Kaempferol
{{cs1 config|name-list-style=vanc}}
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 406555414
| Name = Kaempferol
| ImageFile = Kaempferol.svg
| ImageSize = 250px
| ImageAlt = Skeletal formula of kaempferol
| ImageFile1 = Kaempferol-3D-balls.png
| ImageAlt1 = Ball-and-stick model of the kaempferol molecule
| IUPACName = 3,4′,5,7-Tetrahydroxyflavone
| SystematicName = 3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
| OtherNames = Kaempherol; Robigenin; Pelargidenolon; Rhamnolutein; Rhamnolutin; Populnetin; Trifolitin; Kempferol; Swartziol
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 520-18-3
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 731P2LE49E
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 4444395
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 150
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 28499
| DrugBank = DB01852
| EC_number = 208-287-6
| SMILES = O=c1c(O)c(-c2ccc(O)cc2)oc2cc(O)cc(O)c12
| StdInChI = 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
| StdInChIKey = IYRMWMYZSQPJKC-UHFFFAOYSA-N
| PubChem = 5280863
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = C05903
}}
|Section2={{Chembox Properties
| Formula = C15H10O6
| MolarMass = 286.23 g/mol
| MeltingPt = 276–278 °C
| Density = 1.688 g/mL
}}
}}
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.{{Cite journal|last1=Holland|first1=Thomas M.|last2=Agarwal|first2=Puja|last3=Wang|first3=Yamin|last4=Leurgans|first4=Sue E.|last5=Bennett|first5=David A.|last6=Booth|first6=Sarah L.|last7=Morris|first7=Martha Clare|author-link7=Martha Clare Morris|date=2020-01-29|title=Dietary flavonols and risk of Alzheimer dementia|journal=Neurology|language=en|volume=94|issue=16|pages=e1749–e1756|doi=10.1212/WNL.0000000000008981|issn=0028-3878|pmc=7282875|pmid=31996451}} It is also found in propolis extracts.{{Cite journal |last1=Bertolucci |first1=Vanessa |last2=Ninomiya |first2=André Felipe |last3=Longato |first3=Giovanna Barbarini |last4=Kaneko |first4=Luisa Oliveira |last5=Nonose |first5=Nilson |last6=Scariot |first6=Pedro Paulo Menezes |last7=Messias |first7=Leonardo Henrique Dalcheco |date=2025-01-12 |title=Bioactive Compounds from Propolis on Bone Homeostasis: A Narrative Review |journal=Antioxidants |language=en |volume=14 |issue=1 |pages=81 |doi=10.3390/antiox14010081 |doi-access=free |issn=2076-3921 |pmc=11762496 |pmid=39857415}} Kaempferol is a yellow crystalline solid with a melting point of {{convert|276-278|C|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.[https://www.merriam-webster.com/dictionary/kaempferol Kaempferol] at Merriam-Webster.com; retrieved October 20, 2017
Natural occurrence
=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.{{cite journal | vauthors = Calderón Montaño JM, Burgos Morón E, Pérez Guerrero C, López Lázaro M | title = A review on the dietary flavonoid kaempferol | journal = Mini Reviews in Medicinal Chemistry | volume = 11 | issue = 4 | pages = 298–344 | date = April 2011 | pmid = 21428901 | doi = 10.2174/138955711795305335 }} The total average intake of flavonols and flavones in a normal diet is estimated as 23 mg/day, to which kaempferol contributes approximately 17%.{{cite journal | vauthors = Liu RH | title = Health-promoting components of fruits and vegetables in the diet | journal = Advances in Nutrition | volume = 4 | issue = 3 | pages = 384S–392S | date = May 2013 | pmid = 23674808 | pmc = 3650511 | doi = 10.3945/an.112.003517 }} Common foods that contain kaempferol include: apples,{{cite journal | vauthors = Kim SH, Choi KC | title = Anti-cancer Effect and Underlying Mechanism(s) of Kaempferol, a Phytoestrogen, on the Regulation of Apoptosis in Diverse Cancer Cell Models | journal = Toxicological Research | volume = 29 | issue = 4 | pages = 229–234 | date = December 2013 | pmid = 24578792 | pmc = 3936174 | doi = 10.5487/TR.2013.29.4.229 | bibcode = 2013ToxRe..29..229K }} grapes, tomatoes, green tea, potatoes, onions, broccoli, Brussels sprouts, squash, cucumbers, lettuce, green beans, peaches, blackberries, raspberries, and spinach. Plants that are known to contain kaempferol include Aloe vera, Coccinia grandis, Cuscuta chinensis,{{cite journal | vauthors = Donnapee S, Li J, Yang X, Ge AH, Donkor PO, Gao XM, Chang YX | title = Cuscuta chinensis Lam.: A systematic review on ethnopharmacology, phytochemistry and pharmacology of an important traditional herbal medicine | journal = Journal of Ethnopharmacology | volume = 157 | issue = C | pages = 292–308 | date = November 2014 | pmid = 25281912 | doi = 10.1016/j.jep.2014.09.032 }} Euphorbia pekinensis, Glycine max, Hypericum perforatum, Pinus sylvestris,{{cite journal | vauthors = de la Luz Cádiz-Gurrea M, Fernández-Arroyo S, Segura-Carretero A | title = Pine bark and green tea concentrated extracts: antioxidant activity and comprehensive characterization of bioactive compounds by HPLC-ESI-QTOF-MS | journal = International Journal of Molecular Sciences | volume = 15 | issue = 11 | pages = 20382–20402 | date = November 2014 | pmid = 25383680 | pmc = 4264173 | doi = 10.3390/ijms151120382 | doi-access = free }} Moringa oleifera,{{cite journal | vauthors = Anwar F, Latif S, Ashraf M, Gilani AH | title = Moringa oleifera: a food plant with multiple medicinal uses | journal = Phytotherapy Research | volume = 21 | issue = 1 | pages = 17–25 | date = January 2007 | pmid = 17089328 | doi = 10.1002/ptr.2023 | doi-access = free }} Rosmarinus officinalis, Sambucus nigra, Toona sinensis, and Ilex. It also is present in endive.{{cite journal | vauthors = DuPont MS, Day AJ, Bennett RN, Mellon FA, Kroon PA | title = Absorption of kaempferol from endive, a source of kaempferol-3-glucuronide, in humans | journal = European Journal of Clinical Nutrition | volume = 58 | issue = 6 | pages = 947–954 | date = June 2004 | pmid = 15164116 | doi = 10.1038/sj.ejcn.1601916 | doi-access = | s2cid = 25720976 }}
class="wikitable sortable"
!Foods ! data-sort-type="number" |Kaempferol (mg/100 g) |
capers, raw |
saffron |
capers, canned |
arugula, raw |
kale, raw |
mustard greens, raw |
ginger |
common bean, raw |
chinese cabbage, raw |
dill, fresh |
garden cress, raw |
chive, raw |
dock, raw |
endive, raw |
collard, raw |
broccoli, raw |
fennel leaves |
goji berry, dried |
drumstick leaves, raw |
chard, raw |
Biosynthesis
The biosynthesis of kaempferol occurs in four major steps:
- 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.{{cite journal | vauthors = Vogt T | title = Phenylpropanoid biosynthesis | journal = Molecular Plant | volume = 3 | issue = 1 | pages = 2–20 | date = January 2010 | pmid = 20035037 | doi = 10.1093/mp/ssp106 | doi-access = free }}
The phenylpropanoid pathway is the pathway that converts phenylalanine into tetrahydroxychalcone. Flavonols, including kaempferol, are products of this pathway.{{cite journal | vauthors = Flamini R, Mattivi F, De Rosso M, Arapitsas P, Bavaresco L | title = Advanced knowledge of three important classes of grape phenolics: anthocyanins, stilbenes and flavonols | journal = International Journal of Molecular Sciences | volume = 14 | issue = 10 | pages = 19651–19669 | date = September 2013 | pmid = 24084717 | pmc = 3821578 | doi = 10.3390/ijms141019651 | doi-access = free }}
Notes
{{Reflist}}
External links
- {{Commons category-inline}}
- [https://web.archive.org/web/20070621083657/http://www.nal.usda.gov/fnic/foodcomp/Data/Other/IFT2003_TeaFlav.pdf Flavonoid composition of tea: Comparison of black and green teas ]
{{Antioxidants}}
{{Flavonols}}
{{Cannabinoidergics}}
{{Estrogenics}}
{{Progestogenics}}
{{Purinergics}}
Category:Xanthine oxidase inhibitors