Fagopyrin

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Fagopyrin
Fagopyrin.svg
Fagopyrin 3D ball.png
Names
IUPAC name
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
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=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
    Key: ROFJUMITFMRBRF-UHFFFAOYSA-N
  • 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
Properties
C40H34N2O8
Molar mass 670.718 g·mol−1
AppearanceRed pigment
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Fagopyrin is a term used for several closely related naturally occurring substances in the buckwheat plant. [1] Their chemical structure contains a naphthodianthrone skeleton similar to that of hypericin. [2]

Fagopyrin is located almost exclusively in the cotyledons of the buckwheat herb. When ingested, fagopyrins cause sensitivity to light. [3]

Related Research Articles

<span class="mw-page-title-main">Buckwheat</span> Species of flowering plant in the family Polygonaceae

Buckwheat or common buckwheat is a flowering plant in the knotweed family Polygonaceae cultivated for its grain-like seeds and as a cover crop. Buckwheat originated around the 6th millennium BCE in the region of what is now Yunnan Province in southwestern China. The name "buckwheat" is used for several other species, such as Fagopyrum tataricum, a domesticated food plant raised in Asia.

<span class="mw-page-title-main">Flavonoid</span> Class of plant and fungus secondary metabolites

Flavonoids are a class of polyphenolic secondary metabolites found in plants, and thus commonly consumed in the diets of humans.

<span class="mw-page-title-main">Oxalate</span> Any derivative of oxalic acid; chemical compound containing oxalate moiety

Oxalate is an anion with the chemical formula C2O2−4. This dianion is colorless. It occurs naturally, including in some foods. It forms a variety of salts, for example sodium oxalate, and several esters such as dimethyl oxalate. It is a conjugate base of oxalic acid. At neutral pH in aqueous solution, oxalic acid converts completely to oxalate.

<i>Abies alba</i> Species of conifer tree

Abies alba, the European silver fir or silver fir, is a fir native to the mountains of Europe, from the Pyrenees north to Normandy, east to the Alps and the Carpathians, Slovakia, Slovenia, Croatia, Bosnia and Herzegovina, Montenegro, Serbia, and south to Italy, Bulgaria, Kosovo, Albania and northern Greece.

<i>Fagopyrum</i> Genus of flowering plants

The genus Fagopyrum is in the flowering plant family Polygonaceae. It includes some important food plants, such as F. esculentum (buckwheat) and F. tataricum. The genus is native to the Indian subcontinent, much of Indochina, and central and southeastern China. Species have been widely introduced elsewhere, throughout the Holarctic and parts of Africa and South America.

<span class="mw-page-title-main">Dichromatism</span>

Dichromatism is a phenomenon where a material or solution's hue is dependent on both the concentration of the absorbing substance and the depth or thickness of the medium traversed. In most substances which are not dichromatic, only the brightness and saturation of the colour depend on their concentration and layer thickness.

<span class="mw-page-title-main">Pumpkin seed oil</span> Oil from the seeds of pumpkins

Pumpkin seed oil is a culinary oil, used especially in eastern Europe.

<i>Fagopyrum tataricum</i> Species of plant

Fagopyrum tataricum, also known as Tartary buckwheat, green buckwheat, ku qiao, Tatar buckwheat, or bitter buckwheat, is a domesticated food plant in the genus Fagopyrum in the family Polygonaceae. With another species in the same genus, common buckwheat, it is often counted as a cereal, but the buckwheats are not closely related to true cereals.

<span class="mw-page-title-main">Rutin</span> Chemical compound

Rutin is the glycoside combining the flavonol quercetin and the disaccharide rutinose. It is a flavonoid glycoside found in a wide variety of plants, including citrus.

<span class="mw-page-title-main">Quercitrin</span> Chemical compound

Quercitrin is a glycoside formed from the flavonoid quercetin and the deoxy sugar rhamnose.

