Indicaxanthin
Indicaxanthin is an orally available, blood-brain barrier-permeable bioavailable betalain pigment (Betalain Pigment) found in the fruits of Opuntia ficus-indica. Indicaxanthin exhibits antioxidant, anti-inflammatory, antiproliferative and neuromodulatory activities. Indicaxanthin modulates glutamatergic neurotransmission and inhibits PGE2, TNF-α, IL-1β, iNOS, COX-2 and NF-κB-related inflammatory responses. Indicaxanthin can be used in studies of melanoma, colorectal cancer, acute inflammation, obesity-associated insulin resistance and glutamatergic neuromodulation.
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- CAS No.: 2181-75-1
- Formula: C14H16N2O6
- Molecular Weight:308.29
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Storage:
Please store the product under the recommended conditions in the Certificate of Analysis.
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Biological Activity
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Chemical Information
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Biological Activity
Indicaxanthin (50-200 μM; 72 h) inhibits the proliferation of A375, Sk-Mel-28, MALME and B16/F10 melanoma cells in a concentration-dependent manner, with proliferation inhibition rates of 56%, 24.4%, 30.8% and 69.2% at 200 μM, respectively, while the growth of NHEM is not significantly affected[4].
Indicaxanthin (100 μM; 15 min-48 h) inhibits IκBα degradation and nuclear p65 in A375 cells, and reduces the expression of Bcl-2 and c-FLIP[4].
Indicaxanthin (100 μM; 16 h) reduces the invasive capacity of A375 cells by 71%[4].
Indicaxanthin (100 μM; 48 h) increases the proportion of Annexin V+/PI+ cells in A375 cells to 31.5%, promotes caspase-3 cleavage, and induces the conversion of LC3-I to LC3-II[4].
Indicaxanthin (10-100 μM; 48 h) dose-dependently increases LC3-II in Caco-2 cells, elevates Beclin1 by approximately 3.5-fold at 50 μM, and increases the fluorescence of acidic vesicles by approximately 6- and 9-fold at 50 μM and 100 μM, respectively[6].
Indicaxanthin (1-5 μM; 3 h) concentration-dependently inhibits cigarette smoke extract-induced phosphatidylserine externalization and ceramide production in human erythrocytes, as well as the assembly of the Fas/FasL/FADD/caspase-8 death-inducing signaling complex, p38 phosphorylation, and caspase-8/caspase-3 activation[8].
Indicaxanthin scavenges ABTS cation radicals, and the radical-scavenging activity of purified Indicaxanthin is stronger than that of Trolox[2].
Indicaxanthin (1-25 μM) reduces IL-6, IL-8, PGE2, NO and RONS, and modulates NOX1, COX-2, iNOS and NF-κB in IL-1β-activated Caco-2 assays[1].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:A375, Sk-Mel-28, MALME, B16/F10, NHEM
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Concentration:50 μM, 100 μM, 200 μM
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Incubation Time:72 h
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Result:Inhibited proliferation of A375 cells by 20.7%, 35.7%, and 56% at 50, 100, and 200 μM respectively.
Inhibited proliferation of B16/F10 cells by 33.9%, 46.4%, and 69.2% at 50, 100, and 200 μM respectively.
Inhibited proliferation of Sk-Mel-28 cells by 4.2%, 4.7%, and 24.4% at 50, 100, and 200 μM respectively.
Inhibited proliferation of MALME cells by 4.9%, 12.9%, and 30.8% at 50, 100, and 200 μM respectively.
Did not affect NHEM growth at any tested concentration.
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Cell Line:A375
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Concentration:100 μM
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Incubation Time:48 h
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Result:Increased apoptotic/necroptotic cells (AxV-FITC+/PI+) to 31.5% compared to untreated cells.
Reduced necrotic events (AxV-FITC-/PI+) to 1.3%.
Promoted cleavage and activation of caspase-3.
Increased conversion of LC3-I to LC3-II.
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Cell Line:A375
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Concentration:100 μM
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Incubation Time:15 min, 30 min, 60 min, 6 h, 24 h, 48 h
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Result:Inhibited IκBα degradation, shown by increased band intensity at 30 min.
Reduced nuclear levels of the active NF-κB p65 subunit at 3 and 6 h.
Caused a marked reduction in the expression of NF-κB-dependent anti-apoptotic proteins Bcl-2 and c-FLIP over 6 to 48 h.
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Cell Line:A375
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Concentration:100 μM
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Incubation Time:16 h
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Result:Inhibited the invasiveness of A375 cells by 71% (P < 0.001 vs control; n=3).
