Chrysin
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Chrysin, also called 5,7-dihydroxyflavone, is a
flavone Flavone is an organic compound with the formula . A white solid, flavone is a derivative of chromone with a phenyl (Ph) substituent adjacent to the ether group. The compound is of little direct practical importance, but susbstituted derivatives, ...
found in
honey Honey is a sweet and viscous substance made by several bees, the best-known of which are honey bees. Honey is made and stored to nourish bee colonies. Bees produce honey by gathering and then refining the sugary secretions of plants (primar ...
,
propolis Propolis or bee glue is a resinous mixture that honey bees produce by mixing saliva and beeswax with exudate gathered from tree buds, sap flows, or other botanical sources. It is used as a sealant for unwanted open spaces in the beehive. Prop ...
, the passion flowers, ''
Passiflora caerulea ''Passiflora caerulea'', the blue passionflower, bluecrown passionflower or common passion flower, is a species of flowering plant native to South America. It has been introduced elsewhere. It is a vigorous, deciduous or semi-evergreen tendril vi ...
'' and ''
Passiflora incarnata ''Passiflora incarnata'', commonly known as maypop, purple passionflower, true passionflower, wild apricot, and wild passion vine, is a fast-growing perennial vine with climbing or trailing stems. A member of the passionflower genus ''Passiflora ...
'', and in ''
Oroxylum indicum ''Oroxylum indicum'' is a species of flowering plant belonging to the monotypic genus ''Oroxylum'' and the family Bignoniaceae, and is commonly called Indian trumpet tree, oroxylum, Indian trumpet flower, broken bones, Indian caper, scythe tree o ...
''. It is
extract An extract is a substance made by extracting a part of a raw material, often by using a solvent such as ethanol, oil or water. Extracts may be sold as tinctures, absolutes or in powder form. The aromatic principles of many spices, nuts ...
ed from various plants, such as the blue passion flower (''Passiflora caerulea''). Following oral intake by humans, chrysin has low
bioavailability In pharmacology, bioavailability is a subcategory of absorption and is the fraction (%) of an administered drug that reaches the systemic circulation. By definition, when a medication is administered intravenously, its bioavailability is 100%. Ho ...
and rapid
excretion Excretion is a process in which metabolic waste is eliminated from an organism. In vertebrates this is primarily carried out by the lungs, kidneys, and skin. This is in contrast with secretion, where the substance may have specific tasks after ...
. It is under
basic research Basic research, also called pure research or fundamental research, is a type of scientific research with the aim of improving scientific theories for better understanding and prediction of natural or other phenomena. In contrast, applied rese ...
to evaluate its safety and potential biological effects. Chrysin is an ingredient in
dietary supplement A dietary supplement is a manufactured product intended to supplement one's diet by taking a pill, capsule, tablet, powder, or liquid. A supplement can provide nutrients either extracted from food sources or that are synthetic in order ...
s. As of 2016, there was no clinical use of chrysin, and no evidence for its effect on
testosterone Testosterone is the primary sex hormone and anabolic steroid in males. In humans, testosterone plays a key role in the development of male reproductive tissues such as testes and prostate, as well as promoting secondary sexual characteristi ...
levels. In 2016, the US
Food and Drug Administration The United States Food and Drug Administration (FDA or US FDA) is a federal agency of the Department of Health and Human Services. The FDA is responsible for protecting and promoting public health through the control and supervision of food ...
did not recommend chrysin be included on the list of bulk drug substances that can be used in
compounding In the field of pharmacy, compounding (performed in compounding pharmacies) is preparation of a custom formulation of a medication to fit a unique need of a patient that cannot be met with commercially available products. This may be done for me ...
under section 503A of the
Federal Food, Drug, and Cosmetic Act The United States Federal Food, Drug, and Cosmetic Act (abbreviated as FFDCA, FDCA, or FD&C) is a set of laws passed by the United States Congress in 1938 giving authority to the U.S. Food and Drug Administration (FDA) to oversee the safety of ...
.


