中草藥成分之研究 - 白珠樹、馬藍、三消草、檄樹果實、馬蘭與補骨脂
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2007
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本論文主要是從事植物成分與定量分析之研究，共分六部分:
第一部分為白珠樹(Gaultheria leucocarpa Bl. f. cumingiana ( Vidal ))之成分研究。白珠樹為杜鵑花科(Ericaceae)植物，本實驗自白珠樹地上部之甲醇抽出物經由各種管柱層析進行化學成分之分離，共純化出12-hydroxy-13-acetyl -8,11,13-podocarpatrien-18-oic acid (GL-1), 4,12-dihydroxy-13-acetyl-8,11,13-podocarpatriene (GL-2), 5-methoxy-9- xylopyranosyl-(+)-isolariciresinol (GL-3), schizandriside (GL-4), lyoniside (GL-5), Vanillic acid (GL-6), Scopoletin (GL-7)七個化合物，其中GL-1GL-3三個新化合物經由各種光譜資料分析，已知化合物GL-4GL-7藉由文獻資料比對確立其構造。
第二部分為馬藍(Strobilanthes cusia (Nees) Kuntze)之成分研究。馬藍為爵床科（Acanthaceae）植物，本實驗自馬藍全草之甲醇抽出物經由各種管柱層析進行化學成分之分離，共純化出2-hydroxyquinazolin-4(1H)-one (SC-1), 2,4(1H, 3H)-quinazolinedione (SC-2), 4-methoxy-2(1H)- quinazolineone (SC-3), 2-hydroxy-1,4-benzoxazin-3-one (SC-4), 2- benzoxazolinone (SC-5), indirubin (SC-6), tryptanthrin (SC-7), lupeol (SC-8), betulin (SC-9), 1-hydroxy-3-methyl-5,10anthraquinone (SC-10)十個化合物，其中包含SC-1一個新化合物經由各種光譜資料分析，已知化合物SC-2 SC-10藉由文獻資料比對確立其構造。
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第三部分為三消草(Ruellia tuberosa L.)之成分研究。三消草Ruellia tuberosa L.為爵床科 Acanthaceae 植物，本實驗自三消草全草之甲醇抽出物經由各種管柱層析進行化學成分之分離，共純化出cirsimaritin (RT-1), cirsimarin (RT-2), cirsiliol 4’-glucoside (RT-3), sorbifolin (RT-4), pedalitin (RT-5), Betulin (RT-6), Vanillic acid (RT-7), Indole-3-carboxaldehyde (RT-8)八個已知化合物，藉由文獻資料比對確立其構造。經細胞毒性試驗證實cirsimaritin (RT-1)和cirsiliol 4’-glucoside (RT-3)對 KB 細胞有抑制效果，其IC50分別為95.7及36.4 M而cirsimarin (RT-2)則對 HepG2 cell 有抑制效果，其IC50為81.5 M。
第四部分為檄樹(Morinda citrifolia Linn.)果實noni之成分研究。檄樹為茜草科Rubiaceae植物，本實驗自其果實noni之乙醇抽出物經由各種管柱層析進行化學成分之分離，共純化出1,6-dihydroxy-5-methoxy-2-methoxymethylanthraquinone (MC-1), 1,5,7-trihydroxy -6- methoxy-2-methoxymethylanthraquinone (MC-2), isoamericanoic acid A (MC-3), americanin A (MC-4), americanin D (MC-5), 3,3’-bisdemethylpinoresinol (MC-6), luteolin (MC-7), scopoletin (MC-8), 3-methoxy-2-hydroxyl-cinnamaldehyde (MC-9), p-cresol(MC-10), p-hydroxybenzoic acid (MC-11), p-hydroxybenzaldehyde (MC-12), 3-methoxy-4-hydroxy-benzaldehyde (MC-13), 2,5-dihydroxy-4-methoxybenzaldehyde (MC-14)十四個化合物，其中MC-1 MC-3三個新化合物經由各種光譜資料分析，已知化合物MC-4 MC-14藉由文獻資料比對確立其構造。
第五部分為馬蘭(Aster indicus L.; Kalimeris indica (L.) Sch. Bip.)之成分研究。馬蘭為菊科(Compositae)植物，本實驗自馬蘭全草之酒精抽出物經由各種管柱層析進行化學成分之分離，共純化出4-hydroxy-3-1-(methoxycarbonyl)vinyloxybenzoic acid (AI-1), 5-(1- carboxylvinyloxy)-2-hydroxybenzoic acid (AI-2), 4-allyl-2,6-dimethoxyphenyl 3-methylbutanoate (AI-3), 4-Allyl-2-methoxyphenyl 2-methylbutanoate (AI-4), 3-(1-carbonylvinyloxy -4-hydroxybenzoic acid (AI-5), 4-hydroxybenzaldehyde (AI-6), vanillin (AI-7), vanillic acid (AI-8), friedelin (AI-9), trans-cosanyl ferulate (AI -10), methyl 3-O-caffeoyl quinate (AI-11), 1H-indole -3-carboxaldehyde (AI-12), methyl 3-O-feruloylquinate (AI-13), methyl trans -ferulate (AI -14), arillatoses B (AI -15), erulic acid (AI -16), p-coumaric acid (AI -17), 1H-indole-3-carboxylic acid (AI-18), kaempferol-7-O--D- glucopyranoside (AI-19), isoquercitrin (AI-20), apigenin-7-O-(6-methyl ester) -glucuronide (AI-21), kaempferol (AI-22), quercetin (AI-23), 4-hydroxy benzoic acid (AI-24), 3,4-dihydroxybenzoic acid (AI-25), rutin (AI-26), nicotiflorin (AI-27), methyl 3,4-di-O-caffeoyl quinate (AI-28), 3,5-di-O- caffeoylquinic acid (AI-29), methyl 3,5-di-O-caffeoyl quinate (AI-30), 1,3-di-O-caffeoylquinic acid (AI-31)三十一個化合物，其中AI-1AI-4四個新化合物經由各種光譜資料分析，已知化合物AI-5AI-14藉由文獻資料比對確立其構造。
