Rosmarinic acid

History

Rosmarinic acid was first isolated and characterized in 1958 by the Italian chemists Scarpatti and Oriente from rosemary (Salvia rosmarinus), 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. It has a molecular mass of 360 daltons.

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.

It is found most notably in many Lamiaceae (dicotyledons in the order Lamiales), especially in the subfamily Nepetoideae. 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. It is also found in plants in the family Marantaceae (monocotyledons in the order Zingiberales),

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

Metabolism

The biosynthesis of rosmarinic acid uses 4-coumaroyl-CoA from the general phenylpropanoid pathway as a hydroxycinnamoyl donor. 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. :[[File:Rosmarinic acid biosynthesis.png|600px|Rosmarinic acid biosynthesis]]

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.

References

References

1. (10 July 2021). "Rosmarinic acid". PubChem, US National Library of Medicine.
2. (1958). "Isolamento costituzione e dell'acido rosmarinico (dal ''Rosmarinus off.'')". Ricerca Scientifica.
3. (2009). "Evolution of rosmarinic acid biosynthesis". Phytochemistry.
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. (12 December 2008). "Occurrence of rosmarinic acid, chlorogenic acid and rutin in Marantaceae species". Phytochemistry Letters.
6. (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.
7. (1988). "Two new enzymes of rosmarinic acid biosynthesis from cell cultures of ''Coleus blumei'': hydroxyphenylpyruvate reductase and rosmarinic acid synthase". Zeitschrift für Naturforschung C.