Four new homoisoflavonoids from Caesalpinia pulcherrima

J Asian Nat Prod Res. 2025 Feb;27(2):126-135. doi: 10.1080/10286020.2024.2387307. Epub 2024 Aug 9.

Abstract

Four new homoisoflavonoids, 7-hydroxy-3-[hydroxy(4'-methoxyphenyl)methyl]-benzopyran-4-one (1), (3R)-7, 8-dihydroxy-3-(4'-methoxybenzyl)-chroman-4-one (2), 7-hydroxy-3-(2'-hydroxy-4'-methoxybenzyl)-chroman-4-one (3), and 7-hydroxy-3-(2'-hydroxy-4'-methoxybenzyl)-benzopyran-4-one (4), were isolated from the seeds of Caesalpinia pulcherrima. The structures of new compounds were elucidated by MS and NMR spectra. Their absolute configurations were assigned using electronic circular dichroism spectrum. Compounds 2 and 4 exhibited cytotoxic effects on MCF-7/TAM cells with the IC50 values of 101.4 ± 0.03 and 93.02 ± 0.03 μM, respectively.

Keywords: Caesalpinia pulcherrima; Fabaceae; cytotoxic; homoisoflavonoids.

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Caesalpinia* / chemistry
  • Drug Screening Assays, Antitumor
  • Humans
  • Isoflavones* / chemistry
  • Isoflavones* / isolation & purification
  • Isoflavones* / pharmacology
  • MCF-7 Cells
  • Molecular Structure
  • Seeds / chemistry

Substances

  • Isoflavones
  • Antineoplastic Agents, Phytogenic