# Naringenin Chalcone **Canonical URL:** https://ingredients.hermeticasuperfoods.com/ingredients/naringenin-chalcone **Data Source:** Hermetica Superfoods Ingredient Encyclopedia **Updated:** 2026-03-20 **Evidence Score:** 2 / 10 **Category:** Compound **Also Known As:** 4,2',4',6'-Tetrahydroxychalcone, 2'-Hydroxynaringenin, Naringenin 2'-hydroxychalcone, 4',6'-Dihydroxy-2'-hydroxychalcone, Chalconaringenin, 2',4',6'-Trihydroxychalcone ## Overview Naringenin chalcone is a flavonoid precursor found in citrus peels that exhibits [anti-inflammatory](/ingredients/condition/inflammation) and potential anticancer properties. It works primarily by inhibiting inflammatory cytokine production and inducing apoptosis in cancer cells through multiple cellular pathways. ## Health Benefits • Induces apoptosis, contributing to potential anticancer effects against glioblastoma (Preclinical evidence). • Inhibits MCP-1 production, reducing inflammatory responses (Preclinical evidence). • Decreases nitric oxide production, offering [anti-inflammatory](/ingredients/condition/inflammation) benefits (Preclinical evidence). • Exhibits anti-allergic properties by modulating immune responses (Preclinical evidence). • Potential anticancer activity, specifically noted against glioblastoma cells (Preclinical evidence). ## Mechanism of Action Naringenin chalcone inhibits MCP-1 (monocyte chemoattractant protein-1) production and reduces nitric oxide synthesis through [NF-κB](/ingredients/condition/inflammation) pathway modulation. The compound induces apoptosis in glioblastoma cells by activating caspase cascades and disrupting [mitochondrial](/ingredients/condition/energy) membrane potential. It also demonstrates [antioxidant activity](/ingredients/condition/antioxidant) by scavenging free radicals and upregulating endogenous antioxidant enzymes. ## Clinical Summary Current evidence for naringenin chalcone is limited to preclinical studies using cell cultures and animal models. In vitro studies show significant reduction in [inflammatory](/ingredients/condition/inflammation) markers and cancer cell viability at concentrations ranging from 10-100 μM. Glioblastoma cell studies demonstrate 50-80% reduction in cell proliferation after 48-72 hours of treatment. Human clinical trials are lacking, making it impossible to confirm therapeutic efficacy or optimal dosing in humans. ## Nutritional Profile Naringenin Chalcone (systematic name: (E)-1-(2,4,6-trihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one) is a pure bioactive flavonoid compound, not a whole food, so it has no macronutrient, vitamin, or mineral profile in the traditional sense. Molecular weight: 272.25 g/mol. Molecular formula: C15H12O5. It is the open-chain chalcone precursor to naringenin (a flavanone), formed via enzymatic isomerization by chalcone isomerase. As a compound: Protein: 0g, Fat: 0g, Carbohydrates: 0g, Fiber: 0g. Bioactive compound concentration: Found naturally in tomato skin at approximately 0.3–1.2 mg/g dry weight, making tomato peel one of the richest dietary sources. Also present in citrus peel (grapefruit, oranges) at trace levels typically <0.1 mg/g. Structurally contains three hydroxyl groups (-OH) at positions 2', 4', 6' on the A-ring and position 4 on the B-ring, which confer [antioxidant](/ingredients/condition/antioxidant) radical-scavenging capacity (DPPH IC50 approximately 15–30 µM in vitro). Bioavailability notes: Oral bioavailability is limited due to rapid isomerization to naringenin in acidic gastric conditions and first-pass [metabolism](/ingredients/condition/weight-management); estimated systemic absorption <10% in its intact chalcone form. Lipophilicity (LogP ~2.3) suggests moderate membrane permeability. Intestinal microbiota further metabolize it to phenolic acids including phloroglucinol and 3-(4-hydroxyphenyl)propionic acid. No dietary reference intake (DRI) established. ## Dosage & Preparation No clinically studied dosage ranges are available due to the absence of human studies. Laboratory solubility data indicate various solubilities in DMSO, DMF, ethanol, and PBS. Consult a healthcare provider before starting any new supplement. ## Safety & Drug Interactions Safety data for naringenin chalcone supplementation in humans is extremely limited due to lack of clinical trials. As a citrus-derived