Apigenin-7-O-glucoside (Flavonoid Glycoside)

Apigenin-7-O-glucoside is a flavonoid glycoside that consists of apigenin bound to glucose, primarily derived from chamomile and other plants in the Asteraceae family. This compound exhibits anti-inflammatory activity by inhibiting LPS-induced nitric oxide production in macrophages and demonstrates antioxidant effects through reactive oxygen species scavenging.

Origin & History

Apigenin-7-O-glucoside is a flavonoid glycoside where apigenin is substituted at the 7-position with a β-D-glucopyranosyl moiety, with molecular formula C21H20O10. It occurs naturally in various plants as a bioactive compound and appears as a pale yellow to yellow solid with a melting point of 230-237°C.

Historical & Cultural Context

No information on historical or traditional medicinal uses is available in current research sources.

Health Benefits

• Anti-inflammatory effects demonstrated in vitro through inhibition of LPS-induced nitric oxide production in RAW 264.7 macrophage cells (preliminary evidence)
• Antioxidant activity shown through reactive oxygen species scavenging in laboratory studies (preliminary evidence)
• Anti-proliferative effects observed in cell culture studies (preliminary evidence)
• Potential anxiolytic properties reported in preclinical research (preliminary evidence)
• May support cellular health through multiple bioactive mechanisms (preliminary evidence)

How It Works

Apigenin-7-O-glucoside inhibits lipopolysaccharide-induced nitric oxide synthase (iNOS) expression in RAW 264.7 macrophage cells, reducing inflammatory nitric oxide production. The compound scavenges reactive oxygen species including superoxide anions and hydroxyl radicals through its phenolic hydroxyl groups. Upon metabolism, the glucose moiety is cleaved to release free apigenin, which can interact with cyclooxygenase enzymes and nuclear factor-kappa B signaling pathways.

Scientific Research

No human clinical trials, randomized controlled trials (RCTs), or meta-analyses specifically on apigenin-7-O-glucoside were identified. Current research is limited to preclinical in vitro studies demonstrating anti-inflammatory and antioxidant activities.

Clinical Summary

Current evidence for apigenin-7-O-glucoside is limited to preliminary in vitro studies using cell culture models. Laboratory studies have demonstrated anti-inflammatory effects in RAW 264.7 macrophage cells and antioxidant activity in chemical assays, but specific quantified outcomes and sample sizes are not well-documented in published literature. Anti-proliferative effects have been observed in preliminary research, though complete data on these studies is limited. Human clinical trials specifically investigating apigenin-7-O-glucoside are currently lacking, making it difficult to establish therapeutic efficacy and optimal dosing protocols.

Nutritional Profile

Apigenin-7-O-glucoside is a flavonoid glycoside (a glycosylated form of the aglycone apigenin) and is not a macronutrient source; it contributes negligible calories, protein, fat, or fiber when consumed in typical dietary or supplemental amounts. Molecular weight: 432.38 g/mol (apigenin aglycone: 270.24 g/mol; glucose moiety adds ~162 g/mol). Bioactive compound classification: flavone glycoside, subclass of flavonoids. Naturally found in parsley (Petroselinum crispum) at concentrations of approximately 1,500–4,500 mg/kg dry weight, chamomile (Matricaria chamomilla) flowers at approximately 3–8 mg/g dry weight, celery (Apium graveolens) at 10–300 mg/kg fresh weight, and artichoke leaves at variable concentrations of 50–200 mg/kg. Typical supplemental doses studied range from 25–100 mg per dose. Bioavailability: the glucose moiety at the 7-position renders the compound more water-soluble than the aglycone apigenin, improving oral absorption; intestinal and colonic microbiota hydrolyze the glycosidic bond releasing free apigenin, which is subsequently absorbed in the small intestine and colon. Peak plasma concentrations occur approximately 1–2 hours post-ingestion for the glycoside form. Apigenin undergoes phase II conjugation (glucuronidation and sulfation) in intestinal epithelium and liver, with metabolites excreted renally. Absolute oral bioavailability remains low (estimated <10–20% for the aglycone after hydrolysis), though the glycoside form shows improved solubility compared to apigenin alone. No meaningful vitamin or mineral content is contributed by this isolated compound.

Preparation & Dosage

No clinically studied dosage ranges are available as human trials are lacking. Forms, standardization details, and therapeutic doses have not been established. Consult a healthcare provider before starting any new supplement.

Synergy & Pairings

Other flavonoids, quercetin, vitamin C, green tea extract, curcumin

Safety & Interactions

Safety data specific to apigenin-7-O-glucoside is limited due to lack of human studies, though the parent compound apigenin is generally well-tolerated in dietary amounts. Potential interactions may occur with anticoagulant medications due to flavonoid effects on platelet aggregation and cytochrome P450 enzymes. Individuals with allergies to plants in the Asteraceae family (chamomile, ragweed, chrysanthemums) should exercise caution. Pregnancy and breastfeeding safety has not been established for concentrated apigenin-7-O-glucoside supplements.