Adhyperforin

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Adhyperforin
Adhyperforin2DACS.svg
Adhyperforin3Dan2.gif
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administration
Oral
ATC code
  • none
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Legal status
Identifiers
  • (1R,5S,6R,7S)-4-Hydroxy-6-methyl-5-(2-methylbutanoyl)-1,3,7-tris(3-methyl-2-buten-1-yl)-6-(4-methyl-3-penten-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione
CAS Number
PubChem CID
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Chemical and physical data
Formula C36H54O4
Molar mass 550.824 g·mol−1
3D model (JSmol)
  • CCC(C)C(=O)C12C(=C(C(=O)C(C1=O)(CC(C2(C)CCC=C(C)C)CC=C(C)C)CC=C(C)C)CC=C(C)C)O
  • InChI=1S/C36H54O4/c1-12-27(10)30(37)36-32(39)29(18-16-25(6)7)31(38)35(33(36)40,21-19-26(8)9)22-28(17-15-24(4)5)34(36,11)20-13-14-23(2)3/h14-16,19,27-28,39H,12-13,17-18,20-22H2,1-11H3/t27?,28-,34+,35+,36-/m0/s1 X mark.svgN
  • Key:DHPDSOCOUJHGHE-ACJQSPJVSA-N X mark.svgN
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Adhyperforin is a phytochemical found in the members of the plant genus Hypericum including St. John's Wort. [1] It has a very similar pharmacological profile to hyperforin and acts as a TRPC6 ion channel activator, [1] thereby inhibiting the reuptake of various neurotransmitters including serotonin, norepinephrine, dopamine, GABA, and glutamate. [1] Adhyperforin is found in St. John's Wort in levels approximately 1/10 those of hyperforin. [1]

See also

Related Research Articles

<i>Hypericum perforatum</i> Flowering plant in the St Johns wort family Hypericaceae

Hypericum perforatum, known as St. John's wort, is a flowering plant in the family Hypericaceae and the type species of the genus Hypericum.

<i>Hypericum</i> Genus of flowering plants known as St. Johns worts

Hypericum is a genus of flowering plants in the family Hypericaceae. The genus has a nearly worldwide distribution, missing only from tropical lowlands, deserts and polar regions. Many Hypericum species are regarded as invasive species and noxious weeds. All members of the genus may be referred to as St. John's wort, and some are known as goatweed. The white or pink flowered marsh St. John's worts of North America and eastern Asia are generally accepted as belonging to the separate genus TriadenumRaf.

<i>Hypericum calycinum</i> Species of flowering plant in the St Johns wort family Hypericaceae

Hypericum calycinum is a species of prostrate or low-growing shrub in the flowering plant family Hypericaceae. Widely cultivated for its large yellow flowers, its names as a garden plant include Rose-of-Sharon in Britain and Australia, and Aaron's beard, great St-John's wort, creeping St. John's wort and Jerusalem star. Grown in Mediterranean climates, widely spread in the Strandja Mountains along the Bulgarian and Turkish Black Sea coast, and also in Flanders in Belgium.

Hypericaceae Family of flowering plants (St. Johns wort family)

Hypericaceae is a plant family in the order Malpighiales, comprising six to nine genera and up to 700 species, and commonly known as the St. John's wort family. Members are found throughout the world apart from extremely cold or dry habitats. Hypericum and Triadenum occur in temperate regions but other genera are mostly tropical.

Hypericin Chemical compound

Hypericin is a naphthodianthrone, an anthraquinone derivative which, together with hyperforin, is one of the principal active constituents of Hypericum. Hypericin is believed to act as an antibiotic, antiviral and non-specific kinase inhibitor. Hypericin may inhibit the action of the enzyme dopamine β-hydroxylase, leading to increased dopamine levels, although thus possibly decreasing norepinephrine and epinephrine.

Hyperforin Chemical compound

Hyperforin is a phytochemical produced by some of the members of the plant genus Hypericum, notably Hypericum perforatum. Hyperforin may be involved in the pharmacological effects of St. John's wort, specifically in its antidepressant effects.

Dopaminergic Substance related to dopamine functions

Dopaminergic means "related to dopamine" (literally, "working on dopamine"), dopamine being a common neurotransmitter. Dopaminergic substances or actions increase dopamine-related activity in the brain. Dopaminergic brain pathways facilitate dopamine-related activity. For example, certain proteins such as the dopamine transporter (DAT), vesicular monoamine transporter 2 (VMAT2), and dopamine receptors can be classified as dopaminergic, and neurons that synthesize or contain dopamine and synapses with dopamine receptors in them may also be labeled as dopaminergic. Enzymes that regulate the biosynthesis or metabolism of dopamine such as aromatic L-amino acid decarboxylase or DOPA decarboxylase, monoamine oxidase (MAO), and catechol O-methyl transferase (COMT) may be referred to as dopaminergic as well. Also, any endogenous or exogenous chemical substance that acts to affect dopamine receptors or dopamine release through indirect actions (for example, on neurons that synapse onto neurons that release dopamine or express dopamine receptors) can also be said to have dopaminergic effects, two prominent examples being opioids, which enhance dopamine release indirectly in the reward pathways, and some substituted amphetamines, which enhance dopamine release directly by binding to and inhibiting VMAT2.

