Acid, Rosemary, Acid, Rosmarinic, Rosemary Acid, Rosmarinate, rosmarinic acid, rosmarinic acid, (R-(E))-isomer
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 |
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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 |
Download
2D
MOL
3D
MOL
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Chineses Pinyin | MiDieXiang | ||
Use Part | Whole herb | ||
Species |
>Kingdom: Viridiplantae
-->Phylum: Streptophyta
-->Class: Equisetopsida
-->Order: Lamiales
-->Family: Lamiaceae
-->Genus: Salvia
-->Species: Salvia rosmarinus
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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In Vivo Model | Ascitic fluid of Ehrlich ascites carcinoma-infected mice was withdrawn then mixed with normal saline to form a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. |
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. |
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. |
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 |
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. |
Pair Name | Rosmarinic acid, Inhibit UGT1A1-mediated bilirubin glucuronidation | |||
Partner Name | Inhibit UGT1A1-mediated bilirubin glucuronidation | |||
Result | Jaundice; hyperbilirubinemia |
No. | Title | Href |
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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 |