Kaempferol
Encyclopedia
Kaempferol is a natural flavonol, a type of flavonoid, that has been isolated from tea
, broccoli
, Delphinium
, Witch-hazel
, grapefruit
,cabbage, kale, beans, endive, leek, tomato, strawberries, grapes, brussels sprouts, apples 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 ethanol
and diethyl ether
.
Many glycoside
s of kaempferol, such as kaempferitrin
and astragalin
, have been isolated as natural products from plants. Kaempferol consumption in tea and broccoli has been associated with reduced risk of heart disease. A related compound, Naringenin
may be present at the same time, such as in grapefruit.
Kaempferol is what gives the flowers of Acacia decurrens
and Acacia longifolia
their color. Antidepressant properties have been reported in tests on animals.,
An 8-year study found that three flavonols (kaempferol, quercetin
, and myricetin
) reduced the risk of pancreatic cancer
by 23 percent.
Kaempferol consumption appears to reduce lung cancer incidence.
Kaempferol may be a potent prophylactic against NOX-mediated neurodegeneration.
uses S-adenosyl methionine and kaempferol to produce S-adenosylhomocysteine and kaempferide
.
Kaempferol has been identified in many plant species commonly used in traditional medicine. It has been found in Acacia nilotica, Adansonia digitata, Albizia lebbeck, Aloe vera, Amburana cearensis, Ammi majus, Angelica keiskei, Ardisia japonica, Bauhinia forficata, Bauhinia microstachya, Bunium persicum, Capparis spinosa, Cassia alata, Centella asiatica, Chromolaena odorata, Cissus sicyoides, Coccinia grandis, Crassocephalum crepidioides, Crocus sativus, Cynanchum acutum, Cynanchum chinense, Dicliptera chinensis, Equisetum arvense, Euphorbia pekinensis, Ficaria verna, Foeniculum vulgare, Galega officinalis, Ginkgo biloba, Glycine max, Grindelia robusta, Gymnema sylvestre, Helleborus niger, Hippophae rhamnoides, Houttuynia cordata, Hypericum perforatum, Impatiens balsamina, Lamium album, Laurus nobilis, Lonicera japonica, Lycium barbarum, Lycium chinense, Lysimachia vulgaris, Malva parviflora, Peumus boldus, Phyllanthus emblica, Ribes nigrum, Rosmarinus officinalis, Sambucus nigra, Sanguisorba minor, Siraitia grosvenori, Solanum nigrum, Solenostemma argel, Solidago virgaaurea, Sutherlandia frutescens, Symphytum officinale, Syzygium aromaticum, Tilia americana, Toona sinensis, Trigonella foenum-graecum, Tropaeolum majus, Vaccinium vitis-idaea, Warburgia ugandensis and Wedelia trilobata.
Kaempferol is also present in Kaempferia galanga
and Opuntia ficus-indica var. saboten.
ref>Jang YJ. Kim J. Shim J. Kim J. Byun S. Oak MH. Lee KW. Lee HJ.,"Kaempferol attenuates 4-hydroxynonenal-induced apoptosis in PC12 cells by directly inhibiting NADPH oxidase". Journal of Pharmacology & Experimental Therapeutics. 337(3):747-54, 2011 Jun.
deacetylases has been shown, along with PGC-1α, to mediate the life span
extension associated with caloric restriction. SIRT1 deacetylates protein substrates, thus altering their activity or function. SIRT1 interacts directly with PGC-1α to mediate gluconeogenesis and mitochondrial biogenesis by deacetylating and activating PGC-1α. The activators of SIRT1 polyphenols resveratrol
and kaempferol have been shown to increase mitochondrial function and energy expenditure.
A study used the multicellular model organism nematode Caenorhabditis elegans
to examine the effects of the flavonoids kaempferol and fisetin
on their protective action in individual living worms. The results showed that both flavonoids increased the survival of C. elegans, reduced the intracellular reactive oxygen species
(ROS) accumulation at lethal thermal stress, and diminished the extent of induced oxidative stress. Kaempferol had a stronger impact. Kaempferol also attenuated the accumulation of the ageing marker lipofuscin
suggesting a life prolonging activity of this flavonoid. Fisetin
did not have this effect.
Tea
Tea is an aromatic beverage prepared by adding cured leaves of the Camellia sinensis plant to hot water. The term also refers to the plant itself. After water, tea is the most widely consumed beverage in the world...
, broccoli
Broccoli
Broccoli is a plant in the cabbage family, whose large flower head is used as a vegetable.-General:The word broccoli, from the Italian plural of , refers to "the flowering top of a cabbage"....
