Apigenin (Flavonoid) — Hermetica Encyclopedia
Named Bioactive Compounds · Compound

Apigenin (Flavonoid)

Moderate Evidenceflavonoid

Hermetica Superfood Encyclopedia

The Short Answer

Apigenin is a flavone compound found in parsley, celery, and chamomile that exhibits anti-inflammatory and antioxidant properties through its unique C2-C3 double bond structure. This bioactive flavonoid works primarily by inhibiting inflammatory enzymes like cyclooxygenase and lipoxygenase while scavenging free radicals.

PubMed Studies
0
Validated Benefits
Synergy Pairings
At a Glance
CategoryNamed Bioactive Compounds
GroupCompound
Evidence LevelModerate
Primary Keywordapigenin benefits
Synergy Pairings3
Apigenin (Flavonoid) — botanical
Apigenin (Flavonoid) — botanical close-up

Health Benefits

Origin & History

Apigenin (Flavonoid) — origin
Natural habitat

Apigenin is a flavone compound (C15H10O5) that appears as a pale yellow crystalline solid with a melting point of 345-350°C. It occurs naturally in high concentrations in parsley, celery, celeriac, and chamomile flowers, and is biosynthesized through the phenylpropanoid pathway from phenylalanine or tyrosine via enzymes including chalcone synthase and flavone synthase.

The research dossier did not provide information on traditional or historical uses of apigenin in any traditional medicine systems. No historical context or duration of traditional use was documented.Traditional Medicine

Scientific Research

The research dossier reveals a significant gap in clinical evidence - no human clinical trials, randomized controlled trials, or meta-analyses for apigenin were identified. All available evidence comes from preclinical laboratory and cell culture studies examining antioxidant, anti-inflammatory, and anti-tumor properties.

Preparation & Dosage

Apigenin (Flavonoid) — preparation
Traditional preparation

No clinically studied dosage ranges for apigenin in any form (extract, powder, or standardized preparations) were identified in the available research. Consult a healthcare provider before starting any new supplement.

Nutritional Profile

Apigenin (4',5,7-trihydroxyflavone) is a pure flavonoid compound (molecular weight: 270.24 g/mol), not a whole food, so traditional macronutrient/micronutrient profiling does not apply. As a bioactive compound: Primary identity: Flavone subclass of flavonoids, comprising a phenyl-benzopyranone backbone with hydroxyl groups at positions 4', 5, and 7. Natural dietary concentrations: Parsley (dried): 45,000–180,000 mg/kg dry weight (highest known source); Chamomile flowers (dried): 3,000–5,000 mg/kg; Celery: 19–100 mg/kg fresh weight; Artichokes: 3–11 mg/kg fresh weight; Oregano (dried): ~1,500–4,000 mg/kg. Typical dietary intake: Estimated 0.45–1.5 mg/day in Western diets. Bioavailability: Oral bioavailability is low (estimated <1–5% in free aglycone form) due to poor water solubility (logP ~2.7) and rapid Phase II metabolism (glucuronidation and sulfation in intestinal epithelium and liver). Glycosylated forms (e.g., apigenin-7-glucoside from parsley) require gut microbiota hydrolysis before absorption, delaying but potentially enhancing bioavailability. Peak plasma concentrations in human studies: approximately 0.1–0.5 µmol/L following typical dietary intake. Half-life: approximately 91 hours (extended due to enterohepatic recirculation). Protein binding: >95% bound to serum albumin. No caloric, fiber, vitamin, or mineral content as an isolated compound.

How It Works

Mechanism of Action

Apigenin exerts its effects through multiple molecular pathways, primarily inhibiting cyclooxygenase (COX) and lipoxygenase (LOX) enzymes that produce inflammatory mediators. The compound's C2-C3 double bond and B-ring hydroxyl groups enable direct free radical scavenging and metal ion chelation. Apigenin also modulates nuclear factor-kappa B (NF-κB) signaling pathways, reducing inflammatory cytokine production.

Clinical Evidence

Current evidence for apigenin consists primarily of preclinical studies in cell cultures and animal models, with limited human clinical trials available. Laboratory studies demonstrate significant anti-inflammatory activity with IC50 values ranging from 10-50 μM for COX inhibition. Small human studies on chamomile extract (containing apigenin) suggest mild anti-anxiety effects, but isolated apigenin supplementation lacks robust clinical validation. Most research focuses on apigenin's potential anti-cancer properties, though human efficacy data remains insufficient.

