Cardiovascular protective flavonolignans and flavonoids from Calamus quiquesetinervius |
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Authors: | Chao-Lin Chang Guei-Jane Wang Li-Jie Zhang Wen-Jen Tsai Ru-Yin Chen Yang-Chang Wu Yao-Haur Kuo |
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Institution: | 1. Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 807, Taiwan, ROC;2. Division of Herbal Drugs and Natural Products, National Research Institute of Chinese Medicine, Taipei 112, Taiwan, ROC;3. Food Industry Research and Development Institute, Hsinchu 300, Taiwan, ROC;4. Graduate Institute of Integrated Medicine, China Medical University, Taichung 404, Taiwan, ROC |
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Abstract: | Tricin-type flavonolignans, (2S)-dihydrotricin 4′-O-(erythro-β-guaiacylglyceryl) ether, (2S)-dihydrotricin 4′-O-(threo-β-guaiacylglyceryl) ether, (2S)-dihydrotricin 4′-O-(threo-β-4-hydroxyphenylglyceryl) ether, tricin 4′-O-(erythro-β-4-hydroxyphenylglyceryl) ether, tricin 4′-O-(threo-β-4-hydroxylphenylglyceryl) ether, and (2S)-dihydrotricin 4′-O-(β-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 μM. 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. |
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