第一部分 菲律賓楠葉部之成份研究(II)
第二部分 香桂葉部之成份研究

第一部分菲律賓楠葉部之成份研究(II) 甲型葡萄糖水解酶為一種位在小腸刷狀緣的酵素，可將含1→4和1→6鍵結之葡萄糖聚合物之食物水解得到葡萄糖，因而抑制此酵素可減緩飯後血糖之上升，達到治療糖尿病的效果，其抑制劑使用於臨床治療糖尿病者有：acarbose、voglibose和miglitol等。在我們先前的研究中顯示，自菲律賓楠葉部之二氯甲烷可溶部分分離出的兩個acylated flavonol monorhamnosides化合物對於甲型葡萄糖水解酶(Bacillus stearothermophilus, type IV)具有強抑制效果，由於乙酸乙酯和正丁醇可溶部分亦具抑制活性，因此本論文第一部分繼續探究這些部份之活性成分，共分離出21個成分，包括7個原花青素(2−8)和epicatechin (1)以及13個黃酮糖苷類(9−15, 19−21, 23, 25和26)。另外，應用液相層析-固相萃取-核磁共振儀連接技術，分析具有抑制活性的黃酮類混合物，又鑑定出5個黃酮糖苷類(16−18, 22和24)。其中，machiphilitannins A (7)、B (8)、kaempferol 3-O-(2-O-β-D-apiofuranosyl)-α-L -rhamnopyranoside (9)和kaempferol 3-O-(2-O-β-D-apiofuranosyl)-α-L- arabinofuranoside (10)為新天然物。對於甲型葡萄糖水解酶(type IV from Bacillus stearothermophilus)之活性測試顯示，化合物aesculitannin B (2)、7、8、quercetin 3-O-(6-O-α-L-rhamnopyranosyl)-β-D-galactopyranoside (13)和kaempferol 3-O-α-L-arabinopyranoside (23)之IC50分為3.5、31.3、18.4、19.5和19.0 μM。第二部分香桂葉部之成份研究香桂為中型常綠喬木，分布於台灣海拔700至2100公尺的中部山區、中國、緬甸、柬埔寨、越南、馬來西亞和印度尼西亞等地。甲型葡萄糖水解酶在人類腸道中消化碳水化合物扮演著重要的角色，其抑制劑使用於臨床治療糖尿病者有acarbose和miglitol等。本研究以抑制活性為導向，利用Sephadex LH-20管柱、矽膠管柱、逆相層析管柱以及半製備高壓液相層析管柱自香桂葉部之酒精萃取物分離並鑑定出36個化合物，分別屬於dibenzocycloheptenes (27−29, 31, 32和34)、倍半萜類(35−43)、新木脂素(44)、苷類(45, 46和48)、苯乙醇(47)、黃酮類(49−59)、單寧類(3, 4)。其中，cinnasubavene A−H (27−34)、1β,6α,9β-trihydroxy-cis- eudesm-3-ene-6-O-β-D-glucopyranoside (39)以及其衍生物(40−43)和kaempferol-3-O- (4'-Z-p-coumaroyl)-α-L-rhamnopyranoside (57)為新天然物。

