関: catechin、catechinic acid

WordNet

a tannic acid that is extracted from black catechu as a white crystalline substance

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/09/15 14:47:50」(JST)

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Catechin /ˈkætɪtʃɪn/ is a flavan-3-ol, a type of natural phenol and antioxidant. It is a plant secondary metabolite. It belongs to the group of flavan-3-ols (or simply flavanols), part of the chemical family of flavonoids.

The name of the catechin chemical family derives from catechu, which is the tannic juice or boiled extract of Mimosa catechu (Acacia catechu L.f).^[1]

1 Chemistry
- 1.1 Oxidation
- 1.2 Spectral data
2 Natural occurrences
- 2.1 In food
  - 2.1.1 Taste
3 Metabolism
- 3.1 Biosynthesis
- 3.2 Biodegradation
- 3.3 Humans
- 3.4 Research
- 3.5 Biotransformation
- 3.6 Glycosides
4 Bioactivity studies
- 4.1 Vascular function
- 4.2 Possible immune effects
5 Botanical effects
6 References
7 External links

Chemistry

Catechin numbered

Catechin possesses two benzene rings (called the A- and B-rings) and a dihydropyran heterocycle (the C-ring) with a hydroxyl group on carbon 3. The A ring is similar to a resorcinol moiety while the B ring is similar to a catechol moiety. There are two chiral centers on the molecule on carbons 2 and 3. Therefore, it has four diastereoisomers. Two of the isomers are in trans configuration and are called catechin and the other two are in cis configuration and are called epicatechin.

The most common catechin isomer is the (+)-catechin. The other stereoisomer is (-)-catechin or ent-catechin. The most common epicatechin isomer is (-)-epicatechin (also known under the names L-epicatechin, epicatechol, (-)-epicatechol, l-acacatechin, l-epicatechol, epi-catechin, 2,3-cis-epicatechin or (2R,3R)-(-)-epicatechin).

The different epimers can be distinguished using chiral column chromatography.^[2]

Making reference to no particular isomer, the molecule can just be called catechin. Mixtures of the different enantiomers can be called (+/-)-catechin or DL-catechin and (+/-)-epicatechin or DL-epicatechin.

Catechin and epicatechin are the building blocks of the proanthocyanidins, a type of condensed tannin.

Diastereoisomers gallery
(+)-catechin (2R,3S)
(-)-catechin (2S,3R)
(-)-epicatechin (2R,3R)
(+)-epicatechin (2S,3S)

3D view of "pseudoequatorial" (E) conformation of(+)-catechin

Moreover, the flexibility of the C-ring allows for two conformation isomers, putting the B ring either in a pseudoequatorial position (E conformer) or in a pseudoaxial position (A conformer). Studies confirmed that (+)-catechin adopts a mixture of A- and E-conformers in aqueous solution and their conformational equilibrium has been evaluated to be 33:67.^[3]

As flavonoids, catechins can act as antioxidants when in high concentration in vitro, but compared with other flavonoids, their antioxidant potential is low.^[4] The ability to quench singlet oxygen seems to be in relation with the chemical structure of catechin, with the presence of the catechol moiety on ring B and the presence of a hydroxyl group activating the double bond on ring C.^[5]

Oxidation

Electrochemical experiments show that (+)-catechin oxidation mechanism proceeds in sequential steps, related with the catechol and resorcinol groups and the oxidation is pH-dependent. The oxidation of the catechol 3',4'-dihydroxyl electron-donating groups occurs first, at very low positive potentials, and is a reversible reaction. The hydroxyl groups of the resorcinol moiety oxidised afterwards were shown to undergo an irreversible oxidation reaction.^[6]

The laccase/ABTS system oxidizes (+)-catechin to oligomeric products^[7] of which proanthocyanidin A2 is a dimer.

Spectral data

UV spectrum of catechin.

UV-Vis
Lambda-max:	276 nm
Extinction coefficient (log ε)	4.01
IR
Major absorption bands	1600 cm⁻¹(benzene rings)
NMR
Proton NMR (500 MHz, CD3OD): Reference^[8] d : doublet, dd : doublet of doublets, m : multiplet, s : singlet	δ : 2.49 (1H, dd, J = 16.0, 8.6 Hz, H-4a), 2.82 (1H, dd, J = 16.0, 1.6 Hz, H-4b), 3.97 (1H, m, H-3), 4.56 (1H, d, J = 7.8 Hz, H-2), 5.86 (1H, d, J = 2.1 Hz, H-6), 5.92 (1H, d, J = 2.1 Hz, H-8), 6.70 (1H, dd, J = 8.1, 1.8 Hz, H-6'), 6.75 (1H, d, J = 8.1 Hz, H-5'), 6.83 (1H, d, J = 1.8 Hz, H-2')
Carbon-13 NMR
Other NMR data
MS
Masses of main fragments	ESI-MS [M+H]+ m/z : 291.0 273 water loss 139 Retro Diels Alder 123 165 147

Natural occurrences

(+)-Catechin and (-)-epicatechin as well as their gallic acid conjugates are ubiquitous constituents of vascular plants, and frequent components of traditional herbal remedies, such as the Chinese medicine plant Uncaria rhynchophylla and others. The two isomers are mostly found as cacao and tea constituents.

