Heartwood extractives from the Amazonian trees Dipteryx odorata, Hymenaea courbaril, and Astronium lecointei and their antioxidant activities
Heartwood extractives from the Amazonian trees Dipteryx odorata, Hymenaea courbaril, and Astronium lecointei and their antioxidant activities
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DOI：
10.1007/s10086-008-0975-3
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发表时间：
2008-12-01
影响因子：
2.9
通讯作者：
Fukushima, Kazuhiko
中科院分区：
文献类型：
--
作者：
Imai, Takanori;Inoue, Sousuke;Fukushima, Kazuhiko
来自亚马逊河树木的心材提取物cumaru-ferro（Dipteryx odorata）、贾托巴（Hymenaea courbaril）和guarita（Astronium lecointei）表现出与α-生育酚（一种众所周知的抗氧化剂）相当的抗氧化活性。本文报道了三种心材提取物中抗氧化成分的表征。将cumaru-ferro EtOAc提取物进行硅胶柱色谱，得到（-）-（3R）-7，2 ′，3 ′-三羟基-4 ′-甲氧基异黄烷和（+）-（3R）-8，2 ′，3 ′-三羟基-7，4 ′-二甲氧基异黄烷。硅胶柱色谱法，然后对贾托巴EtOAc提取物进行制备型高效液相色谱法，得到（-）-非塞替尼醇和（+）-反式-紫杉叶素。使用电子电离质谱、（1）H和（13）C核磁共振（NMR）光谱（包括核奥弗豪泽效应光谱（NOESY））以及旋光度和圆二色性对化学结构进行归属。气相色谱-质谱联用表明，分离的化合物在乙酸乙酯提取物中占主导地位。在guarita乙酸乙酯提取物，儿茶素和没食子酸进行了鉴定，通过比较其保留时间和质量碎片模式与真实的样品。通过1，1-二苯基-2-苦基肼测定确定的抗氧化活性表明，所有这些化合物具有与α-生育酚相当的活性。
Heartwood extracts from Amazonian trees cumaru-ferro (Dipteryx odorata), jatoba (Hymenaea courbaril), and guarita (Astronium lecointei) exhibit antioxidant activities comparable with that of alpha-tocopherol, a well-known antioxidant. This article reports the characterization of the antioxidant compounds in the extracts of the three heartwoods. Silica gel column chromatography of the cumaru-ferro EtOAc extract yielded (-)-(3R)-7,2',3'-trihydroxy-4'-methoxyisoflavan and (+)-(3R)-8,2',3'-trihydroxy-7,4'-dimethoxyisoflavan. Silica gel column chromatography followed by preparative high-performance liquid chromatography of the jatoba EtOAc extract yielded (-)-fisetinidol and (+)-trans-taxifolin. Chemical structures were assigned using electron-ionization mass spectrometry, (1)H and (13)C nuclear magnetic resonance (NMR) spectroscopy including nuclear Overhauser effect spectroscopy (NOESY), as well as optical rotation and circular dichroism. Gas chromatography-mass spectrometry demonstrated that the isolated compounds were predominant in the EtOAc extracts. In the guarita EtOAc extract, catechin and gallic acid were identified by comparing their retention times and mass fragmentation patterns with those of authentic samples. Antioxidant activity determined by the 1,1-diphenyl-2-picrylhydrazyl assay demonstrated that all these compounds had activities comparable with that of alpha-tocopherol.