Rosmarinic acid
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Rosmarinic acid
| Rosmarinic acid | |
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(2''R'')-2-[[(2''E'')-3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]]oxy]-3-(3,4-dihydroxyphenyl)propanoic acid |
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| Identifiers | |
| CAS number | 20283-92-5  |
| PubChem | 5315615 |
| ChemSpider | 4474888 |
| ChEBI | CHEBI:17226 |
| ChEMBL | CHEMBL324842  |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C18H16O8 |
| Molar mass | 360.31 g/mol |
| Exact mass | 360.084517 u |
| Melting point |
171-175 °C |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Rosmarinic acid is a natural phenol antioxidant carboxylic acid found in many Lamiaceae herbs used commonly as culinary herbs such as lemon balm, rosemary, oregano, sage, thyme and peppermint.[1] Chemically, rosmarinic acid is an ester of caffeic acid with 3,4-dihydroxyphenyl lactic acid. It is a red-orange powder that is slightly soluble in water, but well soluble in most organic solvents.[2]
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Contents
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Natural occurrences
Rosmarinic acid and a rosmarinic acid 3′-O-β-D-glucoside can be found in Anthoceros agrestis, a hornwort (Anthocerotophyta).[3]
Biological importance
Because of the antioxidant activity of Lamiaceaeous herbs in laboratory test models they have been suggested to have beneficial effects in humans.[4] Rosmarinic acid has a number of interesting biological activities, e.g. antiviral, antibacterial, antiinflammatory and antioxidant. It is also a potential anxiolytic as it acts as a GABA transaminase inhibitor. The presence of rosmarinic acid in medicinal plants, herbs and spices has beneficial and health promoting effects. In plants, rosmarinic acid is supposed to act as a preformed constitutively accumulated defense compound. [5]
Metabolism
Rosmarinic acid is known to undergo metabolism in humans and rats to methylated rosmarinic acid, coumaric acid, ferulic acid and caffeic acid.[citation needed]. However, unconjugated rosmarinic acid and its metabolites remain in the bloodstream of rats for enough time to reach the brain and decrease acetylcholineterase activity, which is useful in the treatment of Alzheimer's disease[6]. Rosmarinic acid may be transported in the bloodstream bound to human serum albumin and lysozyme[7].
References
- ^ Clifford, M.N. Chlorogenic acids and other cinnamates. Nature, occurrence and dietary burden. J. Sci. Food. Agric. (79) 362-372, 1999
- ^ MSDS for rosmarinic acid
- ^ 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
- ^ Triantaphyllou, K.;Blekas, G.; Boskou, D. Antioxidative properties of water extracts obtained from herbs of the species Lamiacaea. Int. J. Food. Sci. Nutr. (52) 313-317, 2001
- ^ Petersen M, Simmonds MSJ (2003) Rosmarinic acid. Phytochemistry 61: 121-125
- ^ Pedro L. V. Falé, Paulo J. Amorim Madeira, M. Helena Florêncio, Lia Ascensão and Maria Luísa M. Serralheiro. Function of Plectranthus barbatus herbal tea as neuronal acetylcholinesterase inhibitor. Food Funct., 2011, 2, 130-136.
- ^ Pedro L.V. Falé, Lia Ascensão, Maria L.M. Serralheiro, Parvez I. Haris. Interaction between Plectranthus barbatus herbal tea components and human serum albumin and lysozyme: Binding and activity studies. Spectroscopy, 2011, 26, 79-92.
See also
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