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 of ...

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 medicinal ...

s, including

(''Salvia rosmarinus'' L.),

perilla ''Perilla'' is a genus consisting of one major Asiatic crop species ''Perilla frutescens'' and a few wild species in nature belonging to the mint family, Lamiaceae. The genus encompasses several distinct varieties of Asian herb, seed, and veget ...

(''Perilla frutescens'' L.),

sage Sage or SAGE may refer to: Plants * ''Salvia officinalis'', common sage, a small evergreen subshrub used as a culinary herb ** Lamiaceae, a family of flowering plants commonly known as the mint or deadnettle or sage family ** ''Salvia'', a large ...

(''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, XaA ...

(''Mentha arvense'' L.), and

basil Basil (, ; ''Ocimum basilicum'' , also called great basil, is a culinary herb of the family Lamiaceae (mints). It is a tender plant, and is used in cuisines worldwide. In Western cuisine, the generic term "basil" refers to the variety also kno ...

(''Ocimum basilicum'' L.).

History

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

('' Salvia rosmarinus''), after which the acid is named.

Chemistry

Chemically, rosmarinic acid is a

caffeic acid Caffeic acid is an organic compound that is classified as a hydroxycinnamic acid. This yellow solid consists of both phenolic and acrylic functional groups. It is found in all plants because it is an intermediate in the biosynthesis of lignin, one ...

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 ar ...

, 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 natu ...

. 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 quanti ...

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 2016 ( ...

, 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-cyc ...

and dicotyledonous

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 th ...

. 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, Bi ...

), especially in the subfamily

Nepetoideae Nepetoideae is a subfamily of plants in the family Lamiaceae. , the Angiosperm Phylogeny Website (APweb) accepted the following genera: The format of the authorities is not the IPNI standard. *''Acanthomintha'' (A. Gray) Bentham & J. D. Hooker ...

. It is found in species used commonly as culinary

s such as ''

Ocimum basilicum Basil (, ; ''Ocimum basilicum'' , also called great basil, is a culinary herb of the family Lamiaceae (mints). It is a tender plant, and is used in cuisines worldwide. In Western cuisine, the generic term "basil" refers to the variety also kno ...

'' (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 mar ...

), ''

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, thoug ...

'' (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 indigenou ...

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 Plantbas ...

. 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 mechan ...

(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'') and ''

Thalia Thalia, Thalía, Thaleia or Thalian may refer to: People * Thalia (given name), including a list of people with the name * Thalía (born 1971), Mexican singer and actress Mythological and fictional characters * Thalia (Grace), one of the three ...

'' ('' Thalia geniculata''). 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. F ...

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 o ...

can be found in '' Anthoceros agrestis'', a

(Anthocerotophyta).

Metabolism

The biosynthesis of rosmarinic acid uses 4-coumaroyl-CoA 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 The shikimate pathway (shikimic acid pathway) is a seven-step metabolic pathway used by bacteria, archaea, fungi, algae, some protozoans, and plants for the biosynthesis of folates and aromatic amino acids (tryptophan, phenylalanine, and tyrosine) ...

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 ...

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

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 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, h ...

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 protect ...

, 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