Scopoletin: Difference between revisions

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 449725580

| ImageFile = Scopoletin.svg

| PIN = 7-Hydroxy-6-methoxy-2''H''-1-benzopyran-2-one

| OtherNames = 7-Hydroxy-6-methoxy-2''H''-chromen-2-one<br />7-Hydroxy-6-methoxychromen-2-one<br />Gelseminic acid<br />Chrysatropic acid<br />Scopoletine<br />6-Methylesculetin<br />Murrayetin<br />Scopoletol<br />Escopoletin<br />Methylesculetin<br />6-O-Methylesculetin<br />Esculetin-6-methyl ether<br />7-Hydroxy-5-methoxycoumarin<br />6-Methoxyumbelliferone

|Section1={{Chembox Identifiers

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

| CASNoOther =

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

| UNII = KLF1HS0SXJ

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 4444113

| InChI = 1/C10H8O4/c1-13-9-4-6-2-3-10(12)14-8(6)5-7(9)11/h2-5,11H,1H3

| InChIKey = RODXRVNMMDRFIK-UHFFFAOYAG

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C10H8O4/c1-13-9-4-6-2-3-10(12)14-8(6)5-7(9)11/h2-5,11H,1H3

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = RODXRVNMMDRFIK-UHFFFAOYSA-N

|Section2={{Chembox Properties

| MeltingPt =

| BoilingPt =

'''Scopoletin''' is a [[coumarin]] found in the root of plants in the genus ''[[Scopolia]]'' such as ''[[Scopolia carniolica]]'' and ''[[Scopolia japonica]]'', in [[chicory]], in ''[[Artemisia scoparia]]'', in the roots and leaves of stinging nettle (''[[Urtica dioica]]''), in the [[passion flower]], in ''[[Brunfelsia]]'', in ''[[Viburnum prunifolium]]'', in ''[[Solanum nigrum]]'',<ref>{{Cite journal | pmid = 20845784 | journal = Zhong Yao Cai | date = 2010 | volume = 33 | issue = 4 | pages = 555–556 | title= [Studies on the chemical constituents of Solanum nigrum] | language = zh |author1=Zhao Y |author2=Liu F |author3=Lou HX }}</ref> in ''[[Datura metel]]'',<ref name="pmid26983236">{{cite journal |vauthors=Han XL, Wang H, Zhang ZH, Tan Y, Wang JH |title=[Study on Chemical Constituents in Seeds of Datura metel from Xinjiang] |language=zh |journal=[[Zhong Yao Cai = Zhongyaocai = Journal of Chinese Medicinal Materials]] |volume=38 |issue=8 |pages=1646–8 |date=August 2015 |pmid=26983236 }}</ref> in ''[[Mallotus resinosus]]'',<ref>{{cite journal | pmid = 15387675 | journal = J Nat Prod | date = 2004 | volume = 67 | issue = 9 | pages = 1614–1616 | title = A coumarin from Mallotus resinosus that mediates DNA cleavage |author1=Ma J |author2=Jones SH |author3=Hecht SM | doi=10.1021/np040129c}}</ref> or and in ''[[Kleinhovia hospita]]''. It can also be found in [[fenugreek]],<ref name=fenugreek/> [[vinegar]],<ref>Analysis of polyphenolic compounds of different vinegar samples. Miguel Carrero Gálvez, Carmelo García Barroso and Juan Antonio Pérez-Bustamante, Zeitschrift für Lebensmitteluntersuhung und -Forschung A, Volume 199, Number 1, pages 29-31, {{doi|10.1007/BF01192948}}</ref><ref name=fenugreek>{{cite journal|last1=Ouzir|first1=M|last2=El Bairi|first2=K|last3=Amzazi|first3=S|title=Toxicological properties of fenugreek (Trigonella foenum graecum).|journal=Food and Chemical Toxicology |date=October 2016|volume=96|pages=145–54|pmid=27498339|doi=10.1016/j.fct.2016.08.003}}</ref> some [[whisky|whiskies]] or in [[dandelion coffee]]. A similar [[coumarin]] is [[scoparone]]. Scopoletin is highly fluorescent when dissolved in [[DMSO]] or water and is regularly used as a fluorimetric assay for the detection of hydrogen peroxide in conjunction with [[horseradish peroxidase]]. When oxidized, its fluorescence is strongly suppressed.

