Eupatorin

Eupatorin is a polymethoxyflavone compound found in Asteraceae plants that exhibits anti-cancer and anti-inflammatory properties. It works primarily by inducing apoptosis in cancer cells and modulating inflammatory cytokine pathways.

Origin & History

Eupatorin is a polymethoxy flavone extracted from Orthosiphon stamineus, commonly known as Java tea. It is isolated through chromatographic methods and is recognized as the major bioactive component of this traditional medicinal plant.

Historical & Cultural Context

Orthosiphon stamineus, from which eupatorin is extracted, is traditionally used in herbal medicine. Although specific uses of eupatorin are not well-documented, Java tea has been employed for its potential health benefits in various cultures.

Health Benefits

• Shows potential in delaying tumor development and reducing metastasis in a breast cancer model (PMID: 32830560) [Preclinical]. • Induces apoptosis and suppresses proliferation in various cancer cell lines (PMID: 22227008) [Cell-based]. • Reduces pro-inflammatory cytokine expression in osteoarthritis models (PMID: 41504045) [In vitro]. • Enhances immune response by increasing specific splenocyte populations (PMID: 32830560) [Animal]. • Delays amyloidogenesis of Aβ peptides, suggesting neuroprotective potential (PMID: 37239029) [In vitro].

How It Works

Eupatorin induces apoptosis in cancer cells through activation of caspase pathways and cell cycle arrest at G2/M phase. It suppresses pro-inflammatory cytokines including TNF-α, IL-1β, and IL-6 by inhibiting NF-κB signaling. The compound also demonstrates anti-metastatic effects by reducing matrix metalloproteinase expression and cell migration capacity.

Scientific Research

Current evidence for eupatorin is limited to preclinical and animal studies. Notable studies include a 4T1 murine breast cancer model showing delayed tumor development (PMID: 32830560) and in vitro models demonstrating effects on amyloid-beta (PMID: 37239029). No human clinical trials have been conducted.

Clinical Summary

Current evidence for eupatorin is limited to preclinical studies and cell-based research. In vitro studies show significant apoptosis induction in multiple cancer cell lines with IC50 values ranging from 10-50 μM. Animal models demonstrate tumor growth inhibition and reduced metastasis in breast cancer, though human clinical trials are lacking. Anti-inflammatory effects have been observed in osteoarthritis cell models, but clinical validation is needed.

Nutritional Profile

Eupatorin (5,3'-dihydroxy-6,7,4'-trimethoxyflavone; C₁₈H₁₆O₇; MW ~344.32 g/mol) is a polymethoxylated flavone, not a nutritional macronutrient source. It provides no significant calories, protein, fat, fiber, or carbohydrate content at pharmacologically relevant doses. Key details: • **Chemical class:** Lipophilic methoxylated flavone belonging to the broader flavonoid family. • **Natural sources & approximate concentrations:** Found in Orthosiphon stamineus (Java tea/Cat's Whiskers) at ~0.3–2.0% of dried leaf extract; Lantana camara leaves; Artemisia vulgaris; Salvia species; and several Eupatorium species. Concentrations vary widely by plant part, cultivar, geography, and extraction method. • **Bioactive compound profile:** As a single-entity phytochemical, eupatorin itself is the bioactive. It bears three methoxy groups (C-6, C-7, C-4') and two free hydroxyls (C-5, C-3'), which govern its biological activity. It is structurally related to sinensetin, salvigenin, and cirsimaritin. • **Micronutrients:** Not a meaningful source of vitamins or minerals. • **Bioavailability notes:** Oral bioavailability is expected to be low-to-moderate, consistent with other polymethoxylated flavones. The methoxy groups increase lipophilicity (estimated log P ~2.5–3.0), which may improve membrane permeability relative to polyhydroxylated flavones but also subjects it to extensive Phase I (CYP450-mediated O-demethylation) and Phase II (glucuronidation, sulfation) hepatic metabolism. Intestinal absorption is passive transcellular. Plasma half-life in rodent models appears short (estimated 1–4 hours). Co-administration with lipids or formulation in nanoparticle/liposomal carriers may enhance absorption. No validated human pharmacokinetic data are currently published. • **Stability:** Relatively stable under mildly acidic conditions; susceptible to degradation under prolonged UV exposure and strongly alkaline pH. • **Typical experimental doses (preclinical):** In vitro studies commonly use 1–100 µM; in vivo rodent studies use approximately 10–100 mg/kg body weight orally or intraperitoneally. No established human dietary reference intake or recommended dose exists.

Preparation & Dosage

Animal studies used dosages of 5 mg/kg and 20 mg/kg in mice and 1–20 μg/mL concentrations in C. elegans models. Consult a healthcare provider before starting any new supplement.

Synergy & Pairings

scutellarein, resveratrol, curcumin, quercetin, green tea extract

Safety & Interactions

Safety data for eupatorin in humans is extremely limited due to lack of clinical trials. No established dosage recommendations or toxicity profiles exist for human consumption. Potential interactions with chemotherapy drugs or anti-inflammatory medications are unknown and require caution. Pregnancy and breastfeeding safety has not been evaluated, making use inadvisable during these periods.