Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 807, Taiwan, ROC.
Phytochemistry. 2010 Feb;71(2-3):271-9. doi: 10.1016/j.phytochem.2009.09.025. Epub 2009 Dec 16.
Tricin-type flavonolignans, (2S)-dihydrotricin 4'-O-(erythro-beta-guaiacylglyceryl) ether, (2S)-dihydrotricin 4'-O-(threo-beta-guaiacylglyceryl) ether, (2S)-dihydrotricin 4'-O-(threo-beta-4-hydroxyphenylglyceryl) ether, tricin 4'-O-(erythro-beta-4-hydroxyphenylglyceryl) ether, tricin 4'-O-(threo-beta-4-hydroxylphenylglyceryl) ether, and (2S)-dihydrotricin 4'-O-(beta-6''-methoxy-4''-oxo-chroman-3''-yloxy) ether namely calquiquelignan A-F, respectively, were isolated and characterized from the EtOAc extract of Calamus quiquesetinervius. Additionally, six known phenolic compounds, including dihydrotricin, tricin, salcolin A, p-hydroxybenzoic acid, (2S, 3S)-trans-dihydrokapempferol and (2S)-naringenin, were also obtained and identified from the extract. Structures of the flavonolignans were assigned based on spectroscopic analyses that included 1D and 2D NMR spectroscopic techniques, such as HMQC, HMBC, and NOESY. Bioassay results showed that calquiquelignan A, dihydrotricin and (2S)-naringenin exhibited significant vasodilatory potencies, as indicated by 60.3%, 80.3% and 60.9% relaxations, respectively, at 100 microM. Salcolin A showed potent platelet aggregation inhibition, compared with aspirin. Most of the tricin-type derivatives (calquiquelignan A-B, dihydrotricin and tricin) also exhibited more potent hydroxyl radical ((.)OH) scavenging activity than trolox as characterized by the ultraweak chemiluminescence assay.
三嗪型黄酮木脂素，（2S）-二氢圣草酚 4'-O-（赤型-β-愈创木基甘油醚），（2S）-二氢圣草酚 4'-O-（苏型-β-愈创木基甘油醚），（2S）-二氢圣草酚 4'-O-（苏型-β-对羟基苯基甘油醚），圣草酚 4'-O-（赤型-β-对羟基苯基甘油醚），圣草酚 4'-O-（苏型-β-对羟基苯基甘油醚），以及（2S）-二氢圣草酚 4'-O-（β-6''-甲氧基-4''-氧代-色原烷-3''-氧基）醚，分别为卡拉奎木脂素 A-F，从 Calamus quiquesetinervius 的乙酸乙酯提取物中分离和鉴定出来。此外，从提取物中还获得并鉴定出六种已知的酚类化合物，包括二氢圣草酚、圣草酚、沙醇 A、对羟基苯甲酸、（2S，3S）-反式-二氢卡姆波酚和（2S）-柚皮素。根据包括 1D 和 2D NMR 光谱技术（如 HMQC、HMBC 和 NOESY）在内的光谱分析，确定了黄酮木脂素的结构。生物测定结果表明，卡拉奎木脂素 A、二氢圣草酚和（2S）-柚皮素在 100 μM 时分别表现出 60.3%、80.3%和 60.9%的显著舒张作用，具有显著的血管舒张活性。与阿司匹林相比，沙醇 A 显示出强大的血小板聚集抑制作用。大多数三嗪型衍生物（卡拉奎木脂素 A-B、二氢圣草酚和圣草酚）也表现出比 Trolox 更强的羟基自由基（.OH）清除活性，这是通过超弱化学发光法测定的。
