A limonoid triterpenoid with diverse biological activities
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Nomilin

Item No. 20836

Technical Information
Formal Name
(1S,3aS,4aR,4bR,6aR,11S,11aR,11bR,13aS)-11-(acetyloxy)-1-(3-furanyl)decahydro-4b,7,7,11a,13a-pentamethyl-oxireno[4,4a]-2-benzopyrano[6,5-g][2]benzoxepin-3,5,9(3aH,4bH,6H)-trione
CAS Number
1063-77-0
Synonyms
  • NSC 297134
Molecular Formula
C28H34O9
Formula Weight
Purity
≥98%
A crystalline solid
DMF: 30 mg/mlDMSO: 30 mg/ml
SMILES
CC([C@@](C1)([H])[C@@]([C@@H](OC(C)=O)C2)(C)[C@@]([C@@]3(C)C1=O)([H])CC[C@]4(C)[C@]3(O5)[C@H]5C(O[C@H]4C6=COC=C6)=O)(C)OC2=O
InChi Code
InChI=1S/C28H34O9/c1-14(29)34-19-12-20(31)36-24(2,3)17-11-18(30)27(6)16(26(17,19)5)7-9-25(4)21(15-8-10-33-13-15)35-23(32)22-28(25,27)37-22/h8,10,13,16-17,19,21-22H,7,9,11-12H2,1-6H3/t16-,17+,19+,21+,22-,25+,26-,27+,28-/m1/s1
InChi Key
KPDOJFFZKAUIOE-WNGDLQANSA-N
Origin
Plant/Aurantii fructus immaturus
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Nomilin is a limonoid triterpenoid that has been found in grapefruit seeds and has diverse biological activities, including antiviral, antiproliferative, and anti-obesity properties.1 It dose-dependently reduces HIV-1 replication in infected human peripheral blood mononuclear cells (PBMCs; EC50 = 52.2 μM) and reduces human umbilical vein endothelial cell (HUVEC) proliferation, invasion, tube formation, and matrix metalloproteinase-2 (MMP-2) and MMP-9 activity without reducing cell viability when used at concentrations ranging from 5 to 25 µg/ml.2,3 Nomilin (100 μM) increases luciferase activity 5.5-fold when the G protein-coupled receptor TGR5 is expressed in HEK293 cells with a TGR5-dependent reporter gene.4 It increases GST activity in the small intestinal mucosa, liver, and forestomach of mice by 4.17-, 3.44-, and 1.16-fold, respectively, when administered at a dose of 10 mg/kg.1 Nomilin (0.2% w/w, p.o.) completely prevents weight gain and reduces serum glucose and insulin levels by 30 and 89.8%, respectively, in mice fed a high-fat diet.4 It also increases the white blood cell count and the specific antibody titer in blood by approximately 10-fold in mice in response to sheep red blood cells when administered at a dose of 10 μmol/kg.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lam, L., Li, Y., and Hasegawa, S. Effects of citrus limonoids on glutathione S-transferase activity in mice. J. Agric. Food Chem. 37(4), 878-880 (1989).

    2. Battinelli, L., Mengoni, F., Lichtner, M., et alEffect of limonin and nomilin on HIV-1 replication on infected human mononuclear cells. Planta Med. 69(10), 910-913 (2003).

    3. Pratheeshkumar, P., and Kuttan, G. Nomilin inhibits tumor-specific angiogenesis by downregulating VEGF, NO and proinflammatory cytokine profile and also by inhibiting the activation of MMP-2 and MMP-9. Eur. J. Pharmacol. 668(3), 450-458 (2011).

    4. Ono, E., Inoue, J., Hashidume, T., et alAnti-obesity and anti-hyperglycemic effects of the dietary citrus limonoid nomilin in mice fed a high-fat diet. Biochem. Biophys. Res. Commun. 410(3), 677-681 (2011).

    5. Raphael, T.J., and Kuttan, G. Effect of naturally occurring triterpenoids glycyrrhizic acid, ursolic acid, oleanolic acid and nomilin on the immune system. Phytomedicine 10(6-7), 483-489 (2003).