Rosmarinic acid, named after

rosemary ''Salvia rosmarinus'' (), commonly known as rosemary, is a shrub with fragrant, evergreen, needle-like leaves and white, pink, purple, or blue flowers, native plant, native to the Mediterranean Region, Mediterranean region. Until 2017, it was kn ...

(''Salvia rosmarinus'' Linn.), is a

polyphenol Polyphenols () are a large family of naturally occurring organic compounds characterized by multiples of phenol units. They are abundant in plants and structurally diverse. Polyphenols include flavonoids, tannic acid, and ellagitannin, some ...

constituent of many culinary

herb In general use, herbs are a widely distributed and widespread group of plants, excluding vegetables and other plants consumed for macronutrients, with savory or aromatic properties that are used for flavoring and garnishing food, for medicina ...

s, including

(''Salvia rosmarinus'' L.), perilla (''Perilla frutescens'' L.), sage (''Salvia officinalis'' L.),

mint MiNT is Now TOS (MiNT) is a free software alternative operating system kernel for the Atari ST system and its successors. It is a multi-tasking alternative to TOS and MagiC. Together with the free system components fVDI device drivers, XaAE ...

(''Mentha arvense'' L.), and basil (''Ocimum basilicum'' L.).

History

Rosmarinic acid was first isolated and characterized in 1958 by the Italian chemists Scarpatti and Oriente from

(''

Salvia rosmarinus ''Salvia rosmarinus'' (), commonly known as rosemary, is a shrub with fragrant, evergreen, needle-like leaves and white, pink, purple, or blue flowers, native to the Mediterranean region. Until 2017, it was known by the scientific name ''Rosmari ...

''), after which the acid is named.

Chemistry

Chemically, rosmarinic acid is a caffeic acid

ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ...

, with tyrosine providing another phenolic ring via dihydroxyphenyl-

lactic acid Lactic acid is an organic acid. It has a molecular formula . It is white in the solid state and it is miscible with water. When in the dissolved state, it forms a colorless solution. Production includes both artificial synthesis as well as nat ...

. It has a

molecular mass The molecular mass (''m'') is the mass of a given molecule: it is measured in daltons (Da or u). Different molecules of the same compound may have different molecular masses because they contain different isotopes of an element. The related quant ...

of 360 daltons.

Natural occurrences

Rosmarinic acid accumulation is shown in

hornwort Hornworts are a group of non-vascular Embryophytes (land plants) constituting the division Anthocerotophyta (). The common name refers to the elongated horn-like structure, which is the sporophyte. As in mosses and liverworts, hornworts have a ...

s, in the fern family

Blechnaceae Blechnaceae is a family of ferns in the order Polypodiales, with a cosmopolitan distribution. Its status as a family and the number of genera included have both varied considerably. In the Pteridophyte Phylogeny Group classification of 201 ...

, and in species of several orders of

mono- Numeral or number prefixes are prefixes derived from numerals or occasionally other numbers. In English and many other languages, they are used to coin numerous series of words. For example: * unicycle, bicycle, tricycle (1-cycle, 2-cycle, 3-cy ...

and

dicotyledon The dicotyledons, also known as dicots (or, more rarely, dicotyls), are one of the two groups into which all the flowering plants (angiosperms) were formerly divided. The name refers to one of the typical characteristics of the group: namely, t ...

ous

angiosperms Flowering plants are plants that bear flowers and fruits, and form the clade Angiospermae (), commonly called angiosperms. The term "angiosperm" is derived from the Greek words ('container, vessel') and ('seed'), and refers to those plants ...

. It is found most notably in many

Lamiaceae The Lamiaceae ( ) or Labiatae are a family of flowering plants commonly known as the mint, deadnettle or sage family. Many of the plants are aromatic in all parts and include widely used culinary herbs like basil, mint, rosemary, sage, savory ...

(dicotyledons in the order

Lamiales The order Lamiales (also known as the mint order) are an order in the asterid group of dicotyledonous flowering plants. It includes about 23,810 species, 1,059 genera, and is divided into about 25 families. These families include Acanthaceae, Big ...

), especially in the subfamily Nepetoideae. It is found in species used commonly as culinary

s such as '' Ocimum basilicum'' (basil), ''

Ocimum tenuiflorum ''Ocimum tenuiflorum'', commonly known as holy basil, ''tulsi'' or ''tulasi'', is an aromatic perennial plant in the family Lamiaceae. It is native to the Indian subcontinent and widespread as a cultivated plant throughout the Southeast Asian ...

'' (holy basil), ''

Melissa officinalis Lemon balm (''Melissa officinalis'') is a perennial herbaceous plant in the mint family and native to south-central Europe, the Mediterranean Basin, Iran, and Central Asia, but now naturalised elsewhere. It grows to a maximum height of . The ...

'' (lemon balm), ''Salvia rosmarinus'' (

), ''Origanum majorana'' (

marjoram Marjoram (; ''Origanum majorana'') is a cold-sensitive perennial herb or undershrub with sweet pine and citrus flavours. In some Middle Eastern countries, marjoram is synonymous with oregano, and there the names sweet marjoram and knotted marj ...

