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{{cs1 config|name-list-style=vanc}} |
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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 405238677 |
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| Watchedfields = changed |
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| Name = Kaempferol |
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| verifiedrevid = 406555414 |
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| ImageFile = Kaempferol.svg |
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| Name = Kaempferol |
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| ImageSize = 250px |
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| ImageName = Kaempferol |
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| ImageFile = Kaempferol.svg |
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| ImageSize = 250px |
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| IUPACName = 3,5,7-trihydroxy-2-<br />(4-hydroxyphenyl)-4H-1-<br />benzopyran-4-one |
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| ImageAlt = Skeletal formula of kaempferol |
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| OtherNames = Kaempherol; Robigenin; Pelargidenolon; Rhamnolutein; Rhamnolutin; Populnetin; Trifolitin; Kempferol; Swartziol |
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| ImageFile1 = Kaempferol-3D-balls.png |
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| Section1 = {{Chembox Identifiers |
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| ImageAlt1 = Ball-and-stick model of the kaempferol molecule |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| IUPACName = 3,4′,5,7-Tetrahydroxyflavone |
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| SystematicName = 3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-4''H''-1-benzopyran-4-one |
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| OtherNames = Kaempherol; Robigenin; Pelargidenolon; Rhamnolutein; Rhamnolutin; Populnetin; Trifolitin; Kempferol; Swartziol |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 520-18-3 |
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| CASNo = 520-18-3 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| SMILES = |
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| PubChem = 5280863 |
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| UNII = 731P2LE49E |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 4444395 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 150 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 28499 |
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| SMILES = O=c1c(O)c(-c2ccc(O)cc2)oc2cc(O)cc(O)c12 |
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| 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 |
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| StdInChIKey = IYRMWMYZSQPJKC-UHFFFAOYSA-N |
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| PubChem = 5280863 |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| KEGG = C05903 |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>15</sub>H<sub>10</sub>O<sub>6</sub> |
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| Formula = C<sub>15</sub>H<sub>10</sub>O<sub>6</sub> |
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| MolarMass = 286.23 g/mol |
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| MolarMass = 286.23 g/mol |
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| MeltingPt = 276–278 °C |
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| ExactMass = 286.047738 |
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| MeltingPt = 276-278 °C |
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| Density = 1.688 g/mL |
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'''Kaempferol''' is a natural ], a type of flavonoid, that has been isolated from ],<ref name="tea">{{cite journal | title = Enzymatic Preparation of Kaempferol from Green Tea Seed and Its Antioxidant Activity | author = Jun Seong Park, Ho Sik Rho, Duck Hee Kim, and Ih Seop Chang | journal = ] | volume = 54 | issue = 8 | pages = 2951–2956 | year = 2006 | pmid = 16608214| doi = 10.1021/jf052900a}}</ref> ], '']'', ], ], ], ] and other plant sources. Kaempferol is a yellow crystalline solid with a melting point of 276-278 °C. It is slightly soluble in water but soluble in hot ] and ]. |
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'''Kaempferol''' (3,4′,5,7-tetrahydroxyflavone) is a natural ], a type of ], found in a variety of plants and plant-derived foods including ], ]s, ], ], and ].<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> 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 ], ], and ]. Kaempferol is named for 17th-century German naturalist ].<ref name=MW> at ].com; retrieved October 20, 2017</ref> |
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==Natural occurrence== |
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Many ]s of kaempferol, such as ] and ], have been isolated as natural products from plants. Kaempferol consumption in tea and broccoli has been associated with reduced risk of heart disease.{{Citation needed|date=November 2007}} |
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Kaempferol is a secondary metabolite found in many plants, plant-derived foods, and traditional medicines.<ref name="calderon" /> Its flavor is considered bitter. |
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===In plants and food=== |
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Kaempferol is what gives the flowers of '']'' and '']'' their color.<ref></ref> The compound has antidepressant properties.<ref>{{cite journal|title=ANTIDEPRESSANT EFFECT OF KAEMPFEROL, A CONSTITUENT OF SAFFRON (CROCUS SATIVUS) PETAL, IN MICE AND RATS|journal=Pharmacologyonline|date=|first=|last=|coauthors=|volume=|issue=|pages=|id= |url=|format=|accessdate=2008-03-03 }}</ref>{{Verify credibility|date=December 2008}} |
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Kaempferol is common in ], ], and ]. Within Pteridophyta and Pinophyta, kaempferol has been found in diverse families. Kaempferol has also been identified in ] and ] 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 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: ]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> ]s,<ref name="kim" /> ]es,<ref name="kim" /> ],<ref name="kim" /> ]es,<ref name="liu" /> ]s,<ref name="calderon" /> ],<ref name="calderon" /> ]s,<ref name="calderon" /> ],<ref name="calderon" /> ]s,<ref name="calderon" /> ],<ref name="calderon" /> ]s,<ref name="calderon" /> ]es,<ref name="calderon" /> ],<ref name="calderon" /> ],<ref name="calderon" /> and ].<ref name="calderon" /> Plants that are known to contain kaempferol include '']'',<ref name="calderon" /> '']'',<ref name="calderon" /> '']'',<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> '']'',<ref name="calderon" /> '']'',<ref name="calderon" /> '']'',<ref name="calderon" /> '']'',<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> '']'',<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> '']'',<ref name="calderon" /> '']'',<ref name="calderon" /> '']'',<ref name="calderon" /> and '']''.<ref name="calderon" /> It also is present in ].<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> |
