5,6-Dihydro-α-pyrones from the leaves of Cryptocarya pulchinervia (Lauraceae)

J Nat Med. 2020 Jun;74(3):584-590. doi: 10.1007/s11418-020-01397-7. Epub 2020 Mar 23.

Abstract

Three new 5,6-dihydro-α-pyrones derivatives, named (S)-rugulactone (1) pulchrinervialactone A (2), and pulchrinervialactone B (4), along with one known pyrone, cryptobrachytone C (3), and three known amide derivatives (5-7) have been isolated from the leaves of Cryptocarya pulchrinervia. The structures of 1-7 were elucidated based on extensive spectroscopic data and comparison with literatures. The configurations of compounds 3 and 4 were established by single crystal X-ray diffraction analysis. This is also the first report in finding (S)-rugulactone (1) as a natural product. In addition, the preliminary cytotoxic activity of the isolated compounds was evaluated against P-388 cells using the [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide] assay. All the pyrones, except compound 4, were active significantly inhibiting the growth of P-388 cells, while the amides derivatives (5-7) showed moderate to weak activities. Therefore, compounds 1-3 could be potentially examined further for anticancer agents.

Keywords: (S)-rugulactone; Cryptobrachitone C; Cryptocarya pulchrinervia; P-388 cells; Pulchrinervialactone A; Pulchrinervialactone B.

MeSH terms

  • Animals
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / pharmacokinetics*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects*
  • Cryptocarya / chemistry*
  • Lactones / isolation & purification
  • Lactones / pharmacology*
  • Mice
  • Molecular Structure
  • Neoplasms / drug therapy
  • Plant Leaves / chemistry
  • Pyrones / isolation & purification
  • Pyrones / pharmacology*

Substances

  • Antineoplastic Agents
  • Lactones
  • Pyrones
  • rugulactone