, Delphinium
Delphinium
Delphinium is a genus of about 300 species of perennial flowering plants in the buttercup family Ranunculaceae, native throughout the Northern Hemisphere and also on the high mountains of tropical Africa. The common name, larkspur, is shared with the closely related genus Consolida...
, Witch-hazel
Witch-hazel
Witch-hazel is a genus of flowering plants in the family Hamamelidaceae, with three species in North America , and one each in Japan and China...
, grapefruit
Grapefruit
The grapefruit , is a subtropical citrus tree known for its sour fruit, an 18th-century hybrid first bred in Barbados. When found, it was named the "forbidden fruit"; it has also been misidentified with the pomelo or shaddock , one of the parents of this hybrid, the other being sweet orange The...
,cabbage, kale, beans, endive, leek, tomato, strawberries, grapes, brussels sprouts, apples 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 ethanol
Ethanol
Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatile, flammable, colorless liquid. It is a psychoactive drug and one of the oldest recreational drugs. Best known as the type of alcohol found in alcoholic beverages, it is also used in thermometers, as a...
and diethyl ether
Diethyl ether
Diethyl ether, also known as ethyl ether, simply ether, or ethoxyethane, is an organic compound in the ether class with the formula . It is a colorless, highly volatile flammable liquid with a characteristic odor...
.
Biological activity
Some epidemiological studies have found a positive association between the consumption of foods containing kaempferol and a reduced risk of developing several disorders such as cancer and cardiovascular diseases. Numerous preclinical studies have shown that kaempferol and some glycosides of kaempferol have a wide range of pharmacological activities, including antioxidant, anti-inflammatory, antimicrobial, anticancer, cardioprotective, neuroprotective, antidiabetic, anti-osteoporotic, estrogenic/antiestrogenic, anxiolytic, analgesic and antiallergic activities (see review article).Many glycoside
Glycoside
In chemistry, a glycoside is a molecule in which a sugar is bound to a non-carbohydrate moiety, usually a small organic molecule. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. These can be activated by enzyme...
s of kaempferol, such as kaempferitrin
Kaempferitrin
Kaempferitrin is a chemical compound. It can be isolated from the leaves of Hedyotis verticillata.Kaempferitrin is the 3,7-dirhamnoside of kaempferol....
and astragalin
Astragalin
Astragalin is a chemical compound. It can be isolated from Phytolacca americana .Astragalin is a 3-O-glucoside of kaempferol....
, have been isolated as natural products from plants. Kaempferol consumption in tea and broccoli has been associated with reduced risk of heart disease. A related compound, Naringenin
Naringenin
Naringenin is a flavanone, a type of flavonoid, that is considered to have a bioactive effect on human health as antioxidant, free radical scavenger, anti-inflammatory, carbohydrate metabolism promoter, and immune system modulator. It is the predominant flavanone in grapefruit.-Biological...
may be present at the same time, such as in grapefruit.
Kaempferol is what gives the flowers of Acacia decurrens
Acacia decurrens
Acacia decurrens is a perennial tree or shrub native to eastern New South Wales...
and Acacia longifolia
Acacia longifolia
Acacia longifolia is a species of Acacia native to southeastern Australia, from the extreme southeast of Queensland, eastern New South Wales, eastern and southern Victoria, and southeastern South Australia. Common names for it include Acacia Trinervis, Aroma Doble, Golden Wattle, Coast Wattle,...
their color. Antidepressant properties have been reported in tests on animals.,
An 8-year study found that three flavonols (kaempferol, quercetin
Quercetin
Quercetin , a flavonol, is a plant-derived flavonoid found in fruits, vegetables, leaves and grains. It also may be used as an ingredient in supplements, beverages or foods.-Occurrence:...
, and myricetin
Myricetin
Myricetin is a naturally occurring flavonol, a flavonoid found in many grapes, berries, fruits, vegetables, herbs, as well as other plants. Walnuts are a rich dietary source. Trace amounts can be found as glycosides. It is one of the phenolic compounds present in red wine.Myricetin has antioxidant...
) reduced the risk of pancreatic cancer
Pancreatic cancer
Pancreatic cancer refers to a malignant neoplasm of the pancreas. The most common type of pancreatic cancer, accounting for 95% of these tumors is adenocarcinoma, which arises within the exocrine component of the pancreas. A minority arises from the islet cells and is classified as a...
by 23 percent.
Kaempferol consumption appears to reduce lung cancer incidence.
Kaempferol may be a potent prophylactic against NOX-mediated neurodegeneration.
