mezerein
Sign in to saveMezerein is a toxic diterpene ester found in the sap of Daphne mezereum and related plants. Plants of the genera Euphorbiaceae and Thymelaeaceae possess a wide variety of different phorbol esters, which share the capacity of mimicking diacylglycerol (DAG) and thus activating different isoforms of protein kinase C. Mezerein was first isolated in 1975. It has antileukemic properties in mice, but it is also defined as a weak promoter of skin cancers in the same species. All parts of the plants contain an acrid and irritant sap that contains mezerein, thought to be the principal poison. The sap is
Research
603 papers- Tigliane Diterpenoids.Progress in the chemistry of organic natural products · 2024
- Mezerein: antileukemic principle isolated from Daphne mezereum L.Science (New York, N.Y.) · 1975
- Non-genotoxic carcinogens (TPA and mezerein) activate tumourous transformation through miR let-7-mediated Hmga2 expression in Bhas42 cells.Environmental epigenetics · 2025
- Further characterization of skin tumor promotion and progression by mezerein in SENCAR mice.Journal of the National Cancer Institute · 1989
- Enhancement of mezerein-promoted papilloma formation by treatment with 12-O-tetradecanoylphorbol-13-acetate or mezerein prior to initiation.Carcinogenesis · 1988
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 654.2464974159999
Show 4 more facts
- chemical formula
- C₃₈H₃₈O₁₀
- canonical SMILES
- CC1C(C2(C3C4C1(C5C=C(C(=O)C5(C(C6(C4O6)CO)O)O)C)OC(O3)(O2)C7=CC=CC=C7)C(=C)C)OC(=O)C=CC=CC8=CC=CC=C8
- Commons category
- Mezerein
- isomeric SMILES
- C=C(C)[C@@]12OC3(c4ccccc4)O[C@@H]1[C@@H]1[C@@H]4O[C@]4(CO)[C@@H](O)[C@]4(O)C(=O)C(C)=C[C@H]4[C@@]1(O3)[C@H](C)[C@H]2OC(=O)/C=C/C=C/c1ccccc1
Sources (2)
via Wikidata · CC0
~7 min read
Encyclopedic overview
5 sectionsContents
- History and alternative uses
- Mezerein and daphnetoxin
- Mechanism of action
- Dose-response relationships
- References
Mezerein is a toxic diterpene ester found in the sap of Daphne mezereum and related plants. Plants of the genera Euphorbiaceae and Thymelaeaceae possess a wide variety of different phorbol esters, which share the capacity of mimicking diacylglycerol (DAG) and thus activating different isoforms of protein kinase C. Mezerein was first isolated in 1975. It has antileukemic properties in mice, but it is also defined as a weak promoter of skin cancers in the same species. All parts of the plants contain an acrid and irritant sap that contains mezerein, thought to be the principal poison. The sap is especially prevalent in the bark and berries.
Mezerein is highly liposoluble and can cause vomiting, diarrhea and burning of the mouth. When a large dose is taken, there can be shivering, dilation of the pupils, damage to the oral passages and the intestine and even death. It can also irritate the skin, resulting in redness by slight damage of the veins. Because of causing this redness, the sap used to be applied as rouge.
Excerpted from Wikipedia’s “mezerein” article, available under the CC BY-SA 4.0 licence.