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研究生: 莊武璋
Chuang, Wu-Chang
論文名稱: 中藥成份高效能液相層析研究
The research of analyzing chemical constituents in Chinese herbs
指導教授: 許順吉
Xu, Shun-Ji
學位類別: 博士
Doctor
系所名稱: 化學系
Department of Chemistry
畢業學年度: 84
語文別: 中文
論文頁數: 5
中文關鍵詞: 高效能液相層析人參芍藥吳茱萸液相層析質譜黃連
英文關鍵詞: HPLC, Ginseng Radix, Paeoniae Radix, Evodia Fructus, LC-MS, Coptidis Rhizoma
論文種類: 學術論文
相關次數: 點閱:455下載:9
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  • 高效能液相層析法 (HPLC) 是目前最為普通中藥的分析
    方法。本論文包含三部分,第一部分是開發出分析人參、芍藥和吳茱萸的
    HPLC 分析方法,並對流動相的組成與管柱的選擇作一系統探討。人參中
    的十二個人參皂素 (ginsenoside Rb1、 Rb2、 Rc、 Rd、 Re、 Rf、
    Rg1、 Rg2、 Ro 、mRb1、 mRb2、 mRc) 可用 Cosmosil 5C18 分離管柱
    在 10 mM KH2PO4-CH3CN 流動相系統,配合梯度沖提在 45 分鐘內完成分
    析定量。芍藥中的八個藥效成分 (gallic acid、 oxypaeoniflorin、
    albiflorin、 paeoniflorin、 benzoic acid、 pentagalloylglucose、
    paeonol、 benzoylalbiflorin) 可用 Cosmosil 5C18-MS 分離管柱在
    0.1% H3PO4-50 mM KH2PO4-CH3CN 流動相系統,配合梯度沖提在 60 分鐘
    內完成分析定量。吳茱萸中的十二個生物鹼成分 (carboxyevodiamine、
    dehydroevodiamine、 evodiamine、 rutaecarpine、 1-methyl-2-
    nonyl-4(1H)-quinolone、 1-methyl-2-[(Z)-6-undecenyl]-4(1H)-
    quinolone、 1-methyl-2-undecyl-4(1H)-quinolone、 evocarpine、
    1-methyl-2-[(6Z,9Z)-6,9-pentadecadienyl]-4(1H)-quinolone、
    dihydroevocarpine、 1-methyl-2-[(Z)-10-pentadecenyl]-4(1H)-
    quinolone、 1-methyl-2-[(Z)-6-pentadecenyl]-4(1H)-quinolone) 可
    用 Capcell SG-120 分離管柱在 1.25% HOAC-30 mM NaOAc-CH3CN-CH3OH
    流動相系統,配合梯度沖提在 45 分鐘內完成分析定量。第二部分是將由
    第一部分所開發的分析方法應用於市售藥材的比較研究,利用特有成分的
    定量結果及各成分間的比例關係,建立植物的化學成分指紋圖譜,推斷藥
    材基源,並獲知藥物品質。粉光參和三七人參的人參皂素總含量高於高麗
    人參,白參、紅參和石柱參中較高含量的成分是 Rb1 和 Rg1 ,參鬚則是
    Rb1 和 Re,三七人參是 Rb1、 Rg1 和 Rd,粉光參是 Rb1、 Re 和 mRb1
    ,另外粉光參中不含 Rf 和 Rg2,紅參和石柱參中幾不含
    malonylginsenosides。白芍的藥效成分總含量高於赤芍,白芍中較高含
    量的成分為 paeoniflorin、 albiflorin 和 pentagalloylglucose,赤
    芍中為 paeoniflorin、 pentagalloylglucose 和 oxypaeoniflorin,白
    芍的 albiflorin/oxypaeoniflorin 比值高於 1,而赤芍則是小於 1,可
    用來區辨兩者。吳茱萸藥材中開口者的含量遠高於閉口者,開口者中含量
    較高者為 dehydroevodiamine、 evodiamine、 evocarpine 和
    rutaecarpine,閉口者中含量較高者則為 dehydroevodiamine、
    evodioside B 和 epimedoside C。液相層析質譜法 (LC/MS) 是將液相層
    析儀 (LC) 和質譜儀 (MS) 相銜接的一種分析技術,第三部分乃利用 LC-
    UV-ESI-MS 的連線作業發展一種分析鑑定黃連中七個生物鹼 (berberine
    、 palmatine、 coptisine、 epiberberine、 jatrorrhizine、
    columbamine 和 berberastine) 的方法,萃取液不需經前處理,可直接
    分析。並利用此方法辨識黃連成分熱解產物 berberrubine、
    palmatrubine、 jatrorrhizrubine 和 columbamrubine。

    The chemical constituents in Chinese herb drugs are
    always very complicated and HPLC is regarded as their most
    conveniently analytical tool up to now. This dissertation
    contains three parts. The first part concerns the development of
    three direct and rapid HPLC methods for determining the chemical
    constituents in Ginseng Radix, Paeoniae Radix and Evodiae
    Fructus respectively. The effects of mobile phase and column
    selectivity and the validation of of these methods are also
    discussion.In Ginseng Radix, components such as ginsnosides-Rb1,
    Rb2, Rc, Rd, Re, Rf, Rg1, Rg2, Ro and malonylginsenosides Rb1,
    Rb2 and mRc could be separated successfully. Detection at 198 nm
    by using a Cosmosil 5C18 column with a linear gradient elution
    of 10 mM KH2PO4-CH3CN (far-UV grade) was found to be the most
    suitable and the contents of the ginsenosides in a non-
    pretreated methanol-water extract could easily be determined
    within 45 min. In Paeoniae Radix, eight compounds (gallic acid,
    oxypaeoniflorin, albiflorin, paeoniflorin, benzoic acid,
    pentagalloylglucose, paeonol and benzoylalbiflorin) could be