Metabolism
The enzyme kaempferol 4'-O-methyltransferaseKaempferol 4'-O-methyltransferase
In enzymology, a kaempferol 4'-O-methyltransferase is an enzyme that catalyzes the chemical reactionThus, the two substrates of this enzyme are S-adenosyl methionine and kaempferol, whereas its two products are S-adenosylhomocysteine and kaempferide....
uses S-adenosyl methionine and kaempferol to produce S-adenosylhomocysteine and kaempferide
Kaempferide
Kaempferide is an O-methylated flavonol, a type of chemical compound. It can be found in Kaempferia galanga .-Metabolism:...
.
Glycosides
- AstragalinAstragalinAstragalin is a chemical compound. It can be isolated from Phytolacca americana .Astragalin is a 3-O-glucoside of kaempferol....
(Astragaline, asragalin, kaempferol-3-O-glucosideGlucosideA glucoside is a glycoside that is derived from glucose. Glucosides are common in plants, but rare in animals. Glucose is produced when a glucoside is hydrolysed by purely chemical means, or decomposed by fermentation or enzymes....
) - Sophoraflavonoloside (kaempferol 3-O-sophoroside)
- Kaempferol-3-O-β-D-glucopyranoside-7-O-α-L-rhamnopyranoside, a known bitter-tasting flavonoid glycoside, can be isolated from the rhizomes of Selliguea feeiSelliguea feeiSelliguea feei is a plant species belonging to the Selliguea genus. This fern can be collected in Indonesia. The species name feei commemorates the botanist Antoine Laurent Apollinaire Fée.-Biochemistry:...
.
List of the plants that contains the chemical
Kaempferol has been identified in many edible plants. It has been found in Allium ampeloprasum (leek), Allium cepa (onion), Allium schoenoprasum (chives), Amaranthus lividus (amaranth), Angelica keiskei (ashitaba), Armoracia rusticana (horseradish), Artemisia dracunculus (tarragon), Atriplex hortensis (orach), Brassica campestris (Chinese cabbage), Brassica juncea (mustard), Brassica napobrassica (rutabagas), Brassica oleracea (broccoli, brussels sprouts, green cabbage and kale), Brassica rapa (turnip greens), Bunias orientalis (Turkish rocket), Camellia sinensis (tea), Capparis spinosa (capers), Celosia argentea (feather cockscomb), Cichorium endivia (endive), Citrus paradisi (grapefruit), Cnidoscolus aconitifolius and C. chayamansa(tree spinach), Coccinia grandis (ivy gourd), Cucumis sativus (cucumber), Cucurbita maxima (squash), Cyamopsis tetragonoloba (cluster bean), Diplotaxis erucoides (wall rocket), Diplotaxis tenuifolia (wild rocket), Eruca sativa (rocket-salad), Foeniculum vulgare (fennel), Fragaria vesca (strawberry), Houttuynia cordata (fishwort), Ipomoea batatas (sweet potato), Lactuca sativa (lettuce), Lepidium sativum (cress), Levisticum officinale (lovage), Lycium barbarum and L. chinense (goji berries), Malus domestica (apple), Momordica cochinchinensis (gac), Morinda citrifolia (Indian mulberry), Nasturtium officinale (watercress), Olea europaea (olive oil), Petroselinum crispum (parsley), Phaseolus vulgaris (green beans), Pistacia vera (pistachio), Prunus persica (peach), Raphanus sativus (radishes), Ribes uva-crispa (gooseberries), Rubís fruticosus (blackberries), Rubus idaeus (raspberry), Sambucus nigra (elderberry), Sauropus androgynus (star gooseberry), Sesbania grandiflora (sesbania), Solanum lycopersicum (tomatoes), Solanum nigrum (nightshade), Solanum tuberosum (potatoes), Spinacia oleracea (spinach), Vaccinium erythrocarpum, V. acrocarpon, V. microcarpum and V. oxycoccos (cranberries), Vaccinium vitis-idaea (cowberries), Vicia faba (broadbeans) Vigna unguiculata (cowpea), Vitis rotundifolia (muscadine grapes) and Vitis vinífera (grapes).Kaempferol has been identified in many plant species commonly used in traditional medicine. It has been found in Acacia nilotica, Adansonia digitata, Albizia lebbeck, Aloe vera, Amburana cearensis, Ammi majus, Angelica keiskei, Ardisia japonica, Bauhinia forficata, Bauhinia microstachya, Bunium persicum, Capparis spinosa, Cassia alata, Centella asiatica, Chromolaena odorata, Cissus sicyoides, Coccinia grandis, Crassocephalum crepidioides, Crocus sativus, Cynanchum acutum, Cynanchum chinense, Dicliptera chinensis, Equisetum arvense, Euphorbia pekinensis, Ficaria verna, Foeniculum vulgare, Galega officinalis, Ginkgo biloba, Glycine max, Grindelia robusta, Gymnema sylvestre, Helleborus niger, Hippophae rhamnoides, Houttuynia cordata, Hypericum perforatum, Impatiens balsamina, Lamium album, Laurus nobilis, Lonicera japonica, Lycium barbarum, Lycium chinense, Lysimachia vulgaris, Malva parviflora, Peumus boldus, Phyllanthus emblica, Ribes nigrum, Rosmarinus officinalis, Sambucus nigra, Sanguisorba minor, Siraitia grosvenori, Solanum nigrum, Solenostemma argel, Solidago virgaaurea, Sutherlandia frutescens, Symphytum officinale, Syzygium aromaticum, Tilia americana, Toona sinensis, Trigonella foenum-graecum, Tropaeolum majus, Vaccinium vitis-idaea, Warburgia ugandensis and Wedelia trilobata.