Occurrence

A component in various
medicinal plants Medicinal plants, also called medicinal herbs, have been discovered and used in traditional medicine practices since prehistoric times. Plants synthesize hundreds of chemical compounds for various functions, including defense and protection ag ...
(e.g. ''
Scutellaria baicalensis ''Scutellaria baicalensis'', with the common name Baikal skullcap or Chinese skullcap, is a species of flowering plant in the family Lamiaceae. Distribution The plant is native to China, Korea, Mongolia, and Russia in the Russian Far East and Si ...
''), chrysin is a dihydroxyflavone, 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 ...
. It is also found in
honey Honey is a sweet and viscous substance made by several bees, the best-known of which are honey bees. Honey is made and stored to nourish bee colonies. Bees produce honey by gathering and then refining the sugary secretions of plants (primar ...
,
propolis Propolis or bee glue is a resinous mixture that honey bees produce by mixing saliva and beeswax with exudate gathered from tree buds, sap flows, or other botanical sources. It is used as a sealant for unwanted open spaces in the beehive. Prop ...
, the passion flowers, ''
Passiflora caerulea ''Passiflora caerulea'', the blue passionflower, bluecrown passionflower or common passion flower, is a species of flowering plant native to South America. It has been introduced elsewhere. It is a vigorous, deciduous or semi-evergreen tendril vi ...
'' and ''
Passiflora incarnata ''Passiflora incarnata'', commonly known as maypop, purple passionflower, true passionflower, wild apricot, and wild passion vine, is a fast-growing perennial vine with climbing or trailing stems. A member of the passionflower genus ''Passiflora ...
'', in ''
Oroxylum indicum ''Oroxylum indicum'' is a species of flowering plant belonging to the monotypic genus ''Oroxylum'' and the family Bignoniaceae, and is commonly called Indian trumpet tree, oroxylum, Indian trumpet flower, broken bones, Indian caper, scythe tree o ...
'', carrots,
chamomile Chamomile (American English) or camomile (British English; see spelling differences) ( or ) is the common name for several plants of the family Asteraceae. Two of the species, ''Matricaria recutita'' and ''Anthemis nobilis'', are commonly us ...
, many fruits, and in
mushroom A mushroom or toadstool is the fleshy, spore-bearing fruiting body of a fungus, typically produced above ground, on soil, or on its food source. ''Toadstool'' generally denotes one poisonous to humans. The standard for the name "mushroom" is ...
s, such as the mushroom ''
Pleurotus ostreatus ''Pleurotus ostreatus'', the oyster mushroom, oyster fungus, or hiratake, is a common edible mushroom. It was first cultivated in Germany as a subsistence measure during World War I and is now grown commercially around the world for food. It is ...
''. It is
extract An extract is a substance made by extracting a part of a raw material, often by using a solvent such as ethanol, oil or water. Extracts may be sold as tinctures, absolutes or in powder form. The aromatic principles of many spices, nuts ...
ed from various plants, such as the blue passion flower (''Passiflora caerulea''). The amount of chrysin in honey from various plant sources is about 0.2 mg per 100 g. Chrysin is typically found at higher amounts in propolis than in honey. A 2010 study found the amount of chrysin was 0.10 mg/kg in honeydew honey, and 5.3 mg/kg in forest honeys. A 2010 study found the amount of chrysin in propolis was as much as 28 g/L. A 2013 study found the amount of chrysin in various mushrooms from the island of Lesvos, Greece, varied between 0.17 mg/kg in ''
Lactarius deliciosus ''Lactarius deliciosus'', commonly known as the saffron milk cap and red pine mushroom, is one of the best known members of the large milk-cap genus ''Lactarius'' in the order Russulales. It is native to Europe, but has been accidentally introd ...
'' to 0.34 mg/kg in ''
Suillus bellinii ''Suillus bellinii'', the Champagne bolete, is a pored mushroom of the genus ''Suillus'' in the family Suillaceae. It is found in coastal pine forests of southern Europe. Description The cap is initially convex and irregular, but becomes flatt ...
''.