(-)-Epicatechin can be found in cacao beans and was first called kakaool or cacao-ol.^[9] It was isolated from green tea by Michiyo Tsujimura in 1929.^[10] Maximilian Nierenstein was among those who proved the presence of catechin in cocoa beans in 1931.^[11]

Catechin is also found as glycoside^[12] and the glycosidic form has also antioxidant properties "in vitro".

In food

The main dietary sources of catechins in Europe and the United States are tea and pome fruits.^[13]^[14]

Catechins and epicatechins are found in cocoa,^[15] which, according to one database, has the highest content (108 mg/100 g) of catechins among foods analyzed, followed by prune juice (25 mg/100 ml) and broad bean pod (16 mg/100 g).^[16] Açaí oil, obtained from the fruit of the açaí palm (Euterpe oleracea), contains (+)-catechins (67 mg/kg).^[17] (-)-Epicatechin and (+)-catechin are among the main natural phenols in argan oil.^[18]

Catechins are diverse among foods,^[16] from peaches^[19] to green tea and vinegar.^[16]^[20] Catechins are found in barley grain where they are the main phenolic compound responsible for dough discoloration.^[21]

Taste

The taste associated with monomeric (+)-catechin or (-)-epicatechin is described as not exactly astringent, nor exactly bitter.^[22]

Metabolism

Biosynthesis

The biosynthesis of catechin begins with a 4-hydroxycinnamoyl CoA starter unit which undergoes chain extension by the addition of three malonyl-CoAs through a PKSIII pathway. 4-hydroxycinnamoyl CoA is biosynthesized from L-phenylalanine through the Shikimate pathway. L-phenylalanine is first deaminated by phenylalanine ammonia lyase (PAL) forming cinnamic acid which is then oxidized to 4-hydroxycinnamic acid by cinnamate 4-hydroyxylase. Chalcone synthase then catalyzes the condensation of 4-hydroxycinnamoyl CoA and three molecules of malonyl-CoA to form chalcone. Chalcone is then isomerized to naringenin by chalcone isomerase which is oxidized to eriodictyol by flavonoid 3'- hydroxylase and further oxidized to taxifolin by flavanone 3-hydroxylase. Taxifolin is then reduced by dihydroflavanol 4-reductase and leucoanthocyanidin reductase to yield catechin. The biosynthesis of catechin is shown below^[23]^[24]^[25]

Leucocyanidin reductase (LCR) uses 2,3-trans-3,4-cis-leucocyanidin to produce (+)-catechin and is the first enzyme in the proanthocyanidins (PA)-specific pathway. Its activity has been measured in leaves, flowers, and seeds of the legumes Medicago sativa, Lotus japonicus, Lotus uliginosus, Hedysarum sulfurescens, and Robinia pseudoacacia.^[26] The enzyme is also present in Vitis vinifera (grape).^[27]

Biodegradation

Catechin oxygenase, a key enzyme in the degradation of catechin, is present in fungi and bacteria.^[28]

Among bacteria, degradation of (+)-catechin can be achieved by Acinetobacter calcoaceticus. Catechin is metabolized to protocatechuic acid (PCA) and phloroglucinol carboxylic acid (PGCA).^[29] It is also degraded by Bradyrhizobium japonicum. Phloroglucinol carboxylic acid is further decarboxylated to phloroglucinol, which is dehydroxylated to resorcinol. Resorcinol is hydroxylated to hydroxyquinol. Protocatechuic acid and hydroxyquinol undergo intradiol cleavage through protocatechuate 3,4-dioxygenase and hydroxyquinol 1,2-dioxygenase to form β-carboxy cis, cis-muconic acid and maleyl acetate.^[30]

Among fungi, degradation of catechin can be achieved by Chaetomium cupreum.^[31]

Humans

Human metabolites of epicatechin (excluding colonic metabolites)^[32]