Indicaxanthin (0.4 mg/kg; twice daily; 4 weeks; p.o.) reduces MDA, RONS and NO levels in the liver and adipose tissue of HFD-fed C57BL/6J mice, and decreases macrophage infiltration, as well as the levels of TNF-α, CCL2, F4-80, iNOS, COX-2, nuclear p65 and p-JNK[5].
Ndicaxanthin (3.2 mg/kg; 14 days; p.o. gavage) reduces tumor volume by 86%, tumor weight by 83%, and plasma CXCL1 levels by 42% in the B16/F10-C57BL/6 melanoma model[4].
Indicaxanthin (0.4 mg/kg; twice daily; 4 weeks; p.o.) reduces body weight gain, visceral fat, fasting blood glucose and plasma insulin, improves glucose tolerance and insulin sensitivity, and restores HOMA-IR and adipose insulin receptor expression in HFD-fed C57BL/6J mice[5].
Indicaxanthin (0.085-0.34 ng/neuron; 5 min; hippocampal microiontophoresis) reduces the spontaneous firing of hippocampal neurons in Wistar rats in a dose-dependent manner, and decreases glutamate-induced neuronal excitation by approximately 52.14% at 0.34 ng/neuron[3].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:Male Wistar rats, 175-200 g; carrageenin-induced pleurisy[7]
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Dosage:0.5, 1, or 2 μmol/kg; 30 min before carrageenin and every 8 h thereafter up to 40 h
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Administration:p.o.
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Result:Reduced pleural exudate and leukocyte recruitment dose-dependently; maximal reductions reached about 70% and 95%, respectively. Reduced PGE2, NO, IL-1β, TNF-α, iNOS, COX-2, and NF-κB activation.
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Animal Model:Male C57BL/6 mice, 6-7 weeks, 18-20 g; s.c. B16/F10 melanoma
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Dosage:3.2 mg/kg; 14 days; frequency reported inconsistently as 3 times/day in Methods and twice daily in Results
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Administration:p.o.
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Result:Reduced tumor volume by 86%, tumor weight by 83%, and plasma CXCL1 by 42%.
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Animal Model:Male C57BL/6J mice; HFD with 60% energy from fat for 10 weeks before Indicaxanthin administration
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Dosage:0.4 mg/kg; twice daily; 4 weeks
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Administration:p.o.
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Result:Reduced body-weight gain and visceral adiposity; improved fasting glycaemia, GTT, ITT, plasma insulin, HOMA-IR and insulin receptor expression; reduced hepatic/adipose oxidative and inflammatory markers.
Chemical Information
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CAS No. 2181-75-1
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Molecular Weight 308.29
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Formula C14H16N2O6
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SMILES
OC(C1=N[C@@H](CC(/C=C/N2CCC[C@H]2C(O)=O)=C1)C(O)=O)=O
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Structure Classification
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Initial Source
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Purity & Documentation
References
[1]. Butera D, et al. Antioxidant activities of sicilian prickly pear (Opuntia ficus indica) fruit extracts and reducing properties of its betalains: betanin and indicaxanthin. Journal of agricultural and food chemistry. 2002 Nov 06;50(23):6895-901. [Content Brief]
[2]. Ragusa MA, et al. Indicaxanthin Induces Autophagy in Intestinal Epithelial Cancer Cells by Epigenetic Mechanisms Involving DNA Methylation. Nutrients. 2023 Aug 07;15(15):3495. [Content Brief]
[3]. Restivo I, et al. Indicaxanthin prevents eryptosis induced by cigarette smoke extract by interfering with active Fas-mediated signaling. BioFactors (Oxford, England). 2024;50(5):997-1008. [Content Brief]
[4]. Allegra M, et al. Indicaxanthin from Opuntia ficus indica (L. Mill) impairs melanoma cell proliferation, invasiveness and tumor progression. Phytomedicine. 2018. [Content Brief]
[5]. Terzo S, et al. Indicaxanthin from Opuntia ficus-indica Fruit Ameliorates Glucose Dysmetabolism and Counteracts Insulin Resistance in High-Fat-Diet-Fed Mice. Antioxidants. 2022;11:80. [Content Brief]
[6]. Ragusa MA, et al. Indicaxanthin Induces Autophagy in Intestinal Epithelial Cancer Cells by Epigenetic Mechanisms Involving DNA Methylation. Nutrients. 2023;15:3495. [Content Brief]
[7]. Allegra M, et al. Indicaxanthin from Opuntia Ficus Indica (L. Mill) impairs melanoma cell proliferation, invasiveness, and tumor progression. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2018 Nov 15;50:19-24. [Content Brief]
[8]. Restivo I, et al. Indicaxanthin prevents eryptosis induced by cigarette smoke extract by interfering with active Fas-mediated signaling. [Content Brief]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
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