Safety & Interactions

Apigenin appears generally safe when consumed through food sources, with no significant adverse effects reported in preclinical studies at typical supplemental doses (50-100mg daily). The compound may interact with cytochrome P450 enzymes, potentially affecting drug metabolism of medications like warfarin and certain chemotherapy agents. Limited data exists regarding safety during pregnancy and lactation, so avoidance is recommended. High-dose supplementation may cause mild gastrointestinal upset in sensitive individuals.

Drug & Supplement Interactions

9 documented interactions for Apigenin (Flavonoid). Click any row to read the full explanation. Always consult your healthcare provider before combining supplements with medications.

Moderate9
  • Alprazolam

    Both Apigenin and Alprazolam work on the same calming brain receptors (GABA). Taking them together may cause excessive drowsiness, sedation, or impaired coordination beyond what either would cause alone.

    What to do: Avoid taking Apigenin at the same time as Alprazolam. If using both, start with a low dose of Apigenin (50mg) and monitor for excessive drowsiness. Do not drive or operate heavy machinery until you know how the combination affects you.

    Timing: Separate by at least 4-6 hours if possible. Avoid taking Apigenin at bedtime if you also take Alprazolam at night.

    Full interaction details →
  • Lorazepam

    Apigenin and Lorazepam both work on GABA brain receptors. Together they may cause excessive calming effects including heavy drowsiness.

    What to do: Reduce Apigenin dose when using Lorazepam. Do not take together before activities requiring alertness.

    Timing: Take Lorazepam only as prescribed. Apigenin (a flavonoid found in chamomile) has mild GABA-ergic and sedative properties — it acts on the same receptor pathway as benzodiazepines. Taking both may amplify sedation. Space at least 4-6 hours apart, and take Apigenin at a lower dose. Avoid driving or operating machinery if using both. Discuss this combination with your prescriber.

    Full interaction details →
  • Clonazepam

    Both Apigenin and Clonazepam activate the same calming brain receptors. Taking them together could cause too much sedation.

    What to do: Use low-dose Apigenin if combining. Avoid concurrent dosing. Monitor for next-day drowsiness given Clonazepam long half-life.

    Timing: Given Clonazepam long half-life, timing separation may be less effective. Use lower doses of both.

    Full interaction details →
  • Diazepam

    Both substances calm the brain through GABA receptors. Together they may cause excessive sedation, drowsiness, and impaired reflexes.

    What to do: Use caution. Reduce Apigenin dose or separate timing. Do not combine at bedtime without medical guidance. Avoid driving.

    Timing: Separate by 4-6 hours. Avoid concurrent nighttime dosing.

    Full interaction details →
  • Warfarin

    Apigenin can slow down how your body processes Warfarin by blocking a liver enzyme (CYP2C9). This could make Warfarin more potent than expected, increasing the risk of dangerous bleeding.

    What to do: CRITICAL: Inform your anticoagulation clinic that you take Apigenin. Request more frequent INR monitoring (weekly) when starting or stopping Apigenin. Do not change Apigenin dose without informing your prescriber. Watch for signs of bleeding.

    Timing: CYP inhibition effects are cumulative. Timing separation does not eliminate the risk. Consistent daily dosing is more predictable than intermittent use.

    Full interaction details →
  • Combined Oral Contraceptives

    Apigenin has mild estrogen-like effects in the body. This could theoretically interfere with how your birth control pill works, though this has not been proven in human studies. It is a precautionary concern.

    What to do: The risk is theoretical, not proven. If using hormonal birth control, keep Apigenin doses moderate (under 100mg/day). Consider backup contraception if taking high doses. Report any breakthrough bleeding to your gynecologist.

    Timing: Take Combined Oral Contraceptives at the same time every day — consistency is essential for contraceptive efficacy. Apigenin can be taken with a separate meal. Apigenin has mild estrogenic activity in some studies, which could theoretically interact with hormonal contraception, though clinical significance at supplement doses is likely minimal. Monitor for any changes in breakthrough bleeding.

    Full interaction details →
  • Zolpidem

    Both Apigenin and Zolpidem (Ambien) make you sleepy by acting on the same brain receptors. Together, they could cause excessive sedation or dangerous oversedation.

    What to do: Do not take these together without medical guidance. If using both for sleep, start Apigenin at a very low dose. Consider using one or the other, not both.

    Timing: Do not take simultaneously at bedtime. If using both, take Apigenin earlier in the evening and Zolpidem at bedtime.

