CYP2C8, CYP2C9, CYP2C19, CYP2D6, and P-gp. However, potent inhibition of CYP3A4 by Limonin is observed with IC50 values of 6.20 μM (CYP3A4/testosterone) and 19.10 μM (CYP3A4/midazolam).
CONCLUSIONS:
This finding has important implications with regard to food-drug interactions between Limonin and several narrow therapeutic index drugs that are metabolized by CYP3A4.

Cell Research

Effect of limonin and nomilin on HIV-1 replication on infected human mononuclear cells.[Pubmed: 14648393]

Planta Med. 2003 Oct;69(10):910-3.

Cell lines:PBMC, and M/M cells
Concentrations: 20, 40 , 60,80 and 100 μM /mL
Incubation Time: ---
Method:
Limonin and nomilin were found to inhibit the HIV-1 replication in all cellular systems used. A dose-dependent inhibition of viral replication was observed in PBMC isolated from healthy donors and infected with HIV-1 strain after incubation with Limonin and nomilin (EC (50) values: 60.0 microM and 52.2 microM, respectively). The two terpenoids inhibited at all concentrations studied the production of HIV-p24 antigen even when the PBMC employed were chronically infected (EC (50) values of 61.0 microM for Limonin and 76.2 microM for nomilin).

Limonin Dilution Calculator

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Limonin Molarity Calculator

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Preparing Stock Solutions of Limonin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.1254 mL 10.627 mL 21.254 mL 42.508 mL 53.135 mL
5 mM 0.4251 mL 2.1254 mL 4.2508 mL 8.5016 mL 10.627 mL
10 mM 0.2125 mL 1.0627 mL 2.1254 mL 4.2508 mL 5.3135 mL
50 mM 0.0425 mL 0.2125 mL 0.4251 mL 0.8502 mL 1.0627 mL
100 mM 0.0213 mL 0.1063 mL 0.2125 mL 0.4251 mL 0.5313 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Limonin

Limonin is a chemically-induced carcinogenesis inhibitor and HIV-1 replication inhibitor.The human immunodeficiency virus (HIV) is a lentivirus that causes the acquired immunodeficiency syndrome (AIDS).
When culturing the HIV-1 in human peripheral blood mononuclear cells (PBMC) and monocytes/macrophages (M/M), Limonin inhibit the HIV-1 replication in all cellular systems and inhibit HIV-1 replication with EC50 value of 60u μM in PBMC cells in a dose-dependent way [1]. In human hepatoma HepG2 cells, limonin can induced apoptosis, which was evidenced by WB analysis of some apoptosis factors [2].
In the female Syrian hamsters treated with DMBA, which can cause tumor, limonin showed a 60% reduction in tumor burden. It decreased 20% tumor number and 50% tumor mass [3]. In male F344 rats treated with azoxymethane (AOM), 0.05% limonin in diet significantly reduced (65%-92% inhibition) the incidence of colonic adenocarcinoma. Thus, limonin has chemopreventive effects on chemically induced carcinogenesis [4].
References:
[1]. Battinelli L, Mengoni F, Lichtner M, et al. Effect of limonin and nomilin on HIV-1 replication on infected human mononuclear cells. Planta medica, 2003, 69(10): 910-913.
[2]. Langeswaran K, Gowthamkumar S, Vijayaprakash S, et al. Influence of limonin on Wnt signalling molecule in HepG2 cell lines. J Nat Sci Biol Med, 2013, 4(1): 126-133.
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3633262/?report=reader
[3]. Miller EG, Fanous R, Rivera-Hidalgo, et al. The effect of citrus limonoids on hamster buccal pouch carcinogenesis. Carcinogenesis, 1989, 10(8): 1535-1537.
[4]. Tanaka T, Kohno H, Tsukio Y, et al. Citrus limonoids obacunone and limonin inhibit azoxymethane-induced colon carcinogenesis in rats. BioFactors (Oxford, England), 2000,  13(1-4): 213-8.

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References on Limonin

Limonin attenuates hepatocellular injury following liver ischemia and reperfusion in rats via toll-like receptor dependent pathway.[Pubmed:24967531]

Eur J Pharmacol. 2014 Oct 5;740:676-82.

