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    Limonin
    Limonin

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    This product is for research use only, not for human use. We do not sell to patients.
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    InvivoChem Cat #: V0734
    CAS #: 1180-71-8Purity ≥98%

    Description: Limonin (also known as NSC-36508; Obaculactone; limonoate D-ring-lactone and limonoic acid di-delta-lactone), a naturally occurring limonoid, is a hexacyclic triterpenoid isolated in citrus fruits and other plants, which has antivirus and antitumor ability. It is a bitter, white, crystalline substance. Chemically, it is a member of the class of compounds known as furanolactones. 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.

    References: Planta Med. 2003 Oct;69(10):910-3; Planta Med. 1998 May;64(4):339-42.

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    Molecular Weight (MW)470.51
    FormulaC26H30O8
    CAS No.1180-71-8
    Storage-20℃ for 3 years in powder form
    -80℃ for 2 years in solvent
    Solubility (In vitro)DMSO: 44 mg/mL (93.5 mM)
    Water: <1 mg/mL
    Ethanol: <1 mg/mL
    Other info

    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[[email protected]]2([H])OC(C)(C)[[email protected]]3([H])CC([[email protected]@]4(C)[[email protected]@]56[[email protected]@](O6)([H])C(O[[email protected]@H](C7=COC=C7)[[email protected]]5(C)CC[[email protected]]4([H])[[email protected]@]23CO1)=O)=O

    Synonyms

    Citro; Dictamnolactone; NSC36508; Limonin; Evodin; Limonine; NSC-36508; NSC 36508; Obaculactone.


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    In Vitro

    In vitro activity: Limonin is a furanolactone enriched in citrus fruits, which has antivirus and antitumor ability. Limonin inhibits the replication of human immunodeficiency virus-1 (HIV-1) in culture of human peripheral blood mononuclear cells (PBMC) with an EC50 of 60 μM. Limonin also shows antinociceptive and anti-inflammatory effects in vivo. Limonin is a potent anti proliferative agent against human hepatoma HepG2 cells via regulation of apoptosis and Wnt signallings.


    Cell Assay: 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. In human hepatoma HepG2 cells, limonin can induced apoptosis, which was evidenced by WB analysis of some apoptosis factors.

    In VivoIn 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. 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.
    Animal modelFemale Syrian hamsters and rats
    Formulation & Dosage0.05% limonin in diet
    References

    Carcinogenesis. 1989 Aug;10(8):1535-7; Biofactors. 2000;13(1-4):213-8.


    These protocols are for reference only. InvivoChem does not independently validate these methods.

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