Two structurally distinct chalcone dimers from Helichrysum zivojinii and their activities in cancer cell lines

Chalcone dimers tomoroside A (1) and tomoroside B (2), along with eight known flavonoid glucosides were isolated from the aerial parts of Helichrysum zivojinii. Cell growth inhibition in cancer cell lines and modulation of mRNAs expression by novel chalcone dimers have been assessed. •A phytochemica...

Full description

Saved in:
Bibliographic Details
Published in:Phytochemistry (Oxford) 2014-02, Vol.98, p.190-196
Main Authors: Aljančić, Ivana S., Vučković, Ivan, Jadranin, Milka, Pešić, Milica, Đorđević, Iris, Podolski-Renić, Ana, Stojković, Sonja, Menković, Nebojša, Vajs, Vlatka E., Milosavljević, Slobodan M.
Format: Article
Language:English
Subjects:
Antineoplastic Agents, Phytogenic - chemistry
Antineoplastic Agents, Phytogenic - isolation & purification
Antineoplastic Agents, Phytogenic - pharmacology
Asteraceae
Cell Proliferation - drug effects
Chalcone - analogs & derivatives
Chalcone - chemistry
Chalcone - pharmacology
Chalcone glucoside dimers
Dimerization
Dose-Response Relationship, Drug
Drug combination
Drug Screening Assays, Antitumor
Flavonoid glucoside
Flowers - chemistry
Helichrysum - chemistry
Helichrysum zivojinii
HIF-1α
Humans
MAP kinase pathway
Molecular Structure
Structure-Activity Relationship
Topoisomerase IIα
Tumor Cells, Cultured
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Chalcone dimers tomoroside A (1) and tomoroside B (2), along with eight known flavonoid glucosides were isolated from the aerial parts of Helichrysum zivojinii. Cell growth inhibition in cancer cell lines and modulation of mRNAs expression by novel chalcone dimers have been assessed. •A phytochemical study was carried out on the aerial parts of Helichrysum zivojinii.•Two dimer chalcone glucosides and eight known flavonoid glucosides were isolated.•The structures of compounds were elucidated by spectroscopic techniques.•Activities in cancer cell lines of both chalcone dimer glucosides have been assessed. Dimers tomoroside A (1) and tomoroside B (2) of the co-occuring known chalcone monomer (3), along with the seven known flavonoid glucosides (4–10), were isolated from the aerial parts of Helichrysum zivojinii Černjavski & Soška. The structures of the isolated compounds were elucidated by spectroscopic techniques. Compound 1 inhibited topo IIα and hif-1α expression and stimulated doxorubicin anticancer effect, while 2 increased the expression of hif-1α, probably acting as antioxidant and redox status modulator. Notably, 2 synergized with Tipifarnib showing potential to improve the action of this new chemotherapeutic involved in the modulation of mitogene activated protein (MAP) kinase signaling pathway.
ISSN:0031-9422
1873-3700
DOI:10.1016/j.phytochem.2013.11.025