Further Investigation into Maple Syrup Yields 3 New Lignans, a New Phenylpropanoid, and 26 Other Phytochemicals
Abstract
Maple syrup is made by boiling the sap collected from certain maple (Acer) species. During this process, phytochemicals naturally present in tree sap are concentrated in maple syrup. Twenty-three phytochemicals from a butanol extract of Canadian maple syrup (MS-BuOH) had previously been reported; this paper reports the isolation and identification of 30 additional compounds (1–30) from its ethyl acetate extract (MS-EtOAc) not previously reported from MS-BuOH. Of these, 4 compounds are new (1–3, 18) and 20 compounds (4–7, 10–12, 14–17, 19, 20, 22–24, 26, and 28–30) are being reported from maple syrup for the first time. The new compounds include 3 lignans and 1 phenylpropanoid: 5-(3″,4″-dimethoxyphenyl)-3-hydroxy-3-(4′-hydroxy-3′-methoxybenzyl)-4-(hydroxymethyl)dihydrofuran-2-one (1), (erythro,erythro)-1-[4-[2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-1-(hydroxymethyl)ethoxy]-3,5-dimethoxyphenyl]-1,2,3-propanetriol (2), (erythro,threo)-1-[4-[2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-1-(hydroxymethyl)ethoxy]-3,5-dimethoxyphenyl]-1,2,3-propanetriol (3), and 2,3-dihydroxy-1-(3,4- dihydroxyphenyl)-1-propanone (18), respectively. In addition, 25 other phenolic compounds were isolated including (threo,erythro)-1-[4-[(2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-1-(hydroxymethyl)ethoxy]-3-methoxyphenyl]-1,2,3-propanetriol (4), (threo,threo)-1-[4-[(2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-1-(hydroxymethyl)ethoxy]-3-methoxyphenyl]-1,2,3-propanetriol (5), threo-guaiacylglycerol-β-O-4′-dihydroconiferyl alcohol (6), erythro-1-(4-hydroxy-3-methoxyphenyl)-2-[4-(3-hydroxypropyl)-2,6-dimethoxyphenoxy]-1,3-propanediol (7), 2-[4-[2,3-dihydro-3-(hydroxymethyl)-5-(3-hydroxypropyl)-7-methoxy-2-benzofuranyl]-2,6-dimethoxyphenoxy]-1-(4-hydroxy-3-methoxyphenyl)-1,3-propanediol (8), acernikol (9), leptolepisol D (10), buddlenol E (11), (1S,2R)-2-[2,6-dimethoxy-4-[(1S,3aR,4S,6aR)-tetrahydro-4-(4-hydroxy-3,5-dimethoxyphenyl)-1H,3H-furo[3,4-c]furan-1-yl]phenoxy]-1-(4-hydroxy-3-methoxyphenyl)-1,3-propanediol (12), syringaresinol (13), isolariciresinol (14), icariside E4 (15), sakuraresinol (16), 1,2-diguaiacyl-1,3-propanediol (17), 2,3-dihydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-1-propanone (19), 3-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propan-1-one (20), dihydroconiferyl alcohol (21), 4-acetylcatechol (22), 3′,4′,5′-trihydroxyacetophenone (23), 3,4-dihydroxy-2-methylbenzaldehyde (24), protocatechuic acid (25), 4-(dimethoxymethyl)pyrocatechol (26), tyrosol (27), isofraxidin (28), and 4-hydroxycatechol (29). One sesquiterpene, phaseic acid (30), which is a known metabolite of the phytohormone abscisic acid, was also isolated from MS-EtOAc. The antioxidant activities of MS-EtOAc (IC50 = 75.5 μg/mL) and the pure isolates (IC50 ca. 68–3000 μM) were comparable to that of vitamin C (IC50 = 40 μM) and the synthetic commercial antioxidant butylated hydroxytoluene (IC50 = 3000 μM), in the diphenylpicrylhydrazyl radical scavenging assay. The current study advances scientific knowledge of maple syrup constituents and suggests that these diverse phytochemicals may impart potential health benefits to this natural sweetener.
