Fagopyrin

Fagopyrin

Fagopyrin is a naturally occurring compound found in the Polygonaceae family of plants, most notably in buckwheat (Fagopyrum spp.). It is a naphthodianthrone, a type of phytochemical that is structurally similar to many compounds with known biological activity. Fagopyrin is known for its phototoxic effects, which can cause skin inflammation in individuals exposed to sunlight after consuming large amounts of buckwheat.

Chemical Structure and Properties

Fagopyrin is a polycyclic aromatic compound with a complex structure that includes five fused rings. It is a member of the naphthodianthrone class of compounds, which also includes the well-known compound hypericin, found in St. John's wort (Hypericum perforatum). Fagopyrin is a lipophilic compound, meaning it is soluble in fats and oils but not in water.

Occurrence and Extraction

Fagopyrin is found in several species of the genus Fagopyrum, including Fagopyrum esculentum (common buckwheat) and Fagopyrum tataricum (Tartary buckwheat). The compound is concentrated in the leaves and flowers of the plant, but can also be found in the seeds. Extraction of fagopyrin is typically achieved using organic solvents such as ethanol or methanol.

Biological Effects

The most notable effect of fagopyrin is its phototoxicity. When an individual consumes a large amount of fagopyrin and is then exposed to sunlight, the compound can cause a skin reaction known as fagopyrism. This condition is characterized by inflammation, redness, and itching of the skin. The mechanism of action is thought to involve the generation of reactive oxygen species when fagopyrin absorbs light, leading to cellular damage.

Safety and Toxicity

While fagopyrin is toxic in large amounts, the levels found in commonly consumed parts of buckwheat plants are generally considered safe. However, individuals with a sensitivity to the compound or those who consume large amounts of buckwheat may be at risk of developing fagopyrism. It is recommended to limit consumption of buckwheat greens and to avoid exposure to sunlight after consuming large amounts of buckwheat.

See Also

• Buckwheat
• Phytochemical
• Phototoxicity

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