An antileukotriene, also known as leukotriene modifier and leukotriene receptor antagonist, is a medication which functions as a leukotriene-related enzyme inhibitor or leukotriene receptor antagonist and consequently opposes the function of these inflammatory mediators; leukotrienes are produced by the immune system and serve to promote bronchoconstriction, inflammation, microvascular permeability, and mucus secretion in asthma and COPD. Leukotriene receptor antagonists are sometimes colloquially referred to as leukasts.

TRPC6 Protein-coding gene in the species Homo sapiens

Transient receptor potential cation channel, subfamily C, member 6, also known as TRPC6, is a human gene encoding a protein of the same name. TRPC6 is a transient receptor potential channel of the classical TRPC subfamily. It has been associated with depression and anxiety, as well as with focal segmental glomerulosclerosis (FSGS).

Reuptake inhibitor Type of drug

A reuptake inhibitor (RI) is a type of drug known as a reuptake modulator that inhibits the plasmalemmal transporter-mediated reuptake of a neurotransmitter from the synapse into the pre-synaptic neuron. This leads to an increase in extracellular concentrations of the neurotransmitter and an increase in neurotransmission. Various drugs exert their psychological and physiological effects through reuptake inhibition, including many antidepressants and psychostimulants.

<i>Hypericum androsaemum</i> Species of flowering plant in the St Johns wort family Hypericaceae

Hypericum androsaemum, also referred to as Tutsan, Shrubby St. John's Wort, or sweet-amber, is a flowering plant in the family Hypericaceae. It is a perennial shrub reaching up to 70 cm in height, native to open woods and hillsides in Eurasia.

<i>Hypericum gentianoides</i> Species of flowering plant in the St Johns wort family Hypericaceae

Hypericum gentianoides is a species of flowering plant in the St. John's wort family Hypericaceae. Its common names include orangegrass and pineweed.

<i>Hypericum humifusum</i> Species of flowering plant in the St Johns wort family Hypericaceae

Hypericum humifusum is a prostrate flowering plant in the St. John's wort family Hypericaceae commonly known as trailing St John's-wort. It is found in Western Europe.

<i>Hypericum hirsutum</i> Species of flowering plant in the St Johns wort family Hypericaceae

Hypericum hirsutum is a species of flowering plant in the family Hypericaceae, commonly known as hairy St John's-wort. It is found in Western Europe.

<i>Hypericum pulchrum</i> Species of flowering plant in the St Johns wort family Hypericaceae

Hypericum pulchrum is a flowering plant in the family Hypericaceae, commonly known as slender St John's-wort. It is native to Western Europe.

<i>Hypericum kalmianum</i> Species of flowering plant in the St Johns wort family Hypericaceae

Hypericum kalmianum, commonly called Kalm's St. Johns wort or Kalm's St. Johnswort, is a flowering plant in the St. John's wort family Hypericaceae. It is native to the Great Lakes region in the northern United States and southern Canada. Hypericum kalmianum was named after its discoverer, Swedish botanist Pehr Kalm (1715-1779).

<i>Hypericum swinkianum</i> Species of plant

Hypericum swinkianum, known as Swink's St. John's wort, is a shrub in the St. John's wort family. It was named after Chicago Region botanist Floyd Swink (1921-2000).

<i>Hypericum punctatum</i> Species of flowering plant

Hypericum punctatum, the spotted St. John's wort, is a perennial herb native to North America. The yellow-flowered herb occurs throughout eastern North America into southern Canada. The process of microsporogenesis carried out by this plant is prone to errors in chromosomal segregation. It has a diploid number of 14 or 16. Insects are attracted to the plant's pollen and the hypericin in the plant's leaves is toxic to mammals.

Hypericum edisonianum, known as Arcadian St. John's wort, Edison's St. John's wort, and Edison ascyrum, is a species of flowering plant in the St. John's wort family, Hypericaceae. It is endemic to Florida.

<i>Hypericum japonicum</i> Species of flowering plant in the St Johns wort family Hypericaceae

Hypericum japonicum, known as matted St. John's-wort, is an annual herbaceous flowering plant in the St. John's wort family Hypericaceae, in Hypericum sect. Trigynobrathys.

References

  1. 1 2 3 4 Jensen AG, Hansen SH, Nielsen EO (2001). "Adhyperforin as a contributor to the effect of Hypericum perforatum L. in biochemical models of antidepressant activity". Life Sci. 68 (14): 1593–1605. doi:10.1016/S0024-3205(01)00946-8. PMID   11263672.