第六部分為補骨脂(Fructus Psoraleae)及其濃縮製劑中bakuchiol、psoralen 及angelicin之含量分析研究。補骨脂(Fructus Psoraleae)為豆科植物(Psoralea corylifolia L.)補骨脂的成熟果實，本實驗利用高效液相層析儀開發補骨脂 Psoralea corylifolia L. 中 bakuchiol, psoralen 和 angelicin 三種指標成分之同時定量分析方法。三種指標成分之intra-day試驗RSD值為 0.32~1.50 % ; inter-day試驗 RSD值為 0.20~1.03 %。針對十八種樣品進行定量分析，結果 bakuchiol, psoralen 和 angelicin 於十種生藥材中之含量範圍分別為 36.2971.06, 2.5413.07 和 2.279.21 mg/g；而於八種市售濃縮製劑中之含量範圍則分別為 0.6221.16, 0.635.23 和 0.675.37 mg/g。
The purpose of this study is to investigate the chemical constituents and quantitative analysis. There are six parts in this study. The first part is the study on the constituents of Gaultheria leucocarpa Bl. f. cumingiana ( Vidal ). The methanolic extract of the aerial part of G. leucocarpa (Ericaceae) was separated by column chromatography to afford seven compounds, including 12-hydroxy-13-acetyl-8,11,13-podocarpatrien -18-oic acid (GL-1), 4,12-hydroxy-13-acetyl-8,11,13-podocarpatriene (GL- 2), 5-methoxy-9-xylopyranosyl-(+)-isolariciresinol (GL-3), schizandriside (GL-4), lyoniside (GL-5), vanillic acid (GL-6), scopoletin (GL-7). The structures of new compounds GL-1GL-3 were established by spectral analyses. The known compounds GL-4GL-7 were identified by comparison of their spectral data with those in the literature. The second part is the study on the constituents of Strobilanthes cusia (Nees) O. Kuntze. The methanolic extract of the whole herbs of S. cusia （Acanthaceae） was separated by column chromatography to afford ten compounds, including 2-hydroxyquinazolin-4(1H)-one (SC-1), 2,4(1H, 3H)-quinazolinedione (SC-2), 4-methoxy-2(1H)-quinazolineone (SC-3), 2-hydroxy-1,4-benzoxazin-3-one (SC-4), 2-benzoxazolinone (SC-5), indirubin (SC-6), tryptanthrin (SC-7), lupeol (SC-8), betulin (SC-9), 1-hydroxy -3-methyl-5,10anthraquinone (SC-10). The structure of new compound SC-1 was established by spectral analyses. The known compounds SC-2SC-10 were identified by comparison of their spectral data with those in the literature. The third part is the study on the constituents of Ruellia tuberosa L.. The methanolic extract of the whole herbs of R. tuberosa （Acanthaceae） was separated by column chromatography to afford eight compounds, including cirsimaritin (RT-1), cirsimarin (RT-2), cirsiliol 4’-glucoside (RT-3), sorbifolin (RT-4), pedalitin (RT-5), Betulin (RT-6), Vanillic acid (RT-7), Indole-3- carboxaldehyde (RT-8). The structures of these compounds were identified by comparison of their spectral data with those in the literature. Furthermore, these compounds were also examined for their antiproliferative effects on HepG2 and KB cancer cell lines. Compounds cirsimaritin (RT-1) and cirsiliol 4’-glucoside (RT-3) showed