Hermetica Superfood Encyclopedia
The Short Answer
Bergapten (5-methoxypsoralen) is a naturally occurring furanocoumarin found in citrus peels, parsley, and angelica root that functions as a photosensitizing agent. Its primary mechanism involves intercalating into DNA strands upon UVA activation, forming cyclobutane adducts that modulate cellular proliferation and immune responses in skin tissue.
CategoryNamed Bioactive Compounds
GroupCompound
Evidence LevelModerate
Primary Keywordbergapten benefits
Synergy Pairings5
Bergapten (5-methoxypsoralen) — botanical close-up
Health Benefits
Origin & History
Natural habitat
Bergapten (5-methoxypsoralen) is a naturally occurring furanocoumarin found in essential oils from bergamot (Citrus bergamia) and other citrus species. It is typically extracted from bergamot oil or citrus fruits via solvent extraction or steam distillation of plant materials.
“While no specific traditional medicine systems are documented for bergapten use, it represents a modern application of natural psoralen derivatives from citrus plants for photochemotherapy. This builds upon historical psoralen traditions for treating skin disorders.”Traditional Medicine
Scientific Research
Clinical trials have primarily evaluated bergapten in photochemotherapy for skin disorders, with one randomized trial (n=169) comparing oral bergapten at 0.6-1.2 mg/kg to 8-MOP showing similar efficacy with minimal side effects. A trial in 40 atopic dermatitis patients demonstrated bergapten's superiority over UVA1 alone with 12-month follow-up benefits (PMID: 3279089 for related psoriasis photochemotherapy summary).
Preparation & Dosage
Traditional preparation
Clinically studied oral doses for psoriasis photochemotherapy range from 0.6-1.2 mg/kg body weight, administered before UVA exposure. No standardized extract forms have been studied in humans. Consult a healthcare provider before starting any new supplement.
Nutritional Profile
Bergapten (5-methoxypsoralen) is a naturally occurring furocoumarin compound, not a nutritional ingredient, and thus lacks conventional macronutrient or micronutrient content. It is a pure bioactive phytochemical with molecular formula C12H8O4 and molecular weight of 216.19 g/mol. Found naturally in plants at varying concentrations: bergamot oil contains approximately 0.3–1.8% bergapten by weight, celery (Apium graveolens) contains roughly 0.004–0.085 mg/g fresh weight, parsley contains approximately 0.003–0.02 mg/g, and fig leaves contain up to 0.12 mg/g. Grapefruit juice contains trace amounts (~0.001–0.01 mg/mL). As a furocoumarin, it contains no protein, fat, carbohydrates, fiber, vitamins, or minerals. Its biological activity is not nutritional but pharmacological, acting as a photosensitizing agent that intercalates with DNA upon UVA activation (320–400 nm). Bioavailability when ingested orally is moderate, with peak plasma concentrations reached within 1–2 hours; it undergoes hepatic first-pass metabolism via CYP450 enzymes (notably CYP3A4 inhibition). Lipophilic in nature (logP approximately 1.9), facilitating membrane permeability. Used therapeutically at doses of approximately 20–40 mg per session in photochemotherapy (PUVA) protocols, considerably lower than 8-methoxypsoralen.
How It Works
Mechanism of Action
Bergapten absorbs UVA radiation (320–400 nm) and undergoes a photochemical reaction to form mono- and bi-functional covalent crosslinks with pyrimidine bases in DNA, inhibiting replication in hyperproliferating keratinocytes central to psoriasis pathology. It also modulates the expression of cytokines including IL-2 and TNF-α and suppresses T-lymphocyte activity by inhibiting calmodulin-dependent processes. Additionally, bergapten interacts with melanocyte-stimulating pathways, upregulating tyrosinase activity and promoting melanin synthesis relevant to vitiligo repigmentation.
Clinical Evidence
Randomized controlled trials comparing bergapten-PUVA (photochemotherapy) to 8-methoxypsoralen (8-MOP)-PUVA in psoriasis patients have demonstrated equivalent clearance rates—typically 70–85% improvement in PASI scores—while bergapten produced significantly lower rates of nausea and hepatotoxicity. A double-blind crossover study in approximately 50 psoriasis patients found that 5-MOP required modestly higher UVA doses for equivalent response but caused gastrointestinal side effects in fewer than 10% of subjects versus roughly 40% with 8-MOP. Evidence for vitiligo is moderate, with open-label and small controlled studies showing partial to complete repigmentation in 40–60% of patients after 6–12 months of topical or oral 5-MOP-PUVA therapy. Preliminary in vitro and animal data suggest antifungal properties against dermatophytes, though human clinical trials in this application remain limited.
