Studies on the Chemical Constituents and BiologicalActivities from Calamus quiquesetinervius Burret

Autor: Chao-Lin Chang, 張肇麟
Rok vydání: 2010
Druh dokumentu: 學位論文 ; thesis
Popis: 98
Calamus quiquesetinervius Burret, the most abundant species of Calamus (Arecaceae) endemic to Taiwan, is a clustered prickly rattan palm that grows at low and medium elevations. It has also been used as a treatment for several diseases, such as hypertension, stroke and hepatitis in folk herbal medicine. As part of our discovery of bioactive constituents from the titled plant, twenty-nine rivatives, including fifteen tricin-type flavonolignans (1–15), six 8-O-4′ neolignans (16–21), two dihydrobenzofuran neolignans (22, 23), and six phenylpropanoid glycosides (24–29), and eighteen known phenolic compounds (30–48), were isolated from the ethanol extract of the stems C. quiquesetinervius. These new lignoids are named as calquiquelignans A–O (1–15) and calquiquesides A–F (24–29). Structural elucidation of the new isolates was accomplished on the basis of their spectroscopic data, including 1D and 2D NMR techniques (COSY, HMQC, HMBC and NOESY) and mass spectrometry. Biological evaluations of the fractionated layers resulted from the ethanol extracts of the title plant were also carried out in vitro. The EtOAc fraction (KCQSE) showed the most potency for anti-platelet aggregation, vasodilatory activities, free-radical scavenging activities, and anti-inflammatory activities employing the inhibition of nitric oxide (NO) production. Furthermore, KCQSE and its subfraction, SE2, possessed strong inhibitory effects on TNF-α, IL-1 and IL-6 in the acute inflammatory stage on 12-O-tetradecanoylphorbol-13-acetate (TPA)- induced mouse ear inflammatory model. In the chronic inflammation, the chronic inflammatory symptom can reduce by SE2 via the regulation of up-expression of pro-inflammatory cytokine, the inhibition of adhesion molecules and monocyte chemoattractant protein, and the modulation of arachidonic acid metabolism. A single dose 5 g/kg body weight of KCQSE did not show any adverse effect on clinical sign for two weeks, implying that KCQSE extracts do not cause any acute toxicity. This result indicated the LD50 value of KCQSE could be >5 g/kg body weight/day. Calquiquelignan J (10), salcolin A, and (3, 34) showed potent platelet aggregation inhibition induced by AA and PAF compared with aspirin; calquiquelignan R (18) had three folds collagen-antagonistic activity compared with aspirin, but was inactive against thrombin-induced platelet aggregation. Calquiquelignan A (1), dihydrotricin (31), and (2S)-naringenin (36) exhibited significant vasodilatory potencies at 100 ?嵱, as indicated by 60.3%, 80.3% and 60.9% relaxations, respectively. Calquiquelignan A, B (1, 2), calquiquelignan Q (17), calquiqueside A–C (24–26), E, F (28, 29), dihydrotricin (31), and tricin (32) also exhibited more potent hydroxyl radical (.OH) scavenging activities (IC50 ??10 ?嵱) than Trolox?? as characterized by the ultraweak chemiluminescence assay. The anti-inflammatory potencies of calquiquelignan R (18) and calquiqueside E, F (28, 29) were three to four folds higher compared with quercetin employing the inhibition of nitric oxide (NO) production. Biological evaluations of the fractionated layers resulted from the ethanol extracts of the title plant were also carried out in vitro. The EtOAc fraction (KCQSE) showed the most potency for anti-platelet aggregation,vasodilatory activities, free-radical scavenging activities, and anti-inflammatory activities employing the inhibition of nitric oxide (NO) production. Furthermore, KCQSE and its subfraction, SE2, possessed strong inhibitory effects on TNF-α, IL-1 and IL-6 in the acute inflammatory stage on 12-O-tetradecanoylphorbol-13-acetate (TPA)- induced mouse ear inflammatory model. In the chronic inflammation, the chronic inflammatory symptom can reduce by SE2 via the regulation of up-expression of pro-inflammatory cytokine, the inhibition of adhesion molecules and monocyte chemoattractant protein, and the modulation of arachidonic acid metabolism. A single dose 5 g/kg body weight of KCQSE did not show any adverse effect on clinical sign for two weeks, implying that KCQSE extracts do not cause any acute toxicity. This result indicated the LD50 value of KCQSE could be >5 g/kg body weight/day. Calquiquelignan J (10), salcolin A, and (3, 34) showed potent platelet aggregation inhibition induced by AA and PAF compared with aspirin; calquiquelignan R (18) had three folds collagen-antagonistic activity compared with aspirin, but was inactive against thrombin-induced platelet aggregation. Calquiquelignan A (1), dihydrotricin (31), and (2S)-naringenin (36) exhibited significant vasodilatory potencies at 100 ?嵱, as indicated by 60.3%, 80.3% and 60.9% relaxations, respectively. Calquiquelignan A, B (1,2), calquiquelignan Q (17), calquiqueside A–C (24–26), E, F (28, 29), dihydrotricin (31), and tricin (32) also exhibited more potent hydroxyl radical (.OH) scavenging activities (IC50 ??10 ?嵱) than Trolox?? as characterized by the ultraweak chemiluminescence assay. The anti-inflammatory potencies of calquiquelignan R (18) and calquiqueside E, F (28, 29) were three to four folds higher compared with quercetin employing the inhibition of nitric oxide (NO) production.
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