Synthesis of Nontoxic Protoflavone Derivatives through Selective Continuous-Flow Hydrogenation of the Flavonoid B-Ring

Sándor B. Ötvös, Máté Vágvölgyi, Gábor Girst, Ching Ying Kuo, Hui Chun Wang, F. Fülöp, Attila Hunyadi

Research output: Contribution to journalArticle

Abstract

Protoflavones are unique natural flavonoids with a non-aromatic B-ring, known for their potent antitumor properties. However, their cytotoxicity represents a strong limitation in the further exploration of their pharmacological potential. In the current study, we sought to selectively saturate the p-quinol B-ring of protoapigenone and that of its 1′-O-butyl ether, in order to obtain non-toxic protoflavone analogues expressing the dihydro- or tetrahydroprotoflavone structure also occurring in nature. The benefits of a strictly controlled continuous-flow environment in combination with on-demand electrolytic H2 gas generation were exploited to suppress undesired side reactions and to safely and selectively yield the desired substances. The obtained tetrahydroprotoflavones were free of the cytotoxicity of their parent compounds, and, even though tetrahydroprotoapigenone 1-O-butyl ether showed a weak inhibition of DNA damage response through Chk1, neither compounds influenced the cytotoxicity of doxorubicin either.

Original languageEnglish
Pages (from-to)72-76
Number of pages5
JournalChemPlusChem
Volume83
Issue number2
DOIs
Publication statusPublished - Feb 1 2018

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Cytotoxicity
Flavonoids
Hydrogenation
Derivatives
Ether
Hydroquinones
Doxorubicin
Gases
DNA

Keywords

  • cancer
  • DNA damage
  • flavonoids
  • flow chemistry
  • hydrogenation

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Synthesis of Nontoxic Protoflavone Derivatives through Selective Continuous-Flow Hydrogenation of the Flavonoid B-Ring. / Ötvös, Sándor B.; Vágvölgyi, Máté; Girst, Gábor; Kuo, Ching Ying; Wang, Hui Chun; Fülöp, F.; Hunyadi, Attila.

In: ChemPlusChem, Vol. 83, No. 2, 01.02.2018, p. 72-76.

Research output: Contribution to journalArticle

Ötvös, Sándor B. ; Vágvölgyi, Máté ; Girst, Gábor ; Kuo, Ching Ying ; Wang, Hui Chun ; Fülöp, F. ; Hunyadi, Attila. / Synthesis of Nontoxic Protoflavone Derivatives through Selective Continuous-Flow Hydrogenation of the Flavonoid B-Ring. In: ChemPlusChem. 2018 ; Vol. 83, No. 2. pp. 72-76.
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