Rosmarinic acid

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Rosmarinic acid
Rosmarinic acid.png
Names
Preferred IUPAC name
(2R)-3-(3,4-Dihydroxyphenyl)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanoic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.123.507 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C18H16O8/c19-12-4-1-10(7-14(12)21)3-6-17(23)26-16(18(24)25)9-11-2-5-13(20)15(22)8-11/h1-8,16,19-22H,9H2,(H,24,25)/b6-3+ Yes check.svgY
    Key: DOUMFZQKYFQNTF-ZZXKWVIFSA-N Yes check.svgY
  • InChI=1/C18H16O8/c19-12-4-1-10(7-14(12)21)3-6-17(23)26-16(18(24)25)9-11-2-5-13(20)15(22)8-11/h1-8,16,19-22H,9H2,(H,24,25)/b6-3+
    Key: DOUMFZQKYFQNTF-ZZXKWVIFBW
  • O=C(O)C(OC(=O)\C=C\c1ccc(O)c(O)c1)Cc2cc(O)c(O)cc2
Properties
C18H16O8
Molar mass 360.318 g·mol−1
AppearanceRed-orange powder
Melting point 171 to 175 °C (340 to 347 °F; 444 to 448 K)
Slightly soluble
Solubility in other solventsWell soluble in most organic solvents [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Rosmarinic acid, named after rosemary (Salvia rosmarinus Spenn.), is a polyphenol constituent of many culinary herbs, including rosemary (Salvia rosmarinus L.), perilla (Perilla frutescens L.), sage (Salvia officinalis L.), mint (Mentha arvense L.), and basil (Ocimum basilicum L.). [1]

Contents

History

Rosmarinic acid was first isolated and characterized in 1958 by the Italian chemists Scarpatti and Oriente from rosemary ( Salvia rosmarinus ), [2] after which the acid is named.

Chemistry

Chemically, rosmarinic acid is a caffeic acid ester, with tyrosine providing another phenolic ring via dihydroxyphenyl-lactic acid. [1] It has a molecular mass of 360 daltons. [1]

Natural occurrences

Rosmarinic acid accumulation is shown in hornworts, in the fern family Blechnaceae, and in species of several orders of mono- and dicotyledonous angiosperms. [3]

It is found most notably in many Lamiaceae (dicotyledons in the order Lamiales), especially in the subfamily Nepetoideae. [1] [4] It is found in species used commonly as culinary herbs such as Ocimum basilicum (basil), Ocimum tenuiflorum (holy basil), Melissa officinalis (lemon balm), Salvia rosmarinus (rosemary), Origanum majorana (marjoram), Salvia officinalis (sage), thyme and peppermint. [1] [5] It is also found in plants in the family Marantaceae (monocotyledons in the order Zingiberales) [3] such as species in the genera Maranta ( Maranta leuconeura , Maranta depressa ) and Thalia ( Thalia geniculata ). [6]

Rosmarinic acid and the derivative rosmarinic acid 3′-O-β-D-glucoside can be found in Anthoceros agrestis , a hornwort (Anthocerotophyta). [7]

Metabolism

The biosynthesis of rosmarinic acid uses 4-coumaroyl-CoA from the general phenylpropanoid pathway as a hydroxycinnamoyl donor. [1] The hydroxycinnamoyl acceptor substrate comes from the shikimate pathway: shikimic acid, quinic acid and 3,4-dihydroxyphenyllactic acid derived from L-tyrosine. [3] Thus, chemically, rosmarinic acid is an ester of caffeic acid with 3,4-dihydroxyphenyllactic acid, but biologically, it is formed from 4-coumaroyl-4′-hydroxyphenyllactate. [8] 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. [9]

Rosmarinic acid biosynthesis.png

Uses

When extracted from plant sources or synthesized in manufacturing, rosmarinic acid may be used in foods or beverages as a flavoring, in cosmetics, or as a dietary supplement. [1]

Related Research Articles

<span class="mw-page-title-main">Lamiaceae</span> Family of flowering plants that includes sage and mint

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, marjoram, oregano, hyssop, thyme, lavender, and perilla, as well as other medicinal herbs such as catnip, salvia, bee balm, wild dagga, and oriental motherwort. Some species are shrubs, trees, or, rarely, vines. Many members of the family are widely cultivated, not only for their aromatic qualities, but also their ease of cultivation, since they are readily propagated by stem cuttings. Besides those grown for their edible leaves, some are grown for decorative foliage. Others are grown for seed, such as Salvia hispanica (chia), or for their edible tubers, such as Plectranthus edulis, Plectranthus esculentus, Plectranthus rotundifolius, and Stachys affinis. Many are also grown ornamentally, notably coleus, Plectranthus, and many Salvia species and hybrids.

