Kaempferol (3,4′,5,7-tetrahydroxyflavone) is a natural

flavonol Flavonols are a class of flavonoids that have the 3-hydroxyflavone backbone (IUPAC name: 3-hydroxy-2-phenylchromen-4-one). Their diversity stems from the different positions of the phenolic –OH groups. They are distinct from flavanols (with ...

, a type of

flavonoid Flavonoids (or bioflavonoids; from the Latin word ''flavus'', meaning yellow, their color in nature) are a class of polyphenolic secondary metabolites found in plants, and thus commonly consumed in the diets of humans. Chemically, flavonoids ...

, found in a variety of plants and plant-derived foods including

kale Kale (), also called leaf cabbage, belongs to a group of cabbage (''Brassica oleracea'') cultivars primarily grown for their Leaf vegetable, edible leaves; it has also been used as an ornamental plant. Its multiple different cultivars vary quite ...

bean A bean is the seed of some plants in the legume family (Fabaceae) used as a vegetable for human consumption or animal feed. The seeds are often preserved through drying (a ''pulse''), but fresh beans are also sold. Dried beans are traditi ...

tea Tea is an aromatic beverage prepared by pouring hot or boiling water over cured or fresh leaves of '' Camellia sinensis'', an evergreen shrub native to East Asia which probably originated in the borderlands of south-western China and nor ...

spinach Spinach (''Spinacia oleracea'') is a leafy green flowering plant native to Central Asia, Central and Western Asia. It is of the order Caryophyllales, family Amaranthaceae, subfamily Chenopodioideae. Its leaves are a common vegetable consumed eit ...

, and

broccoli Broccoli (''Brassica oleracea'' var. ''italica'') is an edible green plant in the Brassicaceae, cabbage family (family Brassicaceae, genus ''Brassica'') whose large Pseudanthium, flowering head, plant stem, stalk and small associated leafy gre ...

. It is also found in propolis extracts. Kaempferol is a yellow crystalline solid with a melting point of . It is slightly soluble in water and highly soluble in hot

ethanol Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the ps ...

ethers In organic chemistry, ethers are a class of compounds that contain an ether group, a single oxygen atom bonded to two separate carbon atoms, each part of an organyl group (e.g., alkyl or aryl). They have the general formula , where R and R′ r ...

, and

DMSO Dimethyl sulfoxide (DMSO) is an organosulfur compound with the formula . This colorless liquid is the sulfoxide most widely used commercially. It is an important polar aprotic solvent that dissolves both polar and nonpolar compounds and is ...

. Kaempferol is named for 17th-century German naturalist

Engelbert Kaempfer Engelbert Kaempfer (16 September 16512 November 1716) was a German natural history, naturalist, physician, exploration, explorer, and writer known for his tour of Russia, Iran, Persia, India, Southeast Asia, and Japan between 1683 and 1693. He ...

.Kaempferol
at

Merriam-Webster Merriam-Webster, Incorporated is an list of companies of the United States by state, American company that publishes reference work, reference books and is mostly known for Webster's Dictionary, its dictionaries. It is the oldest dictionary pub ...

.com; retrieved October 20, 2017

Natural occurrence

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

In plants and food

Kaempferol is common in

Pteridophyta A pteridophyte is a vascular plant (with xylem and phloem) that reproduces by means of spores. Because pteridophytes produce neither flowers nor seeds, they are sometimes referred to as " cryptogams", meaning that their means of reproduction is h ...

Pinophyta Conifers () are a group of cone-bearing seed plants, a subset of gymnosperms. Scientifically, they make up the division Pinophyta (), also known as Coniferophyta () or Coniferae. The division contains a single extant class, Pinopsida. All ...

, and

Angiospermae Flowering plants are plants that bear flowers and fruits, and form the clade Angiospermae (). The term angiosperm is derived from the Greek words (; 'container, vessel') and (; 'seed'), meaning that the seeds are enclosed within a fruit. The ...