關鍵字

菲律賓楠；香桂；甲型葡萄糖水解酶

並列摘要

Part I: Chemical investigation of the leaves of Machilus philippinensis (II) α-Glucosidase is an enzyme which is located in the small intestine brush broader and responsible for digestion of dietary carbohydrate with α-(1→4) and (1→6) linkage. Inhibition of this enzyme could improve postprandial glucose control in the treatment of diabetes mellitus. Currently, α-glucosidase inhibitors, acarbose, voglibose and miglitol, are used in clinic. Our recent studies have revealed that two acylated flavonol monorhamnosides from the leaf of Machilus philippinensis Merr. (Lauraceae) displayed potent inhibitory activities against α-glucosidase (Bacillus stearothermophilus, type IV). Continuing investigation of the α-glucosidase inhibitors in the EtOAc and n-BuOH soluble fraction of the EtOH extract of the M. philippinensis leaf via the bioassay-guided approach, 21 compounds, including seven proanthocyanidins (2−8), epicatechin (1) and 13 flavonoid glycosides (9−15, 19−21, 23, 25, and 26), were isolated. Application of high performance liquid chromatography–solid phase extraction–nuclear magnetic resonance (HPLC–SPE–NMR) hyphenated technique in characterization of the active compounds in a fraction rich in flavonol glycosides led to the identification of five additional flavonol glycosides (16−18, 22 and 24). Of these, machiphilitannins A (7), B (8), kaempferol 3-O-(2-O-β-D-apiofuranosyl)-α-L -rhamnopyranoside (1) and kaempferol 3-O-(2-O-β-D-apiofuranosyl)-α-L -arabinofuranoside (2) are new natural products. Bioassay of the isolated compounds showed the IC50 value of aesculitannin B (2), 7, 8, quercetin 3-O-(6-O-α-L-rhamnopyranosyl)-β-D-galactopyranoside (13) and kaempferol 3-O-α-L-arabinopyranoside (23) to be 3.5, 31.3, 18.4, 19.5 and 19.0 μM, respectively. Part II: Chemical investigation of the leaves of Cinnamomum subavenium Cinnamomum subavenium Miq. (Lauraceae) is a medium-sized evergreen tree distributed at an attitude of 700 to 2100 meters in central mountains in Taiwan and found in central to south China, Burma, Cambodia, Vietnam, Malaysia, Indonesia. α-Glucosidase is an enzyme which is located in the small intestine brush broader and responsible for digestion of dietary carbohydrate. Currently, α-glucosidase inhibitors such as acarbose and miglitol are used in clinic. Guided by bioassay against α-glucosidase (Bacillus stearothermophilus, type IV), 36 compounds were characterized and isolated by Sephadex LH-20 column, silica gel column, Lobar RP-18 column, and semi-preparative RP-18 HPLC. They belong to dibenzocycloheptenes (27−29, 31, 32 and 34), sesquiterpenoids (35−43), neolignan (44), glycosides (45, 46 and 48), phenethnol (47), flavonoids (49−59) and tannins (3, 4). Among them, cinnasubavene A−H (27−34), 1β,6α,9β-trihydroxy-cis-eudesm -3-ene-6-O-β-D-glucopyranoside (39) and its four derivatives (40−43) and kaempferol-3-O- (4'-Z-p-coumaroyl)-α-L-rhamnopyranoside (57) are new natural products.

並列關鍵字

Machilus philippinensis ； Cinnamomum subavenium ； α-glucosidase

參考文獻

1. Lee, S. S.; Lin, H. C.; Chen, C. K. Acylated flavonol monorhamnosides, α-glucosidase inhibitors, from Machilus philippinensis Merr. Phytochemistry 2008, 69, 2347–2353.

2. Seger, C.; Godejohann, M.; Tseng, L. H.; Spraul, M.; Girtler, A.; Sturm, S.; Stuppner, H. LC-DAD-MS/SPE-NMR hyphenation. A tool for the analysis of pharmaceutically used plant extracts: identification of isobaric iridoid glycoside regioisomers from Harpagophytum procumbens. Anal. Chem. 2005, 77, 878–885.

4. Komae, H., Hayashi, N. Terpenes from Actinodaphne, Machilus and Neolitsea species, Phytochemistry 1972 , 11, 1181–1182

5. Cheng, M. J.; Jayaprakasam, B.; Ishikawa, T.; Seki H.; Tsai, I. L.; Wang, J. J.; Chen, I. S. Chemical and Cytotoxic Constituents from the Stem of Machilus zuihoensis. Helv. Chim. Acta. 2002 , 85, 1909–1914.

6. Chung, Y. C.; Cheng, M. J.; Chiang, Y. J.; Baic, J. C.; Chiuc, C. T.; Lind, R. J.; Hsuie, Y. R.; Lo, W. L. Chemical constituents from the leaves of Machilus zuihoensis Hayata var. mushaensis (Lu) Y.C. Liu. Nat. Prod. Res. 2009, 23, 871–875.

國際替代計量

第一部分菲律賓楠葉部之成份研究(II) 第二部分香桂葉部之成份研究

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