Identification of chemical constituents from the bark of Larix kaempferi and their tyrosinase inhibitory effect
Identification of chemical constituents from the bark of Larix kaempferi and their tyrosinase inhibitory effect
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DOI：
10.1515/hf-2018-0267
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发表时间：
2019-07-01
期刊：
影响因子：
2.4
通讯作者：
Mitsunaga, Tohru
中科院分区：
文献类型：
--
作者：
Kakumu, Yuya;Yamauchi, Kosei;Mitsunaga, Tohru
尽管树皮含有多种植物化学成分，但林业生产中产生的大部分树皮被丢弃。本研究的目的是确定次生代谢产物从日本落叶松树皮产生的废料，并评估其作为化妆品剂的潜力。从白花木树皮中分得18个化合物，其中包括一个新的菲类化合物4，6，7-三羟基菲-2-O-β-D-吡喃葡萄糖苷（16）。通过基质辅助激光解吸电离飞行时间质谱（MALDI-TOF-MS）和核磁共振（NMR）鉴定。此外，评价了这些化合物的酪氨酸酶抑制活性。当使用L-酪氨酸和L-多巴作为底物时，原花青素B7（18）表现出最强的抑制作用，IC 50值分别为31.0 μ M和61.8 μ M，这与阳性对照曲酸的IC 50值相似。有趣的是，槲皮素-3-O-α-L-吡喃鼠李糖苷（10）显示出具有酪氨酸酶抑制作用，而其他系列的3-糖基化黄酮醇没有活性，这表明C-3位的鼠李糖基和C-3'位的羟基在抗酪氨酸酶活性中起着不可或缺的作用。这些结果表明，L.山柰树皮可能具有作为化妆品添加剂的潜力。
Most of the wood bark produced by the forestry production is discarded in spite of containing many kinds of the phytochemical ingredients. The aim of the present study was to identify secondary metabolites from the bark of Larix kaempferi generated as waste material and evaluate their potential as cosmetic agents. Eighteen compounds, including a novel phenanthrene, 4,6,7-trihydroxyphenanthrene-2-O-beta-D-glucopyranoside (16), were isolated from the bark of L. kaempferi and identified by matrix assisted laser desorption ionization-time of flight mass spectrometry (MALDI-TOF-MS) and nuclear magnetic resonance (NMR). In addition, the tyrosinase inhibitory activity of these compounds was evaluated. Procyanidin B7 (18) exhibited the most potent inhibition with IC50 values of 31.0 mu M and 61.8 mu M when using L-tyrosine and L-dopa as the substrate, respectively, which were similar to those of the positive control, kojic acid. Interestingly, quercetin-3-O-alpha-L-rhamnopyranoside (10) was shown to possess the tyrosinase inhibition although the other series of 3-glycoylated flavonols were not active, suggesting that the rhamnosyl group at C-3 and the hydroxyl group at C-3' played an indispensable role in the anti-tyrosinase activity. These findings indicate that a number of constituents from L. kaempferi bark may have potential as additives in cosmetics.