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- Xiao-Li Zeng, Guang-Miao Fu, Kai Tian, Jing-Xian Sun, Hua-Bin Xiong, Xiang-Zhong Huang, Zhi-Yong Jiang. Acutissimanide, a new lignan with antioxidant activity isolated from the bark of Quercus acutissima Carruth. Natural Product Research 2014, 28 (17) , 1364-1370. https://doi.org/10.1080/14786419.2014.905557
- Qing-Bo Liu, Xiao-Xiao Huang, Xin-Jia Yan, Ming Bai, Li-Hong Yu, Chong Hu, Tao Zhu, Ling-Zhi Li, Shao-Jiang Song. Neolignans from the seeds of Prunus tomentosa (Rosaceae) and their chemotaxonomic interest. Biochemical Systematics and Ecology 2014, 55 , 236-240. https://doi.org/10.1016/j.bse.2014.03.030
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- Pragati P. Nahar, Maureen V. Driscoll, Liya Li, Angela L. Slitt, Navindra P. Seeram. Phenolic mediated anti-inflammatory properties of a maple syrup extract in RAW 264.7 murine macrophages. Journal of Functional Foods 2014, 6 , 126-136. https://doi.org/10.1016/j.jff.2013.09.026
- Tao Yuan, Liya Li, Yan Zhang, Navindra P. Seeram. Pasteurized and sterilized maple sap as functional beverages: Chemical composition and antioxidant activities. Journal of Functional Foods 2013, 5 (4) , 1582-1590. https://doi.org/10.1016/j.jff.2013.06.009
- Sébastien Cardinal, Normand Voyer. Total synthesis of quebecol. Tetrahedron Letters 2013, 54 (38) , 5178-5180. https://doi.org/10.1016/j.tetlet.2013.07.048
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- Qi Zeng, Ji Ye, Jie Ren, Xiang-rong Cheng, Jiang-jiang Qin, Hui-Zi Jin, Wei-Dong Zhang. Chemical Constituents from Aphanamixis grandifolia. Chemistry of Natural Compounds 2013, 49 (3) , 486-492. https://doi.org/10.1007/s10600-013-0644-7
- Mustapha Sadiki, Nathalie Martin. Solid-Phase Extraction and Procedure for Determination of Phenolic Compounds in Maple Syrup. Food Analytical Methods 2013, 6 (3) , 737-744. https://doi.org/10.1007/s12161-012-9474-7
- Antonio González-Sarrías, Hang Ma, Maxwell E. Edmonds, Navindra P. Seeram. Maple polyphenols, ginnalins A–C, induce S- and G2/M-cell cycle arrest in colon and breast cancer cells mediated by decreasing cyclins A and D1 levels. Food Chemistry 2013, 136 (2) , 636-642. https://doi.org/10.1016/j.foodchem.2012.08.023
- Noriaki Nagai, Yoshimasa Ito, Atsushi Taga. Comparison of the Enhancement of Plasma Glucose Levels in Type 2 Diabetes Otsuka Long-Evans Tokushima Fatty Rats by Oral Administration of Sucrose or Maple Syrup. Journal of Oleo Science 2013, 62 (9) , 737-743. https://doi.org/10.5650/jos.62.737
- Chunpeng Wan, Tao Yuan, Amanda L. Cirello, Navindra P. Seeram. Antioxidant and α-glucosidase inhibitory phenolics isolated from highbush blueberry flowers. Food Chemistry 2012, 135 (3) , 1929-1937. https://doi.org/10.1016/j.foodchem.2012.06.056
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- Antonio González‐Sarrías, Liya Li, Navindra P. Seeram. Effects of Maple ( Acer ) Plant Part Extracts on Proliferation, Apoptosis and Cell Cycle Arrest of Human Tumorigenic and Non‐tumorigenic Colon Cells. Phytotherapy Research 2012, 26 (7) , 995-1002. https://doi.org/10.1002/ptr.3677
- Emmanouil Apostolidis, Liya Li, Bouhee Kang, Chong M. Lee, Navindra P. Seeram. Seasonal influence on phenolic-mediated antihyperglycemic properties of Canadian sugar and red maple leaves using in vitro assay models. Food Science and Biotechnology 2012, 21 (3) , 753-760. https://doi.org/10.1007/s10068-012-0098-x
- Antonio González-Sarrías, Tao Yuan, Navindra P. Seeram. Cytotoxicity and structure activity relationship studies of maplexins A–I, gallotannins from red maple (Acer rubrum). Food and Chemical Toxicology 2012, 50 (5) , 1369-1376. https://doi.org/10.1016/j.fct.2012.02.031
- Chunpeng Wan, Tao Yuan, Liya Li, Vamsikrishna Kandhi, Nadja B. Cech, Mingyong Xie, Navindra P. Seeram. Maplexins, new α-glucosidase inhibitors from red maple (Acer rubrum) stems. Bioorganic & Medicinal Chemistry Letters 2012, 22 (1) , 597-600. https://doi.org/10.1016/j.bmcl.2011.10.073
- Antonio González-Sarrías, Liya Li, Navindra P. Seeram. Anticancer effects of maple syrup phenolics and extracts on proliferation, apoptosis, and cell cycle arrest of human colon cells. Journal of Functional Foods 2012, 4 (1) , 185-196. https://doi.org/10.1016/j.jff.2011.10.004
- Tao Yuan, Chunpeng Wan, Ke Liu, Navindra P. Seeram. New maplexins F–I and phenolic glycosides from red maple (Acer rubrum) bark. Tetrahedron 2012, 68 (4) , 959-964. https://doi.org/10.1016/j.tet.2011.11.062