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

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Bioactive Botanical Research Laboratory, Department of Biomedical and Pharmaceutical Sciences, College of Pharmacy, University of Rhode Island, 7 Greenhouse Road, Kingston, Rhode Island 02881, United States
*(N.P.S.) Phone: (401) 874-9367. Fax: (401) 874-5787. E-mail: [email protected]
Cite this: J. Agric. Food Chem. 2017, 65, 21, 4289–4295
Publication Date (Web):May 12, 2017
https://doi.org/10.1021/acs.jafc.7b01969
Copyright © 2017 American Chemical Society
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    Abstract

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    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.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jafc.7b01969.

    • HPLC-DAD chromatograms of maple syrup and maple sugar ethyl acetate extracts (Figure S1); Kaplan–Meier survival curves of juglone-exposed wild type Caenorhabditis elegans after treatment with the 20 maple sugar isolates (Figure S2); 13C NMR spectra of compounds 29 and 30 in CD3OD (Figures S3 and S4, respectively) (PDF)

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