| Summary: | 博士 === 中國醫藥學院 === 中國藥學研究所 === 89 === This study was first based on the investigations and literature survey of plant origin, phytochemistry and pharmacology of Dendrobium genus and Anoectochilus genus. We could understand the plant taxonomy and position of Shi-Hu and Kinsenren. This research provided some information for chemical and pharmacological studies of Shi-Hu and Kinsenren.
In the course of our studies on the constituents and pharmacolo- gical activity of Taiwanese Orchidaceae plants, this study carried out the chemical analysis and in vitro bioactivity tests of three species of Orchidaceae plants－Dendrobium moniliforme SWARTZ, Dendrobium nakaharai SCHLECHTER and Anoectochilus formosanus HAYATA.
Studies on the constituents of D. moniliforme resulted in the isolation of fourteen compounds from n-hexane extract of stems, including heptacosane (1), octacosanyl hexadecanoate (2), methyl and ethyl linolenates (3), 4-methoxybenzaldehyde (4), alkyl trans-ferulates (5), pheophytin a (6), alkyl 4''-hydroxy-cis-cinnamates (7), alkyl 4''-hydroxy-trans-cinnamates (8), stigmast-4-en-3-one (9), phytosterols (10), denbinobin (11), vanillin (12), linoleic acid (13) and heptatriaconsanoic acid (14). Eleven compounds were isolated from ethyl acetate extract of the stems, including alkyl trans-ferulates (5), alkyl 4''-hydroxy-cis-cinnamates (7), alkyl 4''-hydroxy-trans-cinnamates (8), denbinobin (11), aliphatic acids (14), alkyl hexadecanoates (15), alkyl acetates (16), dengibsin (17), moniliquinone (18), moniliformol (19) and diethyl glycol (20). Six compounds were isolated from n-hexane extract of the roots, including alkyl trans-ferulates (5), phytosterols (10), denbinobin (11), aliphatic acids (14), ergosterol (21) and ergosterol peroxide (22). Among these, 18 and 19 were new compounds, and 2, 12, 13, 15, 16, 17 and 20 were the first report of Dendrobium genus.
Studies on the constituents of whole plants of D. nakaharai, seventeen compounds were isolated from n-hexane extract, including alkyl trans-ferulates (5), pheophytin a (6), stigmast-4-en-3-one (9), phytosterols (10), linoleic acid (13), aliphatic acids (14), ergosterol (21), trans-β-carotene (23), 2,3,4,7-tetramethoxyphenanthrene (24), nakaharain (25), aliphatic alcohols (26), nakaquinone (27), 2,5-dihydroxy-3,4-dimethoxyphenanthrene (28), confusarin (29), nudol (30), bulbophyllanthrin (31) and nakaharaiquinone (32). Ten compounds were isolated from ethyl acetate extract, including alkyl trans-ferulates (5), alkyl 4''-hydroxy- cis-cinnamates (7), alkyl 4''-hydroxy-trans-cinnamates (8), protocatechuic acid (33), nakaharain (25), 2,5-dihydroxy-3,4-dimethoxyphenanthrene (28), uracil (34), nakaharoside A (35), nakaharoside B (36) and vitexin (37). Among these, 25, 27, 32, 35 and 36 were new compounds, and 23, 24, 28, 31, 33, 34 and 37 were the first report of Dendrobium genus.
Studies on the constituents of whole plants of A. formosanus, six compounds were isolated from n-hexane extract, including pheophytin a (6), linoleic acid (13), trans-β-carotene (23), 2-methoxy-4-vinylphenol (38), 4-vinylphenol (39) and lutein (40). Five compounds were isolated from ethyl acetate extract, including pheophytin a (6), phytosterols (10), uracil (34), pheophytin b (41) and anoectolide A (42). Four compounds were isolated from methanol extract, including phytosterols (10), anoectolide A (42), anoectolide B (43) and ethyl β-D-glucopyranoside (44). Among these, 42 and 43 were new compounds, and 6, 13, 23, 34, 38, 39, 40, 41 and 44 were first report of A. formosanus.
