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

Ivana S Aljančić; Ivan Vučković; Milka Jadranin; Milica Pešić; Iris Dorđević; Ana Podolski-Renić; Sonja Stojković; Nebojša Menković; Vlatka E Vajs; Slobodan M Milosavljević

doi:10.1016/j.phytochem.2013.11.025

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

Phytochemistry. 2014 Feb:98:190-6. doi: 10.1016/j.phytochem.2013.11.025. Epub 2013 Dec 19.

Affiliations

¹ Institute of Chemistry, Technology and Metallurgy, Center for Chemistry, University of Belgrade, Njegoševa 12, 11001 Belgrade, Serbia. Electronic address: [email protected].
² Faculty of Chemistry, University of Belgrade, Studentski trg 12-16, 11158 Belgrade, Serbia.
³ Institute of Chemistry, Technology and Metallurgy, Center for Chemistry, University of Belgrade, Njegoševa 12, 11001 Belgrade, Serbia.
⁴ Institute for Biological Research, Department of Neurobiology, University of Belgrade, Bulevar Despota Stefana 142, 11060 Belgrade, Serbia.
⁵ Faculty for Veterinary Medicine, University of Belgrade, Bulevar Oslobodenja 18, 11000 Belgrade, Serbia.
⁶ Institute for Medicinal Plant Research, "Dr. Josif Pančić", Tadeuša Košćuška 1, 11000 Belgrade, Serbia.
⁷ Institute of Chemistry, Technology and Metallurgy, Center for Chemistry, University of Belgrade, Njegoševa 12, 11001 Belgrade, Serbia; Faculty of Chemistry, University of Belgrade, Studentski trg 12-16, 11158 Belgrade, Serbia.

PMID: 24361288
DOI: 10.1016/j.phytochem.2013.11.025

Abstract

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.

Keywords: Asteraceae; Chalcone glucoside dimers; Drug combination; Flavonoid glucoside; HIF-1α; Helichrysum zivojinii; MAP kinase pathway; Topoisomerase IIα.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antineoplastic Agents, Phytogenic / chemistry
Antineoplastic Agents, Phytogenic / isolation & purification
Antineoplastic Agents, Phytogenic / pharmacology*
Cell Proliferation / drug effects
Chalcone / analogs & derivatives
Chalcone / chemistry
Chalcone / pharmacology*
Dimerization
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
Flowers / chemistry*
Helichrysum / chemistry*
Humans
Molecular Structure
Structure-Activity Relationship
Tumor Cells, Cultured

Substances

Antineoplastic Agents, Phytogenic
Chalcone