Kaempferol

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Kaempferol
Skeletal formula of kaempferol
Ball-and-stick model of the kaempferol molecule
Names
IUPAC name
3,4′,5,7-Tetrahydroxyflavone
Preferred IUPAC name
3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
Other names
Kaempherol; Robigenin; Pelargidenolon; Rhamnolutein; Rhamnolutin; Populnetin; Trifolitin; Kempferol; Swartziol
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.535 Edit this at Wikidata
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
SMILES
  • C1=CC(=CC=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O
Properties
Chemical formula
 C15H10O6
Molar mass 286.23 g/mol
Density 1.688 g/mL
Melting point 276–278 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Kaempferol (3,4′,5,7-tetrahydroxyflavone) is a natural flavonol, a type of flavonoid, found in a variety of plants and plant-derived foods including kale, beans, tea, spinach, and broccoli.[1] Kaempferol is a yellow crystalline solid with a melting point of 276–278 °C (529–532 °F). It is slightly soluble in water and highly soluble in hot ethanol, ethers, and DMSO. Kaempferol is named for 17th-century German naturalist Engelbert Kaempfer.[2]

Natural occurrence[]

Kaempferol is a secondary metabolite found in many plants, plant-derived foods, and traditional medicines.[3] Its flavor is considered bitter.

In plants and food[]

Kaempferol is common in Pteridophyta, Pinophyta, and Angiospermae. Within Pteridophyta and Pinophyta, kaempferol has been found in diverse families. Kaempferol has also been identified in Dicotyledons and Monocotyledons of Angiosperms.[3] The total average intake of flavonols and flavones in a normal diet is estimated as 23 mg/day, to which kaempferol contributes approximately 17%.[4] Common foods that contain kaempferol include: apples,[5] grapes,[5] tomatoes,[5] green tea,[5] potatoes,[4] onions,[3] broccoli,[3] Brussels sprouts,[3] squash,[3] cucumbers,[3] lettuce,[3] green beans,[3] peaches,[3] blackberries,[3] raspberries,[3] and spinach.[3] Plants that are known to contain kaempferol include Aloe vera,[3] Coccinia grandis,[3] Cuscuta chinensis,[6] Euphorbia pekinensis,[3] Glycine max,[3] Hypericum perforatum,[3] Pinus sylvestris,[7] Moringa oleifera,[8] Rosmarinus officinalis,[3] Sambucus nigra,[3] and Toona sinensis,[3] and Ilex.[3] It also is present in endive.[9]

Foods Kaempferol

(mg/100g)

capers, raw 259[10]
saffron 205[10]
capers, canned 131[10]
arugula, raw 59[10]
kale, raw 47[10]
mustard greens, raw 38[10]
ginger 34[10]
common bean, raw 26[10]
chinese cabbage, raw 23[10]
dill, fresh 13[10]
garden cress, raw 13[10]
chive, raw 10[10]
dock, raw 10[10]
endive, raw 10[10]
collard, raw 9[10]
broccoli, raw 8[10]
fennel leaves 7[10]
goji berry, dried 6[10]
drumstick leaves, raw 6[10]
chard, raw 4[10]

Biosynthesis[]

The biosynthesis of kaempferol occurs in four major steps:[3]

  • Phenylalanine is converted into 4-coumaroyl-CoA
  • 4-coumaroyl-CoA combines with three molecules of malonyl-coA to form naringenin chalcone (tetrahydroxychalcone) through the action of the enzyme chalcone synthase
  • Naringenin chalcone is converted to naringenin and then a hydroxyl group is added to form dihydrokaempferol
  • Dihydrokaempferol has a double bond introduced into it to form kaempferol

The amino acid phenylalanine is formed from the Shikimate pathway, which is the pathway that plants use in order to make aromatic amino acids. This pathway is located in the plant plastid, and is the entry to the biosynthesis of phenylpropanoids.[11]