Schematic representation of (−)-epicatechin metabolism in humans as a function of time post-oral intake. SREM: structurally related (−)-epicatechin metabolites. 5C-RFM: 5-carbon ring fission metabolites. 3/1C-RFM: 3- and 1-carbon-side chain ring fission metabolites. The structures of the most abundant (−)-epicatechin metabolites present in the systemic circulation and in urine are depicted.^[32]

Catechins are metabolised upon uptake from the gastrointestinal tract, in particular the jejunum,^[33] and in the liver, resulting in so-called structurally-related epicatechin metabolites (SREM).^[34] The main metabolic pathways for SREMs are glucuronidation, sulphation and methylation of the catechol group by catechol-O-methyl transferase, with only small amounts detected in plasma.^[35]^[32] The majority of dietary catechins are however metabolised by the colonic microbiome to gamma-valerolactones and hippuric acids which undergo further biotransformation, glucuronidation, sulphation and methylation in the liver.^[35]

The stereochemical configuration of catechins has a strong impact on their uptake and metabolism as uptake is highest for (-)-epicatechin and lowest for (-)-catechin.^[36]

Research

Inter-species differences in (-)-epicatechin metabolism.^[32]

Plasma catechin metabolites are present as conjugated forms and mainly constituted by glucuronidated and sulphated derivatives. There are large inter-species differences in metabolism, making comparisons between data from rodents and humans difficult. The primary metabolite of (+)-catechin in rat plasma is a glucuronide in the nonmethylated form. In contrast, the primary metabolites of (-)-epicatechin in rat plasma are glucuronide and sulfoglucuronide in nonmethylated forms, and sulfate in the 3'-O-methylated forms (3'OMC).^[37] The recent use of radiocarbon-labeled epicatechin (¹⁴C₂-(−)-epicatechin) demonstrated significant species-dependent differences in the metabolism of (-)-epicatechin in rat, mouse and human.^[32]

In rats, the concentrations of catechin derivatives in the liver are lower than in plasma, and no accumulation is observed after adaptation for 14 days to the supplemented diets. The hepatic metabolites are intensively methylated (90–95%), but in contrast to plasma, some free aglycones can be detected.^[38] Rats fed with (+)-catechin and (-)-epicatechin exhibit (+)-catechin 5-O-β-glucuronide and (-)-epicatechin 5-O-β-glucuronide in their body fluids.^[39] Catechin is absorbed into intestinal cells and metabolized extensively because no native catechin can be detected in plasma from the mesenteric vein.^[35] Additional methylation and sulfation occur in the liver, and glucuronide or sulfate conjugates of 3'OMC are excreted extensively in bile. Circulating forms are mainly glucuronide conjugates of catechin and 3'OMC.^[40] Another study shows that catechin undergoes enzymatic oxidation by tyrosinase in the presence of glutathione (GSH) to form mono-, bi-, and tri-glutathione conjugates of catechin and mono- and bi-glutathione conjugates of a catechin dimer.^[41]

In the crab-eating macaque (Macaca iris), (+)-catechin administered orally or intraperitonally leads to the formation of 10 metabolites and notably to m-hydroxyphenylhydracrylic acid excreted in the urine.^[42]

Biotransformation

Biotransformation of (+)-catechin into taxifolin by a two-step oxidation can be achieved by Burkholderia sp.^[43]

(+)-Catechin and (-)-epicatechin are transformed by the endophytic filamentous fungus Diaporthe sp. into the 3,4-cis-dihydroxyflavan derivatives, (+)-(2R,3S,4S)-3,4,5,7,3',4'-hexahydroxyflavan (leucocyanidin) and (-)-(2R,3R,4R)-3,4,5,7,3',4'-hexahydroxyflavan, respectively, whereas (-)-catechin and (+)-epicatechin with a 2S-phenyl group resisted the biooxidation.^[44]

Leucoanthocyanidin reductase (LAR) uses (2R,3S)-catechin, NADP⁺ and H₂O to produce 2,3-trans-3,4-cis-leucocyanidin, NADPH, and H⁺. Its gene expression has been studied in developing grape berries and grapevine leaves.^[45]

Glycosides

(2R,3S)-Catechin-7-O-β-D-glucopyranoside can be isolated from barley (Hordeum vulgare L.) and malt.^[46]
Epigeoside (Catechin-3-O-alpha-L-rhamnopyranosyl-(1-4)-beta-D-glucopyranosyl-(1–6)-beta-D-glucopyranoside) can be isolated from the rhizomes of Epigynum auritum.^[47]

Bioactivity studies

Vascular function

Association between flavan-3-ol intake and incidence of cardiovascular disease in different cohort studies.^[48] Data compare the bottom and top quintiles of intake.

