Scopoletin is a

coumarin Coumarin () or 2''H''-chromen-2-one is an aromatic organic chemical compound with formula . Its molecule can be described as a benzene molecule with two adjacent hydrogen atoms replaced by a lactone-like chain , forming a second six-membered ...

. It found in the root of plants in the genus '' Scopolia'' such as '' Scopolia carniolica'' and '' Scopolia japonica'', in chicory, in ''

Artemisia scoparia ''Artemisia scoparia'' is a Eurasian species in the genus ''Artemisia (plant), Artemisia'', in the Asteraceae, sunflower family. It is widespread across much of Eurasia from France to Japan, including China, India, Russia, Germany, Poland, central ...

'', in the roots and leaves of stinging nettle ('' Urtica dioica''), in the passion flower, in ''

Brunfelsia ''Brunfelsia'' is a genus of flowering plants belonging to subfamily Petunioideae of the nightshade family Solanaceae. The 50 or so species have been grouped into the three sections: ''Brunfelsia'' (circa 22 species), ''Franciscea'' (circa 18 spe ...

'', in '' Viburnum prunifolium'', in '' Solanum nigrum'', in '' Datura metel'', in ''

Mallotus resinosus ''Mallotus resinosus'', the resinous kamala , is a species of 12m tall shrub, evergreen plant in the family Euphorbiaceae. It is native to India, Sri Lanka to New Guinea and Australia. The plant is known as "கருவாளிச்சீ / k ...

'', or and in ''

Kleinhovia hospita ''Kleinhovia hospita'' (guest tree syn. ''Kleinhovia serrata'' Blanco, ''Grewia meyeniana'' Walp.) is an evergreen, tropical tree native to Indonesia, Malaysia and other parts of tropical Asia. It is monotypic, being the only species in the genu ...

''. It can also be found in fenugreek,

vinegar Vinegar is an aqueous solution of acetic acid and trace compounds that may include flavorings. Vinegar typically contains 5–8% acetic acid by volume. Usually, the acetic acid is produced by a double fermentation, converting simple sugars to ...

, some whiskies or in

dandelion coffee Dandelion 'coffee' (also dandelion tea) is a herbal tea, tisane made from the root of the Taraxacum, dandelion plant. The roasted dandelion root pieces and the beverage have some resemblance to coffee in appearance and taste, and it is thus commo ...

. A similar

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 Coumaroyl-coenzyme A is the thioester of coenzyme-A and coumaric acid. Coumaroyl-coenzyme A is a central intermediate in the biosynthesis of myriad natural products found in plants. These products include Monolignol, lignols (precursors to lignin ...

. Scopoletin is derived from 1,2-benzopyrones which is the core structure of coumarins formed through hydroxylation of cinnamates, trans/cis isomerization of the side chain, and lactonization. And CYP98A (C3’H) are enzymes belonging to the

cytochrome P450 Cytochromes P450 (CYPs) are a superfamily of enzymes containing heme as a cofactor that functions as monooxygenases. In mammals, these proteins oxidize steroids, fatty acids, and xenobiotics, and are important for the clearance of various compo ...

family that catalyze the meta-hydroxylation of p-coumarate derivatives, an important step in the phenylpropanoid pathway. For scopoletin, most of biosynthetic investigations are based on

Arabidopsis thaliana ''Arabidopsis thaliana'', the thale cress, mouse-ear cress or arabidopsis, is a small flowering plant native to Eurasia and Africa. ''A. thaliana'' is considered a weed; it is found along the shoulders of roads and in disturbed land. A winter ...

Derivatives/Related Compounds

Scopolin Scopolin is a glucoside of scopoletin formed by the action of the enzyme scopoletin glucosyltransferase In enzymology, a scopoletin glucosyltransferase () is an enzyme that catalysis, catalyzes the chemical reaction :UDP-glucose + scopoletin \ri ...

is a glucoside of scopoletin formed by the action of the

enzyme Enzymes () are proteins that act as biological catalysts by accelerating chemical reactions. The molecules upon which enzymes may act are called substrate (chemistry), substrates, and the enzyme converts the substrates into different molecule ...

scopoletin glucosyltransferase In enzymology, a scopoletin glucosyltransferase () is an enzyme that catalyzes the chemical reaction :UDP-glucose + scopoletin \rightleftharpoons UDP + scopolin Thus, the two substrates of this enzyme are UDP-glucose and scopoletin, whereas i ...

Uses

Traditional Medicine

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

References

O-methylated coumarins {{aromatic-stub