Dalbergia ecastaphyllum (L.) Taub. and Symphonia globulifera L.f.: The Botanical Sources of Isoflavonoids and Benzophenones in Brazilian Red Propolis

Molecules. 2020 Apr 28;25(9):2060. doi: 10.3390/molecules25092060.

Abstract

The Brazilian red propolis (BRP) constitutes an important commercial asset for northeast Brazilian beekeepers. The role of Dalbergia ecastaphyllum (L.) Taub. (Fabaceae) as the main botanical source of this propolis has been previously confirmed. However, in addition to isoflavonoids and other phenolics, which are present in the resin of D. ecastaphyllum, samples of BRP are reported to contain substantial amounts of polyprenylated benzophenones, whose botanical source was unknown. Therefore, field surveys, phytochemical and chromatographic analyses were undertaken to confirm the botanical sources of the red propolis produced in apiaries located in Canavieiras, Bahia, Brazil. The results confirmed D. ecastaphyllum as the botanical source of liquiritigenin (1), isoliquiritigenin (2), formononetin (3), vestitol (4), neovestitol (5), medicarpin (6), and 7-O-neovestitol (7), while Symphonia globulifera L.f. (Clusiaceae) is herein reported for the first time as the botanical source of polyprenylated benzophenones, mainly guttiferone E (8) and oblongifolin B (9), as well as the triterpenoids β-amyrin (10) and glutinol (11). The chemotaxonomic and economic significance of the occurrence of polyprenylated benzophenones in red propolis is discussed.

Keywords: botanical sources; isoflavonoids; polyisoprenylated benzophenones; propolis.

MeSH terms

  • Benzophenones / analysis
  • Benzophenones / chemistry
  • Brazil
  • Chalcones / analysis
  • Chromatography, High Pressure Liquid
  • Clusiaceae / chemistry*
  • Dalbergia / chemistry*
  • Drug Design
  • Flavanones / analysis
  • Flavonoids / analysis
  • Isoflavones / analysis
  • Isoflavones / chemistry*
  • Magnetic Resonance Spectroscopy
  • Oleanolic Acid / analogs & derivatives
  • Oleanolic Acid / analysis
  • Phytochemicals / analysis*
  • Phytochemicals / chemistry*
  • Plant Extracts / analysis
  • Pterocarpans / analysis
  • Terpenes / analysis
  • Triterpenes / analysis

Substances

  • Benzophenones
  • Chalcones
  • Flavanones
  • Flavonoids
  • Isoflavones
  • Phytochemicals
  • Plant Extracts
  • Pterocarpans
  • Terpenes
  • Triterpenes
  • glutinol
  • neovestitol
  • formononetin
  • Oleanolic Acid
  • medicarpin
  • guttiferone E
  • isoliquiritigenin
  • beta-amyrin
  • liquiritigenin
  • vestitol