Kaempferolのソースを表示

{{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)-4''H''-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 = C<sub>15</sub>H<sub>10</sub>O<sub>6</sub>
| MolarMass = 286.23 g/mol
| MeltingPt = 276–278&nbsp;°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]], [[bean]]s, [[tea]], [[spinach]], and [[broccoli]].<ref>{{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}}</ref>  It is also found in propolis extracts.<ref>Bertolucci, V., Ninomiya, A. F., Longato, G. B., Kaneko, L. O., Nonose, N., Scariot, P. P. M., & Messias, L. H. D. (2025). Bioactive Compounds from Propolis on Bone Homeostasis: A Narrative Review. Antioxidants, 14(1), 81. https://doi.org/10.3390/antiox14010081</ref> 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 [[Dimethyl sulfoxide|DMSO]]. Kaempferol is named for 17th-century German naturalist [[Engelbert Kaempfer]].<ref name=MW>[https://www.merriam-webster.com/dictionary/kaempferol Kaempferol] at [[Merriam-Webster]].com; retrieved October 20, 2017</ref>

==Natural occurrence==
Kaempferol is a secondary metabolite found in many plants, plant-derived foods, and traditional medicines.<ref name="calderon" /> 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.<ref name=calderon>{{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 }}</ref> The total average intake of flavonols and flavones in a normal diet is estimated as 23&nbsp;mg/day, to which kaempferol contributes approximately 17%.<ref name=liu>{{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 }}</ref> Common foods that contain kaempferol include: [[apple]]s,<ref name=kim>{{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 }}</ref> [[grape]]s,<ref name="kim" /> [[tomato]]es,<ref name="kim" /> [[green tea]],<ref name="kim" /> [[potato]]es,<ref name="liu" /> [[onion]]s,<ref name="calderon" /> [[broccoli]],<ref name="calderon" /> [[Brussels sprout]]s,<ref name="calderon" /> [[Cucurbita|squash]],<ref name="calderon" /> [[cucumber]]s,<ref name="calderon" /> [[lettuce]],<ref name="calderon" /> [[green bean]]s,<ref name="calderon" /> [[peach]]es,<ref name="calderon" /> [[Blackberry|blackberries]],<ref name="calderon" /> [[Raspberry|raspberries]],<ref name="calderon" /> and [[spinach]].<ref name="calderon" />  Plants that are known to contain kaempferol include ''[[Aloe vera]]'',<ref name="calderon" /> ''[[Coccinia grandis]]'',<ref name="calderon" /> ''[[Cuscuta chinensis]]'',<ref>{{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 }}</ref> ''[[Euphorbia pekinensis]]'',<ref name="calderon" /> ''[[Glycine max]]'',<ref name="calderon" /> ''[[Hypericum perforatum]]'',<ref name="calderon" /> ''[[Scots pine|Pinus sylvestris]]'',<ref>{{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 }}</ref> ''[[Moringa oleifera]]'',<ref>{{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 }}</ref> ''[[Rosmarinus officinalis]]'',<ref name="calderon" /> ''[[Sambucus nigra]]'',<ref name="calderon" /> ''[[Toona sinensis]]'',<ref name="calderon" /> and ''[[Ilex]]''.<ref name="calderon" /> It also is present in [[endive]].<ref name="DuPont_2004">{{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 }}</ref>
{| class="wikitable sortable"
!Foods
! data-sort-type="number" |Kaempferol 
<small>(mg/100&nbsp;g)</small>
|-
|[[capers]], raw
|259<ref name="usda">{{cite web|url=http://www.ars.usda.gov/SP2UserFiles/Place/12354500/Data/Flav/Flav_R03.pdf|title=USDA Database for the Flavonoid Content of Selected Foods, Release 3|year=2011|publisher=U.S. Department of Agriculture}}</ref>
|-
|[[saffron]]
|205<ref name="usda" />
|-
|[[capers]], canned
|131<ref name="usda" />
|-
|[[Eruca sativa|arugula]], raw
|59<ref name="usda" />
|-
|[[kale]], raw
|47<ref name="usda" />
|-
|[[Brassica juncea|mustard greens]], raw
|38<ref name="usda" />
|-
|[[ginger]]
|34<ref name="usda" />
|-
|[[Phaseolus vulgaris|common bean]], raw
|26<ref name="usda" />
|-
|[[chinese cabbage]], raw
|23<ref name="usda" />
|-
|[[dill]], fresh
|13<ref name="usda" />
|-
|[[garden cress]], raw
|13<ref name="usda" />
|-
|[[Chives|chive]], raw
|10<ref name="usda" />
|-
|[[Rumex|dock]], raw
|10<ref name="usda" />
|-
|[[endive]], raw
|10<ref name="usda" />
|-
|[[Collard (plant)|collard]], raw
|9<ref name="usda" />
|-
|[[broccoli]], raw
|8<ref name="usda" />
|-
|[[fennel]] leaves
|7<ref name="usda" />
|-
|[[Goji|goji berry]], dried
|6<ref name="usda" />
|-
|[[Moringa oleifera|drumstick]] leaves, raw
|6<ref name="usda" />
|-
|[[chard]], raw
|4<ref name="usda" />
|}

==Biosynthesis==

The biosynthesis of kaempferol occurs in four major steps:<ref name=calderon/>

*[[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.<ref>{{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 }}</ref>

The [[phenylpropanoid pathway]] is the pathway that converts phenylalanine into tetrahydroxychalcone. Flavonols, including kaempferol, are products of this pathway.<ref name="flamini">{{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 }}</ref>

==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:Kaempferol| ]]
[[Category:Antidepressants]]
[[Category:Xanthine oxidase inhibitors]]
[[Category:Flavonoid antioxidants]]
[[Category:Phytoestrogens]]
[[Category:Progestogens]]
[[Category:Tetrols]]