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  1. General Info
  2. Source Info
  3. Effects Info
  4. Reference
Phytochemical Details
01. General Information
Name Rosmarinic acid
PubChem CID 5281792
Molecular Weight 360.3g/mol
Synonyms

Acid, Rosemary, Acid, Rosmarinic, Rosemary Acid, Rosmarinate, rosmarinic acid, rosmarinic acid, (R-(E))-isomer

Formula C₁₈H₁₆O₈
SMILES C1=CC(=C(C=C1CC(C(=O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)O)O
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
InChIKey DOUMFZQKYFQNTF-WUTVXBCWSA-N
CAS Number 20283-92-5
ChEMBL ID CHEMBL324842
ChEBI ID CHEBI:50371
Drug Bank ID DB16865
KEGG ID C01850
Toxicity Organism Test Type Route(Dose)
rat LD50 intraperitoneal(165 mg/kg)
mouse LD50 intraperitoneal(254 mg/kg)
rat LD50 oral(322 mg/kg)
Structure 2D-img
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2D MOL 3D MOL
02. Source Information of Phytochemical
Salvia rosmarinus Warm
Chineses Pinyin MiDieXiang
Use Part Whole herb
Species
>Kingdom: Viridiplantae
 -->Phylum: Streptophyta
  -->Class: Equisetopsida
   -->Order: Lamiales
    -->Family: Lamiaceae
     -->Genus: Salvia
      -->Species: Salvia rosmarinus
03. Combinatorial Therapeutic Effect(s)
Synergistic Effect
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Drug(s) whose efficacy can be enhanced by this phytochemical
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Combination Pair ID: 319
Pair Name Rosmarinic acid, Paclitaxel
Partner Name Paclitaxel
Disease Info [ICD-11: 2C60] Breast cancer Investigative
Biological Phenomena Inhibition-->Angiogenesis
Gene Regulation Up-regulation Expression BAX hsa581
Down-regulation Expression BCL2 hsa596
Up-regulation Expression CASP3 hsa836
Down-regulation Expression NFKB1 hsa4790
Down-regulation Expression TNF hsa7124
Up-regulation Expression TP53 hsa7157
Down-regulation Expression VEGFA hsa7422
In Vivo Model Ascitic fluid of Ehrlich ascites carcinoma-infected mice was withdrawn then mixed with normal saline to form a suspen_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x005f_x0002_sion of 2×10⁶ cells and used as a source of Ehrlich carcinoma cells.
Result Rosmarinic acid exerted chemo-preventive and therapeutic potential alone or in combination with Paclitaxel. Moreover, rosmarinic acid targets numerous signaling pathways associated with breast cancer.
Combination Pair ID: 320
Pair Name Rosmarinic acid, Anti-MUC1 antibody
Partner Name Anti-MUC1 antibody
Disease Info [ICD-11: 2B72] Gastric cancer Investigative
Biological Phenomena Induction-->Apoptosis
Gene Regulation Down-regulation Expression BCL2 hsa596
Down-regulation Expression BCL-xL hsa598
Up-regulation Expression CASP3 hsa836
Up-regulation Expression CASP9 hsa842
Down-regulation Expression LGALS3 hsa3958
Up-regulation Expression MUC1 hsa4582
Up-regulation Expression TP53 hsa7157
In Vitro Model AGS Gastric adenocarcinoma Homo sapiens (Human) CVCL_0139
Result Results of the study indicate that combined action of anti-MUC1 and RA is more effective than monotherapy in relation to examined cancer related factors. Such treatment can be considered as new, promising strategy in gastric cancer therapy.
Combination Pair ID: 778
Pair Name Rosmarinic acid, Indoleamine 2,3-dioxygenase 1
Partner Name Indoleamine 2,3-dioxygenase 1
Disease Info [ICD-11: 2C12] Hepatocellular carcinoma Investigative
Biological Phenomena Induction-->Immunomodulatory
Gene Regulation Up-regulation Expression IFNG hsa3458
Down-regulation Expression IL10 hsa3586
Up-regulation Expression IL2 hsa3558
Down-regulation Expression TNF hsa7124
In Vivo Model The H22 cells were inoculated into the peritoneal cavity of the mice. After three passages in cell ascites, the ascites was extracted and diluted to the concentration of 1.5×10⁷/ml with normal saline. The H22 cell suspension (3×106 cell /mouse) was subcutaneously injected into the right side of the axillary of mice.
