台灣苧麻莖部暨塊莖蘆莉草化學成分之研究

Abstract

第一部分:台灣苧麻莖部化學成分之研究 台灣苧麻 (Boehmeria formosana) 為台灣原生之蕁麻科植物，分布於台灣還有日本及中國大陸。同屬植物具有降血糖、抗B型肝炎，與抗癌等活性。而在本實驗室先前研究中，發現台灣苧麻葉部具有多種菲併吲哚啶(phenanthroindolizidine)與菲併喹啉(phenathroquinolizidine)類生物鹼的成分，文獻中報導具有抗發炎、抗微生物、抗癌、抗痢疾等生物活性。基於上述原因，本研究進而探討此植物之莖部中生物鹼及其他生物活性成分，藉以評估台灣苧麻莖部對於藥用的潛力。 莖部乙醇萃取物以液相-液相分配進行極性分割，得到二氯甲烷、乙酸乙酯、正丁醇層與水四個可溶部分。乙酸乙酯及二氯甲烷可溶部分利用Sephadex LH-20、矽膠正相及逆相和半製備高效能液相層析管柱進行分離，純化並鑑定出10個化合物: para-coumaric acid (1)、5-O-caffeoylshikimic acid (2) taxifolin (3)、eriodictyol (4)、luteolin (5)、quercetin 3-O-α-L-rhamnoside (6)、5,7-dihydroxychromone (7)、ficuseptine (8)、4a,4b-seco-dehydroantofine (9)及(+)-antofine (10)。 上述成分之化學結構主要係藉由一維與二維解析核磁共振譜並搭配質譜資料而得到。文獻報導4a,4b-seco-dehydroantofine (9)及(+)-antofine (10)對於肺癌、肝癌細胞具有抑制作用。 第二部分:塊莖蘆莉草化學成分之研究 塊莖蘆莉草 (Ruellia tuberosa) 原產於中美洲和南美洲熱帶地區，分佈於東南亞印尼、印度、巴基斯坦和臺灣等熱帶地區。此植物為爵床科之蘆利草屬植物，同屬植物具有調控血糖、抗氧化、抗發炎與抗癌等生物活性。因此探討此植物之化學成分，藉以釐清本植物之活性來源成分。 全株乙醇萃取物依序以等體積之正己烷、乙酸乙酯、正丁醇層與水層，以液相-液相分配進行極性分割，共得到四個可溶部分。乙酸乙酯可溶部分利用Sephadex LH-20、矽膠管柱、逆向層析管柱及半製備高效能液相層析管柱進行分離，並純化鑑定出16個化合物: para-hydroxylbenzaldehyde (11)、vanillin (12)、indole-3-carboxaldehyde (13)、cirsimatin (14)、caffeic acid (15)、acteoside (16)、isoacteoside (17)、isonuomioside (18)、fucatoside A (19)、cirsimarin (20)、allantoin (21)、adenine (22)、indole-3-carboxylic acid (23)、tyrosol (24)、stigmasterol (25)、lupeol (26)。 上述成分之結構主要係藉由解析核磁共振譜(氫、碳-13與二維圖譜)並搭配質譜資料而得到。而其中acteoside (16) 具有抗氧化活性，對於血糖與血管收縮素轉換酶(anti-angiotensin-converting enzyme)皆具有抑制效果；isoacteoside (17) 具有抗菌、抗氧化、抗發炎，與肝保護等生物活性。

Part 1: Chemical investigations on the stem of Boehmeria formosana Boehmeria formosana is an indogenous Urticaceae plant of Taiwan, distributed not only in Taiwan, but also in Japan and mainland China. The species from the same genus possess the activities of anti-hyperglycemia, inhibition of HBV production anti-cancer, etc. In the previous studies of our lab, aboundant phenanthroindolizidines and phenathroquinolizidines were isolated from the leaves of B. formosana, and these compounds are reported to demonstrate many biological activities, such as anti-inflammation, anti-microorganism, anti-cancer and anti-dysentery. Thus, the aim of the present study was to investigate the chemical constituents from B. formosana stem and evaluate the potential of B. formosana in medicinal uses. The ethanol extract of the B. formosana stem was divided into four fractions (dichloromethane-, ethyl acetate-, n-butanol-, and water- soluble fractions) by liquid-liquid partition. The ethyl acetate- and dichloromethane- soluble fractions were further separated by Sephadex LH-20, silica gel, RP-18 and semi-preparative RP-18 HPLC chromatography to give 10 compounds, including para-coumaric acid (1), 5-O-caffeoylshikimic acid (2), taxifolin (3), eriodictyol (4), luteolin (5), quercetin 3-O-α-L-rhamnoside (6), 5,7-dihydroxychromone (7), ficuseptine (8), 4a,4b-seco-dehydroantofine (9), and (+)-antofine (10). The structures of the aforementioned compounds were elucidated mainly by spectroscopic analyses of 1D and 2D NMR and assisted by MS data. 4a,4b-seco-dehydroantofine (9) and (+)-antofine (10) were reported to inhibit the growth of lung, liver cancer cells. Part 2: Chemical investigations on whole plant of Ruellia tuberosa Ruellia tuberosa is Acanthaceous herb native to tropical regions of central and south America, and is distributed in Southeast Asia, Indonesia, India, Pakistan and Taiwan. The species of the same genus were reported to possess bioactivities such as anti-glycemia, antioxidation, anti-inflammation, anti-cancer, etc. Therefore, the present study was to investigate the chemical constituents to clarify the resource compounds of its activities. The ethanol extract plant of R. tuberosa was divided into four soluble fractions (n-hexane-, ethyl acetate-, n-butanol-, and water- soluble fractions) by liquid-liquid partition. The ethyl acetate-soluble fraction were further separated by Sephadex LH-20, silica gel, RP-18 and semi-preparative RP-18 HPLC chromatography to give 16 compounds, including para-hydroxylbenzaldehyde (11), vanillin (12), indole-3-carboxaldehyde (13), cirsimatin (14), caffeic acid (15), acteoside (16), isoacteoside (17), isonuomioside (18), fucatoside A (19), cirsimarin (20), allantoin (21), adenine (22), indole-3-carboxylic acid (23), tyrosol (24), stigmasterol (25), and lupeol (26). The structures of the aforementioned compounds were elucidated mainly by 1D and 2D NMR spectroscopic analyses and assisted by MS data. Acteoside (16) was reported to demonstrate antioxidant, anti-angiotensin converting enzyme (ACE) activities and anti-hyperglycemic effect in vitro, isoacteoside (17) exhibited antimicrobial activity against Gram-positive and negative bacteria.