    determined easily within 40 min. The method is carried out by
    using a Cosmosil 5C18-MS column with a gradient solvent system
    of 0.1% H3PO4-50 mM KH2PO4-CH3CN and a UV detector (254 nm). And
    a method for the simultaneous determination of four
    indolequinazoline alkaloids (carboxyevodiamine,
    dehydroevodiamine, evodiamine and rutaecarpine) and eight
    quinolone alkaloids (1-methyl-2-nonyl-4(1H)-quinolone,
    1-methyl-2-[(Z)-6-undecenyl]-4(1H)-quinolone, 1-methyl-2-
    undecyl-4(1H)-quinolone, evocarpine, 1-methyl-2-[(6Z,9Z)-6,9-
    pentadecadienyl]-4(1H)-quinolone, dihydroevocarpine, 1-methyl-2-
    [(Z)-10-pentadecenyl]-4(1H)-quinolone and 1-methyl-2-[(Z)-6-
    pentadecenyl]-4(1H)-quinolone) in Evodiae Fructus was also
    developed. The method was carried out by using a Capcell C18
    SG-120 column with a gradient solvent system of acetate buffer-
    acetonitrile-methanol and a UV detector (250 nm), and the
    contents of the alkaloids in a non-pretreatment Evodiae Fructus
    extract could easily be determined within 40 minutes. In the
    second part, we used these methods listed above to evaluate the
    three Chinese herb drugs and found that there were great
    difference existed in each herb either the ratios or amounts of
    the individual constituents. After closely comparing the HPLC
    chromatogram and the morphological characters of various
    samples, a significant relationship between the species and the
    chemical constituents have been postulated. It was found that
    the saponin contents in P. notoginseng and P. quinquefolia were
    generally higher than in P. ginseng. The ginsenosides that were
    of the highest contents in the white-ginseng, red-ginseng and
    shihchu-ginseng samples of P. ginseng were Rb1 and Rg1, that in
    the root-hair of P. ginseng were Rb1 and Re, that in P.
    notoginseng were Rb1, Rg1 and Rd, and that in P. quinquefolia
    were Rb1, Re and mRb1. Among the samples, those of P.
    quinquefolia did not contain Rf and Rg2, whilst those of
    shihchu-ginseng and red-ginseng of P. ginseng contained none or
    only trace of malonylginsenosides. In Paeoniae Radix, P.
    lactiflora articles were generally higher than in P. vitchii
    articles in constituent contents except the albiflorin/
    oxypaeoniflorin ratio and paeonol content. The top high contents
    of in P. lactiflora were paeoniflorin, albiflorin and
    pentagalloylglucose in the order named, but those in P. vitchii
    were paeoniflorin, pentagalloylglucose and oxypaeoniflorin. The
    peak-area ratio of albiflorin/oxypaeoniflorin was higher than
    unity in P. lactiflora samples but lower than unity in P.
    vitchii samples. Among the samples of Evodiae Fructus, there
    included mainly two categories: opened tip and unopened tip. The
    former had dehydroevodiamine, evodiamine, evocarpine and
    rutaecarpine as the most aboundant components. And the latter,
    however, had higher contents in dehydroevodiamine、 evodioside
    B and epimedoside C。By use of this LC-UV-ESI-MS method, these
    protoberberine alkaloids (berberine, palmatine, coptisine,
    epiberberine, jatrorrhizine, columbamine and berberastine) in a
    crude extract of Coptidis Rhizoma can be easily separated and
    identified within 50 minutes. And the method had been used to
    identify the pyrolyzed products, berberrubine, palmatrubine,
    jatrorrhizrubine and columbamrubine。
    The chemical constituents in Chinese herb drugs are

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