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MedKoo Cat#: 326788 | Name: Limonin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Limonin, is a limonoid, and a bitter, white, crystalline substance found in citrus and other plants. It is also known as limonoate D-ring-lactone and limonoic acid di-delta-lactone. Chemically, it is a member of the class of compounds known as furanolactones. Ongoing research programs are examining the effects of limonin in human diseases. Citrus seed extracts reportedly have antiviral properties, inhibiting replication of retroviruses like HIV-1 and HTLV-I. Neuroprotective effects of limonin have also been described. Limonin reduces proliferation of colon cancer cells and has been tested as an anti-obesity agent in mice.

Chemical Structure

Limonin
Limonin
CAS#1180-71-8

Theoretical Analysis

MedKoo Cat#: 326788

Name: Limonin

CAS#: 1180-71-8

Chemical Formula: C26H30O8

Exact Mass: 470.1941

Molecular Weight: 470.52

Elemental Analysis: C, 66.37; H, 6.43; O, 27.20

Price and Availability

Size Price Availability Quantity
100mg USD 250.00 2 Weeks
250mg USD 450.00 2 Weeks
500mg USD 750.00 2 Weeks
1g USD 1,250.00 2 Weeks
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Related CAS #
No Data
Synonym
Citro; Dictamnolactone; Limonin; Evodin; Limonine; NSC 36508; Obaculactone.
IUPAC/Chemical Name
(4aS,6aR,8aR,8bR,9aS,12S,12aS,14aR,14bR)-12-(furan-3-yl)-6,6,8a,12a-tetramethyldecahydro-1H,3H-oxireno[2,3-d]pyrano[4',3':3,3a]isobenzofuro[5,4-f]isochromene-3,8,10(6H,9aH)-trione
InChi Key
KBDSLGBFQAGHBE-MSGMIQHVSA-N
InChi Code
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
SMILES Code
O=C1C[C@]2([H])OC(C)(C)[C@]3([H])CC([C@@]4(C)[C@@]56[C@@](O6)([H])C(O[C@@H](C7=COC=C7)[C@]5(C)CC[C@]4([H])[C@@]23CO1)=O)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Limonin is a triterpenoid enriched in citrus fruits, which has antivirus and antitumor ability.
In vitro activity:
Preliminarily, the anti-proliferative effect of limonin on HepG2 cells was tested by MTT method, which is reliable to detect proliferation of cells. Figure 1 shows the exposure of different concentrations of limonin (20, 40, 60, 80 and 100 μM) for 24 and 48 hours, which resulted in decreased cell proliferation in a dose and time dependent manner when compared with control cells. Reference: J Nat Sci Biol Med. 2013 Jan;4(1):126-33. https://pubmed.ncbi.nlm.nih.gov/23633848/
In vivo activity:
In a subsequent long-term experiment (38 weeks), in which rats were initiated with AOM and fed 0.05% obacunone or 0.05% limonin during the initiation or post-initiation phase, both compounds in diet caused significant reduction (65%-92% inhibition) in the incidence of colonic adenocarcinoma. Thus, citrus bitter limonoids obacunone and limonin possess chemopreventive effects on chemically induced rat colon carcinogenesis. Reference: Biofactors. 2000;13(1-4):213-8. https://pubmed.ncbi.nlm.nih.gov/11237184/
Solvent mg/mL mM comments
Solubility
DMF 25.0 53.13
DMF:PBS (pH 7.2) (1:1) 0.5 1.06
DMSO 31.9 67.78
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 470.52 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Langeswaran K, Gowthamkumar S, Vijayaprakash S, Revathy R, Balasubramanian MP. Influence of limonin on Wnt signalling molecule in HepG2 cell lines. J Nat Sci Biol Med. 2013 Jan;4(1):126-33. doi: 10.4103/0976-9668.107276. PMID: 23633848; PMCID: PMC3633262. 2. Han YL, Yu HL, Li D, Meng XL, Zhou ZY, Yu Q, Zhang XY, Wang FJ, Guo C. Inhibitory effects of limonin on six human cytochrome P450 enzymes and P-glycoprotein in vitro. Toxicol In Vitro. 2011 Dec;25(8):1828-33. doi: 10.1016/j.tiv.2011.09.023. Epub 2011 Oct 5. PMID: 22001672. 3. Tanaka T, Kohno H, Tsukio Y, Honjo S, Tanino M, Miyake M, Wada K. Citrus limonoids obacunone and limonin inhibit azoxymethane-induced colon carcinogenesis in rats. Biofactors. 2000;13(1-4):213-8. doi: 10.1002/biof.5520130133. PMID: 11237184. 4. Matsuda H, Yoshikawa M, Iinuma M, Kubo M. Antinociceptive and anti-inflammatory activities of limonin isolated from the fruits of Evodia rutaecarpa var. bodinieri. Planta Med. 1998 May;64(4):339-42. doi: 10.1055/s-2006-957447. PMID: 9619117.
