2-(3,4-dihydroxyphenyl)ethyl (2S-(2alpha,3E,4beta))-3-ethylidene-2-(beta-D-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-2H-pyran-4-acetate, oleoeuropein, oleoeuropeine, oleuropein
Name | Oleuropein | ||
PubChem CID | 5281544 | ||
Molecular Weight | 540.5g/mol | ||
Synonyms |
2-(3,4-dihydroxyphenyl)ethyl (2S-(2alpha,3E,4beta))-3-ethylidene-2-(beta-D-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-2H-pyran-4-acetate, oleoeuropein, oleoeuropeine, oleuropein |
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Formula | C₂₅H₃₂O₁₃ | ||
SMILES | CC=C1C(C(=COC1OC2C(C(C(C(O2)CO)O)O)O)C(=O)OC)CC(=O)OCCC3=CC(=C(C=C3)O)O | ||
InChI | 1S/C25H32O13/c1-3-13-14(9-19(29)35-7-6-12-4-5-16(27)17(28)8-12)15(23(33)34-2)11-36-24(13)38-25-22(32)21(31)20(30)18(10-26)37-25/h3-5,8,11,14,18,20-22,24-28,30-32H,6-7,9-10H2,1-2H3/b13-3+/t14-,18+,20+,21-,22+,24-,25-/m0/s1 | ||
InChIKey | RFWGABANNQMHMZ-ZCHJGGQASA-N | ||
CAS Number | 32619-42-4 | ||
ChEMBL ID | CHEMBL1911053 | ||
ChEBI ID | CHEBI:7747 | ||
Herb ID | HBIN038054 | ||
Structure |
Download
2D
MOL
3D
MOL
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Chineses Pinyin | NvZhenZi | ||
Use Part | Fruit | ||
Habitat | ZheJiang, JiangSu, HuNan, FuJian, GuangXi, JiangXi, SiChuan | ||
Flavor | Sweet, Bitter | ||
Meridian Tropism | Liver, Kidney | ||
Species |
>Kingdom: Viridiplantae
-->Phylum: Streptophyta
-->Class: Equisetopsida
-->Order: Lamiales
-->Family: Oleaceae
-->Genus: Ligustrum
-->Species: Ligustrum lucidum
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Chineses Pinyin | QinPi | ||
Use Part | Bark | ||
Habitat | Shaanxi, HeBei, JiLin, LiaoNing | ||
Flavor | Bitter, Astringent | ||
Meridian Tropism | Liver, Gallbladder, Large intestine | ||
Species |
>Kingdom: Viridiplantae
-->Phylum: Streptophyta
-->Class: Equisetopsida
-->Order: Lamiales
-->Family: Oleaceae
-->Genus: Fraxinus
-->Species: Fraxinus rhynchophylla
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Chineses Pinyin | YouGanLan | ||
Use Part | Fruit | ||
Habitat | HuNan, JiangXi, ZheJiang, FuJian, GuangDong, GuiZhou, YunNan, HaiNan, XiZang, TaiWan | ||
Species |
>Kingdom: Viridiplantae
-->Phylum: Streptophyta
-->Class: Equisetopsida
-->Order: Lamiales
-->Family: Oleaceae
-->Genus: Olea
-->Species: Olea europaea
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Chineses Pinyin | GanLan | ||
Use Part | leaf | ||
Habitat | FuJian, SiChuan, GuangDong, YunNan, GuangXi | ||
Flavor | Sweet; Sour; Punkery | ||
Meridian Tropism | Lung | ||
Species |
>Kingdom: Viridiplantae
-->Phylum: Streptophyta
-->Class: Equisetopsida
-->Order: Sapindales
-->Family: Burseraceae
-->Genus: Canarium
-->Species: Canarium album
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Pair Name | Oleuropein, Doxorubicin | |||
Partner Name | Doxorubicin | |||
Disease Info | [ICD-11: 2C60] | Breast cancer | Investigative | |
Biological Phenomena | Induction-->Apoptosis | |||
Gene Regulation | Down-regulation | Expression | BCL2 | hsa596 |
Down-regulation | Expression | BIRC5 | hsa332 | |
Down-regulation | Expression | CCND1 | hsa595 | |
Down-regulation | Expression | NFKB1 | hsa4790 | |
In Vitro Model | MDA-MB-231 | Breast adenocarcinoma | Homo sapiens (Human) | CVCL_0062 |
In Vivo Model | The study involved 40 female, nude mice (BALB/c OlaHsd-foxn1),the volume of the tumor increased aggressively, reaching 173 mm3 in the control animals in a time-dependent manner. On the other hand, a sharp drop, to 48.7 mm3, in the volume of the tumor was observed with the 2 drugs combined, a more than 3-fold decrease. | |||
Result | The key findings clearly indicate the synergistic efficacy of DOX with natural and nontoxic OL against breast tumor xenografts. |
Pair Name | Oleuropein, Cisplatin | |||
Partner Name | Cisplatin | |||
Disease Info | [ICD-11: 2C73] | Ovarian cancer | Investigative | |
Gene Regulation | Down-regulation | Expression | BCL2 | hsa596 |
Up-regulation | Expression | CDKN1A | hsa1026 | |
Up-regulation | Expression | GDE1 | hsa51573 | |
Down-regulation | Expression | MCL1 | hsa4170 | |
Up-regulation | Expression | TNFRSF10B | hsa8795 | |
Up-regulation | Expression | TP53 | hsa7157 | |
In Vitro Model | A2780 | Ovarian endometrioid adenocarcinoma | Homo sapiens (Human) | CVCL_0134 |
A2780/CP70 | Ovarian endometrioid adenocarcinoma | Homo sapiens (Human) | CVCL_0135 | |
Result | These data revealed that oleuropein regulated the expression of the above-mentioned miRNAs in ovarian cancer cells, which potentially resulted in apoptosis induction, cell proliferation inhibition, and cisplatin resistance decline in ovarian cancer cells. To confirm the results of this study, it is suggested that similar experiments be performed in animal models of ovarian cancer. |
Pair Name | Oleuropein, Cisplatin | |||
Partner Name | Cisplatin | |||
Disease Info | [ICD-11: 2C12] | Hepatocellular carcinoma | Investigative | |
Gene Regulation | Up-regulation | Expression | CASP3 | hsa836 |
Down-regulation | Expression | MMP7 | hsa4316 | |
Down-regulation | Expression | NGF | hsa4803 | |
In Vitro Model | Hep-G2 | Hepatoblastoma | Homo sapiens (Human) | CVCL_0027 |
Result | Our results showed for the first time that the anti-tumor activity of oleuropein against HCC could be attributed to influencing the pro-NGF/NGF balance via affecting MMP-7 activity without affecting the gene expression of NGF. Concurrent treatment with both oleuropein and cisplatin could lead to more effective chemotherapeutic combination against HCC. |
No. | Title | Href |
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1 | Synergistic Anti-Breast-Cancer Effects of Combined Treatment With Oleuropein and Doxorubicin In Vivo. Altern Ther Health Med. 2019 May;25(3):17-24. | Click |
2 | Oleuropein reduces cisplatin resistance in ovarian cancer by targeting apoptotic pathway regulators. Life Sci. 2021 Aug 1;278:119525. doi: 10.1016/j.lfs.2021.119525. | Click |
3 | Oleuropein potentiates anti-tumor activity of cisplatin against HepG2 through affecting proNGF/NGF balance. Life Sci. 2018 Apr 1;198:87-93. doi: 10.1016/j.lfs.2018.02.027. | Click |