Centuries ago, catechin-containing extracts were thought to be useful for treating heart diseases,^[49]^[50] and an effect on the permeability of capillaries was shown in 1936.^[51] Limited evidence from dietary studies indicates that catechins may have an effect on endothelium-dependent vasodilation which could contribute to normal blood flow regulation in humans.^[52]^[53] Green tea catechins may improve blood pressure, especially when systolic blood pressure is above 130 mmHg.^[54] Due to extensive metabolism during digestion, the fate and activity of catechin metabolites responsible for this effect on blood vessels, as well as the actual mode of action, are unknown.^[35]^[55]

The European Food Safety Authority established that cocoa flavanols have an effect on vascular function in healthy adults by concluding: "cocoa flavanols help maintain endothelium-dependent vasodilation, which contributes to normal blood flow".^[56] Data from observational cohort studies have not shown a consistent association between flavan-3-ol intake and risk of cardiovascuar diseases.^[48]

A meta-analysis also indicated that green tea catechins may favorably affect cholesterol.^[54]

Possible immune effects

Depending on dose consumed, catechins and their metabolites can bind to red blood cells and possibly induce release of autoantibodies, resulting in haemolytic anaemia and renal failure.^[57] This resulted in the withdrawal of the catechin-containing drug Catergen, used to treat viral hepatitis, from the European market in 1985.^[58]^[59]

Botanical effects

Catechins released into the ground by some plants may hinder the growth of their neighbors, a form of allelopathy.^[60] Centaurea maculosa, the spotted knapweed often studied for this behavior, releases catechin isomers into the ground through its roots, potentially having effects as an antibiotic or herbicide. One hypothesis is that it causes a reactive oxygen species wave through the target plant's root to kill root cells by apoptosis.^[61] Most plants in the European ecosystem have defenses against catechin, but few plants are protected against it in the North American ecosystem where Centaurea maculosa is an invasive, uncontrolled weed.^[60]

Catechin acts as an infection-inhibiting factor in strawberry leaves.^[62] Epicatechin and catechin may prevent coffee berry disease by inhibiting appressorial melanization of Colletotrichum kahawae.^[63]

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External links

English Journal

Preparative HSCCC isolation of phloroglucinolysis products from grape seed polymeric proanthocyanidins as new powerful antioxidants.

Zhang S1, Cui Y2, Li L2, Li Y2, Zhou P2, Luo L2, Sun B3.
Food chemistry.Food Chem.2015 Dec 1;188:422-9. doi: 10.1016/j.foodchem.2015.05.030. Epub 2015 May 7.
Polymeric proanthocyanidins isolated from a grape seed phenolic extract were hydrolysed in the presence of phloroglucinol into monomer catechins and their nucleophile derivatives. Each of the phloroglucinolysis products was successfully separated and isolated in large amount by semi-preparative HSCC
PMID 26041213

Phenolic compounds, organic acids and antioxidant activity of grape juices produced in industrial scale by different processes of maceration.

Lima Mdos S1, da Conceição Prudêncio Dutra M1, Toaldo IM2, Corrêa LC3, Pereira GE3, de Oliveira D4, Bordignon-Luiz MT2, Ninow JL5.
Food chemistry.Food Chem.2015 Dec 1;188:384-92. doi: 10.1016/j.foodchem.2015.04.014. Epub 2015 Apr 11.
The effect of maceration process on the profile of phenolic compounds, organic acids composition and antioxidant activity of grape juices from new varieties of Vitis labrusca L. obtained in industrial scale was investigated. The extraction process presented a high yield without pressing the grapes.
PMID 26041208

Hydrogenolytic depolymerization of procyanidin polymers from hi-tannin sorghum bran.

Li Z1, Zeng J2, Tong Z2, Qi Y3, Gu L4.
Food chemistry.Food Chem.2015 Dec 1;188:337-42. doi: 10.1016/j.foodchem.2015.05.021. Epub 2015 May 6.
Depolymerization of procyanidin polymers into oligomers enhances their bioavailability and bioactivity because oligomers are bioavailable. Hydrogenolysis was applied in this study to depolymerize hi-tannin sorghum bran procyanidin polymers into oligomers. The yield and composition of oligomers under
PMID 26041201

Japanese Journal

新規環状ジスルフィド化合物ＳＡ３４４３のＡｃｅｔａｍｉｎｏｐｈｅｎ誘発肝障害に対する防御作用

田中美保子 [他],中田勝彦,高瀬謙二,三田四郎
日本薬理学雑誌 97(4), 191-198, 1991
… 性と共に肝の病理組織学的変化を用量依存的に抑制し，また，acetaminophen(350mg/kg)による急性肝不全死に対しても同用量で抑制した．このBALB/cマウスの急性肝不全死モデルに対して，他の肝疾患治療薬であるcianidanol(500mg/kg)，malotilate(100mg/kg)，glycyrrhizine(10mg/kg)およびcystein(300mg/kg)も同様に抑制した．一方，SA3443は正常マウスの肝GSH量に対して何等影響を与えなかったが，acetaminophen投与による肝GSH量の低下を用量依存的に抑 …
NAID 130000758963

Liver injury model in mice for immunopharmacological study.