In vitro protocol:
1. Langeswaran K, Gowthamkumar S, Vijayaprakash S, Revathy R, Balasubramanian MP. Influence of limonin on Wnt signalling molecule in HepG2 cell lines. J Nat Sci Biol Med. 2013 Jan;4(1):126-33. doi: 10.4103/0976-9668.107276. PMID: 23633848; PMCID: PMC3633262. 2. Han YL, Yu HL, Li D, Meng XL, Zhou ZY, Yu Q, Zhang XY, Wang FJ, Guo C. Inhibitory effects of limonin on six human cytochrome P450 enzymes and P-glycoprotein in vitro. Toxicol In Vitro. 2011 Dec;25(8):1828-33. doi: 10.1016/j.tiv.2011.09.023. Epub 2011 Oct 5. PMID: 22001672.
In vivo protocol:
1. Tanaka T, Kohno H, Tsukio Y, Honjo S, Tanino M, Miyake M, Wada K. Citrus limonoids obacunone and limonin inhibit azoxymethane-induced colon carcinogenesis in rats. Biofactors. 2000;13(1-4):213-8. doi: 10.1002/biof.5520130133. PMID: 11237184. 2. Matsuda H, Yoshikawa M, Iinuma M, Kubo M. Antinociceptive and anti-inflammatory activities of limonin isolated from the fruits of Evodia rutaecarpa var. bodinieri. Planta Med. 1998 May;64(4):339-42. doi: 10.1055/s-2006-957447. PMID: 9619117.
1: Eraky MA, El-Kholy AA, Rashed GA, Hammam OA, Moharam AF, Abou-Ouf EA, Aly NS, Kishik SM, Abdallah KF, Hamdan DI. Dose-response relationship in Schistosoma mansoni juvenile and adult stages following limonin treatment in experimentally infected mice. Parasitol Res. 2016 Jun 20. [Epub ahead of print] PubMed PMID: 27325399. 2: Wang F, Yu X, Liu X, Shen W, Zhu S, Zhao X. Temporal and spatial variations on accumulation of nomilin and limonin in the pummelos. Plant Physiol Biochem. 2016 Apr 23;106:23-29. doi: 10.1016/j.plaphy.2016.04.039. [Epub ahead of print] PubMed PMID: 27135815. 3: Zunino SJ, Storms DH, Freytag TL, Adkins YC, Bonnel EL, Woodhouse LR, Breksa AP 3rd, Manners GD, Mackey BE, Kelley DS. Dietary supplementation with purified citrus limonin glucoside does not alter ex vivo functions of circulating T lymphocytes or monocytes in overweight/obese human adults. Nutr Res. 2016 Jan;36(1):24-30. doi: 10.1016/j.nutres.2015.10.011. Epub 2015 Oct 31. PubMed PMID: 26773778. 4: Yoon YC, Kim SH, Kim MJ, Yang HJ, Rhyu MR, Park JH. Limonin, a Component of Dictamni Radicis Cortex, Inhibits Eugenol-Induced Calcium and cAMP Levels and PKA/CREB Signaling Pathway in Non-Neuronal 3T3-L1 Cells. Molecules. 2015 Dec 10;20(12):22128-36. doi: 10.3390/molecules201219840. PubMed PMID: 26690397. 5: Zhang A, Wang H, Sun H, Zhang Y, An N, Yan G, Meng X, Wang X. Metabolomics strategy reveals therapeutical assessment of limonin on nonbacterial prostatitis. Food Funct. 2015 Nov;6(11):3540-9. doi: 10.1039/c5fo00489f. Epub 2015 Aug 24. PubMed PMID: 26302114. 6: Shimizu S, Miyamoto S, Fujii G, Nakanishi R, Onuma W, Ozaki Y, Fujimoto K, Yano T, Mutoh M. Suppression of intestinal carcinogenesis in Apc-mutant mice by limonin. J Clin Biochem Nutr. 2015 Jul;57(1):39-43. doi: 10.3164/jcbn.15-28. Epub 2015 Jun 17. PubMed PMID: 26236099; PubMed Central PMCID: PMC4512898. 7: Yamashita S, Naruko A, Nakazawa Y, Zhao L, Hayashi Y, Hirama M. Total Synthesis of Limonin. Angew Chem Int Ed Engl. 2015 Jul 13;54(29):8538-41. doi: 10.1002/anie.201503794. Epub 2015 Jun 3. PubMed PMID: 26036432. 8: Ren W, Li Y, Zuo R, Wang HJ, Si N, Zhao HY, Han LY, Yang J, Bian BL. Species-related difference between limonin and obacunone among five liver microsomes and zebrafish using ultra-high-performance liquid chromatography coupled with a LTQ-Orbitrap mass spectrometer. Rapid Commun Mass Spectrom. 2014 Nov 15;28(21):2292-300. doi: 10.1002/rcm.7026. PubMed PMID: 25279742. 