Limonin has been shown to exhibit anti-inflammatory and antioxidant properties in the settings of chemically induced hepatic injury. The current study aimed to investigate the protective effects of Limonin on experimentally-induced hepatic ischemia reperfusion (I/R) injury in rats. Rats were injected IP with either DMSO or Limonin (100 mg/kg BW), 30 min before submission to 45 min of ischemia, followed by 1 h of reperfusion. Limonin ameliorated the deleterious effects of I/R as indicated by improvement in liver function tests, reduction of lactate dehydrogenase, reduction of oxidative stress, decrease in hepatocyte degeneration, and pyknosis. Furthermore, pretreatment of I/R rats with Limonin, induced a significant down regulation in the various elements of the toll like receptor (TLR)pathway including TLR-2 and TLR-4, myeloid differentiation factor 88 (MYD88) and toll/IR-1(TIR)-domain-containing adaptor protein inducing interferon-beta (TRIF) and the downstream effectors TNF-alpha, TNF-alpha/IL-10 ratio and nuclear factor-kappaB (NF-kappaB). It also increased the anti-inflammatory cytokine IL-10 and decreased the activity of the apoptotic marker, caspase-3. These data indicate that Limonin exerts antioxidant and anti-inflammatory effects in ischemic liver, thus, protecting hepatocytes against I/R injury in rats. The mechanism of these hepatoprotective effects appears to be related to the antioxidant and anti-inflammatory potential of Limonin mediated by the down regulation of TLR- signaling pathway.

Influence of limonin on Wnt signalling molecule in HepG2 cell lines.[Pubmed:23633848]

J Nat Sci Biol Med. 2013 Jan;4(1):126-33.

OBJECTIVE: The role of Limonin as potent anti carcinogenic, apoptosis and chemotherapeutic agents has been supported by limited studies. MATERIALS AND METHODS: In this study, Limonin is identified as a potent anti proliferative agent against human hepatoma HepG2 cells based on the cell viability study, LDH leakage assay. Induction of apoptosis in HepG2 cells by Limonin was evidenced by western blot analysis of Bax, Cyclin D1, Caspase 3 and Caspase9. RESULTS: Since Wnt signalling is involved in the initiation and sustaining of hepatocellular carcinoma we studied differential expression of LRP5, LRP6 and DKK wnt players. CONCLUSION: Limonin found to down regulate these players which forms a rationale for further investigation on effect on Limonin in cancer therapy.

Inhibitory effects of limonin on six human cytochrome P450 enzymes and P-glycoprotein in vitro.[Pubmed:22001672]

Toxicol In Vitro. 2011 Dec;25(8):1828-33.

Among the various possible causes for drug interactions, pharmacokinetic factors such as inhibition of drug-metabolizing enzymes and transporters, especially cytochrome P450 (CYP) isoenzymes and P-glycoprotein (P-gp), are regarded as the most frequent and clinically important. Limonin is a widely used dietary supplement and one of the most prevalent citrus limonoids, which are known to have inhibitory effects on CYPs and P-gp. In this study, the in vitro inhibitory effects of Limonin on the major human CYP isoenzymes (CYP1A2, CYP2C8, CYP2C9, CYP2C19, CYP2D6, and CYP3A4) activities in human liver microsomes were examined using liquid chromatography-tandem mass spectrometry. The inhibitory effects of Limonin on P-gp activity in a human metastatic malignant melanoma cell line WM-266-4 were examined using a calcein-AM fluorometry screening assay. It demonstrates that Limonin has negligible inhibitory effects on human CYP1A2, CYP2C8, CYP2C9, CYP2C19, CYP2D6, and P-gp. However, potent inhibition of CYP3A4 by Limonin is observed with IC50 values of 6.20 muM (CYP3A4/testosterone) and 19.10 muM (CYP3A4/midazolam). This finding has important implications with regard to food-drug interactions between Limonin and several narrow therapeutic index drugs that are metabolized by CYP3A4.

Description

Limonin is a triterpenoid enriched in citrus fruits, which has antivirus and antitumor ability.

Keywords:

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