Safety & Interactions
Bergapten carries a significant phototoxicity risk; sun or UVA exposure within 8–12 hours of oral ingestion or topical application can cause severe erythema, blistering, and hyperpigmentation. Long-term PUVA therapy using bergapten is associated with increased risk of squamous cell carcinoma and melanoma, necessitating periodic skin surveillance. It is a known inhibitor of CYP1A2 and CYP3A4 enzymes, potentially elevating plasma concentrations of substrates such as warfarin, caffeine, and certain statins; co-administration requires clinical monitoring. Bergapten is contraindicated in pregnancy due to mutagenic potential demonstrated in vitro, in patients with lupus erythematosus or xeroderma pigmentosum, and in individuals with a history of photosensitizing conditions.
Synergy Stack
Hermetica Formulation Heuristic
Also Known As
5-methoxypsoralen5-MOPBergamot psoralenCitrus bergamia extract5-methoxy-7H-furo[3,2-g]chromen-7-oneBergamot furanocoumarin
Frequently Asked Questions
How does bergapten compare to 8-methoxypsoralen for psoriasis treatment?
Bergapten (5-MOP) achieves clinically equivalent PASI score reductions to 8-MOP in PUVA therapy but requires approximately 20–30% higher UVA doses to reach the same therapeutic endpoint. Its primary advantage is a substantially lower incidence of nausea and vomiting—under 10% versus up to 40% with 8-MOP—making patient compliance significantly better in comparative trials.
What foods contain bergapten naturally?
Bergapten is found in highest concentrations in bergamot orange peel (Citrus bergamia), from which it was first isolated, as well as in grapefruit, lime, and lemon rind, parsley (Petroselinum crispum), celery (Apium graveolens), and angelica root (Angelica archangelica). Bergamot essential oil can contain 0.3–0.5% bergapten by weight, though bergapten-free variants are produced for cosmetic use specifically to eliminate phototoxicity risk.
What is the typical dose of bergapten used in PUVA therapy?
In oral PUVA protocols, bergapten is typically administered at 1.2–1.5 mg/kg body weight approximately 2 hours before UVA exposure, compared to 0.6–0.8 mg/kg for 8-MOP, reflecting its lower intrinsic photosensitivity potency. Topical formulations for localized psoriasis or vitiligo commonly use 0.001–0.01% bergapten solutions applied 15–30 minutes prior to controlled UVA irradiation.
Can bergapten cause skin cancer with long-term use?
Yes, long-term PUVA therapy involving bergapten is associated with a dose-dependent elevated risk of squamous cell carcinoma, estimated to be 10–100 times higher than the general population after more than 200 treatment sessions in studies of psoralen-PUVA cohorts. Melanoma risk is also modestly increased with prolonged exposure, and current guidelines recommend limiting cumulative lifetime UVA dose and conducting annual full-body skin examinations for patients undergoing extended PUVA regimens.
Does bergapten interact with any medications?
Bergapten inhibits cytochrome P450 enzymes CYP1A2 and CYP3A4, which are responsible for metabolizing drugs including warfarin, theophylline, cyclosporine, and certain calcium channel blockers, potentially increasing their plasma levels and risk of toxicity. Concurrent use with other photosensitizing agents—such as fluoroquinolone antibiotics, tetracyclines, thiazide diuretics, or amiodarone—can synergistically amplify phototoxic reactions and should be avoided or managed with adjusted UVA dosing.
Is bergapten safe for children or the elderly during photochemotherapy treatment?
Bergapten use in children requires careful medical supervision due to increased photosensitivity risk and developing skin, making pediatric PUVA therapy less common than in adults. Elderly patients may use bergapten safely but should be monitored closely for cumulative UV exposure effects and potential interactions with age-related medications or skin conditions.
What is the evidence quality for bergapten's effectiveness in treating mycosis fungoides?
Clinical evidence for bergapten in mycosis fungoides treatment is currently preliminary, based on limited case reports and small studies showing good patient tolerance and promising response rates. Larger, randomized controlled trials are needed to establish bergapten as a standard photochemotherapy option for this condition compared to established treatments like 8-MOP.
How does bergapten absorption vary based on food intake or formulation type?
Bergapten bioavailability is typically enhanced when taken with fatty foods, which improve intestinal absorption of this lipophilic compound. Pharmaceutical formulations (tablets, solutions) show more consistent absorption compared to dietary sources, making standardized dosing in clinical settings more reliable for PUVA therapy applications.
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