Isolation, Identification, and Biological Evaluation of Phenolic Compounds from a Traditional North American Confectionery, Maple Sugar

J Agric Food Chem. 2017 May 31;65(21):4289-4295. doi: 10.1021/acs.jafc.7b01969. Epub 2017 May 18.

Abstract

Maple sap, collected from the sugar maple (Acer saccharum) tree, is boiled to produce the popular plant-derived sweetener, maple syrup, which can then be further evaporated to yield a traditional North American confectionery, maple sugar. Although maple sap and maple syrup have been previously studied, the phytochemical constituents of maple sugar are unknown. Herein, 30 phenolic compounds, 1-30, primarily lignans, were isolated and identified (by HRESIMS and NMR) from maple sugar. The isolates included the phenylpropanoid-based lignan tetramers (erythro,erythro)-4″,4‴-dihydroxy-3,3',3″,3‴,5,5'-hexamethoxy-7,9';7',9-diepoxy-4,8″;4',8‴-bisoxy-8,8'-dineolignan-7″,7‴,9″,9‴-tetraol, 29, and (threo,erythro)-4″,4‴-dihydroxy-3,3',3″,3‴,5,5'-hexamethoxy-7,9';7',9-diepoxy-4,8″;4',8‴-bisoxy-8,8'-dineolignan-7″,7‴,9″,9‴-tetraol, 30, neither of which have been identified from maple sap or maple syrup before. Twenty of the isolates (selected on the basis of sample quantity available) were evaluated for their potential biological effects against lipopolysaccharide-induced inflammation in BV-2 microglia in vitro and juglone-induced oxidative stress in Caenorhabditis elegans in vivo. The current study increases scientific knowledge of possible bioactive compounds present in maple-derived foods including maple sugar.

Keywords: bioactive; lignans; maple sugar; maple syrup; phenolics.

MeSH terms

  • Acer / chemistry*
  • Animals
  • Caenorhabditis elegans / drug effects
  • Caenorhabditis elegans / metabolism
  • Microglia / drug effects
  • Microglia / immunology
  • Molecular Structure
  • Oxidative Stress / drug effects
  • Phenols / chemistry*
  • Phenols / isolation & purification
  • Phenols / pharmacology*
  • Plant Extracts / chemistry*
  • Plant Extracts / isolation & purification
  • Plant Extracts / pharmacology*
  • Sweetening Agents / chemistry*
  • Sweetening Agents / isolation & purification
  • Sweetening Agents / pharmacology*
  • United States

Substances

  • Phenols
  • Plant Extracts
  • Sweetening Agents