9: Rahman A, Siddiqui SA, Jakhar R, Kang SC. Growth inhibition of various human cancer cell lines by imperatorin and limonin from poncirus trifoliata rafin. Seeds. Anticancer Agents Med Chem. 2015;15(2):236-41. PubMed PMID: 25244913. 10: Xiang Y, Cao J, Luo F, Wang D, Chen W, Li X, Sun C, Chen K. Simultaneous purification of limonin, nomilin and isoobacunoic acid from pomelo fruit (Citrus grandis) segment membrane. J Food Sci. 2014 Oct;79(10):C1956-63. doi: 10.1111/1750-3841.12581. Epub 2014 Sep 11. PubMed PMID: 25212475. 11: Zhao Y, Zhao Y, Zhou X, Gong X. Development and validation of an UPLC-ESI-MS/MS method for determination of dehydroevodiamine, limonin, evodiamine, and rutaecarpine in Evodiae Fructus. Pharmacogn Mag. 2014 Jul;10(39):374-83. doi: 10.4103/0973-1296.137381. PubMed PMID: 25210328; PubMed Central PMCID: PMC4159934. 12: Yang N, Wang J, Liu C, Song Y, Zhang S, Zi J, Zhan J, Masilamani M, Cox A, Nowak-Wegrzyn A, Sampson H, Li XM. Berberine and limonin suppress IgE production by human B cells and peripheral blood mononuclear cells from food-allergic patients. Ann Allergy Asthma Immunol. 2014 Nov;113(5):556-564.e4. doi: 10.1016/j.anai.2014.07.021. Epub 2014 Aug 22. PubMed PMID: 25155085. 13: Mahmoud MF, Gamal S, El-Fayoumi HM. Limonin attenuates hepatocellular injury following liver ischemia and reperfusion in rats via toll-like receptor dependent pathway. Eur J Pharmacol. 2014 Oct 5;740:676-82. doi: 10.1016/j.ejphar.2014.06.010. Epub 2014 Jun 23. PubMed PMID: 24967531. 14: Yang Y, Wang X, Zhu Q, Gong G, Luo D, Jiang A, Yang L, Xu Y. Synthesis and pharmacological evaluation of novel limonin derivatives as anti-inflammatory and analgesic agents with high water solubility. Bioorg Med Chem Lett. 2014 Apr 1;24(7):1851-5. doi: 10.1016/j.bmcl.2014.02.003. Epub 2014 Feb 10. PubMed PMID: 24569111. 15: Mahmoud MF, Hamdan DI, Wink M, El-Shazly AM. Hepatoprotective effect of limonin, a natural limonoid from the seed of Citrus aurantium var. bigaradia, on D-galactosamine-induced liver injury in rats. Naunyn Schmiedebergs Arch Pharmacol. 2014 Mar;387(3):251-61. doi: 10.1007/s00210-013-0937-1. Epub 2013 Nov 21. PubMed PMID: 24258286. 16: Zhang PT, Pan BY, Liao QF, Yao MC, Xu XJ, Wan JZ, Liu D, Xie ZY. Simultaneous Quantification of Limonin, Two Indolequinazoline Alkaloids, and Four Quinolone Alkaloids in Evodia rutaecarpa (Juss.) Benth by HPLC-DAD Method. J Anal Methods Chem. 2013;2013:827361. doi: 10.1155/2013/827361. Epub 2013 May 8. PubMed PMID: 23738236; PubMed Central PMCID: PMC3664498. 17: Langeswaran K, Gowthamkumar S, Vijayaprakash S, Revathy R, Balasubramanian MP. Influence of limonin on Wnt signalling molecule in HepG2 cell lines. J Nat Sci Biol Med. 2013 Jan;4(1):126-33. doi: 10.4103/0976-9668.107276. PubMed PMID: 23633848; PubMed Central PMCID: PMC3633262. 18: Wang P, Sun J, Gao E, Zhao Y, Qu W, Yu Z. Simultaneous determination of limonin, dictamnine, obacunone and fraxinellone in rat plasma by a validated UHPLC-MS/MS and its application to a pharmacokinetic study after oral administration of Cortex Dictamni extract. J Chromatogr B Analyt Technol Biomed Life Sci. 2013 Jun 1;928:44-51. doi: 10.1016/j.jchromb.2013.03.018. Epub 2013 Mar 26. PubMed PMID: 23611843. 19: Xu H, Li Q, Yin Y, Lv C, Sun W, He B, Liu R, Chen X, Bi K. Simultaneous determination of three alkaloids, four ginsenosides and limonin in the plasma of normal and headache rats after oral administration of Wu-Zhu-Yu decoction by a novel ultra fast liquid chromatography-tandem mass spectrometry method: application to a comparative pharmacokinetics and ethological study. J Mass Spectrom. 2013 Apr;48(4):519-32. doi: 10.1002/jms.3183. PubMed PMID: 23584945. 20: Liu SJ, Zhou L, Zhang J, Yu BY, Li CY, Liu ZX, Ju WZ. Determination of limonin in dog plasma by liquid chromatography-tandem mass spectrometry and its application to a pharmacokinetic study. Biomed Chromatogr. 2013 Apr;27(4):515-9. doi: 10.1002/bmc.2821. Epub 2012 Sep 27. PubMed PMID: 23018841.