Scopoletin

Scopoletin

Chemical structure of scopoletin
Names
Preferred IUPAC name 7-Hydroxy-6-methoxy-2H-1-benzopyran-2-one
Other names 7-Hydroxy-6-methoxy-2H-chromen-2-one 7-Hydroxy-6-methoxychromen-2-one Gelseminic acid Chrysatropic acid Scopoletine 6-Methylesculetin Murrayetin Scopoletol Escopoletin Methylesculetin 6-O-Methylesculetin Esculetin-6-methyl ether 7-Hydroxy-5-methoxycoumarin 6-Methoxyumbelliferone
Identifiers
CAS Number	92-61-5  Y
3D model (JSmol)	Interactive image
ChemSpider	4444113  N
ECHA InfoCard	100.001.975
PubChem CID	5280460
UNII	KLF1HS0SXJ  Y
CompTox Dashboard (EPA)	DTXSID0075368
InChI InChI=1S/C10H8O4/c1-13-9-4-6-2-3-10(12)14-8(6)5-7(9)11/h2-5,11H,1H3 N Key: RODXRVNMMDRFIK-UHFFFAOYSA-N N InChI=1/C10H8O4/c1-13-9-4-6-2-3-10(12)14-8(6)5-7(9)11/h2-5,11H,1H3 Key: RODXRVNMMDRFIK-UHFFFAOYAG
SMILES COC1=C(C=C2C(=C1)C=CC(=O)O2)O
Properties
Chemical formula	C10H8O4
Molar mass	192.16 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N  verify  (what is  YN ?) Infobox references

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 , ^[1] in Datura metel , ^[2] in Mallotus resinosus , ^[3] and in Kleinhovia hospita . It can also be found in fenugreek, ^[4] vinegar, ^{[5] [4]} some whiskies and 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 phenylpropanoids, the biosynthetic precursor to scopoletin acid is 4-coumaroyl-CoA. ^[6] Scopoletin is derived from 1,2-benzopyrones ^[7] which is the core structure of coumarins formed through hydroxylation of cinnamates, trans/cis isomerization of the side chain, and lactonization. ^[8] 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. ^[9] For scopoletin, most of biosynthetic investigations are based on Arabidopsis thaliana .

Biosynthetic pathway of Scopoletin

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.^{[ citation needed ]}

References

1. Zhao Y; Liu F; Lou HX (2010). "[Studies on the chemical constituents of Solanum nigrum]". Zhong Yao Cai (in Chinese). 33 (4): 555–556. PMID   20845784.
2. Han XL, Wang H, Zhang ZH, Tan Y, Wang JH (August 2015). "[Study on Chemical Constituents in Seeds of Datura metel from Xinjiang]". Zhong Yao Cai = Zhongyaocai = Journal of Chinese Medicinal Materials (in Chinese). 38 (8): 1646–8. PMID   26983236.
3. Ma J; Jones SH; Hecht SM (2004). "A coumarin from Mallotus resinosus that mediates DNA cleavage". J Nat Prod. 67 (9): 1614–1616. doi:10.1021/np040129c. PMID   15387675.
4. Ouzir, M; El Bairi, K; Amzazi, S (October 2016). "Toxicological properties of fenugreek (Trigonella foenum graecum)". Food and Chemical Toxicology. 96: 145–54. doi:10.1016/j.fct.2016.08.003. PMID   27498339.
5. 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
6. Vogt, T. (2010). "Phenylpropanoid Biosynthesis". Molecular Plant. 3: 2–20. doi: 10.1093/mp/ssp106 . PMID   20035037.
7. Beeching, John R.; Han, Yuanhuai; Gómez-Vásquez, Rocío; Day, Robert C.; Cooper, Richard M. (1998), "Wound and Defense Responses in Cassava as Related to Post-Harvest Physiological Deterioration", Phytochemical Signals and Plant—Microbe Interactions, Springer US, pp. 231–248, doi:10.1007/978-1-4615-5329-8_12, ISBN   9780306459177
8. Kai, Kosuke; Mizutani, Masaharu; Kawamura, Naohiro; Yamamoto, Ryotaro; Tamai, Michiko; Yamaguchi, Hikaru; Sakata, Kanzo; Shimizu, Bun-ichi (September 2008). "Scopoletin is biosynthesized viaortho-hydroxylation of feruloyl CoA by a 2-oxoglutarate-dependent dioxygenase in Arabidopsis thaliana". The Plant Journal. 55 (6): 989–999. doi: 10.1111/j.1365-313x.2008.03568.x . ISSN   0960-7412. PMID   18547395.
9. Schoch, Guillaume; Goepfert, Simon; Morant, Marc; Hehn, Alain; Meyer, Denise; Ullmann, Pascaline; Werck-Reichhart, Danièle (2001-06-27). "CYP98A3 from Arabidopsis thaliana Is a 3′-Hydroxylase of Phenolic Esters, a Missing Link in the Phenylpropanoid Pathway" (PDF). Journal of Biological Chemistry. 276 (39): 36566–36574. doi: 10.1074/jbc.m104047200 . ISSN   0021-9258. PMID   11429408. S2CID   11765327.