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研究生： 郭亦顓
Kuo, Yi-zhuan
論文名稱： 菲律賓楠莖部之成分研究
Studies on the stem constituents of Machilus philippinensis Merr
指導教授： 吳天賞
Wu, Tian-Shung
學位類別： 碩士
Master
系所名稱： 理學院 - 化學系
Department of Chemistry
論文出版年： 2007
畢業學年度： 95
語文別： 中文
論文頁數： 169
中文關鍵詞： 楠屬 、樟科 、菲律賓楠
外文關鍵詞： Lauraceae, Machilus philippinensis, Machilus
相關次數： 點閱：68  下載：2 
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    • 中文摘要
    由菲律賓楠莖部分離出43個化合物，經光譜分析化學方法及文獻比對後鑑定出40個化合物的構造，分別為13個neolignans：cinnamophilin、lyoniresol、biscinnamophilin、oleiferin D、lyoniside、meso-dihydroguaiaretic acid、dehydroguaiaretic acid、9,9'-Ο-diferuloyl-seco-isolariciresinol、machilupin A、machilupin B、machiphilin A、machilutone A、machilutone B；10個benzenoids：methyl syringate、3,4,5-trimethoxyphenyl-β-D-glucopyranoside、5,6-dimethoxy-
    benzene-1,3-diol、4'-hydroxy-2,3-dihydrocinnamic acid、syringic acid、vanillic acid、(E)-ferulic acid octacosyl ester、methyl-4-hydroxybenzoate、2,4,6-trimethoxy-
    phenol、homovanillyl alcohol；2個amides：N-trans-feruioyl tyramine、N-cis-feruioyl tyramine; 3個flavonoids: (-)-epicatechin、(+)-epicatechin、(+)-catechin；1個ionone：grasshopperketone；3個sesquiterpenes：sesquichamaenol、machilusoxide A、machilusoxide B；2個steroils：β-sitosterol、β-sitosteryl glucoside；3個coumarins：scopoletin、isofraxidin、scopolin；3個isoquinolines：thalifoline、tetrahydroisoquinolinone、6,7-dimethoxyisoquinoline。其中biscinnamophilin、machilupin A、machilupin B、machilusoxide A、machilusoxide B為首次發現的新化合物，machiphilin A、machilutone A、machilutone B為首次發現的新骨架化合物。

    Abstract
    A series of chromatographic separations of the methanolic extract of Machilus philipinensis Merr. has led to the isolation of forty-three compounds. Among these isolates, forty compounds were characterized by comprehensive analyses of their 1D and 2D NMR and mass spectral data. They include thirteen neolignans:
    cinnamophilin, biscinnamophilin, oleiferin D, meso-dihydroguaiaretic acid, lyoniresol, lyoniside, dehydroguaiaretic acid, machilupin A and B, machiphilin A, machilutone A, machilutone B and 9,9'-Ο-diferuloyl-seco-isolariciresinol; three flavonoids: (-)-epicatechin, (+)-epicatechin, and (+)-catechin; three coumarins: scopoletin, isofraxidin, and scopolin; ten benzenoids: methyl syringate, 3,4,5-trimethoxyphenyl-β-D-glucopyranoside, 5,6-dimethoxybenzene-1,3-diol, 4'-
    hydroxy-2, 3-dihydrocinnamic acid, syringic acid, vanillic acid, (E)-ferulic acid octacosyl ester, methyl-4-hydroxybenzoate, 2,4,6-trimethoxyphenol, and homovanillyl alcohol; two amides, namely N-trans-feruioyl tyramine, and N-cis-feruioyl tyramine; three isoquinolines: tetrahydroisoquinolinone, 6,7-dimethoxyisoquinoline, and thalifoline; one ionones: grasshopperketone; three sesquiterpenes: sesquichamaenol, machilusoxide A and B; and two sterols: namely β-sitosterol and β-sitosteryl glucoside. Among them, machilupin A and B, machilusoxide A and B were new compounds. Compounds, machiphilin A, and machilutone A and B were reported for the first time new skeleton from the natural source.

