Cardiovascular protective flavonolignans and flavonoids from Calamus quiquesetinervius.
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.
Chang
Chao-Lin
CL
Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 807, Taiwan, ROC.
Wang
Guei-Jane
GJ
Zhang
Li-Jie
LJ
Tsai
Wen-Jen
WJ
Chen
Ru-Yin
RY
Wu
Yang-Chang
YC
Kuo
Yao-Haur
YH
D000818:Animals; D000975:Antioxidants / Q000302:isolation & purification / Q000494:pharmacology*; D031081:Calamus / Q000737:chemistry*; D044947:Flavonolignans / Q000302:isolation & purification / Q000494:pharmacology*; D008297:Male; D015394:Molecular Structure; D010636:Phenols / Q000302:isolation & purification / Q000494:pharmacology*; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology*; D018547:Plant Stems; D051381:Rats; D017207:Rats, Sprague-Dawley; D014661:Vasoconstriction / Q000187:drug effects*; D014665:Vasodilator Agents / Q000302:isolation & purification / Q000494:pharmacology*
D000975:Antioxidants; D044947:Flavonolignans; D010636:Phenols; D010936:Plant Extracts; D014665:Vasodilator Agents