Result The mechanism might be related to regulating immune response and immunocytokines, as well as alleviating immunosuppression induced by Tregs in the tumor immune microenvironment.
Drug(s) whose resistance can be reversed by this phytochemical
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Combination Pair ID: 321
Pair Name Rosmarinic acid, Cisplatin
Partner Name Cisplatin
Disease Info [ICD-11: 2C25] Lung cancer Investigative
Biological Phenomena Induction-->Blockade of cell cycle in G0/G1 phase
Gene Regulation Down-regulation Expression ABCB1 hsa5243
Up-regulation Expression CDKN1A hsa1026
Up-regulation Activity MAPK1 hsa5594
Up-regulation Expression TP53 hsa7157
In Vitro Model A-549 Lung adenocarcinoma Homo sapiens (Human) CVCL_0023
In Vivo Model A549 (3×10⁶) and A549DDP (3×10^6) cells were injected subcutaneously (s.c.) into the flanks of the mice.
Result Rosmarinic acid reverses non-small cell lung cancer cisplatin resistance by activating the MAPK signaling pathway
Combination Pair ID: 777
Pair Name Rosmarinic acid, Cisplatin
Partner Name Cisplatin
Disease Info [ICD-11: 2C73] Ovarian cancer Investigative
Biological Phenomena Inhibition-->Cell migration
Gene Regulation Down-regulation Expression FOXM1 hsa2305
In Vitro Model SK-OV-3 Ovarian serous cystadenocarcinoma Homo sapiens (Human) CVCL_0532
Result Our research suggests that RAME is a promising option in treating ovarian cancer patients, as it revealed a novel molecular pathway underlying its anti-tumor effects.
Antagonistic Effect
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Drug(s) whose toxicity can be increased by this phytochemical
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Combination Pair ID: 1084
Pair Name Rosmarinic acid, Inhibit UGT1A1-mediated bilirubin glucuronidation
Partner Name Inhibit UGT1A1-mediated bilirubin glucuronidation
Result Jaundice; hyperbilirubinemia
04. Reference
No. Title Href
1 Inhibition of Human UGT1A1-Mediated Bilirubin Glucuronidation by Polyphenolic Acids Impact Safety of Popular Salvianolic Acid A/B-Containing Drugs and Herbal Products. Mol Pharm. 2017;14(9):2952-2966. doi:10.1021/acs.molpharmaceut.7b00365 Click
2 Rosmarinic acid suppresses inflammation, angiogenesis, and improves paclitaxel induced apoptosis in a breast cancer model via NF3 κB-p53-caspase-3 pathways modulation. J Appl Biomed. 2021 Dec;19(4):202-209. doi: 10.32725/jab.2021.024. Click
3 Anti-cancer effect of combined action of anti-MUC1 and rosmarinic acid in AGS gastric cancer cells. Eur J Pharmacol. 2021 Jul 5;902:174119. doi: 10.1016/j.ejphar.2021.174119. Click
4 Effects of gene silencing of indoleamine 2,3-dioxygenase 1 combined with rosmarinic acid on tumor immune microenvironment in H22 tumor-bearing mice. Int Immunopharmacol. 2023 Jun;119:110193. doi: 10.1016/j.intimp.2023.110193. Click
5 Rosmarinic acid reverses non-small cell lung cancer cisplatin resistance by activating the MAPK signaling pathway. Phytother Res. 2020 May;34(5):1142-1153. doi: 10.1002/ptr.6584. Click
6 Rosmarinic Acid Methyl Ester Regulates Ovarian Cancer Cell Migration and Reverses Cisplatin Resistance by Inhibiting the Expression of Forkhead Box M1. Pharmaceuticals (Basel). 2020 Oct 12;13(10):302. doi: 10.3390/ph13100302. Click
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