指甲花葉部的化學成分及其抗發炎活性之研究

Study on Chemical Constituents from the Leaves of Lawsonia inermis Linn. and their Anti-inflammatory Activity

劉金茹(Jing-Rou Liou)

指導教授 ： 張芳榮

高雄醫學大學/藥學院/天然藥物研究所碩士班/碩士(2011年)

摘要

千屈菜科(Lythraceae)指甲花是單種屬指甲花屬，原生於北非和西南亞洲，廣泛作為栽培做庭園裝飾和染料使用。此藥用植物指甲花具有廣泛抗菌效果，包括抗菌、抗病毒、抗黴菌和抗原蟲活性。在本篇研究中，我們將針對研究指甲花的葉部進行化學成分分離、結構鑑定，以及生物活性探討。
台灣產的指甲花(Lawsonia inermis Linn.)葉部之甲醇抽取物，進行分配萃取，得四個萃取物並依極性高低分別為水層、正丁醇層、75%甲醇水溶液層和正己烷層。將四個萃取物分別經過抗發炎活性藥理活性篩選，發現正己烷層和75%甲醇水溶液層具有強抑制人類fMLP/CB 所誘導之superoxide anion generation和elastase release的活性，其有效抑制濃度值10 μg/mL時，分別為(正己烷層：75.33 ± 7.69 %、78.79 ± 5.51 %；75%甲醇水溶液層：80.52 ± 6.56 %、98.38 ± 1.41 % 抑制百分率。正丁醇層也顯示具有抗發炎之能力(55.91 ± 5.50 %、62.82 ± 7.12 % 抑制百分率)。
經由活性導引分析，由75%甲醇水溶液層和正丁醇層分離得到19個化合物，分別為luteolin (1) 、apigenin (2) 、luteolin 4?S-O-glucoside (3) 、1,2,4-trihydroxynaphthalene-1-O-β-D-glycopyranoside (4) 、2,4,6-
trihydroxyacetophenone-2-O-β-D-glucopyranoside (5) 、Lawacetophenol (6) 、2-butoxy-tetrahydro-6-(hydroxymethyl)-2H-pyran-3,4,5-triol (7) 、D-glucopyranose (8) 、D-mannitol (9) 、methyl pheophorbide b (10) 、 linolenic acid (11) 、 oleic acid (12) 、oleamide (13) 、 4-hydroxy-4H-isochromene-1,3-dione (14) 、 a mixture of trans-p-coumaric acid (15) and cis-p-coumaric acid (16) 、 a mixture of (E)-3-(4-hydroxyphenyl) acrylamide (17) and (Z)-3-(4-hydroxyphenyl)-acrylamide (18) 、 a mixture of β-stigmasteryl (19) and β-sitosterol (20) 、 a mixture of β-sitostery-3-O-β-D-glucoside (21) and stigmasteryl-3-O-β-D-glucoside (22) 、 2-butoxysuccinic acid (23)。化合物4是2011年其他研究團隊剛發表的新化合物、該論文中化合物5也被同時發表為首次分離於此植物之化合物。化合物6和化合物14為本研究首次發現之新化合物。

關鍵字

千屈菜科 ； 指甲花

並列摘要

Lawsonia is a monotypic genus represented by Lawsonia inermis Linn. (syn. Lawsonia alba Lam, Lythraceae), a native plant of North Africa and Southwestern Asia, widely cultivated as an ornamental hedge and dye-plant. The medicinal plant, henna (L. inermis), has a wide spectrum of antimicrobial activity including antibacterial, antiviral, antimycotic and antiparasitic activities. In the present study, we reported bioactivity-guided fractionation and isolation as well as structural elucidation of isolates from leaves of henna.
The MeOH extract of the leaves was partitioned into n-hexane, 75% MeOH(aq), n-BuOH, and H2O-soluble fractions. Among them, n-hexane and 75% MeOH(aq) fractions showed strong inhibitory effect on superoxide anion and elastase release of neutrophils induced by fMLP at 10 μg/mL with inhibitory percentage values of 75.33 ± 7.69 % , 78.79 ± 5.51 % , and 80.52 ± 6.56 % , 98.38 ± 1.41 %. n-BuOH fraction also showed moderate inhibitory effect (55.91 ± 5.50 %, 62.82 ± 7.12 %).
Nineteen compounds, including luteolin (1), apigenin (2), luteolin 4?S-O-glucoside (3), 1,2,4-trihydroxynaphthalene-1-O-β-D-glycopyranoside (4), 2,4,6-trihydroxyacetophenone-2-O-β-D-glucopyranoside (5), lawacetophenol (6), 2-butoxy-tetrahydro-6-(hydroxymethyl)-2H-pyran-3,4,5-triol (7), D-glucopyranose (8), D-mannitol (9), methyl pheophorbide b (10), linolenic acid (11), oleic acid (12), oleamide (13), 4-hydroxy-4H-isochromene-1,3-dione (14), a mixture of trans-p-coumaric acid (15) and cis-p-coumaric acid (15), a mixture of (E)-3-(4-hydroxyphenyl)acrylamide (17) and (Z)-3-(4-hydroxyphenyl)-acrylamide (18), a mixture of β-stigmasteryl (19) and β-sitosterol (20), a mixture of β-sitostery-3-O-β-D-glucoside (21) and stigmasteryl-3-O-β-D-glucoside (22), and 2-butoxysuccinic acid (23) were isolated from the 75% MeOH(aq) and n-BuOH fractions. Compound 4 was new and compound 5 was reported for the first time from this plant, which were revealed by the other research team in 2011. Compound 6 and compound 14 are new compounds.

並列關鍵字

Lythraceae ； Lawsonia inermis Linn.

參考文獻

1. 樓迎統, 陳君侃, 黃榮棋, 王錫五, 實用生理學 三版,偉華書局有限公司, 2003, 473-477.

2. 吳天鳴, 朱延和, 細菌的抗藥性,科學發展, 2003, 364, 64-73.

3. Y. L. Chuang, Studies on the chemical constituents and anti-inflammatory activity of stems of Lawsonia inermis Linn, Master thesis, Graduate Institute of Natural products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan, 2007.

4. J. Auboyer, Daily Life in Ancient India from 200 BC to 700 AD. London: Phoenix Press, 1965.

5. R. Fletcher, Moorish Spain Henry Holt and Company, New York, 1992.