Retrieval of High Added Value Natural Bioactive Coumarins from Mandarin Juice-Making Industrial Byproduct

Molecules. 2021 Dec 12;26(24):7527. doi: 10.3390/molecules26247527.

Abstract

Cold pressed essential oil (CPEO) of mandarin (Citrus reticulata Blanco), a by-product of the juice-making industrial process known to contain large amounts of polymethoxyflavones, was exploited for its content in high added value natural coumarins. The study herein afforded a method referring to the evaporation of CPEO volatile fraction under mild conditions (reduced pressure and temperature below 35 °C) as azeotrope with isopropanol. This allowed the isolation of high added value coumarins from the non-volatile fragment using preparative High Performance Liquid Chromatography (HPLC). Pilot-scale application of this procedure afforded for each kg of CPEO processed the following natural bioactive coumarins in chemically pure forms: heraclenol (38-55 mg), 8-gerayloxypsoralen (35-51 mg), auraptene (22-33 mg), and bergamottin (14-19 mg). The structures of coumarins were verified by Nuclear Magnetic Resonance (NMR) spectroscopy and HPLC co-injection with authentic standards. Thus, the low market value mandarin CPEO with current value of 17 to 22 EUR/kg can be valorized through the production of four highly bioactive natural compounds worth 3479 to 5057 EUR/kg, indicating the great potentials of this methodology in the terms of the circular economy.

Keywords: 8-geranylpsoralen; auraptene; bergamottin; circular economy; coumarin; furanocoumarin; heraclenol; mandarin (Citrus reticulata).

MeSH terms

  • Beverages / analysis*
  • Biological Products / analysis*
  • Chromatography, High Pressure Liquid
  • Citrus / chemistry*
  • Coumarins / analysis*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Oils, Volatile / analysis*

Substances

  • Biological Products
  • Coumarins
  • Oils, Volatile