NAGAI Hiroichi,YAKUO Ikuhisa,YAMADA Hiroaki,SHIMAZAWA Tsukasa,KODA Akihide,NIU Kazumi,ASANO Kyouichi,SHIMIZU Tamotsu,KASAHARA Masao
The Japanese Journal of Pharmacology 46(3), 247-254, 1988
… Cianidanol and sylibin inhibited the elevation of GOT and GPT in anti-BLP induced liver injured mice. …
NAID 130000832117

シアニダノールの免疫賦活作用について

溝口靖紘,阪上吉秀,筒井ひろ子,山本祐夫,森沢成司
アレルギー 35(6), 422-427, 1986-06-30
HBe抗原陽性慢性肝炎患者の末梢血単核細胞をHBs抗原あるいは精製ツベルクリン蛋白(PPD)で刺激し, ^3H-サイミジンの酸不溶性分画へのとりこみでリンパ球幼若化反応を検討した.その結果, フラボノイド化合物であるシアニダノールを抗原をともに加えるとリンパ球幼若化反応が増幅した.この増幅作用は, シアニダノールがマクロファージを活性化し, さらにこの薬剤がマクロファージのインターリュウキン-1産 …
NAID 110002414799

Related Pictures

★リンクテーブル★

リンク元	「catechin」「シアニダノール」「catechinic acid」

「catechin」

Catechin
Names
	IUPAC name (2R,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
	Other names Cianidanol; Cyanidanol; (+)-catechin; D-Catechin; Catechinic acid; Catechuic acid; Cianidol; Dexcyanidanol; (2R,3S)-Catechin; 2,3-trans-catechin; 3,3',4',5,7–flavanpentol
Identifiers
CAS Number	7295-85-4 (±) ; 154-23-4 (+) ; 18829-70-4 (-) ; 88191-48-4 (+), hydrate ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:15600 ;
ChemSpider	8711 ;
ECHA InfoCard	100.005.297
PubChem CID	9064;
UNII	8R1V1STN48 ;
	InChI InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15+/m0/s1 Key: PFTAWBLQPZVEMU-DZGCQCFKSA-N ; InChI=1/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15+/m0/s1 Key: PFTAWBLQPZVEMU-DZGCQCFKBX ;
	SMILES Oc1ccc(cc1O)[C@H]3Oc2cc(O)cc(O)c2C[C@@H]3O ;
Properties
Chemical formula	C15H14O6
Molar mass	290.27 g·mol−1
Appearance	Colorless solid
Melting point	175 to 177 °C (347 to 351 °F; 448 to 450 K)
UV-vis (λmax)	276 nm
Chiral rotation ([α]D)	+14.0°
Hazards
Main hazards	Mutagenic for mammalian somatic cells, mutagenic for bacteria and yeast
Safety data sheet	sciencelab AppliChem[permanent dead link]
R-phrases (outdated)	R36/37/38
S-phrases (outdated)	S26-S36
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	(+)-catechin : 10,000 mg/kg in rat (RTECS); 10,000 mg/kg in mouse; 3,890 mg/kg in rat (other source)
Pharmacology
Routes of; administration	Oral
	Pharmacokinetics:
Excretion	Urines
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

　　[★]

カテキン

関: catechinic acid、cianidanol

「シアニダノール」

　　[★]

英: cianidanol
関: カテキン、カテキン酸

「catechinic acid」

　　[★]

