Hydroxylated boswellic and glycyrrhetinic acid derivatives: synthesis and cytotoxicity

Hydroxylated boswellic and glycyrrhetinic acid derivatives: synthesis and cytotoxicity

Authors

  • Immo Serbian Martin-Luther Universität Halle-Wittenberg
  • Ratna Kancana Wolfram Martin-Luther Universität Halle-Wittenberg
  • Lucie Fischer Martin-Luther Universität Halle-Wittenberg
  • Ahmed Al-Harrasi
  • René Csuk Martin-Luther Universität Halle-Wittenberg http://orcid.org/0000-0001-7911-290X

DOI:

https://doi.org/10.13171/mjc74181121-csuk

Abstract

Oxidation of 2,3-dehydro-11-keto--boswellic acid gave derivatives holding extra hydroxyl groups at positions C-1, C-2 or C-1 and C-9, respectively. The synthesis of 2,3-dehydro-1,9-dihydroxy-11-keto--boswellic acid represents the first partial-synthetic access to this class of compounds. The synthetic strategy can be expanded easily, and a corresponding analogue derived from glycyrrhetinic acid was accessed by the same synthetic scheme in good overall yield. Boswellic and glycyrrhetinic acid 1,9-endoperoxides are intermediates for the synthesis of the 1,9-dihydroxylated compounds. These 1,9-endo-peroxides were highly cytotoxic for several human tumor cell lines but only diminished cytotoxicity was observed in SRB assays for the 1,9-dihydroxylated compounds.

Author Biography

René Csuk, Martin-Luther Universität Halle-Wittenberg

Organic Chemistry

Head of Department

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Published

21-11-2018

Issue

Vol. 7 No. 4 (2018)

Section

Medicinal Chemistry

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