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. It is a member of the sage family, Lamiaceae. The species is native to the Mediterranean r ...

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

polyphenol Polyphenols () are a large family of naturally occurring phenols. They are abundant in plants and structurally diverse. Polyphenols include phenolic acids, flavonoids, tannic acid, and ellagitannin, some of which have been used historically as ...

constituent of many culinary

herb Herbs are a widely distributed and widespread group of plants, excluding vegetables, with savory or aromatic properties that are used for flavoring and garnishing food, for medicinal purposes, or for fragrances. Culinary use typically distingu ...

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 vege ...

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

mint Mint or The Mint may refer to: Plants * Lamiaceae, the mint family ** ''Mentha'', the genus of plants commonly known as "mint" Coins and collectibles * Mint (facility), a facility for manufacturing coins * Mint condition, a state of like-new ...

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

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

(''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. It is a member of the sage family, Lamiaceae. The species is native to the Mediterranean re ...

''), after which the acid is named.

Chemistry

Chemically, rosmarinic acid is a

caffeic acid Caffeic acid is an organic compound with the formula . It is a polyphenol with a key role in scavenging reactive oxygen species (ROS) generated in energy metabolism. Caffeic acid is also one major polyphenol responsible for maintaining normal le ...

ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...

, with tyrosine providing another phenolic ring via dihydroxyphenyl-

lactic acid Lactic acid is an organic acid. It has the molecular formula C3H6O3. 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 wel ...

. It has a

molecular mass The molecular mass () is the mass of a given molecule, often expressed in units of daltons (Da). Different molecules of the same compound may have different molecular masses because they contain different isotopes of an element. The derived quan ...

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 (PP ...

, 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: * triangle, quadrilateral, pentagon, hexagon, oc ...

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, ...

ous

angiosperms Flowering plants are plants that bear flowers and fruits, and form the clade Angiospermae (). The term angiosperm is derived from the Greek words (; 'container, vessel') and (; 'seed'), meaning that the seeds are enclosed within a fruit. T ...

. It is found most notably in many

Lamiaceae The Lamiaceae ( ) or Labiatae are a family (biology), 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 (herb), ba ...

(dicotyledons in the order

Lamiales The Lamiales (also known as the mint order) are an order of flowering plants in the asterids clade of the Eudicots. Under the APG IV system of flowering plant classification the order consists of 24 families, and includes about 23,810 species ...

), 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. Hooke ...

. 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 hardiness (plants), tender plant, and is used in cuisines worldwide. In Western cuisine, the generic term "basil" r ...

'' (basil), ''

Ocimum tenuiflorum ''Ocimum tenuiflorum'', commonly known as holy basil, ''tulasi'' or ''tulsi'' (), is an aromatic perennial plant in the family Lamiaceae. It is widely cultivated throughout the Southeast Asian tropics. It is native to tropical and subtropical r ...

'' (holy basil), ''

Melissa officinalis Lemon balm (''Melissa officinalis'') is a perennial herbaceous plant in the mint family. It has lemon-scented leaves, white or pale pink flowers, and contains essential oils and compounds like geranial and neral. It grows to a maximum height of ...

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

), ''Origanum majorana'' (

marjoram Marjoram (, ''Origanum majorana'') is a cold-sensitive perennial plant, 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 ...

), ''

Salvia officinalis ''Salvia officinalis'', the common sage or 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, though it ...

'' (sage),

thyme Thyme () is a culinary herb consisting of the dried aerial parts of some members of the genus ''Thymus (plant), Thymus'' of flowering plants in the mint family Lamiaceae. Thymes are native to Eurasia and north Africa. Thymes have culinary, medici ...

and

peppermint Peppermint (''Mentha'' × ''piperita'') is a Hybrid (biology), hybrid species of Mentha, mint, a cross between Mentha aquatica, watermint and spearmint. Indigenous to Europe and the Middle East, the plant is now widely spread and cultivated in m ...

. It is also found in plants in the family

Marantaceae The Marantaceae are a family, the arrowroot family, or the prayer plant 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). “Diversif ...

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

Maranta leuconeura ''Maranta leuconeura'', widely known as the prayer plant due to its daily sunlight-dependent movements (which are said to resemble hands “in-prayer”), is a species of flowering plant in the family Marantaceae native to the Brazilian tropic ...

'', ''

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) In botanical nomenclature, author citati ...

'') 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 is a fundamental tool that quantifies the sensitivity to change of a function's output with respect to its input. The derivative of a function of a single variable at a chosen input value, when it exists, is t ...

rosmarinic acid 3′-''O''-β-D-

glucoside A glucoside is a glycoside that is chemically 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. Th ...

can be found in ''

Anthoceros agrestis ''Anthoceros agrestis'', commonly called field hornwort, is a bryophyte of the family Anthocerotaceae. ''A. agrestis'' is considered the model species for hornwort biology and is used to study some of the unique traits that hornworts possess, su ...

'', 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 Monolignol, lignols (precursors to lignin ...

from the general

phenylpropanoid pathway The phenylpropanoids are a diverse family of organic compounds that are biosynthesized by plants from the amino acids phenylalanine and tyrosine in the shikimic acid pathway. Their name is derived from the six-carbon, aromatic phenyl group and ...

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 an organic compound with the formula . The compound is classified as 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 p ...

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 (essence) 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 or absolutes or dried and powdered. The aromatic principles of ma ...

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

cosmetics Cosmetics are substances that are intended for application to the body for cleansing, beautifying, promoting attractiveness, or altering appearance. They are mixtures of chemical compounds derived from either Natural product, natural source ...

, or as a

dietary supplement A dietary supplement is a manufactured product intended to supplement a person's diet by taking a pill (pharmacy), pill, capsule (pharmacy), capsule, tablet (pharmacy), tablet, powder, or liquid. A supplement can provide nutrients eithe ...

References

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