<span class="mw-page-title-main">Rosemary</span> Species of plant

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 Rosmarinus officinalis, now a synonym.

<span class="mw-page-title-main">Eugenol</span> Chemical compound

Eugenol is an allyl chain-substituted guaiacol, a member of the allylbenzene class of chemical compounds. It is a colorless to pale yellow, aromatic oily liquid extracted from certain essential oils especially from clove, nutmeg, cinnamon, basil and bay leaf. It is present in concentrations of 80–90% in clove bud oil and at 82–88% in clove leaf oil. Eugenol has a pleasant, spicy, clove-like scent. The name is derived from Eugenia caryophyllata, the former Linnean nomenclature term for cloves. The currently accepted name is Syzygium aromaticum.

<span class="mw-page-title-main">Quercetin</span> Chemical compound

Quercetin is a plant flavonol from the flavonoid group of polyphenols. It is found in many fruits, vegetables, leaves, seeds, and grains; capers, red onions, and kale are common foods containing appreciable amounts of it. It has a bitter flavor and is used as an ingredient in dietary supplements, beverages, and foods.

<span class="mw-page-title-main">Chlorogenic acid</span> Chemical compound

Chlorogenic acid (CGA) is the ester of caffeic acid and (−)-quinic acid, functioning as an intermediate in lignin biosynthesis. The term "chlorogenic acids" refers to a related polyphenol family of esters, including hydroxycinnamic acids with quinic acid.

<span class="mw-page-title-main">Caffeic acid</span> Chemical compound

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 of the principal components of woody plant biomass and its residues.

<span class="mw-page-title-main">Ferulic acid</span> Chemical compound

Ferulic acid is a hydroxycinnamic acid, is an organic compound with the formula (CH3O)HOC6H3CH=CHCO2H. The name is derived from the genus Ferula, referring to the giant fennel (Ferula communis). Classified as a phenolic phytochemical or polyphenol, ferulic acid is an amber colored solid. Esters of ferulic acid are found in plant cell walls, covalently bonded to hemicellulose such as arabinoxylans. Salts and esters derived from ferulic acid are called ferulates.

<span class="mw-page-title-main">Caryophyllene</span> Chemical compound

Caryophyllene, more formally (−)-β-caryophyllene,(BCP), is a natural bicyclic sesquiterpene that is a constituent of many essential oils, especially clove oil, the oil from the stems and flowers of Syzygium aromaticum (cloves), the essential oil of Cannabis sativa, copaiba, rosemary, and hops. It is usually found as a mixture with isocaryophyllene (the cis double bond isomer) and α-humulene (obsolete name: α-caryophyllene), a ring-opened isomer. Caryophyllene is notable for having a cyclobutane ring, as well as a trans-double bond in a 9-membered ring, both rarities in nature.

<span class="mw-page-title-main">Kaempferol</span> Chemical compound

Kaempferol (3,4′,5,7-tetrahydroxyflavone) is a natural flavonol, a type of flavonoid, found in a variety of plants and plant-derived foods including kale, beans, tea, spinach, and broccoli. Kaempferol is a yellow crystalline solid with a melting point of 276–278 °C (529–532 °F). It is slightly soluble in water and highly soluble in hot ethanol, ethers, and DMSO. Kaempferol is named for 17th-century German naturalist Engelbert Kaempfer.

<span class="mw-page-title-main">Edible flower</span> Flowers that may be consumed safely

Edible flowers are flowers that can be consumed safely. Flowers may be eaten as vegetables as a main part of a meal, or may be used as herbs. Flowers are part of many regional cuisines, including Asian, European, and Middle Eastern cuisines.

In enzymology, a rosmarinate synthase is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">Naturally occurring phenols</span> Group of chemical compounds

In biochemistry, naturally occurring phenols are natural products containing at least one phenol functional group. Phenolic compounds are produced by plants and microorganisms. Organisms sometimes synthesize phenolic compounds in response to ecological pressures such as pathogen and insect attack, UV radiation and wounding. As they are present in food consumed in human diets and in plants used in traditional medicine of several cultures, their role in human health and disease is a subject of research. Some phenols are germicidal and are used in formulating disinfectants.

