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 h ...

. It found in the root of plants in the genus ''

Scopolia ''Scopolia'' is a genus of four species of flowering plants in the family Solanaceae, native to Europe and Asia. The genus is named after Giovanni Scopoli (1723–88), a Tyrolean naturalist. The genus has a disjunct distribution, with two reco ...

'' such as ''

Scopolia carniolica ''Scopolia carniolica'', the European scopolia or henbane bell, is a poisonous plant belonging to the family Solanaceae. It has dark violet flowers on long hanging stems. It grows to in height. Its toxicity derives from its high levels of tropan ...

'' and ''

Scopolia japonica ''Scopolia japonica'', also Japanese belladonna or Korean scopolia, is a flowering plant species in the genus ''Scopolia'' - one of the eight genera in tribe Hyoscyameae of the nightshade family Solanaceae. The coumarins umbelliferone and scopol ...

'', in

chicory Common chicory ('' Cichorium intybus'') is a somewhat woody, perennial herbaceous plant of the family Asteraceae, usually with bright blue flowers, rarely white or pink. Native to the Old World, it has been introduced to North America and Austra ...

, in '' Artemisia scoparia'', in the roots and leaves of stinging nettle (''

Urtica dioica ''Urtica dioica'', often known as common nettle, burn nettle, stinging nettle (although not all plants of this species sting) or nettle leaf, or just a nettle or stinger, is a herbaceous perennial flowering plant in the family Urticaceae. Ori ...

''), in the

passion flower ''Passiflora'', known also as the passion flowers or passion vines, is a genus of about 550 species of flowering plants, the type genus of the family Passifloraceae. They are mostly tendril-bearing vines, with some being shrubs or trees. The ...

, in '' Brunfelsia'', in ''

Viburnum prunifolium ''Viburnum prunifolium'' (known as blackhaw or black haw, blackhaw viburnum, sweet haw, and stag bush) is a species of ''Viburnum'' native to eastern North America, from Connecticut west to eastern Kansas, and south to Alabama and Texas. Growth ...

'', in ''

Solanum nigrum ''Solanum nigrum'', the European black nightshade or simply black nightshade or blackberry nightshade, is a species of flowering plant in the genus ''Solanum'', native to Eurasia and introduced in the Americas, Australasia, and South Africa. Ripe ...

'', in ''

Datura metel ''Datura metel'' is a shrub-like annual (zone 5–7) or short-lived, shrubby perennial (zone 8–10), commonly known in Europe as Indian thornapple, Hindu Datura, or metel and in the United States as devil's trumpet or angel's trumpet. ''Datura ...

'', in '' Mallotus resinosus'', or and in '' Kleinhovia hospita''. 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 et ...

, some

whiskies Whisky or whiskey is a type of liquor, distilled alcoholic beverage made from Fermentation in food processing, fermented grain mashing, mash. Various grains (which may be Malting, malted) are used for different varieties, including barley, Maize ...

or in

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

. A similar

is scoparone. Scopoletin is highly fluorescent when dissolved in

DMSO Dimethyl sulfoxide (DMSO) is an organosulfur compound with the formula ( CH3)2. This colorless liquid is the sulfoxide most widely used commercially. It is an important polar aprotic solvent that dissolves both polar and nonpolar compounds an ...

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 The phenylpropanoids are a diverse family of organic compounds that are synthesized by plants from the amino acids phenylalanine and tyrosine. Their name is derived from the six-carbon, aromatic phenyl group and the three-carbon propene tail of ...

s, the biosynthetic precursor to scopoletin acid is 4-coumaroyl-CoA. 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 Protein superfamily, superfamily of enzymes containing heme as a cofactor (biochemistry), cofactor that functions as monooxygenases. In mammals, these proteins oxidize steroids, fatty acids, and xenobiotics, and are ...

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 a ...

Derivatives/Related Compounds

Scopolin Scopolin is a glucoside of scopoletin formed by the action of the enzyme scopoletin glucosyltransferase. References Bibliography

* * O-methylated coumarins Phenol glucosides {{aromatic-stub ...

is a

glucoside A glucoside is a glycoside that is derived from glucose. Glucosides are common in plants, but rare in animals. Glucose is produced when a glucoside is hydrolysed by purely chemical means, or decomposed by fermentation or enzymes. The name was o ...

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 substrates, and the enzyme converts the substrates into different molecules known as products. A ...

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

Uses

Traditional Medicine

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

References

O-methylated coumarins {{aromatic-stub