    Full interaction details →
  • Caffeine

    Apigenin slows down how your body processes caffeine. If you take both, your morning coffee or caffeine supplement may feel stronger and last longer than usual, potentially causing jitteriness or insomnia.

    What to do: If you take Apigenin regularly, you may need less caffeine than usual. Reduce coffee/caffeine intake by 25-50% when starting Apigenin. Avoid caffeine after 2pm if taking Apigenin for sleep.

    Timing: Take Apigenin in the evening and caffeine in the morning for natural separation. CYP1A2 inhibition may still be present but less impactful with 8-10 hour separation.

    Full interaction details →
  • Theophylline

    Apigenin blocks the liver enzyme (CYP1A2) that breaks down Theophylline. This could cause Theophylline to build up in your body to dangerous levels, causing nausea, rapid heartbeat, or seizures.

    What to do: IMPORTANT: If you take Theophylline for asthma or COPD, inform your pulmonologist before using Apigenin. Request theophylline level monitoring. Consider avoiding this combination or using very low Apigenin doses.

    Timing: CYP1A2 inhibition is not eliminated by timing separation. If combining, maintain consistent Apigenin dosing and monitor theophylline levels.

    Full interaction details →

Educational information only. Always consult a qualified healthcare provider before changing your supplement or medication regimen.

Synergy Stack

Hermetica Formulation Heuristic

Also Known As

4',5,7-trihydroxyflavone5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-oneApigenolChamomile flavonoidVersulinC15H10O54',5,7-trihydroxy-2-phenyl-4H-1-benzopyran-4-one

Frequently Asked Questions

What foods contain the most apigenin?
Parsley contains the highest apigenin concentrations at approximately 215mg per 100g fresh weight, followed by celery leaves (19mg/100g) and dried chamomile flowers (3-5mg/g). Other sources include oranges, onions, and wheat sprouts, though in much lower concentrations.
What is the recommended apigenin dosage?
No official dosage guidelines exist for apigenin supplements, but research studies typically use 50-100mg daily. Most commercial supplements contain 25-50mg per serving, often combined with other flavonoids for enhanced absorption.
Does apigenin help with sleep and anxiety?
Apigenin may promote relaxation through its binding to benzodiazepine receptors in the brain, particularly when consumed as chamomile tea. However, isolated apigenin supplements lack clinical evidence for sleep or anxiety benefits, with most positive studies using whole chamomile extracts.
Can apigenin interact with medications?
Apigenin may inhibit CYP3A4 and CYP2C9 enzymes, potentially increasing blood levels of medications like warfarin, some statins, and certain chemotherapy drugs. Consult healthcare providers before combining apigenin supplements with prescription medications.
Is apigenin better absorbed with other compounds?
Apigenin absorption is enhanced when consumed with fats or oils due to its lipophilic nature, and piperine (from black pepper) may increase bioavailability by up to 200%. Many supplements include quercetin or vitamin C to improve stability and absorption.
How does apigenin's chemical structure contribute to its antioxidant and anti-inflammatory effects?
Apigenin's antioxidant and anti-inflammatory properties are primarily attributed to its C2-C3 double bond structure and the positioning of its B-ring, which allow it to neutralize free radicals and modulate inflammatory pathways. These structural features enable apigenin to donate electrons to reactive oxygen species, though most evidence for these mechanisms comes from laboratory and preclinical studies rather than human clinical trials. The specific positioning of hydroxyl groups on the flavonoid backbone also contributes to its ability to inhibit pro-inflammatory enzymes and signaling molecules.
What does current research show about apigenin's potential anti-cancer properties?
Laboratory and preclinical studies demonstrate that apigenin exhibits potential anti-tumor activity through multiple mechanisms, including cell cycle arrest and apoptosis induction in cancer cell lines. However, it is crucial to note that these anti-cancer effects have only been observed in controlled laboratory settings and animal models, not yet conclusively proven in human clinical trials. Current evidence does not support apigenin as a standalone cancer treatment, and anyone with cancer concerns should consult with oncology professionals rather than relying on apigenin supplementation.
Who is most likely to benefit from apigenin supplementation based on current evidence?
Individuals interested in antioxidant and anti-inflammatory support may be candidates for apigenin supplementation, though robust clinical evidence in human populations remains limited. Those already consuming apigenin-rich foods (such as chamomile tea, parsley, and celery) may achieve modest intake without supplements. People with specific health concerns should consult healthcare providers before starting apigenin supplements, particularly those on medications or with pre-existing health conditions, as individual responses and interactions vary significantly.

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