Kaempferol

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Kaempferol
Kaempferol.svg
Kaempferol-3D-balls.png
Names
IUPAC name
3,4′,5,7-Tetrahydroxyflavone
Systematic 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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.007.535 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 208-287-6
KEGG
PubChem CID
UNII
  • InChI=1S/C15H10O6/c16-8-3-1-7(2-4-8)15-14(20)13(19)12-10(18)5-9(17)6-11(12)21-15/h1-6,16-18,20H
    Key: IYRMWMYZSQPJKC-UHFFFAOYSA-N
  • O=c1c(O)c(-c2ccc(O)cc2)oc2cc(O)cc(O)c12
Properties
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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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] Toona sinensis , [3] and Ilex . [3] It also is present in endive. [9]

FoodsKaempferol

(mg/100 g)

capers, raw259 [10]
saffron 205 [10]
capers, canned131 [10]
arugula, raw59 [10]
kale, raw47 [10]
mustard greens, raw38 [10]
ginger 34 [10]
common bean, raw26 [10]
chinese cabbage, raw23 [10]
dill, fresh13 [10]
garden cress, raw13 [10]
chive, raw10 [10]
dock, raw10 [10]
endive, raw10 [10]
collard, raw9 [10]
broccoli, raw8 [10]
fennel leaves7 [10]
goji berry, dried6 [10]
drumstick leaves, raw6 [10]
chard, raw4 [10]

Biosynthesis

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

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 TM, Agarwal P, Wang Y, Leurgans SE, Bennett DA, Booth SL, Morris MC (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. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 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. 1 2 Liu RH (May 2013). "Health-promoting components of fruits and vegetables in the diet". Advances in Nutrition. 4 (3): 384S –392S. doi:10.3945/an.112.003517. PMC   3650511 . PMID   23674808.
  5. 1 2 3 4 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): 229–234. 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): 20382–20402. 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): 947–954. doi:10.1038/sj.ejcn.1601916. PMID   15164116. S2CID   25720976.
  10. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 "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): 19651–19669. doi: 10.3390/ijms141019651 . PMC   3821578 . PMID   24084717.
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