Anti-inflammatory and antiproliferative evaluation of 4β-cinnamoyloxy,1β,3α-dihydroxyeudesm-7,8-ene from Verbesina persicifolia and derivatives

[Display omitted] The anti-inflammatory and antiproliferative activities of 4β-cinnamoyloxy,1β,3α-dihydroxyeudesm-7,8-ene (1) and of three derivatives, namely diacetate (2), hydrogenate (3) and diacetate hydrogenate (4) were evaluated. All derivatives exert an anti-inflammatory effect significantly...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2015-09, Vol.23 (17), p.5816-5828
Main Authors: Dalla Via, L., Mejia, M., García-Argáez, A.N., Braga, A., Toninello, A., Martínez-Vázquez, M.
Format: Article
Language:English
Subjects:
Anti-inflammatory activity
Anti-Inflammatory Agents - pharmacology
Antiproliferative activity
Eudesmane sesquiterpene
Humans
Mitochondria
Mitochondria - metabolism
Molecular Structure
Verbesina - chemistry
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Summary:[Display omitted] The anti-inflammatory and antiproliferative activities of 4β-cinnamoyloxy,1β,3α-dihydroxyeudesm-7,8-ene (1) and of three derivatives, namely diacetate (2), hydrogenate (3) and diacetate hydrogenate (4) were evaluated. All derivatives exert an anti-inflammatory effect significantly lower than that exerted by 1. Otherwise, both the lead compound and 2–4 showed a comparable antiproliferative activity on human tumor cell lines. The investigation of the mechanism of action accountable for cytotoxicity highlighted the capacity to impair mitochondrial functions through two different pathways, depending on chemical structure. In particular, the lead compound 1 and derivative 3 are able to induce mitochondrial permeability transition, while derivatives 2 and 4 inhibit Complex II in the respiratory chain.
ISSN:0968-0896
1464-3391
DOI:10.1016/j.bmc.2015.07.002