Butein: Difference between revisions

(30 intermediate revisions by 21 users not shown)

Line 1:

{{chembox

| Verifiedfields = changed

⚫

| verifiedrevid = ~~404808986~~

| Watchedfields = changed

⚫

| verifiedrevid = 462806316

| Name = Butein

| ImageFile = Butein.svg

| ImageSize = 250px

| ImageName = Chemical structure of butein

| PIN = 2′,3,4,4′-Tetrahydroxychalcone

| IUPACName = (''E'')-1-(2,4-dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one

| OtherNames = 2',3,4~~,4'~~-~~Tetrahydroxychalcone~~ 2',4',3,4-Tetrahydroxychalcone 3,4,~~2',4'-Tetrahydroxychalcone ~~2′,4′~~,3,4~~-Tetrahydroxychalcone

| OtherNames = (2''E'')-1-(2,4-Dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one 2′,4′,3,4-Tetrahydroxychalcone 3,4,2′,4′-Tetrahydroxychalcone

|Section1= {{Chembox Identifiers

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 487-52-5

| UNII_Ref = {{fdacite|correct|FDA}}

| CASNo_Ref =

| ~~CASOther~~ = ~~21849-70-7~~

| UNII = 4WVS5M0LGF

| PubChem = 5281222

| KEGG = C08578

| ChEBI = 3237

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 128000

| SMILES = C1=CC(=C(C=C1C=CC(=O)C2=C(C=C(C=C2)O)O)O)O

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 4444634

| InChI = 1/C15H12O5/c16-10-3-4-11(14(19)8-10)12(17)5-1-9-2-6-13(18)15(20)7-9/h1-8,16,18-20H/b5-1+

| InChIKey = AYMYWHCQALZEGT-ORCRQEGFBV

⚫

| StdInChI = 1S/C15H12O5/c16-10-3-4-11(14(19)8-10)12(17)5-1-9-2-6-13(18)15(20)7-9/h1-8,16,18-20H/b5-1+

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

⚫

| StdInChIKey = AYMYWHCQALZEGT-ORCRQEGFSA-N

⚫

| StdInChI = 1S/C15H12O5/c16-10-3-4-11(14(19)8-10)12(17)5-1-9-2-6-13(18)15(20)7-9/h1-8,16,18-20H/b5-1+

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

⚫

| StdInChIKey = AYMYWHCQALZEGT-ORCRQEGFSA-N

| MeSHName =

}}

|Section2= {{Chembox Properties

|Section2={{Chembox Properties

| C=15 | H=12 | O=5

| Formula = C15H12O5

| MolarMass = 272.25 g/mol

| ExactMass = 272.068473 u

| Appearance =

| Density =

| MeltingPt = ~~~~

| MeltingPt =

| BoilingPt = ~~~~

| BoilingPt =

| Solubility =

}}

'''Butein''' is a [[chalconoid]]. It can be found in ''[[Toxicodendron vernicifluum]]'' (or formerly ''Rhus verniciflua''). It has [[Antioxidant|antioxidative]], [[aldose reductase]] and [[advanced glycation endproduct]]s inhibitory effects<ref name="pmid18670102">{{cite journal |~~author~~=Lee EH, Song DG, Lee JY, Pan CH, Um BH, Jung SH |title=Inhibitory effect of the compounds isolated from Rhus verniciflua on aldose reductase and advanced glycation endproducts |journal=Biol. Pharm. Bull. |volume=31 |issue=8 |pages=1626–30 |~~year~~=2008 ~~|month=August~~ |pmid=18670102 |doi= 10.1248/bpb.31.1626|~~url~~=~~http://joi.jlc.jst.go.jp/JST.JSTAGE/bpb/31.1626?from=PubMed~~}}</ref>. It is also a [[sirtuin-activating compound]], a chemical compound having an effect on sirtuins, a group of enzymes that use NAD+ to remove acetyl groups from proteins.

'''Butein''' is a [[chalcone]] of the [[chalconoid]]s. It can be found in ''[[Toxicodendron vernicifluum]]'' (or formerly ''Rhus verniciflua''), ''[[Dahlia]]'', ''[[Butea]]'' (''[[Butea monosperma]]'') and ''[[Coreopsis]]''.<ref>Semwal, R. B., Semwal, D. K., Combrinck, S., & Viljoen, A. (2015). Butein: From ancient traditional remedy to modern nutraceutical. Phytochemistry Letters, 11, 188-201. {{doi|10.1016/j.phytol.2014.12.014}}</ref> It has [[Antioxidant|antioxidative]], [[aldose reductase]] and [[advanced glycation endproduct]]s inhibitory effects.<ref name="pmid18670102">{{cite journal |vauthors=Lee EH, Song DG, Lee JY, Pan CH, Um BH, Jung SH |title=Inhibitory effect of the compounds isolated from Rhus verniciflua on aldose reductase and advanced glycation endproducts |journal=Biol. Pharm. Bull. |volume=31 |issue=8 |pages=1626–30 |date=August 2008 |pmid=18670102 |doi= 10.1248/bpb.31.1626|doi-access=free }}</ref> It is also a [[sirtuin-activating compound]], a chemical compound having an effect on sirtuins, a group of enzymes that use NAD+ to remove acetyl groups from proteins. Buteins possess a high ability to inhibit aromatase process in the human body, for this reason, the use of these compounds in the treatment of [[breast cancer]] on the estrogen ground has been explored.<ref>Wang Y. "[https://www.ncbi.nlm.nih.gov/pubmed/15848217 The plant polyphenol butein inhibits testosterone-induced proliferation in breast cancer cells expressing aromatase]" Life Sci. 2005 May 20;77(1):39-51.</ref> The first attempts of sport pro-hormone supplementation with the use of buteins took place in Poland.<ref>S.Amboziak "[http://prohormones.info/aromatase.htm Aromatase in the dock"] 09.2012</ref>{{rs|date=March 2024}}

==References==

Line 42:

Line 49:

[[Category:Chalconoids]]