flavonoid, it may interact with cytochrome P450 enzymes, potentially affecting drug [metabolism](/ingredients/condition/weight-management) similar to other citrus compounds. Individuals taking blood thinners should exercise caution as flavonoids can affect platelet function. Pregnancy and breastfeeding safety has not been established, so avoidance is recommended during these periods. ## Scientific Research No human clinical trials or meta-analyses have been conducted on naringenin chalcone. The current research is limited to preclinical studies focusing on its biological activities such as apoptosis induction and [inflammatory](/ingredients/condition/inflammation) inhibition. ## Historical & Cultural Context There are no documented traditional or historical medicinal uses of naringenin chalcone in the provided research sources. ## Synergistic Combinations Quercetin, Resveratrol, Curcumin, Green Tea Extract, Vitamin C ## Frequently Asked Questions ### What foods contain naringenin chalcone naturally? Naringenin chalcone is found primarily in citrus fruit peels, particularly grapefruit and orange peels, where it serves as a precursor to naringenin. It's also present in smaller amounts in tomatoes and certain medicinal plants like Alpinia species. ### How much naringenin chalcone should I take daily? No established human dosage exists for naringenin chalcone supplements due to lack of clinical trials. Preclinical studies used concentrations of 10-100 μM, but this cannot be directly translated to human supplementation without safety studies. ### Can naringenin chalcone help with cancer treatment? Preclinical studies show naringenin chalcone induces apoptosis in glioblastoma cells and reduces tumor cell proliferation by 50-80%. However, these are laboratory studies only, and human clinical evidence is completely lacking for any cancer treatment applications. ### Does naringenin chalcone reduce inflammation better than naringenin? Limited comparative studies suggest naringenin chalcone may have stronger anti-inflammatory effects than naringenin, particularly in inhibiting MCP-1 production. However, naringenin has more extensive research supporting its anti-inflammatory benefits in humans. ### Are there side effects from taking naringenin chalcone supplements? Specific side effects of naringenin chalcone supplementation are unknown due to lack of human studies. As a citrus flavonoid, potential side effects may include digestive upset, drug interactions, or allergic reactions in sensitive individuals. ### Does naringenin chalcone have better bioavailability than other flavonoid forms? Naringenin chalcone is a precursor form of naringenin that may offer superior bioavailability compared to naringenin itself, as it can be more readily absorbed in the small intestine before conversion. However, individual absorption rates vary based on gut microbiota composition and intestinal health. Research suggests that chalcone forms of flavonoids may bypass some metabolic barriers, potentially allowing higher circulating levels of active compounds. ### Is naringenin chalcone safe to use alongside antihistamine or allergy medications? While naringenin chalcone demonstrates anti-allergic properties in preclinical studies, no human clinical trials have directly evaluated interactions with antihistamines or prescription allergy medications. If you are taking medications for allergies or immune conditions, consult your healthcare provider before adding naringenin chalcone supplements, as it modulates immune responses that may theoretically interact with these drugs. ### What is the current state of clinical evidence for naringenin chalcone's health benefits in humans? Most evidence for naringenin chalcone comes from preclinical studies demonstrating apoptosis induction, anti-inflammatory, and anti-allergic effects in cell and animal models. Human clinical trials specifically investigating naringenin chalcone are extremely limited, so the translation of these promising laboratory findings to human efficacy remains largely unproven. Strong clinical evidence is needed to support supplementation claims in humans. --- *Source: Hermetica Superfoods Ingredient Encyclopedia — https://ingredients.hermeticasuperfoods.com* *License: CC BY-NC-SA 4.0 — Attribution required. Commercial use: admin@hermeticasuperfoods.com*