Chemical compound found in a variety of plants
Rosmarinic acid Rosmarinic acid Names Preferred IUPAC name (2R )-3-(3,4-Dihydroxyphenyl)-2-{[(2E )-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanoic acid
Identifiers ChEBI ChEMBL ChemSpider ECHA InfoCard 100.123.507 KEGG 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+
Y Key: DOUMFZQKYFQNTF-ZZXKWVIFSA-N
Y 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
Properties C 18 H 16 O 8 Molar mass −1 Appearance Red-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).
Chemical compound
Rosmarinic acid , named afterrosemary (Salvia rosmarinus Spenn.), is apolyphenol constituent of many culinaryherbs , includingrosemary (Salvia rosmarinus L.),perilla (Perilla frutescens L.),sage (Salvia officinalis L.),mint (Mentha arvense L.), andbasil (Ocimum basilicum L.).[ 1]
Rosmarinic acid was first isolated and characterized in 1958 by the Italian chemists Scarpatti and Oriente fromrosemary (Salvia rosmarinus [ 2]
Chemically, rosmarinic acid is acaffeic acid ester , with tyrosine providing another phenolic ring via dihydroxyphenyl-lactic acid .[ 1] molecular mass of 360daltons .[ 1]
Natural occurrences [ edit ] Rosmarinic acid accumulation is shown inhornworts , in the fern familyBlechnaceae , and in species of several orders ofmono- anddicotyledonous angiosperms .[ 3]
It is found most notably in manyLamiaceae (dicotyledons in the orderLamiales ), especially in the subfamilyNepetoideae .[ 1] [ 4] herbs such asOcimum basilicum Ocimum tenuiflorum Melissa officinalis Salvia rosmarinus (rosemary ),Origanum majorana (marjoram ),Salvia officinalis thyme andpeppermint .[ 1] [ 5] Marantaceae (monocotyledons in the order Zingiberales)[ 3] Maranta Maranta leuconeura Maranta depressa Thalia Thalia geniculata [ 6]
Rosmarinic acid and thederivative rosmarinic acid 3′-O -β-D -glucoside can be found inAnthoceros agrestis hornwort (Anthocerotophyta).[ 7]
The biosynthesis of rosmarinic acid uses4-coumaroyl-CoA from the generalphenylpropanoid pathway as ahydroxycinnamoyl donor.[ 1] shikimate pathway :shikimic acid ,quinic acid and3,4-dihydroxyphenyllactic acid derived fromL -tyrosine[ 3] ester ofcaffeic acid with 3,4-dihydroxyphenyllactic acid, but biologically, it is formed from 4-coumaroyl-4′-hydroxyphenyllactate.[ 8] Rosmarinate synthase is an enzyme that usescaffeoyl-CoA and 3,4-dihydroxyphenyllactic acid to produceCoA and rosmarinate.Hydroxyphenylpyruvate reductase is also an enzyme involved in this biosynthesis.[ 9]
Whenextracted from plant sources or synthesized in manufacturing, rosmarinic acid may be used in foods or beverages as a flavoring, incosmetics , or as adietary supplement .[ 1]
^a b c d e f g h "Rosmarinic acid" . PubChem, US National Library of Medicine. 10 July 2021. Retrieved11 July 2021 .^ Scarpati, M. L.; Oriente, G. (1958). "Isolamento costituzione e dell'acido rosmarinico (dalRosmarinus off. )".Ricerca Scientifica .28 :2329– 2333. ^a b c 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 . ^ 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 ^ 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.Bibcode :1999JSFA...79..362C .doi :10.1002/(SICI)1097-0010(19990301)79:3<362::AID-JSFA256>3.0.CO;2-D . ^ 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 . ^ Vogelsang, Katharina; Schneider, Bernd; Petersen, Maike (2006). "Production of rosmarinic acid and a new rosmarinic acid 3′-O -β-D -glucoside in suspension cultures of the hornwortAnthoceros agrestis Paton".Planta .223 (2):369– 373.doi :10.1007/s00425-005-0089-8 .PMID 16133208 .S2CID 29302603 . ^ "MetaCyc rosmarinic acid biosynthesis I" .biocyc.org .^ Petersen, M.; Alfermann, A. W. (1988)."Two new enzymes of rosmarinic acid biosynthesis from cell cultures ofColeus 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 .
Aglycones
Precursor Monohydroxycinnamic acids Dihydroxycinnamic acids Trihydroxycinnamic acids O -methylated formsothers
Esters
glycoside-likes
Esters of
Glycosides
Tartaric acid estersOther esters Caffeoyl phenylethanoid Echinacoside Calceolarioside A ,B ,C ,F Chiritoside A ,B ,C Cistanoside A ,B ,C ,D ,E ,F ,G ,H Conandroside Myconoside Pauoifloside Plantainoside A Plantamajoside Tubuloside B Verbascoside (Isoverbascoside ,2′-Acetylverbascoside )
Oligomeric forms
Dimers Diferulic acids (DiFA) :5,5′-Diferulic acid ,8-O -4′-Diferulic acid ,8,5′-Diferulic acid ,8,5′-DiFA (DC) ,8,5′-DiFA (BF) ,8,8′-Diferulic acid Trimers Tetramers
Conjugates withcoenzyme A (CoA)
Transporter
GAT Tooltip GABA transporter VIAAT Tooltip Vesicular inhibitory amino acid transporter
Enzyme
GAD Tooltip Glutamate decarboxylase GABA-T Tooltip γ-Aminobutyrate aminotransferase
Other
Receptor (ligands )
DP (D2 ) Tooltip Prostaglandin D2 receptor
DP1 Tooltip Prostaglandin D2 receptor 1 DP2 Tooltip Prostaglandin D2 receptor 2
EP (E2 ) Tooltip Prostaglandin E2 receptor
EP1 Tooltip Prostaglandin EP1 receptor EP2 Tooltip Prostaglandin EP2 receptor EP3 Tooltip Prostaglandin EP3 receptor EP4 Tooltip Prostaglandin EP4 receptor Unsorted
FP (F2α ) Tooltip Prostaglandin F receptor IP (I2 ) Tooltip Prostacyclin receptor TP (TXA2 ) Tooltip Thromboxane receptor Unsorted
Enzyme (inhibitors )
COX PTGS) PGD2 S Tooltip Prostaglandin D synthase PGES Tooltip Prostaglandin E synthase PGFS Tooltip Prostaglandin F synthase PGI2 S Tooltip Prostacyclin synthase TXAS Tooltip Thromboxane A synthase
Others
