Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C18H16O8 |
Molecular Weight | 360.3148 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)[C@@H](CC1=CC=C(O)C(O)=C1)OC(=O)\C=C\C2=CC=C(O)C(O)=C2
InChI
InChIKey=DOUMFZQKYFQNTF-WUTVXBCWSA-N
InChI=1S/C18H16O8/c19-12-4-1-10(7-14(12)21)3-6-17(23)26-16(18(24)25)9-11-2-5-13(20)15(22)8-11/h1-8,16,19-22H,9H2,(H,24,25)/b6-3+/t16-/m1/s1
Molecular Formula | C18H16O8 |
Molecular Weight | 360.3148 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 1 |
Optical Activity | UNSPECIFIED |
Rosmarinic acid (α-o-caffeoyl-3,4-dihydroxyphenyllactic acid; RA) is a naturally occurring hydroxylated compound commonly found in species of the subfamily Nepetoideae of the Lamiaceae and Boraginaceae, such as Rosmarinus officinalis, Salvia officinalis, and Perilla frutescens. RA is biosynthesized from the amino acids L-phenylalanine and L-tyrosine by eight enzymes that include phenylalanine ammonia lyase and cinnamic acid 4-hydroxylase. Recently, RA and its derivatives have attracted interest for their biological activities, which include anti-inflammatory, anti-oxidant, anti-angiogenic, anti-tumor, and anti-microbial functions. Clinically, RA attenuates T cell receptor-mediated signaling, attenuates allergic diseases like allergic rhinitis and asthma, and 2,4-dinitrofluorobenzene-induced atopic dermatitis-like symptoms, protects from neurotoxicity, and slows the development of Alzheimer's disease. Rosmarinic Acid seems to be able to suppress 5-lipoxygenase and 5-HETE synthesis (a pro-inflammatory compound in the omega-6 metabolic chain). Rosmarinic acid appeared to be effective in suppressing allergies in a dose-dependent manner, with 30% of the placebo group reporting symptom relief compared to 55.6% of the 50mg group and 70% of the 200mg group.
Originator
Sources: https://www.rosmarinic-acid.com/
Curator's Comment: Rosmarinic acid is a naturally occurring polyphenolic compound that was first discovered in 1958 by the Italian scientists M. L. Scarpatti and and G. Oriente
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL1951 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27270453 |
50.1 µM [IC50] | ||
Target ID: CHEMBL2039 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27270453 |
184.6 µM [IC50] | ||
Target ID: CHEMBL2023 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27270453 |
26.7 µM [IC50] | ||
Target ID: CHEMBL1841 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17315853 |
1.3 µM [IC50] | ||
Target ID: CHEMBL2366505 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12672152 |
550.0 nM [IC50] | ||
Target ID: CHEMBL215 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20149856 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Curcumin analogs with altered potencies against HIV-1 integrase as probes for biochemical mechanisms of drug action. | 1997 Sep 12 |
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Anti-HIV activities of natural antioxidant caffeic acid derivatives: toward an antiviral supplementation diet. | 2005 |
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Simultaneous determination of six phenolic constituents of danshen in human serum using liquid chromatography/tandem mass spectrometry. | 2005 Jun 5 |
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Rosmarinic acid as a downstream inhibitor of IKK-beta in TNF-alpha-induced upregulation of CCL11 and CCR3. | 2006 Jun |
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Oxidative DNA damage protection and repair by polyphenolic compounds in PC12 cells. | 2008 Dec 28 |
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The effect of dietary polyphenols on the epigenetic regulation of gene expression in MCF7 breast cancer cells. | 2010 Feb 1 |
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Frequent gene hypermethylation in laryngeal cancer cell lines and the resistance to demethylation induction by plant polyphenols. | 2011 Feb |
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Inhibitory effects of caffeic acid phenethyl ester derivatives on replication of hepatitis C virus. | 2013 |
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Protective effect of rosmarinic acid is through regulation of inflammatory cytokine in cadmium-induced ototoxicity. | 2013 |
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Rosmarinic acid down-regulates endothelial protein C receptor shedding in vitro and in vivo. | 2013 Sep |
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Inhibitors of the glyoxylate cycle enzyme ICL1 in Candida albicans for potential use as antifungal agents. | 2014 |
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Rosmarinic acid attenuates hepatic ischemia and reperfusion injury in rats. | 2014 Dec |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14988517
A human study consisting of 30 persons aged 21-53 with mild cedar allergies (who get stuffy noses during allergy season) were given either 50mg Rosmarinic acid, 200mg, or placebo to be taken with breakfast for 21 days. Rosmarinic acid appeared to be effective in suppressing allergies in a dose-dependent manner, with 30% of the placebo group reporting symptom relief compared to 55.6% of the 50mg group and 70% of the 200mg group.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26759705
Curator's Comment: Rosmarinic acid shows antioxidant effects against hydroxyl (HO(•)) and nitric oxide (NO) radicals (IC50 of 29.4 and 140 uM, respectively), and inhibition of lipid peroxidation (IC50 of 19.6 uM). https://www.ncbi.nlm.nih.gov/pubmed/27270453
Rosmarinic acid (RA) exerts a significant cytoprotective effect by scavenging intracellular ROS induced by UVB. In H2O2-treated cells, 2.5 uM Rosmarinic acid scavenges 60% of intracellular ROS compared to 77% of intracellular ROS scavenging effect in N-acetyl-L-cysteine (NAC)
Substance Class |
Chemical
Created
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Edited
Fri Dec 15 18:11:46 GMT 2023
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Record UNII |
MQE6XG29YI
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Record Status |
Validated (UNII)
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Record Version |
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DSLD |
1943 (Number of products:10)
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