Salicylic aldehyde (2-hydroxybenzaldehyde) is an organic compound with the formula C6H4OH(CHO). Along with 3-hydroxybenzaldehyde and 4-hydroxybenzaldehyde, it is one of the three isomers of hydroxybenzaldehyde. This colorless oily liquid has a bitter almond odor at higher concentration. Salicylaldehyde is a precursor to coumarin and a variety of chelating agents.

<span class="mw-page-title-main">Lamellar bodies</span> Secretory organelles

In cell biology, lamellar bodies are secretory organelles found in type II alveolar cells in the lungs, and in keratinocytes in the skin. They are oblong structures, appearing about 300-400 nm in width and 100-150 nm in length in transmission electron microscopy images. Lamellar bodies in the alveoli of the lungs fuse with the cell membrane and release pulmonary surfactant into the extracellular space.

<span class="mw-page-title-main">2-Nonenal</span> Chemical compound

2-Nonenal is an unsaturated aldehyde. The colorless liquid is an important aroma component of aged beer and buckwheat, and is insoluble in water.

Decanal is an organic compound classified as an aldehyde with the chemical formula C10H20O.

<span class="mw-page-title-main">Furaneol</span> Chemical compound

Furaneol, or strawberry furanone, is an organic compound used in the flavor and perfume industry. It is formally a derivative of furan. It is a white or colorless solid that is soluble in water and organic solvents.

(E,E)-2,4-Decadienal is an aromatic substance found in butter, cooked beef, fish, potato chips, roasted peanut, buckwheat and wheat bread crumb. In an isolated state, it smells of deep fat flavor, characteristic of chicken aroma (at 10ppm). At lower concentration, it has the odor of citrus, orange or grapefruit. It might be carcinogenic. It has been used as aroma in the EU, but use restrictions apply until the required data have been submitted.

<span class="mw-page-title-main">Phenylacetaldehyde</span> Chemical compound

Phenylacetaldehyde is an organic compound used in the synthesis of fragrances and polymers. Phenylacetaldehyde is an aldehyde that consists of acetaldehyde bearing a phenyl substituent; the parent member of the phenylacetaldehyde class of compounds. It has a role as a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is an alpha-CH2-containing aldehyde and a member of phenylacetaldehydes.

<span class="mw-page-title-main">2-Methoxy-4-vinylphenol</span> Chemical compound

2-Methoxy-4-vinylphenol is an aromatic substance used as a flavoring agent. It is one of the compounds responsible for the natural aroma of buckwheat.

<span class="mw-page-title-main">Epicatechin gallate</span> Chemical compound

Epicatechin gallate (ECG) is a flavan-3-ol, a type of flavonoid, present in green tea. It is also reported in buckwheat and in grape.

<i>Fagopyrum cymosum</i> Species of grass

Fagopyrum cymosum, also known as tall buckwheat, is a domesticated plant used in traditional Chinese medicine, for animal feed, and as an ornamental plant. It is native to much of China, and to Bhutan, Nepal, India, Burma, and Vietnam.

References

  1. Brockmann, Hans; Weber, Erhard; Sander, Elsbeth (1950). "Fagopyrin, ein photodynamischer Farbstoff aus Buchweizen (Fagopyrum esculentum)". Die Naturwissenschaften. 37 (2): 43. Bibcode:1950NW.....37...43B. doi:10.1007/BF00645366. S2CID   29975083.
  2. Tavčar Benković, Eva; Žigon, Dušan; Friedrich, Miha; Plavec, Janez; Kreft, Samo (2014). "Isolation, analysis and structures of phototoxic fagopyrins from buckwheat". Food Chemistry. 143: 432–439. doi:10.1016/j.foodchem.2013.07.118. PMID   24054263.
  3. Kreft, S.; Janeš, D.; Kreft, I. (2013). "The content of fagopyrin and polyphenols in common and tartary buckwheat sprouts". Acta Pharmaceutica. 63 (4): 553–60. doi: 10.2478/acph-2013-0031 . PMID   24451079.