In the anti-inflammatory and anti-allergic assays, the crude extracts of D. nakaharai and A. formosanus significantly inhibited the release of β-glucuronidase and lysozyme on neutrophil degranulation induced by fMLP in vitro and inhibited the release of β-glucuronidase and histamine on mast cells induced by compound 48/80 in vitro. In addition, the anti-inflammatory and anti-allergic activities of eleven compounds were investigated.
1. The isolated compounds from D. nakaharai showed that a new compound, 25 had not benefit in anti-inflammation and anti-allergy. 28 had better anti-inflammation against neutrophil. 33, 34 and 37 may have inhibition of the inflammatory against neutrophil.
2. The isolated compounds from D. moniliforme showed that 4 may have effect of anti-inflammatory against the neutrophil superoxide formation. 11 may have benefit in controlling central and peripheral inflammation as well as allergy against mast cell. 12 had inhibition against neutrophil.
3. The isolated compounds from A. formosanus showed that 6, 13 and 23 may have benefit in controlling neutrophil and peripheral inflammation.
However, other compounds are still under test.
頁 數
目錄 i
圖表目錄 iv
中文摘要 xv
英文摘要 xviii
第一章 緒論 1
第一節 研究之背景及目的 1
第二節 植物基原考察 2
一、石斛之植物學分類 2
二、金線連之植物學分類 2
三、蘭科植物之特徵 3
四、植物之形態與生長特性 8
第三節 化學成分考察 11
一、石斛屬植物之化學成分 11
二、石斛屬植物成分之化學結構 14
三、開唇蘭屬(金線連屬)植物之化學成分 23
四、開唇蘭屬植物成分之化學結構 24
第四節 藥理活性考察 27
一、石斛之藥理活性 27
二、金線連之藥理活性 31
第五節 抗發炎及抗過敏活性試驗簡介 34
第二章 實驗部分 36
第一節 實驗材料 36
第二節 試藥與材料 36
第三節 實驗儀器 38
第四節 植物成分之抽取與分離 40
一、石斛之抽取與分離 40
二、連珠石斛之抽取與分離 48
三、臺灣金線連之抽取與分離 68
第五節 抗發炎及抗過敏實驗方法 81
一、嗜中性白血球(Neutrophils )的去顆粒作用 81
二、肥滿細胞(Mast cells)的去顆粒作用 82
三、NO的測定 82
四、TNF-α和PGE2的測定 83
五、統計方法 83
第三章 結果與討論 84
第一節 化合物之結構決定 84
一、Phenanthrene類化合物 84
二、Phenanthraquinone (phenanthrene-1,4-quinone)類化合物 117
三、9,10-Dihydrophenanthraquinone 類化合物 130
四、Phenanthradiquinone 類化合物 137
五、Fluorenone類化合物 143
六、Flavonoid類化合物 149
七、Benzene和Phenol 類化合物 173
八、Carotenoid類化合物 217
九、Chlorophyll類化合物 225
十、Sterol類化合物 240
十一、Fatty acid or ester類化合物 256
十二、Pyrimidine類化合物 267
十三、Sugar類化合物 270
十四、其它 275
第二節 抗發炎及抗過敏之藥理活性 286
一、連珠石斛粗抽物之抗發炎及抗過敏試驗 286
二、DNE-I~DNE-VI之抗發炎及抗過敏試驗 288
三、臺灣金線連粗抽物之抗發炎及抗過敏試驗 291
四、化合物之抗發炎及抗過敏試驗 292
第三節 化合物之光譜數據 303
第四節 分離之成分的化學結構 322
第四章 結論 326
第一節 植物化學成分 326
第二節 抗發炎及抗過敏活性試驗 328
參考文獻 329
著者學經歷表 342
學術著作目錄 343
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