A phenylpropanoid dimer from the leaves of Piper betle

Nat Prod Res. 2023 May;37(9):1550-1556. doi: 10.1080/14786419.2022.2025594. Epub 2022 Mar 1.

Abstract

Phytochemical analyses of the chloroform extract of Piper betle L. var. Sanchi, Piperaceae, leaves led to the isolation of a new phenylpropanoid analogue for the first time: hydroxychavicol dimer, 2-(γ'-hydroxychavicol)-hydroxychavicol (S1), on the basis of spectroscopic data 1 D (1H and 13C) and 2 D (1H-1H COSY and HMBC) NMR, as well as ESI-MS, FT-IR, HR-ESI-MS and LC-ESI-MS. Compound S1 exhibited excellent antioxidant DPPH radical scavenging activity with IC50 values of 9.07 μg/mL, compared to ascorbic acid as a standard antioxidant drug with IC50 value of 3.41 μg/mL. Evaluation of cytotoxic activity against two human colon cancer cell lines (HT 29 and COLO-205) showed significant effect with GI50 values of 73.81 and 64.02 μmol/L, compared to Doxorubicin® as a standard cytotoxic drug with GI50 value of <10 μmol/L.

Keywords: Antioxidant; Piper betle; SAR; cytotoxic; phenylpropanoid analogue.

MeSH terms

  • Antineoplastic Agents* / analysis
  • Antioxidants / chemistry
  • Humans
  • Piper betle* / chemistry
  • Plant Extracts / chemistry
  • Plant Leaves / chemistry
  • Spectroscopy, Fourier Transform Infrared

Substances

  • Antioxidants
  • 2-hydroxychavicol
  • Plant Extracts
  • Antineoplastic Agents