cytotoxic effects against the KB cell line with IC50 values of 95.7 and 36.4 M respectively, while cirsimarin (RT-2) exhibited a cytotoxic effect against against the HepG2 cell line with an IC50 value of 81.5 M. The fourth part is the study on the constituents of Morinda citrifolia. The ethanolic extract of the fruit of Morinda citrifolia (Rubiaceae) was separated by column chromatography to afford fourteen compounds, including 1,6-dihydroxy-5-methoxy-2-methoxymethylanthraquinone (MC-1), 1,5,7- trihydroxy-6-methoxy-2-methoxymethylanthraquinone (MC-2), isoamericanoic acid A (MC-3), americanin A (MC-4), americanin D (MC-5), 3,3’- bisdemethylpinoresinol (MC-6), luteolin (MC-7), scopoletin (MC-8), 3-methoxy-2-hydroxyl-cinnamaldehyde (MC-9), p-cresol(MC-10), p-hydroxybenzoic acid (MC-11), p-hydroxybenzaldehyde (MC-12), 3-methoxy-4-hydroxy-benzaldehyde (MC-13), 2,5-dihydroxy-4-methoxy benzaldehyde (MC-14). The structures of new compounds MC-1 MC-3 were established by spectral analyses. The known compounds MC-4 MC-14 were identified by comparison of their spectral data with those in the literature. The fifth part is the study on the constituents of Aster indicus L.. A. indicus. The ethanolic extract of the whole herbs of A. indicus L.(Compositae) was separated by column chromatography to afford thirty-one compounds, including 4-hydroxy-3-1-(methoxycarbonyl)vinyloxybenzoic acid (AI-1), 5-(1-carboxylvinyloxy)-2-hydroxybenzoic acid (AI-2),4-allyl-2,6- dimethoxyphenyl 3-methylbutanoate (AI-3), 4-Allyl-2-methoxyphenyl 2-methylbutanoate (AI-4), 3-(1-carbonylvinyloxy -4-hydroxybenzoic acid (AI-5), 4-hydroxybenzaldehyde (AI-6), vanillin (AI-7), vanillic acid (AI-8), friedelin (AI-9), trans-cosanyl ferulate (AI -10), methyl 3-O-caffeoyl quinate (AI-11), 1H-indole-3-carboxaldehyde (AI-12), methyl 3-O-feruloylquinate (AI-13), methyl trans-ferulate (AI -14), arillatoses B (AI -15), erulic acid (AI -16), p-coumaric acid (AI -17), 1H-indole-3-carboxylic acid (AI-18), kaempferol-7-O--D-glucopyranoside (AI-19), isoquercitrin (AI-20), apigenin-7-O-(6-methyl ester)-glucuronide (AI-21), kaempferol (AI-22), quercetin (AI-23), 4-hydroxybenzoic acid (AI-24), 3,4-dihydroxybenzoic acid (AI-25), rutin (AI-26), nicotiflorin (AI-27), methyl 3,4-di-O-caffeoyl quinate (AI-28), 3,5-di-O-caffeoylquinic acid (AI-29), methyl 3,5-di-O-caffeoyl quinate (AI-30), 1,3-di-O-caffeoylquinic acid (AI-31). The structures of new compounds AI-1AI-4 were established by spectral analyses. The known compounds AI-5AI-31 were identified by comparison of their spectral data with those in the literature. The last part is the study on the bakuchiol, psoralen, and angelicin content of Fructus Psoraleae and its commercial concentrated products. Bakuchiol, psoralen and angelicin are bioactive constituents of Fructus Psoraleae (Buguzhi, the seeds of Psoralea corylifolia). The present study provides details of an HPLC method for the separation of bakuchiol, psoralen, and angelicin in Fructus Psoraleae. The relative standard deviation of the marker substances for intraday and interday analyses were 0.321.50 % and 0.201.03 %, respectively. The bakuchiol, psoralen and angelicin contents ranged between 36.2971.06, 2.5413.07 and 2.279.21 mg/g for ten raw material samples of Fructus Psoraleae, and 0.6221.16, 0.635.23 and 0.675.37 mg/g for eight commercial concentrated products of Fructus Psoraleae.
