Maple Syrup Phytochemicals Include Lignans, Coumarins, a Stilbene, and Other Previously Unreported Antioxidant Phenolic Compounds
Maple Syrup Phytochemicals Include Lignans, Coumarins, a Stilbene, and Other Previously Unreported Antioxidant Phenolic Compounds
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DOI：
10.1021/jf1033398
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发表时间：
2010-11-24
影响因子：
6.1
通讯作者：
Seeram, Navindra P.
中科院分区：
文献类型：
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作者：
Li, Liya;Seeram, Navindra P.
从加拿大枫糖浆的正丁醇提取物（MS-BuOH）中分离出23种酚类化合物。根据核磁共振和质谱数据鉴定了7种木脂素[lyoniresinol（1），secoisolariciresinol（2），dehydroconiferyl alcohol（3），5 '-methoxy-dehydroconiferyl alcohol（4），erythro-guaiacylglycerol-beta-O-4'-coniferyl alcohol（5），erythro-guaiacylglycerol-beta-O-4 '-dihydroconiferyl alcohol（6），和[3-[4-[（6-脱氧-α-L-吡喃甘露糖基）氧基]-3-甲氧基苯基]甲基]-5-（3，4 '-二甲氧基苯基）二氢-3-羟基-4-（羟甲基）-2（3 H）-呋喃酮（7）]，2种香豆素类化合物[东莨菪内酯（8）和秦皮乙素（9）]，一种芪类化合物[（E）-3，3 ′-二甲氧基-4，4 ′-二羟基芪（10）]，和13种酚类衍生物[2-羟基-3 ′，4 ′-二羟基苯乙酮（11），1-（2，3，4-三羟基-5-甲基苯基）乙酮（12），2，4，5-三羟基苯乙酮（13），儿茶醛（14），香草醛（15），丁香醛（16），没食子酸（17），没食子酸三甲基甲酯（18），丁香酸（19），姜黄素（20）、（E）-松柏醇（21）、C-藜芦醇（22）和儿茶酚（23）]。在二苯基苦基肼（DPPH）自由基清除试验中评价了MS-BuOH（IC 50> 1000 μ g/mL）、纯化合物、维生素C（IC 50 = 58 μ M）和合成的商业抗氧化剂丁基化羟基甲苯（IC 50 = 2651 AA）的抗氧化活性。在分离物中，与木脂素和二苯乙烯（IC 50> 100 μ M）相比，酚类衍生物和香豆素显示出优异的上级抗氧化活性（IC 50 <100 μ M）。此外，这是第一次报告的16个这23个酚，即化合物1，2，4-14，18，20和22，在枫糖浆。
Twenty-three phenolic compounds were isolated from a butanol extract of Canadian maple syrup (MS-BuOH) using chromatographic methods. The compounds were identified from their nuclear magnetic resonance and mass spectral data as 7 lignans [lyoniresinol (1), secoisolariciresinol (2), dehydroconiferyl alcohol (3), 5'-methoxy-dehydroconiferyl alcohol (4), erythro-guaiacylglycerol-beta-O-4'-conrferyl alcohol (5), erythro-guaiacylglycerol-beta-O-4'-dihydroconiferyl alcohol (6), and [3-[4-[(6-deoxy-alpha-L-mannopyranosyl)oxy]-3-methoxyphenyl]methyl]-5-(3,4'-dimethoxyphenyl)dihydro-3-hydroxy-4-(hydroxymethyl)-2(3H)-furanone (7)], 2 coumarins [scopoletin (8) and fraxetin (9)], a stilbene [(E)-3,3'-dimethoxy-4,4'-dihydroxystilbene (10)], and 13 phenolic derivatives [2-hydroxy-3',4'-dihydroxyacetophenone (11), 1-(2,3,4-trihydroxy-5-methylphenyl)ethanone (12), 2,4,5-trihydroxyacetophenone (13), catechaldehyde (14), vanillin (15), syringaldehyde (16), gallic acid (17), trimethyl gallic acid methyl ester (18), syringic acid (19), syringenin (20), (E)-coniferol (21), C-veratroylglycol (22), and catechol (23)]. The antioxidant activities of MS-BuOH (IC50 > 1000 mu g/mL), pure compounds, vitamin C (IC50 = 58 mu M), and a synthetic commercial antioxidant, butylated hydroxytoluene (IC50 = 2651 AA), were evaluated in the diphenylpicrylhydrazyl (DPPH) radical scavenging assay. Among the isolates, the phenolic derivatives and coumarins showed superior antioxidant activity (IC50 < 100 mu M) compared to the lignans and stilbene (IC50 > 100 mu M). Also, this is the first report of 16 of these 23 phenolics, that is, compounds 1, 2, 4-14, 18, 20, and 22, in maple syrup.