Rosmarinic acid

Rosmarinic acid
Names
IUPAC name
(2R)-2-[[(2''E'')-3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]]oxy]-3-(3,4-dihydroxyphenyl)propanoic acid
Identifiers
20283-92-5 YesY
ChEBI CHEBI:17226 YesY
ChEMBL ChEMBL324842 N
ChemSpider 4474888 YesY
Jmol interactive 3D Image
PubChem 5315615
Properties
C18H16O8
Molar mass 360.32 g·mol−1
Appearance Red-orange powder
Melting point 171 to 175 °C (340 to 347 °F; 444 to 448 K)
Slightly soluble
Solubility in other solvents Well 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).
N verify (what is YesYN ?)
Infobox references

Rosmarinic acid is a chemical compound found in a variety of plants. It has antioxidant properties.

History

Rosmarinic acid was first isolated and characterized in 1958 by two Italian chemists ML Scarpatti and G. Oriente from rosemary (Rosmarinus officinalis).[2]

Chemistry

Chemically, rosmarinic acid is a caffeic acid ester of salvianic acid A (3,4-dihydroxyphenyllactic acid).

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.[4] It is found in species used commonly as culinary herbs such as Ocimum basilicum (basil), Ocimum tenuiflorum (holy basil), Melissa officinalis (lemon balm), Rosmarinus officinalis (rosemary), Origanum majorana (marjoram), Salvia officinalis (sage), thyme and peppermint[5] or in plants with medicinal properties such as common self-heal (Prunella vulgaris) or species in the genus Stachys.

It is also found in other Lamiales such as Heliotropium foertherianum, a plant in the family Boraginaceae.

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]

Biosynthesis

The biosyntheses of rosmarinic acid uses 4-coumaroyl-CoA from the general phenylpropanoid pathway as hydroxycinnamoyl donor. 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]

The enzymes involved in the biosynthesis pathway probably evolved from those used in the formation of chlorogenic and caffeoylshikimic acids.[3]

In plants, rosmarinic acid is supposed to act as a preformed constitutively accumulated defense compound.[10]

Biochemical activities

Rosmarinic acid is a potential anxiolytic as it acts as a GABA transaminase inhibitor, more specifically on 4-aminobutyrate transaminase.[11] Rosmarinic acid also inhibits the expression of indoleamine 2,3-dioxygenase via its cyclooxygenase-inhibiting properties.[12]

Senescent leaves of Heliotropium foertherianum (Boraginaceae) also known as octopus bush, a plant used in many Pacific islands as a traditional medicine to treat ciguatera fish poisoning, contain rosmarinic acid and derivatives.[13] Rosmarinic acid may remove the ciguatoxins from their sites of action.

The use of rosmarinic acid is effective in a mouse model of Japanese encephalitis.[14]

References

  1. ↑ "Rosmarinic acid". sigmaaldrich.com.
  2. ↑ Isolamento costituzione e dell 'acido rosmarinico (dal rosmarinus off ). ML Scarpati, G. Oriente , Ric. Sci, 1958, volume 28, pages 2329-2333
  3. 1 2 3 4 Evolution of rosmarinic acid biosynthesis. Petersen M, Abdullah Y, Benner J, Eberle D, Gehlen K, Hücherig S, Janiak V, Kim KH, Sander M, Weitzel C and Wolters S, Phytochemistry, Oct-Nov 2009, volume 70, issues 15-16, pages 1663-1679, doi:10.1016/j.phytochem.2009.05.010
  4. ↑ Distribution and taxonomic implications of some phenolics in the family Lamiaceae determindes by ESR spectroscopy. J. A. Pedersen, Biochemical Systematics and Ecology, 2000, volume 28, pages 229–253
  5. ↑ Clifford, M.N. Chlorogenic acids and other cinnamates. Nature, occurrence and dietary burden. J. Sci. Food. Agric. (79) 362-372, 1999
  6. ↑ Occurrence of rosmarinic acid, chlorogenic acid and rutin in Marantaceae species. Yana Abdullah, Bernd Schneider and Maike Petersen, Phytochemistry Letters, 12 December 2008, Volume 1, Issue 4, Pages 199–203, doi:10.1016/j.phytol.2008.09.010
  7. ↑ Production of rosmarinic acid and a new rosmarinic acid 3′- O -β-D -glucoside in suspension cultures of the hornwort Anthoceros agrestis Paton. Katharina Vogelsang, Bernd Schneider and Maike Petersen, Planta, Volume 223, Number 2, 369-373, doi:10.1007/s00425-005-0089-8
  8. ↑ "MetaCyc rosmarinic acid biosynthesis I". biocyc.org.
  9. ↑ Two new enzymes of rosmarinic acid biosynthesis from cell cultures of Coleus blumei: hydroxyphenylpyruvate reductase and rosmarinic acid synthase. Petersen M and Alfermann AW, Z. Naturforsch. C: Biosci., 1988, volume 43, pages 501–504
  10. ↑ Petersen M, Simmonds MSJ (2003) Rosmarinic acid. Phytochemistry 61: 121-125
  11. ↑ Bioassay-guided fractionation of lemon balm (Melissa officinalis L.) using an in vitro measure of GABA transaminase activity. Awad R, Muhammad A, Durst T, Trudeau VL and Arnason JT, Phytother Res., August 2009, volume 23, issue 8, pages 1075-1081, doi:10.1002/ptr.2712
  12. ↑ Lee HJ, Jeong YI, Lee TH, et al. (May 2007). "Rosmarinic acid inhibits indoleamine 2,3-dioxygenase expression in murine dendritic cells". Biochem. Pharmacol. 73 (9): 1412–21. doi:10.1016/j.bcp.2006.12.018. PMID 17229401.
  13. ↑ Protective effect of Heliotropium foertherianum (Boraginaceae) folk remedy and its active compound, rosmarinic acid, against a Pacific ciguatoxin. Rossi F, Jullian V, Pawlowiez R, Kumar-Roiné S, Haddad M, Darius HT, Gaertner-Mazouni N, Chinain M and Laurent D, J Ethnopharmacol., 30 August 2012, volume 143, issue 1, pages 33-40, doi:10.1016/j.jep.2012.05.045
  14. ↑ Swarup V, Ghosh J, Ghosh S, Saxena A, Basu A (September 2007). "Antiviral and anti-inflammatory effects of rosmarinic acid in an experimental murine model of Japanese encephalitis". Antimicrob. Agents Chemother. 51 (9): 3367–70. doi:10.1128/AAC.00041-07. PMC 2043228. PMID 17576830.
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