Kaempferol is also present in Kaempferia galanga
Kaempferia galanga
Kaempferia galanga, commonly known as kencur, aromatic ginger, sand ginger, cutcherry or resurrection lily, is a monocotyledonous plant in the ginger family. It is found primarily in open areas in Indonesia, southern China, Taiwan, Cambodia and India, but is also widely cultivated throughout...
and Opuntia ficus-indica var. saboten.
ref>Jang YJ. Kim J. Shim J. Kim J. Byun S. Oak MH. Lee KW. Lee HJ.,"Kaempferol attenuates 4-hydroxynonenal-induced apoptosis in PC12 cells by directly inhibiting NADPH oxidase". Journal of Pharmacology & Experimental Therapeutics. 337(3):747-54, 2011 Jun.
Kaempferol as a longevity promoting agent
The SIRT1 member of sirtuinSirtuin
Sirtuin or Sir2 proteins are a class of proteins that possess either histone deacetylase or mono-ribosyltransferase activity. Sirtuins regulate important biological pathways in bacteria, archaea and eukaryotes...
deacetylases has been shown, along with PGC-1α, to mediate the life span
Life span
Life span or lifespan may refer to:*Maximum life span, the maximum lifespan observed in a group*Life expectancy, the average lifespan expected of a group*Longevity, the average lifespan expected under ideal conditions...
extension associated with caloric restriction. SIRT1 deacetylates protein substrates, thus altering their activity or function. SIRT1 interacts directly with PGC-1α to mediate gluconeogenesis and mitochondrial biogenesis by deacetylating and activating PGC-1α. The activators of SIRT1 polyphenols resveratrol
Resveratrol
Resveratrol is a stilbenoid, a type of natural phenol, and a phytoalexin produced naturally by several plants when under attack by pathogens such as bacteria or fungi....
and kaempferol have been shown to increase mitochondrial function and energy expenditure.
A study used the multicellular model organism nematode Caenorhabditis elegans
Caenorhabditis elegans
Caenorhabditis elegans is a free-living, transparent nematode , about 1 mm in length, which lives in temperate soil environments. Research into the molecular and developmental biology of C. elegans was begun in 1974 by Sydney Brenner and it has since been used extensively as a model...
to examine the effects of the flavonoids kaempferol and fisetin
Fisetin
Fisetin is a flavonol, a structurally distinct chemical substance that belongs to the flavonoid group of polyphenols. It can be found in many plants, where it serves as a colouring agent...
on their protective action in individual living worms. The results showed that both flavonoids increased the survival of C. elegans, reduced the intracellular reactive oxygen species
Reactive oxygen species
Reactive oxygen species are chemically reactive molecules containing oxygen. Examples include oxygen ions and peroxides. Reactive oxygen species are highly reactive due to the presence of unpaired valence shell electrons....
(ROS) accumulation at lethal thermal stress, and diminished the extent of induced oxidative stress. Kaempferol had a stronger impact. Kaempferol also attenuated the accumulation of the ageing marker lipofuscin
Lipofuscin
Lipofuscin is the name given to finely granular yellow-brown pigment granules composed of lipid-containing residues of lysosomal digestion. It is considered one of the aging or "wear-and-tear" pigments, found in the liver, kidney, heart muscle, adrenals, nerve cells, and ganglion cells...
suggesting a life prolonging activity of this flavonoid. Fisetin
Fisetin
Fisetin is a flavonol, a structurally distinct chemical substance that belongs to the flavonoid group of polyphenols. It can be found in many plants, where it serves as a colouring agent...
did not have this effect.