== Chemistry ==

=== Biosynthesis ===

Like most [[phenylpropanoid]]s, the biosynthetic precursor to scopoletin acid is [[4-Coumaroyl-CoA|4-coumaroyl-CoA]].<ref>{{cite journal|journal=Molecular Plant|volume=3|year=2010|pages=2–20|doi=10.1093/mp/ssp106|pmid=20035037|title=Phenylpropanoid Biosynthesis|author=Vogt, T.|doi-access=free}}

</ref> Scopoletin is derived from 1,2-benzopyrones<ref>{{Citation|last1=Beeching|first1=John R.|title=Wound and Defense Responses in Cassava as Related to Post-Harvest Physiological Deterioration|date=1998|work=Phytochemical Signals and Plant—Microbe Interactions|pages=231–248|publisher=Springer US|isbn=9780306459177|last2=Han|first2=Yuanhuai|last3=Gómez-Vásquez|first3=Rocío|last4=Day|first4=Robert C.|last5=Cooper|first5=Richard M.|doi=10.1007/978-1-4615-5329-8_12}}</ref> which is the core structure of coumarins formed through hydroxylation of cinnamates, trans/cis isomerization of the side chain, and lactonization.<ref>{{Cite journal|last1=Kai|first1=Kosuke|last2=Mizutani|first2=Masaharu|last3=Kawamura|first3=Naohiro|last4=Yamamoto|first4=Ryotaro|last5=Tamai|first5=Michiko|last6=Yamaguchi|first6=Hikaru|last7=Sakata|first7=Kanzo|last8=Shimizu|first8=Bun-ichi|date=September 2008|title=Scopoletin is biosynthesized viaortho-hydroxylation of feruloyl CoA by a 2-oxoglutarate-dependent dioxygenase inArabidopsis thaliana|journal=The Plant Journal|volume=55|issue=6|pages=989–999|doi=10.1111/j.1365-313x.2008.03568.x|pmid=18547395|issn=0960-7412|doi-access=free}}</ref> And CYP98A (C3’H) are enzymes belonging to the [[cytochrome P450]] family that catalyze the meta-hydroxylation of p-coumarate derivatives, an important step in the phenylpropanoid pathway.<ref>{{Cite journal|last1=Schoch|first1=Guillaume|last2=Goepfert|first2=Simon|last3=Morant|first3=Marc|last4=Hehn|first4=Alain|last5=Meyer|first5=Denise|last6=Ullmann|first6=Pascaline|last7=Werck-Reichhart|first7=Danièle|date=2001-06-27|title=CYP98A3 fromArabidopsis thalianaIs a 3′-Hydroxylase of Phenolic Esters, a Missing Link in the Phenylpropanoid Pathway|journal=Journal of Biological Chemistry|volume=276|issue=39|pages=36566–36574|doi=10.1074/jbc.m104047200|pmid=11429408|s2cid=11765327|issn=0021-9258|url=https://hal.archives-ouvertes.fr/hal-01738074/file/schoch_et_al%202001.pdf|doi-access=free}}</ref> For scopoletin, most of biosynthetic investigations are based on [[Arabidopsis thaliana]].

[[File:Wikipedia pathway copy.png|center|Biosynthetic p<span name="OLE_LINK72"></span>athway of Scopoletin|750px]]

=== Derivatives/Related Compounds ===

[[Scopolin]] is a [[glucoside]] of scopoletin formed by the action of the [[enzyme]] [[scopoletin glucosyltransferase]].

== Uses ==

=== Traditional Medicine ===

It was usually used for rheumatic arthritis therapy in Traditional Chinese Medicine.

== References ==

[[Category:O-methylated coumarins]]

{{aromatic-stub}}