カテキン酸

関: catechin、cianidanol

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v t e Antioxidants
Food antioxidants	6-Hydroxymelatonin Acetyl-L-carnitine (ALCAR) Alpha-lipoic acid (ALA) Ascorbic acid (vitamin C) Carotenoids (vitamin A) Curcumin Edaravone Polyphenols Glutathione Hydroxytyrosol L-carnitine Ladostigil Melatonin Mofegiline N-Acetylcysteine (NAC) N-Acetylserotonin (NAS) Oleocanthal Oleuropein Rasagiline Resveratrol Selegiline Selenium Tocopherols (vitamin E) Tocotrienols (vitamin E) Tyrosol Ubiquinone (coenzyme Q) Uric acid
Fuel antioxidants	Butylated hydroxytoluene 2,6-Di-tert-butylphenol 1,2-Diaminopropane 2,4-Dimethyl-6-tert-butylphenol Ethylenediamine
Measurements	Folin method ORAC TEAC FRAP

v t e Opioid receptor modulators
MOR	Agonists (abridged; see here for a full list): 3-HO-PCP 7-Acetoxymitragynine 7-Hydroxymitragynine ψ-Akuammigine α-Chlornaltrexamine α-Narcotine Acetyldihydrocodeine Acetylfentanyl Acrylfentanyl Adrenorphin (metorphamide) AH-7921 Akuammicine Akuammidine Alfentanil Anileridine Apparicine β-Endorphin BAM-12P BAM-18P BAM-22P Benzhydrocodone Benzylmorphine Bezitramide Biphalin BU08070 Buprenorphine Butorphan Butorphanol Butyrfentanyl BW-373U86 Carfentanil Casokefamide Cebranopadol Chloroxymorphamine Codeine DADLE DAMGO (DAGO) Dermorphin Desmetramadol (desmethyltramadol) Desomorphine Dextromoramide Dextropropoxyphene (propoxyphene) Dezocine Dimenoxadol Dimethylaminopivalophenone Eluxadoline Diamorphine (heroin) Dihydrocodeine Dihydroetorphine Dihydromorphine Diphenoxylate Dipipanone Dynorphin A Embutramide Endomorphin-1 Endomorphin-2 Eseroline Ethylmorphine Etorphine Fentanyl Fluorophen Frakefamide Furanylfentanyl Hemorphin-4 Herkinorin Hodgkinsine Hydrocodone Hydromorphinol Hydromorphone IBNtxA Ketamine Ketobemidone Kratom Laudanosine Lefetamine Leu-enkephalin Levacetylmethadol Levomethorphan Levorphanol Lexanopadol Loperamide Loxicodegol Matrine Meptazinol Met-enkephalin (metenkefalin) Methadone Metkefamide Metopon Mitragynine Mitragynine pseudoindoxyl Morphiceptin Morphine Nalbuphine Nalbuphine sebacate NalBzOH Nalmexone Naltalimide Neopine NFEPP Nicocodeine Nicodicodeine Nicomorphine NKTR-181 Norketamine Octreotide Oliceridine OM-3-MNZ Oripavine Oxycodone Oxymorphazone Oxymorphonazine Oxymorphone Oxymorphone phenylhydrazone OxyPNPH Papaver somniferum (opium) Pentazocine Pericine Pethidine (meperidine) Phenazocine Phencyclidine Piminodine Piritramide PL-017 Prodine Propiram PZM21 Racemethorphan Racemorphan Remifentanil Salsolinol SC-17599 Sinomenine Sufentanil Tapentadol Tetrahydropapaveroline TH-030418 Thebaine Thienorphine Tianeptine Tilidine Tramadol Trimebutine TRIMU 5 TRV734 Tubotaiwine U-47700 Valorphin Viminol Xorphanol PAMs: BMS-986121 BMS-986122 Antagonists: (3S,4S)-Picenadol 2-(S)-N,N-(R)-Viminol 3CS-nalmefene 4-Caffeoyl-1,5-quinide 4′-Hydroxyflavanone 4',7-Dihydroxyflavone 6β-Naltrexol 6β-Naltrexol-d4 18-MC α-Gliadin β-Chlornaltrexamine β-Funaltrexamine Akuammine Alvimopan AM-251 Apigenin AT-076 Axelopran Bevenopran Catechin Catechin gallate Clocinnamox CTAP CTOP Cyclofoxy Cyprodime Diacetylnalorphine Diprenorphine ECG EGC Epicatechin Eptazocine Gemazocine Ginsenoside R Hyperoside Ibogaine Levallorphan Lobeline LY-255582 LY-2196044 Methocinnamox Methylnaltrexone Methylsamidorphan chloride Naldemedine Nalmefene Nalodeine (N-allylnorcodeine) Nalorphine Nalorphine dinicotinate Naloxazone Naloxegol Naloxol Naloxonazine Naloxone Naltrexazone Naltrexonazine Naltrexone Naltrindole Naringenin Noribogaine Oxilorphan Pawhuskin A Rimonabant Quadazocine Samidorphan Taxifolin Unknown/unsorted: Cannabidiol Coronaridine Cyproterone acetate Dihydroakuuamine Tabernanthine Tetrahydrocannabinol