. Within Pteridophyta and Pinophyta, kaempferol has been found in diverse families. Kaempferol has also been identified in

Dicotyledons The dicotyledons, also known as dicots (or, more rarely, dicotyls), are one of the two groups into which all the flowering plants (angiosperms) were formerly divided. The name refers to one of the typical characteristics of the group: namely, ...

and

Monocotyledons Monocotyledons (), commonly referred to as monocots, (Lilianae ''sensu'' Chase & Reveal) are flowering plants whose seeds contain only one embryonic leaf, or cotyledon. A monocot taxon has been in use for several decades, but with various ranks and ...

of Angiosperms. The total average intake of flavonols and flavones in a normal diet is estimated as 23 mg/day, to which kaempferol contributes approximately 17%. Common foods that contain kaempferol include:

apple An apple is a round, edible fruit produced by an apple tree (''Malus'' spp.). Fruit trees of the orchard or domestic apple (''Malus domestica''), the most widely grown in the genus, are agriculture, cultivated worldwide. The tree originated ...

grape A grape is a fruit, botanically a berry, of the deciduous woody vines of the flowering plant genus ''Vitis''. Grapes are a non- climacteric type of fruit, generally occurring in clusters. The cultivation of grapes began approximately 8,0 ...

tomato The tomato (, ), ''Solanum lycopersicum'', is a plant whose fruit is an edible Berry (botany), berry that is eaten as a vegetable. The tomato is a member of the nightshade family that includes tobacco, potato, and chili peppers. It originate ...

es,

green tea Green tea is a type of tea made from the leaves and buds of the '' Camellia sinensis'' that have not undergone the withering and oxidation process that creates oolong teas and black teas. Green tea originated in China in the late 1st millenn ...

potato The potato () is a starchy tuberous vegetable native to the Americas that is consumed as a staple food in many parts of the world. Potatoes are underground stem tubers of the plant ''Solanum tuberosum'', a perennial in the nightshade famil ...

es,

onion An onion (''Allium cepa'' , from Latin ), also known as the bulb onion or common onion, is a vegetable that is the most widely cultivated species of the genus '' Allium''. The shallot is a botanical variety of the onion which was classifie ...

Brussels sprout The Brussels sprout is a member of the Gemmifera cultivar group of cabbages (''Brassica oleracea''), grown for its edible buds. Etymology Though native to the Mediterranean region with other cabbage species, Brussels sprouts first appeared i ...

s, squash,

cucumber The cucumber (''Cucumis sativus'') is a widely-cultivated creeping vine plant in the family Cucurbitaceae that bears cylindrical to spherical fruits, which are used as culinary vegetables.

lettuce Lettuce (''Lactuca sativa'') is an annual plant of the family Asteraceae mostly grown as a leaf vegetable. The leaves are most often used raw in Green salad, green salads, although lettuce is also seen in other kinds of food, such as sandwiche ...

green bean Green beans are young, unripe fruits of various cultivars of the common bean ('' Phaseolus vulgaris''), although immature or young pods of the runner bean ('' Phaseolus coccineus''), yardlong bean ( ''Vigna unguiculata'' subsp. ''sesquipedali ...

peach The peach (''Prunus persica'') is a deciduous tree first domesticated and Agriculture, cultivated in China. It bears edible juicy fruits with various characteristics, most called peaches and the glossy-skinned, non-fuzzy varieties called necta ...

es,

blackberries BlackBerry is a discontinued brand of handheld devices and related mobile services, originally developed and maintained by the Canadian company Research In Motion (RIM, later known as BlackBerry Limited) until 2016. The first BlackBerry device ...

raspberries The raspberry is the edible fruit of several plant species in the genus ''Rubus'' of the Rosaceae, rose family, most of which are in the subgenus ''Rubus#Modern classification, Idaeobatus''. The name also applies to these plants themselves. Ras ...

, and

. Plants that are known to contain kaempferol include ''

Aloe vera ''Aloe vera'' () is a succulent plant species of the genus ''Aloe''. It is widely distributed, and is considered an invasive species in many world regions. An evergreen perennial plant, perennial, it originates from the Arabian Peninsula, but ...

'', ''

Coccinia grandis ''Coccinia grandis'', the ivy gourd, also known as scarlet gourd, is a tropical vine. It grows primarily in tropical climates and is commonly found in the Indian states where it forms a part of the local cuisine. ''Coccinia grandis'' is cooked ...

'', '' Cuscuta chinensis'', '' Euphorbia pekinensis'', ''

Glycine max The soybean, soy bean, or soya bean (''Glycine max'') is a species of legume native to East Asia, widely grown for its edible bean. Soy is a staple crop, the world's most grown legume, and an important animal feed. Soy is a key source of f ...

'', ''

Hypericum perforatum ''Hypericum perforatum'', commonly known as St. John's wort (sometimes perforate St. John's wort or common St. John's wort), is a flowering plant in the family Hypericaceae. It is a hairless, Perennial, perennial herb with woody Root, roots, y ...

'', ''

Pinus sylvestris ''Pinus sylvestris'', the Scots pine (UK), Scotch pine (US), Baltic pine, or European red pine is a species of tree in the pine family Pinaceae that is native plant, native to Eurasia. It can readily be identified by its combination of fairly s ...