The purpose of this study is to investigate the chemical constituents and quantitative analysis. There are six parts in this study. The first part is the study on the constituents of Gaultheria leucocarpa Bl. f. cumingiana ( Vidal ). The methanolic extract of the aerial part of G. leucocarpa (Ericaceae) was separated by column chromatography to afford seven compounds, including 12-hydroxy-13-acetyl-8,11,13-podocarpatrien -18-oic acid (GL-1), 4,12-hydroxy-13-acetyl-8,11,13-podocarpatriene (GL- 2), 5-methoxy-9-xylopyranosyl-(+)-isolariciresinol (GL-3), schizandriside (GL-4), lyoniside (GL-5), vanillic acid (GL-6), scopoletin (GL-7). The structures of new compounds GL-1GL-3 were established by spectral analyses. The known compounds GL-4GL-7 were identified by comparison of their spectral data with those in the literature. The second part is the study on the constituents of Strobilanthes cusia (Nees) O. Kuntze. The methanolic extract of the whole herbs of S. cusia （Acanthaceae） was separated by column chromatography to afford ten compounds, including 2-hydroxyquinazolin-4(1H)-one (SC-1), 2,4(1H, 3H)-quinazolinedione (SC-2), 4-methoxy-2(1H)-quinazolineone (SC-3), 2-hydroxy-1,4-benzoxazin-3-one (SC-4), 2-benzoxazolinone (SC-5), indirubin (SC-6), tryptanthrin (SC-7), lupeol (SC-8), betulin (SC-9), 1-hydroxy -3-methyl-5,10anthraquinone (SC-10). The structure of new compound SC-1 was established by spectral analyses. The known compounds SC-2SC-10 were identified by comparison of their spectral data with those in the literature. The third part is the study on the constituents of Ruellia tuberosa L.. The methanolic extract of the whole herbs of R. tuberosa （Acanthaceae） was separated by column chromatography to afford eight compounds, including cirsimaritin (RT-1), cirsimarin (RT-2), cirsiliol 4’-glucoside (RT-3), sorbifolin (RT-4), pedalitin (RT-5), Betulin (RT-6), Vanillic acid (RT-7), Indole-3- carboxaldehyde (RT-8). The structures of these compounds were identified by comparison of their spectral data with those in the literature. Furthermore, these compounds were also examined for their antiproliferative effects on HepG2 and KB cancer cell lines. Compounds cirsimaritin (RT-1) and cirsiliol 4’-glucoside (RT-3) showed cytotoxic effects against the KB cell line with IC50 values of 95.7 and 36.4 M respectively, while cirsimarin (RT-2) exhibited a cytotoxic effect against against the HepG2 cell line with an IC50 value of 81.5 M. The fourth part is the study on the constituents of Morinda citrifolia. The ethanolic extract of the fruit of Morinda citrifolia (Rubiaceae) was separated by column chromatography to afford fourteen compounds, including 1,6-dihydroxy-5-methoxy-2-methoxymethylanthraquinone (MC-1), 1,5,7- trihydroxy-6-methoxy-2-methoxymethylanthraquinone (MC-2), isoamericanoic acid A (MC-3), americanin A (MC-4), americanin D (MC-5), 3,3’- bisdemethylpinoresinol (MC-6), luteolin (MC-7), scopoletin (MC-8), 3-methoxy-2-hydroxyl-cinnamaldehyde (MC-9), p-cresol(MC-10), p-hydroxybenzoic acid (MC-11), p-hydroxybenzaldehyde (MC-12), 3-methoxy-4-hydroxy-benzaldehyde (MC-13), 2,5-dihydroxy-4-methoxy benzaldehyde (MC-14). The structures of new compounds MC-1 MC-3 were established by spectral analyses. The known compounds MC-4 MC-14 were identified by comparison of their spectral data with those in the literature. The fifth part is the study on the constituents of Aster indicus L.. A. indicus. The ethanolic extract of the whole herbs of A. indicus L.(Compositae) was separated by column chromatography to afford thirty-one compounds, including 4-hydroxy-3-1-(methoxycarbonyl)vinyloxybenzoic acid (AI-1), 5-(1-carboxylvinyloxy)-2-hydroxybenzoic acid (AI-2),4-allyl-2,6- dimethoxyphenyl 3-methylbutanoate (AI-3), 4-Allyl-2-methoxyphenyl 2-methylbutanoate (AI-4), 3-(1-carbonylvinyloxy -4-hydroxybenzoic acid (AI-5), 4-hydroxybenzaldehyde (AI-6), vanillin (AI-7), vanillic acid (AI-8), friedelin (AI-9), trans-cosanyl ferulate (AI -10), methyl 3-O-caffeoyl quinate (AI-11), 1H-indole-3-carboxaldehyde (AI-12), methyl 3-O-feruloylquinate (AI-13), methyl trans-ferulate (AI -14), arillatoses B (AI -15), erulic acid (AI -16), p-coumaric acid (AI -17), 1H-indole-3-carboxylic acid (AI-18), kaempferol-7-O--D-glucopyranoside (AI-19), isoquercitrin (AI-20), apigenin-7-O-(6-methyl ester)-glucuronide (AI-21), kaempferol (AI-22), quercetin (AI-23), 4-hydroxybenzoic acid (AI-24), 3,4-dihydroxybenzoic acid (AI-25), rutin (AI-26), nicotiflorin (AI-27), methyl 3,4-di-O-caffeoyl quinate (AI-28), 3,5-di-O-caffeoylquinic acid (AI-29), methyl 3,5-di-O-caffeoyl quinate (AI-30), 1,3-di-O-caffeoylquinic acid (AI-31). The structures of new compounds AI-1AI-4 were established by spectral analyses. The known compounds AI-5AI-31 were identified by comparison of their spectral data with those in the literature. The last part is the study on the bakuchiol, psoralen, and angelicin content of Fructus Psoraleae and its commercial concentrated products. Bakuchiol, psoralen and angelicin are bioactive constituents of Fructus Psoraleae (Buguzhi, the seeds of Psoralea corylifolia). The present study provides details of an HPLC method for the separation of bakuchiol, psoralen, and angelicin in Fructus Psoraleae. The relative standard deviation of the marker substances for intraday and interday analyses were 0.321.50 % and 0.201.03 %, respectively. The bakuchiol, psoralen and angelicin contents ranged between 36.2971.06, 2.5413.07 and 2.279.21 mg/g for ten raw material samples of Fructus Psoraleae, and 0.6221.16, 0.635.23 and 0.675.37 mg/g for eight commercial concentrated products of Fructus Psoraleae.
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Keywords
白珠樹, 馬藍, 三消草, 檄樹, 馬蘭, 補骨脂, Gaultheria leucocarpa, Strobilanthes cusia, Ruellia tuberosa, Morinda citrifolia, noni, Aster indicus, Gaultheria leucocarpa, bakuchiol, psoralen, angelicin