The phenylpropanoid pathway is the pathway that converts phenylalanine into tetrahydroxychalcone. Flavonols, including kaempferol, are products of this pathway.[12]

Notes[]

  1. ^ Holland, Thomas M.; Agarwal, Puja; Wang, Yamin; Leurgans, Sue E.; Bennett, David A.; Booth, Sarah L.; Morris, Martha Clare (2020-01-29). "Dietary flavonols and risk of Alzheimer dementia". Neurology. 94 (16): e1749–e1756. doi:10.1212/WNL.0000000000008981. ISSN 0028-3878. PMC 7282875. PMID 31996451.
  2. ^ Kaempferol at Merriam-Webster.com; retrieved October 20, 2017
  3. ^ a b c d e f g h i j k l m n o p q r s t u v w Calderón-Montaño JM, Burgos-Morón E, Pérez-Guerrero C, López-Lázaro M (April 2011). "A review on the dietary flavonoid kaempferol". Mini Reviews in Medicinal Chemistry. 11 (4): 298–344. doi:10.2174/138955711795305335. PMID 21428901.
  4. ^ a b Liu RH (May 2013). "Health-promoting components of fruits and vegetables in the diet". Advances in Nutrition. 4 (3): 384S–92S. doi:10.3945/an.112.003517. PMC 3650511. PMID 23674808.
  5. ^ a b c d Kim SH, Choi KC (December 2013). "Anti-cancer Effect and Underlying Mechanism(s) of Kaempferol, a Phytoestrogen, on the Regulation of Apoptosis in Diverse Cancer Cell Models". Toxicological Research. 29 (4): 229–34. doi:10.5487/TR.2013.29.4.229. PMC 3936174. PMID 24578792.
  6. ^ Donnapee S, Li J, Yang X, Ge AH, Donkor PO, Gao XM, Chang YX (November 2014). "Cuscuta chinensis Lam.: A systematic review on ethnopharmacology, phytochemistry and pharmacology of an important traditional herbal medicine". Journal of Ethnopharmacology. 157 (C): 292–308. doi:10.1016/j.jep.2014.09.032. PMID 25281912.
  7. ^ de la Luz Cádiz-Gurrea M, Fernández-Arroyo S, Segura-Carretero A (November 2014). "Pine bark and green tea concentrated extracts: antioxidant activity and comprehensive characterization of bioactive compounds by HPLC-ESI-QTOF-MS". International Journal of Molecular Sciences. 15 (11): 20382–402. doi:10.3390/ijms151120382. PMC 4264173. PMID 25383680.
  8. ^ Anwar F, Latif S, Ashraf M, Gilani AH (January 2007). "Moringa oleifera: a food plant with multiple medicinal uses". Phytotherapy Research. 21 (1): 17–25. doi:10.1002/ptr.2023. PMID 17089328.
  9. ^ DuPont MS, Day AJ, Bennett RN, Mellon FA, Kroon PA (June 2004). "Absorption of kaempferol from endive, a source of kaempferol-3-glucuronide, in humans". European Journal of Clinical Nutrition. 58 (6): 947–54. doi:10.1038/sj.ejcn.1601916. PMID 15164116.
  10. ^ a b c d e f g h i j k l m n o p q r s t "USDA Database for the Flavonoid Content of Selected Foods, Release 3" (PDF). U.S. Department of Agriculture. 2011.
  11. ^ Vogt T (January 2010). "Phenylpropanoid biosynthesis". Molecular Plant. 3 (1): 2–20. doi:10.1093/mp/ssp106. PMID 20035037.
  12. ^ Flamini R, Mattivi F, De Rosso M, Arapitsas P, Bavaresco L (September 2013). "Advanced knowledge of three important classes of grape phenolics: anthocyanins, stilbenes and flavonols". International Journal of Molecular Sciences. 14 (10): 19651–69. doi:10.3390/ijms141019651. PMC 3821578. PMID 24084717.

External links[]

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