DOR	Agonists: 3CS-nalmefene 6'-GNTI 7-SIOM ADL-5747 (PF-04856881) ADL-5859 Alazocine (SKF-10047) Amoxapine AR-M100390 (ARM390) AZD2327 β-Endorphin BAM-18P Biphalin BU-48 Butorphan Butorphanol BW-373U86 Casokefamide Cebranopadol Codeine Cyclazocine DADLE Deltorphin A Deltorphin I Deltorphin II Desmethylclozapine Desmetramadol (desmethyltramadol) Dezocine Diamorphine (heroin) Dihydroetorphine Dihydromorphine DPDPE DPI-221 DPI-3290 DSLET Ethylketazocine Etorphine Fentanyl FIT Fluorophen Hemorphin-4 Hydrocodone Hydromorphone Ibogaine Isomethadone JNJ-20788560 KNT-127 Kratom Laudanosine Leu-enkephalin Levomethorphan Levorphanol Lexanopadol Lofentanil Met-enkephalin (metenkefalin) Metazocine Metkefamide Mitragynine Mitragynine pseudoindoxyl Morphine N-Phenethyl-14-ethoxymetopon Norbuprenorphine NalBzOH Oripavine Oxycodone Oxymorphone Pethidine (meperidine) Proglumide Racemethorphan Racemorphan RWJ-394674 Samidorphan SB-235863 SNC-80 SNC-162 TAN-67 (SB-205,607) TH-030418 Thebaine Thiobromadol (C-8813) Tianeptine Tonazocine Tramadol TRV250 Xorphanol Zenazocine Antagonists: 4',7-Dihydroxyflavone 5'-NTII 6β-Naltrexol 6β-Naltrexol-d4 α-Santolol β-Chlornaltrexamine Apigenin AT-076 Axelopran Bevenopran BNTX Catechin Catechin gallate Clocinnamox Diacetylnalorphine Diprenorphine ECG EGC Eluxadoline Epicatechin ICI-154129 ICI-174864 LY-255582 LY-2196044 Methylnaltrexone Methylnaltrindole N-Benzylnaltrindole Nalmefene Nalorphine Naltrexone Naltriben Naltrindole Naloxone Naringenin Noribogaine Pawhuskin A Quadazocine SDM25N SoRI-9409 Taxifolin Thienorphine Unknown/unsorted: 18-MC Cannabidiol Coronaridine Cyproterone acetate Tabernanthine Tetrahydrocannabinol
KOR	Agonists: 3CS-nalmefene 6'-GNTI 8-CAC 18-MC 14-Methoxymetopon β-Chlornaltrexamine β-Funaltrexamine Adrenorphin (metorphamide) Akuuamicine Alazocine (SKF-10047) Allomatrine Apadoline Asimadoline BAM-12P BAM-18P BAM-22P Big dynorphin Bremazocine BRL-52537 Butorphan Butorphanol BW-373U86 Cebranopadol Ciprefadol CR665 Cyclazocine Cyclorphan Cyprenorphine Desmetramadol (desmethyltramadol) Diamorphine (heroin) Diacetylnalorphine Difelikefalin Dihydroetorphine Dihydromorphine Diprenorphine Dynorphin A Dynorphin B (rimorphin) Eluxadoline Enadoline Eptazocine Erinacine E Ethylketazocine Etorphine Fedotozine Fentanyl Gemazocine GR-89696 GR-103545 Hemorphin-4 Herkinorin HS665 Hydromorphone HZ-2 Ibogaine ICI-199,441 ICI-204,448 Ketamine Ketazocine Laudanosine Leumorphin (dynorphin B-29) Levallorphan Levomethorphan Levorphanol Lexanopadol Lofentanil LPK-26 Lufuradom Matrine MB-1C-OH Menthol Metazocine Metkefamide Mianserin Mirtazapine Morphine Moxazocine MR-2034 N-MPPP Nalbuphine Nalbuphine sebacate NalBzOH Nalfurafine Nalmefene Nalodeine (N-allylnorcodeine) Nalorphine Naltriben Niravoline Norbuprenorphine Norbuprenorphine-3-glucuronide Noribogaine Norketamine Oripavine Oxilorphan Oxycodone Pentazocine Pethidine (meperidine) Phenazocine Proxorphan Racemethorphan Racemorphan RB-64 Salvinorin A (salvia) Salvinorin B ethoxymethyl ether Salvinorin B methoxymethyl ether Samidorphan Spiradoline (U-62,066) TH-030418 Thienorphine Tifluadom Tricyclic antidepressants (e.g., amitriptyline, desipramine, imipramine, nortriptyline) U-50,488 U-54,494A U-69,593 Xorphanol Antagonists: 4′-Hydroxyflavanone 4',7-Dihydroxyflavone 5'-GNTI 6'-GNTI 6β-Naltrexol 6β-Naltrexol-d4 β-Chlornaltrexamine Buprenorphine/samidorphan Amentoflavone ANTI Apigenin Arodyne AT-076 Axelopran AZ-MTAB Binaltorphimine BU09059 Buprenorphine Catechin Catechin gallate CERC-501 (LY-2456302) Clocinnamox Cyclofoxy Dezocine DIPPA EGC ECG Epicatechin Hyperoside JDTic LY-255582 LY-2196044 LY-2444296 LY-2459989 LY-2795050 MeJDTic Methylnaltrexone ML190 ML350 MR-2266 N-Fluoropropyl-JDTic Naloxone Naltrexone Naltrindole Naringenin Norbinaltorphimine Noribogaine Pawhuskin A PF-4455242 RB-64 Quadazocine Taxifolin UPHIT Zyklophin Unknown/unsorted: Akuammicine Akuammine Coronaridine Cyproterone acetate Dihydroakuuamine Ibogamine Tabernanthine
NOP	Agonists: (Arg14,Lys15)Nociceptin ((pF)Phe⁴)Nociceptin(1-13)NH₂ (Phe¹Ψ(CH₂-NH)Gly²)Nociceptin(1-13)NH₂ Ac-RYYRWK-NH₂ Ac-RYYRIK-NH₂ BU08070 Buprenorphine Cebranopadol Dihydroetorphine Etorphine JNJ-19385899 Levomethorphan Levorphanol Levorphanol Lexanopadol MCOPPB MT-7716 NNC 63-0532 Nociceptin (orphanin FQ) Nociceptin (1-11) Nociceptin (1-13)NH₂ Norbuprenorphine Racemethorphan Racemorphan Ro64-6198 Ro65-6570 SCH-221510 SCH-486757 SR-8993 SR-16435 TH-030418 Antagonists: (Nphe¹)Nociceptin(1-13)NH₂ AT-076 BAN-ORL-24 J-113397 JTC-801 LY-2940094 NalBzOH Nociceptin (1-7) Nocistatin SB-612111 SR-16430 Thienorphine Trap-101 UFP-101
Unsorted	β-Casomorphins Amidorphin BAM-20P Cytochrophin-4 Deprolorphin Gliadorphin (gluteomorphin) Gluten exorphins Hemorphins Kava constituents MEAGL MEAP NEM Neoendorphins Nepetalactone (catnip) Peptide B Peptide E Peptide F Peptide I Rubiscolins Soymorphins
Others	Enkephalinase inhibitors: Amastatin BL-2401 Candoxatril D -Phenylalanine Dexecadotril (retorphan) Ecadotril (sinorphan) Kelatorphan Racecadotril (acetorphan) RB-101 RB-120 RB-3007 Opiorphan Selank Semax Spinorphin Thiorphan Tynorphin Ubenimex (bestatin) Propeptides: β-Lipotropin (proendorphin) Prodynorphin Proenkephalin Pronociceptin Proopiomelanocortin (POMC) Others: Kyotorphin (met-enkephalin releaser/degradation stabilizer)
See also: Receptor/signaling modulators • Signaling peptide/protein receptor modulators

v t e Flavan-3-ols and their glycosides
Flavan-3-ols	Afzelechin Catechin (Epicatechin) Epicatechin gallate Epigallocatechin Fisetinidol Gallocatechin Guibourtinidol Mesquitol Oritin Robinetinidol
O-methylated flavan-3ols	Meciadanol (3-O-methylcatechin) Ourateacatechin (4′-O-methyl-(−)-epigallocatechin)
Glycosides	Arthromerin A (Afzelechin-3-O-β-D-xylopyranoside) Arthromerin B (Afzelechin-3-O-β-D-glucopyranoside) Catechin-3-O-glucoside Catechin-3'-O-glucoside Catechin-4'-O-glucoside Catechin-5-O-glucoside Catechin-7-O-glucoside (+)-Catechin 7-O-β-D-xylopyranoside Epicatechin-3′-O-glucoside Glochiflavanoside A, B, C D Polydine ((+)-catechin 7-0-α-L-arabinoside) Symplocoside (3’-O-methyl-(-)-epicatechin 7-O-β-D-glucopyranoside)
Acetylated	Phylloflavan
Gallate esters	Epigallocatechin gallate Gallocatechin gallate
Misc.	Thearubigins

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cianidanol