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| 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 |
| KEGG | |
PubChem
CID
|
|
| UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
| Properties | |
| C18H16O8 | |
| Molar mass | 360.318 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).
| |
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]
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]
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]
References
- ^ a b c d e f g h "Rosmarinic acid". PubChem, US National Library of Medicine. 10 July 2021. Retrieved 11 July 2021.
- ^ Scarpati, M. L.; Oriente, G. (1958). "Isolamento costituzione e dell'acido rosmarinico (dal Rosmarinus 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. 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 hornwort Anthoceros 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 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.
|
| |
| 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 |
| KEGG | |
PubChem
CID
|
|
| UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
| Properties | |
| C18H16O8 | |
| Molar mass | 360.318 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).
| |
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]
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]
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]
References
- ^ a b c d e f g h "Rosmarinic acid". PubChem, US National Library of Medicine. 10 July 2021. Retrieved 11 July 2021.
- ^ Scarpati, M. L.; Oriente, G. (1958). "Isolamento costituzione e dell'acido rosmarinico (dal Rosmarinus 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. 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 hornwort Anthoceros 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 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.