Fagopyrin

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Family of organic compounds found in buckwheat

title: "Fagopyrin" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["piperidines", "hydroxyarenes", "plant-toxins", "quinones"] description: "Family of organic compounds found in buckwheat" topic_path: "general/piperidines" source: "https://en.wikipedia.org/wiki/Fagopyrin" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Family of organic compounds found in buckwheat ::

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 455303239 | Name = Fagopyrin | ImageFile = Fagopyrin.svg | ImageClass = skin-invert-image | ImageAlt = Structural formula of fagopyrin | ImageFile1 = Fagopyrin 3D ball.png | ImageClass1 = bg-transparent | ImageAlt1 = Ball-and-stick model of the fagopyrin molecule | IUPACName = 1,3,4,6,8,13-Hexahydroxy-10,11-dimethyl-2,5-di(piperidin-2-yl)fenantro[1,10,9,8-opqra]peryleen-7,14-dion | OtherNames = |Section1={{Chembox Identifiers | CASNo = 72393-03-4 | CASNo_Ref = | ChemSpiderID = 4589856 | PubChem = 5488537 | SMILES = O=C1C2=C(C3=C(O)C(C4CCCCN4)=C2O)C(C5=C6C(C)=CC(O)=C15)=C7C(C3=C(O)C(C8NCCCC8)=C9O)=C9C(C%10=C7C6=C(C)C=C%10O)=O | StdInChI=1S/C40H34N2O8/c1-13-11-17(43)23-25-19(13)20-14(2)12-18(44)24-26(20)28-27(25)29-31(35(45)21(15-7-3-5-9-41-15)37(47)33(29)39(23)49)32-30(28)34(40(24)50)38(48)22(36(32)46)16-8-4-6-10-42-16/h11-12,15-16,41-48H,3-10H2,1-2H3 | StdInChIKey = ROFJUMITFMRBRF-UHFFFAOYSA-N |Section2={{Chembox Properties | C=40|H=34|N=2|O=8 | Appearance = Red pigment | Density = | MeltingPt = | BoilingPt = | Solubility =

Fagopyrin is a phototoxic substance found in the flowers of buckwheat (Fagopyrum esculentum). Their chemical structure contains a naphthodianthrone skeleton similar to that of hypericin. After exposure, fagopyrin can cause sensitivity to light, also called fagopyrism, an itchy skin rash.

History and occurrence

The substance was isolated from flowers of the red-flowering genotype of buckwheat in 1941, and its chemical structure, which is derived from hypericin, was first described in 1979. Within the edible parts of the plant, it is found exclusively in the brown fruit husk of buckwheat grains.

Fagopyrin is located almost exclusively in the cotyledons of the buckwheat herb.

Structure

[[File:Fagopyrum_esculentum_kz14.jpg|thumb|True buckwheat]] Recent literature describes several variants of fagopyrin, referred to as fagopyrins A to F. They differ in methylation at positions C-10 and C-11 and contain piperidineyl or pyrrolidineyl residues at C-2 and C-5.

Biosynthesis and properties

The biosynthetic precursor of fagopyrin is protofagopyrin. This proto-compound converts under the influence of light by cyclization into fagopyrin, which is lipophilic and cannot be extracted with water. The content of fagopyrin in tea preparations is generally below the detection limit (

A solution of fagopyrin in pyridine exhibits a red color.

References

References

  1. (1950). "Fagopyrin, ein photodynamischer Farbstoff aus Buchweizen (Fagopyrum esculentum)". Die Naturwissenschaften.
  2. (2014). "Isolation, analysis and structures of phototoxic fagopyrins from buckwheat". Food Chemistry.
  3. (2013). "The content of fagopyrin and polyphenols in common and tartary buckwheat sprouts". Acta Pharmaceutica.
  4. (2025). "Distribution of photosensitive fagopyrin in buckwheat flowers and its potential biological relevance". Scientific Reports.
  5. Montag, Andreas. (2023). "Pflanzen und Haut Dermatologisch bedeutsame Abwehrstrategien der Pflanzen in Europa". Springer-Verlag.
  6. (2014). "Isolation, analysis and structures of phototoxic fagopyrins from buckwheat". Food Chemistry.
  7. (2006). "Pharmakognosie - Phytopharmazie". Springer-Verlag.
  8. (2011). "Fagopyrin and its derivatives in buckwheat (Fagopyrum sp.)".
  9. (1989). "Fagopyrin". CRC Press.

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piperidineshydroxyarenesplant-toxinsquinones