Daphnanes diterpenes from the latex of Hura crepitans L. And activity against human colorectal cancer cells Caco-2

[Display omitted] •Five daphnane-type diterpenes were isolated from the latex of Hura crepitans L.•Huratoxin induced both cytostatic and morphogenic effects on cancer Caco-2 cells.•Huratoxin inhibited GSK3β and Akt and increased integrin alpha 2 and mucin 2. Hura crepitans (Euphorbiaceae) is a tree...

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Published in:Bioorganic chemistry 2020-10, Vol.103, p.104132-13, Article 104132
Main Authors: Trinel, Manon, Le Lamer, Anne-Cécile, Jullian, Valérie, Jacquemin, Denis, Graton, Jérôme, Cristofoli, Valérie, Crossay, Elise, Yassine, May, Rolland, Corinne, Vergnolle, Nathalie, Mejia, Kember, Joel Cabanillas, Billy, Racaud-Sultan, Claire, Fabre, Nicolas
Format: Article
Language:English
Subjects:
Antineoplastic Agents, Phytogenic - chemistry
Antineoplastic Agents, Phytogenic - isolation & purification
Antineoplastic Agents, Phytogenic - pharmacology
Botanics
Caco-2 Cells
Cancer
Cell Proliferation - drug effects
Colorectal cancer
Cytotoxicity
Daphnane diterpenes
Density Functional Theory
Diterpenes - chemistry
Diterpenes - isolation & purification
Diterpenes - pharmacology
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
Epithelial morphogenesis
Euphorbiaceae - chemistry
Human health and pathology
Humans
Hura crepitans
Latex - chemistry
Life Sciences
Molecular Structure
Structure-Activity Relationship
Tumor Cells, Cultured
Vegetal Biology
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Summary:[Display omitted] •Five daphnane-type diterpenes were isolated from the latex of Hura crepitans L.•Huratoxin induced both cytostatic and morphogenic effects on cancer Caco-2 cells.•Huratoxin inhibited GSK3β and Akt and increased integrin alpha 2 and mucin 2. Hura crepitans (Euphorbiaceae) is a tree from South America that produces an irritant latex used as a fish poison. A bio-guided fractionation of an ethanolic extract of the latex led to the isolation and structural identification of three known daphnane-type diterpenes (1–3) including huratoxin (1), together with two new analogs (4, 5). Compound 1 was found to exhibit significant and selective cell growth inhibition against the colorectal cancer cell line Caco-2, with morphological modifications suggesting formations mimicking the intestinal crypt architecture. The underlying mechanism of 1 was further investigated, in comparison with 12-O-tetradecanoylphorbol-13-acetate (TPA), revealing two different mechanisms.
ISSN:0045-2068
1090-2120
DOI:10.1016/j.bioorg.2020.104132