小錦蘭根部之化學成分及抗發炎活性之研究

Studies on the Chemical Constituents and Anti-inflammatory Activities of the Roots of Anodendron affine

鄭詩蓉(Shih-Jung Cheng)

指導教授 ： 鍾美英

高雄醫學大學/藥學院/藥學系碩士在職專班/碩士(2018年)

摘要

小錦蘭(Anodendron affine Druce)為夾竹桃科(Apocynaceae)之木質藤本植物，分佈於中國南部、琉球群島、日本及台灣。對台灣產植物及中草藥進行抗發炎活性篩選，其中小錦蘭為活性植物之一。
由小錦蘭根部之乙酸乙酯可溶部，目前已分離出一個新的acylquinic acid derivative: methyl 4,5-O-feruloyl-3-methoxyquinate (1) 、一個新的pregnane: 16-pregnen-3,12,20-trione (2)，以及4個已知化合物，包括兩個nervogenic acids: deglucosylanodendrosin A (3) 及 anodendrosin H (4)，一個prenylbenzoic acid: 4-hydroxy-3-(3-methylbut- 2-en-1-yl)benzoic acid (5) 及一個 comarin: scopoletin (6)。已知化合物中，deglucosylanodendrosin A (3)為天然物首次分離得到的化合物。上述化合物之結構，經由各種圖譜分析及文獻數據比對予以確認。
目前分離所得到的化合物中，methyl 4,5-O-feruloyl-3-methoxy- quinate (1)、anodendrosin H (4)及4-hydroxy-3-(3-methylbut-2-en-1-yl) benzoic acid (5) 對於formyl-L-methionyl-L-leuckyl-L-phenylalanine (fMLP)誘導人類 嗜中性白血球產生超氧陰離子(O2•–)，具有良好的抑制活性，其IC50值分別為24.76, 27.37及17.65 M。

關鍵字

小錦蘭 ； 夾竹桃科 ； 抗發炎活性 ； 結構解析

並列摘要

Anodendron affine Druce (Apocynaceae) is a glabrous climbing shrub distributed in southern China, the Ryukyu Islands, Japan, and Taiwan. In our studies on the anti-inflammatory constituents of Formosan plants, many species have been screened for in vitro anti-inflammatory activity, and A. affine has been found to be one of the active species.
Investigation on EtOAc-soluble fraction of roots of this plant led to the isolation of a new acylquinic acid derivative, methyl 4,5-O- feruloyl-3-methoxyquinate (1), a new pregnane derivative, 16-pregnen- 3,12,20-trione (2), together with 4 known compounds, deglucosyl- anodendrosin A (3), anodendrosin H (4), 4-hydroxy-3-(3-methylbut- 2-en-1-yl)benzoic acid (5), and scopoletin (6). From these known compounds, deglucosylanodendrosin A (3) is isolated for the first time from natural sources. The structures of all isolates were determined through spectral analyses and comparison of their physical and spectral data with literatures.
Among the isolated compounds, methyl 4,5-O-feruloyl-3-methoxy- quinate (1), anodendrosin H (4), and 4-hydroxy-3-(3-methylbut-2-en- 1-yl)benzoic acid (5) exhibited potent inhibition against fMLP-induced superoxide (O2•–) production with IC50 values of 24.76 ± 0.45, 27.37 ± 2.28, and 17.65 ± 0.97 M, respectively.

並列關鍵字

Anodendron affine ； Apocynaceae ； anti-inflammatory activity ； structure elucidation

參考文獻

1. Li H. L. & Huang T. C., 1996. ‘Apocynaceae’ in ‘flora of Taiwan’, 2nd ed.; Editorial Committee of the Flora of Taiwan: Taipei, Taiwan, Vol. 4, pp 192-219

2. 呂福原, 歐辰雄, 呂金誠, 臺灣樹木解說(Illustrations of Trees of Taiwan), 行政院農業委員會(Council of Agriculture, Executive Yuan), 2001, Vol. 5; pp 57.

3. 莊溪(2001): 錦蘭。2018年7月24日，取自http://kplant.biodiv.tw/%E9%8C%A6%E8%98%AD/%E9%8C%A6%E8%98%AD.htm

4. Coussens, L.M.; Werb, Z. Inflammation and cancer. Nature, 2002, 420, 860-867.

5. Capece, D.; Fischietti, M.; Verzella, D.; Gaggiano, A.; Cicciarelli, G.; Tessitore A.; Zazzeroni, F.; Alesse, E. The Inflammatory Microenvironment in Hepatocell Carcinoma: A Pivotal Role for Tumor-Associated Macrophages. Biomed Res. Int., 2013, article ID: 187204. (http://dx. doi. org/ 10.1155/2013/187204)