Bioavailability

The effects of chrysin are reliant on its
bioavailability In pharmacology, bioavailability is a subcategory of absorption and is the fraction (%) of an administered drug that reaches the systemic circulation. By definition, when a medication is administered intravenously, its bioavailability is 100%. Ho ...
and
solubility In chemistry, solubility is the ability of a substance, the solute, to form a solution with another substance, the solvent. Insolubility is the opposite property, the inability of the solute to form such a solution. The extent of the solubi ...
. Following oral intake by humans, chrysin has low bioavailability and rapid
excretion Excretion is a process in which metabolic waste is eliminated from an organism. In vertebrates this is primarily carried out by the lungs, kidneys, and skin. This is in contrast with secretion, where the substance may have specific tasks after ...
. As a result, it is poorly absorbed. A 1998 study determined that the highest amounts in plasma was from 12 to 64 nM. As of 2015, the
serum Serum may refer to: * Serum (blood), plasma from which the clotting proteins have been removed **Antiserum, blood serum with specific antibodies for passive immunity * Serous fluid, any clear bodily fluid *Truth serum, a drug that is likely to mak ...
levels of chrysin have not been cited in the literature. Following oral intake by humans, the bioavailability was reported to be from 0.003% to 0.02%.


Oral and topical application

There is insufficient information to determine how long chrysin has been used in pharmacy
compounding In the field of pharmacy, compounding (performed in compounding pharmacies) is preparation of a custom formulation of a medication to fit a unique need of a patient that cannot be met with commercially available products. This may be done for me ...
. Chrysin is used as an ingredient in
dietary supplement A dietary supplement is a manufactured product intended to supplement one's diet by taking a pill, capsule, tablet, powder, or liquid. A supplement can provide nutrients either extracted from food sources or that are synthetic in order ...
s, but there is no information on systemic exposure from
topical application A topical medication is a medication that is applied to a particular place on or in the body. Most often topical medication means application to body surfaces such as the skin or mucous membranes to treat ailments via a large range of classes ...
. As of 2016, there was no evidence to support any effect of oral chrysin on
testosterone Testosterone is the primary sex hormone and anabolic steroid in males. In humans, testosterone plays a key role in the development of male reproductive tissues such as testes and prostate, as well as promoting secondary sexual characteristi ...
levels, or an any disease-modifying activity with oral or topical formulations.


Safety

A daily consumed amount of chrysin of 0.5 to 3 g is considered safe. As of 2016, there was no toxicity attributable to chrysin in
clinical trial Clinical trials are prospective biomedical or behavioral research studies on human participants designed to answer specific questions about biomedical or behavioral interventions, including new treatments (such as novel vaccines, drugs, diet ...
s or
adverse event An adverse event (AE) is any untoward medical occurrence in a patient or clinical investigation subject administered a pharmaceutical product and which does not necessarily have a causal relationship with this treatment. An adverse event can ther ...
reporting. As of 2016, clinical safety issues have not been identified. As of 2016, nonclinical data suggest potential concerns. In 2016, the US
Food and Drug Administration The United States Food and Drug Administration (FDA or US FDA) is a federal agency of the Department of Health and Human Services. The FDA is responsible for protecting and promoting public health through the control and supervision of food ...
did not recommend chrysin be included on the list of bulk drug substances that can be used in compounding under section 503A of the
Federal Food, Drug, and Cosmetic Act The United States Federal Food, Drug, and Cosmetic Act (abbreviated as FFDCA, FDCA, or FD&C) is a set of laws passed by the United States Congress in 1938 giving authority to the U.S. Food and Drug Administration (FDA) to oversee the safety of ...
based on consideration of the following criteria: (1) physicochemical characterization; (2) safety; (3) effectiveness; and (4) historical use of the substance in compounding.


Research

As of 2016, there is no evidence for chrysin being used in human clinical applications. Research showed that orally administered chrysin does not have clinical activity as an
aromatase Aromatase (), also called estrogen synthetase or estrogen synthase, is an enzyme responsible for a key step in the biosynthesis of estrogens. It is CYP19A1, a member of the cytochrome P450 superfamily, which are monooxygenases that catalyze many ...
inhibitor. Nanoformulations of
polyphenol Polyphenols () are a large family of naturally occurring organic compounds characterized by multiples of phenol units. They are abundant in plants and structurally diverse. Polyphenols include flavonoids, tannic acid, and ellagitannin, some ...
s, including chrysin, are made using various carrier methods, such as
liposome A liposome is a small artificial Vesicle (biology and chemistry), vesicle, spherical in shape, having at least one lipid bilayer. Due to their hydrophobicity and/or hydrophilicity, biocompatibility, particle size and many other properties, lipo ...
s and nanocapsules.


Bibliography

*


References

{{Xenobiotic-sensing receptor modulators Aromatase inhibitors Flavones Flavonoids found in Asteraceae Resorcinols