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An 8-year study found that three ]s (kaempferol, ], and ]) reduced the risk of ] by 23 percent.<ref>Ute Nöthlings, Suzanne P. Murphy, Lynne R. Wilkens, Brian E. Henderson & Laurence N. Kolone. 2007. Flavonols and Pancreatic Cancer Risk. ''American Journal of Epidemiology'' '''166'''(8): 924–931. {{DOI|10.1093/aje/kwm172}}</ref> |
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{| class="wikitable sortable" |
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!Foods |
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! data-sort-type="number" |Kaempferol |
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<small>(mg/100 g)</small> |
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|], raw |
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|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> |
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|] |
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|205<ref name="usda" /> |
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|], canned |
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|131<ref name="usda" /> |
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|], raw |
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|59<ref name="usda" /> |
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|], raw |
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|47<ref name="usda" /> |
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|], raw |
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|38<ref name="usda" /> |
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|] |
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|34<ref name="usda" /> |
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|], raw |
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|26<ref name="usda" /> |
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|], raw |
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|23<ref name="usda" /> |
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|], fresh |
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|13<ref name="usda" /> |
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|], raw |
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|13<ref name="usda" /> |
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|], raw |
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|10<ref name="usda" /> |
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|], raw |
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|10<ref name="usda" /> |
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|], raw |
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|10<ref name="usda" /> |
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|], raw |
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|9<ref name="usda" /> |
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|], raw |
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|8<ref name="usda" /> |
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|] leaves |
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|7<ref name="usda" /> |
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|], dried |
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|6<ref name="usda" /> |
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|] leaves, raw |
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|6<ref name="usda" /> |
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|], raw |
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|4<ref name="usda" /> |
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==Biosynthesis== |
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] cancer researchers have found that study participants who ate foods containing certain flavonoids seemed to be protected from developing lung cancer. Dr. Zuo-Feng Zhang, of the UCLA's Jonsson Cancer Center and a professor of public health and epidemiology at the UCLA School of Public Health said the flavonoids that appeared to be the most protective included ], found in strawberries and green and black teas; kaempferol, found in brussels sprouts and apples; and quercetin, found in beans, onions and apples.<ref></ref> |
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The biosynthesis of kaempferol occurs in four major steps:<ref name=calderon/> |
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==Metabolism== |
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The enzyme ] uses S-adenosyl methionine and kaempferol to produce S-adenosylhomocysteine and ]. |
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*] is converted into ] |
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===Glycosides=== |
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*4-Coumaroyl-CoA combines with three molecules of ] to form ] (tetrahydroxychalcone) through the action of the enzyme ] |
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* ] (Astragaline, asragalin, kaempferol-3-O-]) |
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*Naringenin chalcone is converted to ] and then a hydroxyl group is added to form ] |
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* ] (kaempferol 3-O-]) |
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*Dihydrokaempferol has a double bond introduced into it to form kaempferol |
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* ], a known bitter-tasting flavonoid glycoside, can be isolated from the rhizomes of '']''.<ref></ref> |
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The amino acid phenylalanine is formed from the ], which is the pathway that plants use in order to make aromatic amino acids. This pathway is located in the plant ], 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> |
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== List of the plants that contains the chemical == |
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* ] {{Citation needed|date=July 2009}} |
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Opuntia ficus-indica var.saboten <ref>Opuntia ficus indica extract protects against chlorpyrifos-induced damage on mice liver:Available online at www.sciencedirect.com</ref> |
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The ] 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> |
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== Toxicology == |
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{{Empty section|date=July 2009}} |
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==References== |
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==Notes== |
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{{reflist}} |
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{{Reflist}} |
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== External links == |
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*{{Commons category-inline}} |
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==External links== |
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{{Antioxidants}} |
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{{Antioxidants}} |
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{{Flavonols}} |
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{{Flavonols}} |
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{{Cannabinoidergics}} |
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{{Estrogenics}} |
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{{Progestogenics}} |
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{{Purinergics}} |
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-mitochondrial effect. |
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