'', ''

Moringa oleifera ''Moringa oleifera'' is a short-lived, fast-growing, drought-resistant tree of the family Moringaceae, native to northern India and used extensively in South Asia, South and Southeast Asia. Common names include moringa, drumstick tree (from th ...

'', ''

Rosmarinus officinalis ''Salvia rosmarinus'' (), commonly known as rosemary, is a shrub with fragrant, evergreen, needle-like leaves and white, pink, purple, or blue flowers. It is a member of the sage family, Lamiaceae. The species is native to the Mediterranean r ...

'', ''

Sambucus nigra ''Sambucus nigra'' is a species complex of flowering plants in the family Viburnaceae native to most of Europe. Common names include elder, elderberry, black elder, European elder, European elderberry, and European black elderberry. It grows in ...

'', ''

Toona sinensis ''Toona sinensis'', common name, commonly called Chinese mahogany, Chinese cedar, Chinese toon, beef and onion plant, or red toon (; ; ; ; ) is a species of ''Toona'' native to eastern and southeastern Asia, ranging from northern Korean peninsula ...

'', and ''

Ilex ''Ilex'' () or holly is a genus of over 570 species of flowering plants in the family Aquifoliaceae, and the only living genus in that family. ''Ilex'' has the most species of any woody dioecious angiosperm genus. The species are evergreen or ...

''. It also is present in

endive Endive () is a leaf vegetable belonging to the genus ''Cichorium'', which includes several similar bitter-leafed vegetables. Species include ''Cichorium endivia'' (also called endive), ''Cichorium pumilum'' (also called wild endive), and ''Cicho ...

Biosynthesis

The biosynthesis of kaempferol occurs in four major steps: *

Phenylalanine Phenylalanine (symbol Phe or F) is an essential α-amino acid with the chemical formula, formula . It can be viewed as a benzyl group substituent, substituted for the methyl group of alanine, or a phenyl group in place of a terminal hydrogen of ...

is converted into 4-coumaroyl-CoA *4-Coumaroyl-CoA combines with three molecules of

malonyl-CoA Malonyl-CoA is a coenzyme A derivative of malonic acid. Biosynthesis Malonyl-CoA cannot cross membranes and there is no known malonyl-CoA import mechanism. The biosynthesis therefore takes place locally: * cytosol: Malonyl-CoA is formed by c ...

to form naringenin chalcone (tetrahydroxychalcone) through the action of the enzyme

chalcone synthase Chalcone synthase or naringenin-chalcone synthase (CHS) is an enzyme ubiquitous to higher plants and belongs to a family of polyketide synthase enzymes (PKS) known as type III PKS. Type III PKSs are associated with the production of chalcones, a ...

*Naringenin chalcone is converted to

naringenin Naringenin is a flavanone from the flavonoid group of polyphenols. It is commonly found in citrus fruits, especially as the predominant flavonone in grapefruit. The fate and biological functions of naringenin in vivo are unknown, remaining und ...

and then a hydroxyl group is added to form

dihydrokaempferol Aromadendrin (aromodendrin or dihydrokaempferol) is a flavanonol, a type of flavonoid. It can be found in the wood of ''Pinus sibirica''. Metabolism The enzyme dihydrokaempferol 4-reductase uses ''cis''-3,4-leucopelargonidin and NADP+ to prod ...

*Dihydrokaempferol has a double bond introduced into it to form kaempferol The amino acid phenylalanine is formed from the

Shikimate pathway The shikimate pathway (shikimic acid pathway) is a seven-step metabolic pathway used by bacteria, archaea, fungi, algae, some protozoans, and plants for the biosynthesis of folates and aromatic amino acids (tryptophan, phenylalanine, and tyrosine) ...

, which is the pathway that plants use in order to make aromatic amino acids. This pathway is located in the plant

plastid A plastid is a membrane-bound organelle found in the Cell (biology), cells of plants, algae, and some other eukaryotic organisms. Plastids are considered to be intracellular endosymbiotic cyanobacteria. Examples of plastids include chloroplasts ...

, and is the entry to the biosynthesis of phenylpropanoids. The phenylpropanoid pathway is the pathway that converts phenylalanine into tetrahydroxychalcone. Flavonols, including kaempferol, are products of this pathway.

Notes

External links

*
Flavonoid composition of tea: Comparison of black and green teas
{{Purinergics Antidepressants Xanthine oxidase inhibitors Flavonoid antioxidants Phytoestrogens Progestogens Tetrols Resorcinols