Rosmarinic acid, C

Carbon

Carbon is the chemical element with symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalent—making four electrons available to form covalent chemical bonds...

₁₈H

Hydrogen

Hydrogen is the chemical element with atomic number 1. It is represented by the symbol H. With an average atomic weight of , hydrogen is the lightest and most abundant chemical element, constituting roughly 75% of the Universe's chemical elemental mass. Stars in the main sequence are mainly...

₁₆O

Oxygen

Oxygen is the element with atomic number 8 and represented by the symbol O. Its name derives from the Greek roots ὀξύς and -γενής , because at the time of naming, it was mistakenly thought that all acids required oxygen in their composition...

₈, is a natural phenol

Natural phenol

Natural phenols, bioavailable phenols, plant phenolics, low molecular weight phenols or phenoloids are a class of natural products. They are small molecules containing one or more phenolic group. These molecules are smaller in size than polyphenols, containing less than 12 phenolic groups...

 antioxidant

Antioxidant

An antioxidant is a molecule capable of inhibiting the oxidation of other molecules. Oxidation is a chemical reaction that transfers electrons or hydrogen from a substance to an oxidizing agent. Oxidation reactions can produce free radicals. In turn, these radicals can start chain reactions. When...

 carboxylic acid

Carboxylic acid

Carboxylic acids are organic acids characterized by the presence of at least one carboxyl group. The general formula of a carboxylic acid is R-COOH, where R is some monovalent functional group...

 found in many Lamiaceae

Lamiaceae

The mints, taxonomically known as Lamiaceae or Labiatae, are a family of flowering plants. They have traditionally been considered closely related to Verbenaceae, but in the 1990s, phylogenetic studies suggested that many genera classified in Verbenaceae belong instead in Lamiaceae...

herbs used commonly as culinary herbs such as lemon balm

Lemon balm

Lemon balm , not to be confused with bee balm, Monarda species, is a perennial herb in the mint family Lamiaceae, native to southern Europe and the Mediterranean region....

, rosemary

Rosemary

Rosemary, , is a woody, perennial herb with fragrant, evergreen, needle-like leaves and white, pink, purple or blue flowers, native to the Mediterranean region. It is a member of the mint family Lamiaceae, which includes many other herbs, and is one of two species in the genus Rosmarinus...

, oregano

Oregano

Oregano – scientifically named Origanum vulgare by Carolus Linnaeus – is a common species of Origanum, a genus of the mint family . It is native to warm-temperate western and southwestern Eurasia and the Mediterranean region.Oregano is a perennial herb, growing from 20–80 cm tall,...

, sage

Common sage

Salvia officinalis is a small, perennial, evergreen subshrub, with woody stems, grayish leaves, and blue to purplish flowers. It is a member of the family Lamiaceae and is native to the Mediterranean region, though it has naturalized in many places throughout the world...

, thyme

Thyme

Thyme is a culinary and medicinal herb of the genus Thymus.-History:Ancient Egyptians used thyme for embalming. The ancient Greeks used it in their baths and burnt it as incense in their temples, believing it was a source of courage...

 and peppermint

Peppermint

Peppermint is a hybrid mint, a cross between the watermint and spearmint . The plant, indigenous to Europe, is now widespread in cultivation throughout all regions of the world...

. Chemically, rosmarinic acid is an ester of caffeic acid

Caffeic acid

Caffeic acid is a hydroxycinnamic acid, a naturally occurring organic compound. This yellow solid consists of both phenolic and acrylic functional groups...

 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.

Biological importance

Because of the antioxidant

Antioxidant

An antioxidant is a molecule capable of inhibiting the oxidation of other molecules. Oxidation is a chemical reaction that transfers electrons or hydrogen from a substance to an oxidizing agent. Oxidation reactions can produce free radicals. In turn, these radicals can start chain reactions. When...

 activity of Lamiaceae

Lamiaceae

The mints, taxonomically known as Lamiaceae or Labiatae, are a family of flowering plants. They have traditionally been considered closely related to Verbenaceae, but in the 1990s, phylogenetic studies suggested that many genera classified in Verbenaceae belong instead in Lamiaceae...

ous herbs in laboratory test models they have been suggested to have beneficial effects in humans. 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

GABA transaminase inhibitor

A GABA transaminase inhibitor is an enzyme inhibitor that acts upon GABA transaminase.Examples include vigabatrin and ethanolamine-O-sulfate .Certain members of this class are used as anticonvulsants....

. 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.

Metabolism

Rosmarinic acid is known to undergo metabolism

Metabolism

Metabolism is the set of chemical reactions that happen in the cells of living organisms to sustain life. These processes allow organisms to grow and reproduce, maintain their structures, and respond to their environments. Metabolism is usually divided into two categories...

 in humans and rats to methylated rosmarinic acid, coumaric acid

Coumaric acid

Coumaric acid is a hydroxycinnamic acid, an organic compound that is a hydroxy derivative of cinnamic acid. There are three isomers, o-coumaric acid, m-coumaric acid, and p-coumaric acid, that differ by the position of the hydroxy substitution of the phenyl group...

, ferulic acid

Ferulic acid

Ferulic acid is a hydroxycinnamic acid, a type of organic compound. It is an abundant phenolic phytochemical found in plant cell wall components such as arabinoxylans as covalent side chains. It is related to trans-cinnamic acid. As a component of lignin, ferulic acid is a precursor in the...

and caffeic acid.. 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. Rosmarinic acid may be transported in the bloodstream bound to human serum albumin and lysozyme.