), ''

Salvia officinalis ''Salvia officinalis'', the common sage or just sage, is a perennial, evergreen subshrub, with woody stems, grayish leaves, and blue to purplish flowers. It is a member of the mint family Lamiaceae and native to the Mediterranean region, tho ...

'' (sage),

thyme Thyme () is the herb (dried aerial parts) of some members of the genus ''Thymus'' of aromatic perennial evergreen herbs in the mint family Lamiaceae. Thymes are relatives of the oregano genus '' Origanum'', with both plants being mostly indigen ...

and

peppermint Peppermint (''Mentha'' × ''piperita'') is a hybrid species of mint, a cross between watermint and spearmint. Indigenous to Europe and the Middle East, the plant is now widely spread and cultivated in many regions of the world.Euro+Med Plantb ...

. It is also found in plants in the family

Marantaceae The Marantaceae are a family, the arrowroot family, of flowering plants consisting of 31 genera and around 530 species, defining it as one of the most species-rich families in its order.Kennedy, H. (2000). “Diversification in pollination mech ...

(monocotyledons in the order Zingiberales) such as species in the genera '' Maranta'' (''

Maranta leuconeura ''Maranta leuconeura'', also known as prayer plant, is a species of flowering plant in the family Marantaceae, native to the Brazilian tropical forests. It is a variable, rhizomatous perennial, growing to tall and broad, with crowded clumps of ...

'', ''

Maranta depressa Maranta can refer to: *The Marantaceae family of "prayer plants", including arrowroot * ''Maranta'' (plant), a genus within that family Maranta as a personal name may refer to: *In author citation (botany), Maranta is Bartolomeo Maranta, the 16th ...

'') and '' Thalia'' (''

Thalia geniculata ''Thalia geniculata'', the bent alligator-flag, arrowroot, or fire-flag, is a plant species widespread across tropical Africa and much of the Americas. ''Thalia geniculata'' is native to a large region in Africa, from Senegal in the west to Sud ...

''). Rosmarinic acid and the

derivative In mathematics, the derivative of a function of a real variable measures the sensitivity to change of the function value (output value) with respect to a change in its argument (input value). Derivatives are a fundamental tool of calculus. ...

rosmarinic acid 3′-''O''-β-D-

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 ...

can be found in ''

Anthoceros agrestis ''Anthoceros agrestis'', commonly called field hornwort, is a bryophyte of the genus ''Anthoceros''. It has complicated taxonomies. Taxonomy This species of ''Anthoceros'' is known for having enzymes like cinnamic acid 4-hydroxylase (EC 1.1 ...

'', a

(Anthocerotophyta).

Metabolism

The biosynthesis of rosmarinic acid uses

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 lignols (precursors to lignin and ligno ...

from the general

phenylpropanoid pathway 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 ...

as a hydroxycinnamoyl donor. The hydroxycinnamoyl acceptor substrate comes from the shikimate pathway:

shikimic acid Shikimic acid, more commonly known as its anionic form shikimate, is a cyclohexene, a cyclitol and a cyclohexanecarboxylic acid. It is an important biochemical metabolite in plants and microorganisms. Its name comes from the Japanese flower ''shik ...

quinic acid Quinic acid is a cyclitol, a cyclic polyol, and a cyclohexanecarboxylic acid. It is a colorless solid that can be extracted from plant sources. Quinic acid is implicated in the perceived acidity of coffee. Occurrence and preparation The compound i ...

and 3,4-dihydroxyphenyllactic acid derived from L-tyrosine. Thus, chemically, rosmarinic acid is an

of caffeic acid with 3,4-dihydroxyphenyllactic acid, but biologically, it is formed from 4-coumaroyl-4′-hydroxyphenyllactate. Rosmarinate synthase is an enzyme that uses caffeoyl-CoA and 3,4-dihydroxyphenyllactic acid to produce

CoA Coa may refer to: Places * Coa, County Fermanagh, a rural community in County Fermanagh, Northern Ireland * Côa River, a tributary of the Douro, Portugal ** Battle of Coa, part of the Peninsular War period of the Napoleonic Wars ** Côa Valley ...

and rosmarinate. Hydroxyphenylpyruvate reductase is also an enzyme involved in this biosynthesis. : Rosmarinic acid biosynthesis

Uses

When

extract An extract is a substance made by extracting a part of a raw material, often by using a solvent such as ethanol, oil or water. Extracts may be sold as tinctures, absolutes or in powder form. The aromatic principles of many spices, nuts ...

ed from plant sources or synthesized in manufacturing, rosmarinic acid may be used in foods or beverages as a flavoring, in

cosmetics Cosmetics are constituted mixtures of chemical compounds derived from either natural sources, or synthetically created ones. Cosmetics have various purposes. Those designed for personal care and skin care can be used to cleanse or protec ...

, or as a

dietary supplement A dietary supplement is a manufactured product intended to supplement one's diet by taking a pill, capsule, tablet, powder, or liquid. A supplement can provide nutrients either extracted from food sources or that are synthetic in order ...

References

{{Prostanoid signaling modulators Acetylcholinesterase inhibitors GABA transaminase inhibitors Hydroxycinnamic acid esters Nonsteroidal anti-inflammatory drugs Phenol antioxidants Vinylogous carboxylic acids Catechols