<i>Anthoceros agrestis</i> Species of hornwort

Anthoceros agrestis, commonly called field hornwort, is a bryophyte of the genus Anthoceros. It has complicated taxonomies.

<i>p</i>-Coumaroylated anthocyanin

p-Coumaroylated anthocyanins are a type of anthocyanins with a p-coumaric acid unit linked with a sugar to an anthocyanidin aglycone. 3-(6-p-Coumaroyl)glucosides are found in grape and wine. Cyanidin-3-O-(di-p-coumarylglucoside)-5-glucoside is found in dark opal basil. Red leaves of Perilla frutescens also accumulate cyanidin 3-(6-O-p-coumaroyl-β-D-glucoside)-5-(6-O-malonyl-β-D-glucoside).

<i>Maranta leuconeura</i> Species of flowering plant

Maranta leuconeura, widely known as the prayer plant due to its daily sunlight-dependent movements, is a species of flowering plant in the family Marantaceae native to the Brazilian tropical forests. It is a variable, rhizomatous perennial, growing to 30 cm (12 in) tall and broad, with crowded clumps of evergreen, strikingly-marked oval leaves, each up to 12 cm (5 in) long. The plant spreads itself horizontally, carpeting an entire small area of forest floor, sending roots into the substrate at each leaf node.

<span class="mw-page-title-main">Spice use in antiquity</span>

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<span class="mw-page-title-main">Direct linear plot</span> Plot for enzyme kinetics data

In biochemistry, the direct linear plot is a graphical method for enzyme kinetics data following the Michaelis–Menten equation. In this plot, observations are not plotted as points, but as lines in parameter space with axes and , such that each observation of a rate at substrate concentration is represented by a straight line with intercept on the axis and on the axis. Ideally the lines intersect at a unique point whose coordinates provide the values of and .

References

  1. 1 2 3 4 5 6 7 8 "Rosmarinic acid". PubChem, US National Library of Medicine. 10 July 2021. Retrieved 11 July 2021.
  2. Scarpati, M. L.; Oriente, G. (1958). "Isolamento costituzione e dell'acido rosmarinico (dal Rosmarinus off.)". Ricerca Scientifica. 28: 2329–2333.
  3. 1 2 3 Petersen, M.; Abdullah, Y.; Benner, J.; Eberle, D.; Gehlen, K.; Hücherig, S.; Janiak, V.; Kim, K. H.; Sander, M.; Weitzel, C.; Wolters, S. (2009). "Evolution of rosmarinic acid biosynthesis". Phytochemistry. 70 (15–16): 1663–1679. Bibcode:2009PChem..70.1663P. doi:10.1016/j.phytochem.2009.05.010. PMID   19560175.
  4. Distribution and taxonomic implications of some phenolics in the family Lamiaceae determined by ESR spectroscopy. J. A. Pedersen, Biochemical Systematics and Ecology, 2000, volume 28, pages 229–253
  5. Clifford, M. N. (1999). "Chlorogenic acids and other cinnamates. Nature, occurrence and dietary burden". Journal of the Science of Food and Agriculture. 79 (3): 362–372. doi:10.1002/(SICI)1097-0010(19990301)79:3<362::AID-JSFA256>3.0.CO;2-D.
  6. Abdullah, Yana; Schneider, Bernd; Petersen, Maike (12 December 2008). "Occurrence of rosmarinic acid, chlorogenic acid and rutin in Marantaceae species". Phytochemistry Letters. 1 (4): 199–203. Bibcode:2008PChL....1..199A. doi:10.1016/j.phytol.2008.09.010.
  7. Vogelsang, Katharina; Schneider, Bernd; Petersen, Maike. "Production of rosmarinic acid and a new rosmarinic acid 3′-O-β-D-glucoside in suspension cultures of the hornwort Anthoceros agrestis Paton". Planta. 223 (2): 369–373. doi:10.1007/s00425-005-0089-8. PMID   16133208. S2CID   29302603.
  8. "MetaCyc rosmarinic acid biosynthesis I". biocyc.org.
  9. Petersen, M.; Alfermann, A. W. (1988). "Two new enzymes of rosmarinic acid biosynthesis from cell cultures of Coleus blumei: hydroxyphenylpyruvate reductase and rosmarinic acid synthase". Zeitschrift für Naturforschung C. 43 (7–8): 501–504. doi: 10.1515/znc-1988-7-804 . S2CID   35635116.