Further investigation into maple syrup yields 3 new lignans, a new phenylpropanoid, and 26 other phytochemicals.
Further investigation into maple syrup yields 3 new lignans, a new phenylpropanoid, and 26 other phytochemicals.
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对枫糖浆的进一步研究产生了 3 种新的木脂素、一种新的苯丙素和 26 种其他植物化学物质。
DOI：
10.1021/jf2011613
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发表时间：
2011-07-27
影响因子：
6.1
通讯作者：
Seeram NP
中科院分区：
文献类型：
--
作者：
Li L;Seeram NP
枫糖浆是通过煮沸从某些枫树（宏碁）树种收集的汁液制成的。在此过程中，树液中天然存在的植物化学物质浓缩在枫糖浆中。我们之前报道了加拿大枫糖浆丁醇提取物 (MS-BuOH) 中的 23 种植物化学物质。在此，我们报告了从其乙酸乙酯提取物 (MS-EtOAc) 中分离和鉴定了 30 种其他化合物 (1-30)，这是之前从未通过 MS-BuOH 报道过的。其中，4 种化合物是新化合物（1-3、18），20 种化合物（4-7、10-12、14-17、19-20、22-24、26、28-30）是首次从枫糖浆中报道。新化合物包括 3 种木脂素和 1 种苯丙素： 5-(3″,4″-二甲氧基苯基)-3-羟基-3-(4′-羟基-3′-甲氧基苄基)-4-羟甲基-二氢呋喃-2-酮 (1)，(赤式，赤式)-1-[4-[2-羟基-2-(4-羟基-3-甲氧基苯基)-1-(羟甲基)乙氧基]-3,5-二甲氧基苯基]-1,2,3-丙三醇 (2), (赤式,分别为：苏)-1-[4-[2-羟基-2-(4-羟基-3-甲氧基苯基)-1-(羟甲基)乙氧基]-3,5-二甲氧基苯基]-1,2,3-丙三醇(3)和2,3-二羟基-1-(3,4-二羟基苯基)-1-丙酮(18)。此外，还分离出 25 种其他酚类化合物，包括(苏式、赤式)-1-[4-[(2-羟基-2-(4-羟基-3-甲氧基苯基)-1-(羟甲基)乙氧基]-3-甲氧基苯基]-1,2,3-丙三醇(4)、(苏式、苏)-1-[4-[(2-羟基-2-(4-羟基-3-甲氧基苯基)-1-(羟甲基)乙氧基]-3-甲氧基苯基]-1,2,3-丙三醇(5)，苏型愈创木酰甘油-β-O-4'-二氢松柏醇(6)，赤式-1-(4-羟基-3-甲氧基苯基)-2-[4-(3-羟基丙基)-2,6-二甲氧基苯氧基]-1,3-丙二醇(7)， 2-[4-[2,3-二氢-3-(羟甲基)-5-(3-羟丙基)-7-甲氧基-2-苯并呋喃基]-2,6-二甲氧基苯氧基]-1-(4-羟基-3-甲氧基苯基)-1,3-丙二醇(8)、acenikol(9)、lepolepisol D(10)、buddlenol E(11)、 (1S,2R)-2-[2,6-二甲氧基-4-[(1S,3aR,4S,6aR)-四氢-4-(4-羟基-3,5-二甲氧基苯基)-1H,3H-呋喃并[3,4-c]呋喃-1-基]苯氧基]-1-(4-羟基-3-甲氧基苯基)-1,3-丙二醇(12)，丁香树脂醇(13)、异落叶松树脂醇(14)、淫羊藿苷E4(15)、樱花树脂醇(16)、1,2-二愈创木脂基-1,3-丙二醇(17)、2,3-二羟基-1-(4-羟基-3,5-二甲氧基苯基)-1-丙酮(19)、 3-羟基-1-(4-羟基-3,5-二甲氧基苯基)丙-1-酮(20)、二氢松柏醇(21)、4-乙酰儿茶酚(22)、3',4',5'-三羟基苯乙酮(23)、3,4-二羟基-2-甲基苯甲醛(24)、原儿茶酸(25)、 4-(二甲氧基甲基)-邻苯二酚 (26)、酪醇 (27)、异佛西丁 (28) 和 4-羟基儿茶酚 (29) 是一种倍半萜烯，菜豆酸 (30)，它是植物激素脱落酸的已知代谢物，也从 MS-EtOAc 中分离出来。在二苯基三硝苯肼自由基清除测定中，纯分离物（IC50 约 68–3000 μM）与维生素 C（IC50 = 40 μM）和合成商业抗氧化剂丁基羟基甲苯（IC50 = 3000 μM）相当。当前的研究推进了枫糖浆成分的科学知识，并表明这些不同的植物化学物质可能为这种天然甜味剂带来潜在的健康益处。
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. We previously reported 23 phytochemicals from a butanol extract of Canadian maple syrup (MS-BuOH). Here we report 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, 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 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 suggest that these diverse phytochemicals may impart potential health benefits to this natural sweetener.
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影响因子：
6.3
作者：
Guri, Amir J.;Hontecillas, Raquel;Bassaganya-Riera, Josep
通讯作者：
Bassaganya-Riera, Josep
影响因子：
6.1
作者：
Li, Liya;Seeram, Navindra P.
通讯作者：
Seeram, Navindra P.
影响因子：
1.7
作者：
Okuyama, E;Hasegawa, T;Yamazaki, M
通讯作者：
Yamazaki, M
影响因子：
3.4
作者：
Jones, L.;Bartholomew, B.;Nash, R. J.
通讯作者：
Nash, R. J.
影响因子：
1.7
作者：
Yang, Xu-Juan;Wong, Man-Sau;Yao, Xin-Sheng
通讯作者：
Yao, Xin-Sheng