    目錄 Abstract I 中文摘要 II 第一章 緒論 1 第一節 研究動機 1 第二節 植物形態 2 第二章 楨楠屬( Machilus )植物之藥理研究回顧 4 第三章 楨楠屬( Machilus )植物之成分研究回顧 11 第四章 菲律賓楠成分之萃取與分離 31 第五章 化學構造之研究 41 第一節 meso-Dihydroguaiaretic acid (24)之構造研究 41 第二節 Cinnamophilin (38)之構造研究 45 第三節 Biscinnamophilin (127*)之構造研究 50 第四節 Oleiferin D (119)之構造研究 56 第五節 Lyoniresol (120)之構造研究 61 第六節 Lyoniside (28)之構造研究 66 第七節 Dehydroguaiaretic acid (121)之構造研究 71 第八節 Machilupin A (122*)之構造研究 75 第九節 Machilupin B (123*)之構造研究 80 第十節 Machiphilin A (124*)之構造研究 85 第十一節 Machilutone A (125*)之構造研究 90 第十二節 Machilutone B (126*)之構造研究 94 第十三節 Sesquichamaenol (140)之構造研究 98 第十四節 Machilusoxide A (141*)之構造研究 103 第十五節 Machilusoxide B (142*)之構造研究 107 第十六節 Biosynthesis 之研究 111 第十七節 其他化合物之構造研究 112 第六章 結論 113 第七章 實驗部分 114 第一節 本實驗所使用之儀器與藥品 114 第二節 菲律賓楠的萃取與分離 116 第三節 光譜數據 120 參考文獻 148 圖目錄 (圖一) 菲律賓楠(Machilus philipinensis Merr. )之植物外觀 2 (圖二) 菲律賓楠( Machilus philipinensis Merr. )之植物莖部外觀 3 (圖三) 菲律賓楠( Machilus philipinensis Merr. )之莖部外觀 3 Fig. 1-1 EI-MS spectrum of meso-dihydroguaiaretic acid (24) 42 Fig. 1-2 IR spectrum of meso-dihydroguaiaretic acid (24) 42 Fig. 1-3 1H-NMR spectrum of meso-dihydroguaiaretic acid (24) 43 Fig. 1-4 13C-NMR spectrum of meso-dihydroguaiaretic acid (24) 43 Fig. 1-5 NOESY spectrum of meso-dihydroguaiaretic acid (24) 44 Fig. 1-6 HMBC spectrum of meso-dihydroguaiaretic acid (24) 44 Fig. 2-1 EI-MS spectrum of cinnamophilin (38) 46 Fig. 2-2 IR spectrum of cinnamophilin (38) 47 Fig. 2-3 1H-NMR spectrum of cinnamophilin (38) 47 Fig. 2-4 13C-NMR spectrum of cinnamophilin (38) 48 Fig. 2-5 NOESY spectrum of cinnamophilin (38) 48 Fig. 2-6 HMBC spectrum of cinnamophilin (38) 49 Fig. 2-7 CD spectrum of cinnamophilin (38) 49 Fig. 3-1 FAB-MS spectrum of biscinnamophilin (127*) 51 Fig. 3-2 ESI-MS spectrum of biscinnamophilin (127*) 52 Fig. 3-3 IR spectrum of biscinnamophilin (127*) 52 Fig. 3-4 1H-NMR spectrum of biscinnamophilin (127*) 53 Fig. 3-5 13C-NMR spectrum of biscinnamophilin (127*) 53 Fig. 3-6 NOESY spectrum of biscinnamophilin (127*) 54 Fig. 3-7 HMBC spectrum of biscinnamophilin (127*) 54 Fig. 3-8 CD spectrum of biscinnamophilin (127*) 55 Fig. 4-1 EI-MS spectrum of oleiferin D (119) 57 Fig. 4-2 IR spectrum of oleiferin D (119) 58 Fig. 4-3 1H-NMR spectrum of oleiferin D (119) 58 Fig. 4-4 13C-NMR spectrum of oleiferin D (119) 59 Fig. 4-5 NOESY spectrum of oleiferin D (119) 59 Fig. 4-6 HMBC spectrum of oleiferin D (119) 60 Fig. 4-7 CD spectrum of oleiferin D (119) 60 Fig. 5-1 EI-MS spectrum of echioidinin lyoniresol (120) 62 Fig. 5-2 IR spectrum of echioidinin lyoniresol (120) 62 Fig. 5-3 1H-NMR spectrum of lyoniresol (120) 63 Fig. 5-4 13C-NMR spectrum of lyoniresol (120) 63 Fig. 5-5 COSY spectrum of lyoniresol (120) 64 Fig. 5-6 NOESYspectrum of lyoniresol (120) 64 Fig. 5-7 HMBC spectrum of lyoniresol (120) 65 Fig. 5-8 CD spectrum of lyoniresol (120) 65 Fig. 6-1 IR spectrum of lyoniside (28) 67 Fig. 6-2 1H-NMR spectrum of lyoniside (28) 68 Fig. 6-3 13C-NMR spectrum of lyoniside (28) 68 Fig. 6-4 COSY spectrum of lyoniside (28) 69 Fig. 6-5 NOESY spectrum of lyoniside (28) 69 Fig. 6-6 HMBC spectrum of lyoniside (28) 70 Fig. 6-6 CD spectrum of lyoniside (28) 70 Fig. 7-1 EI-MS spectrum of dehydroguaiaretic acid (121) 72 Fig. 7-2 IR spectrum of dehydroguaiaretic acid (121) 72 Fig. 7-3 1H-NMR spectrum of dehydroguaiaretic acid (121) 73 Fig. 7-4 13C-NMR spectrum of dehydroguaiaretic acid (121) 73 Fig. 7-5 NOESY spectrum of dehydroguaiaretic acid (121) 74 Fig. 7-6 HMBC spectrum of dehydroguaiaretic acid (121) 74 Fig. 8-1 EI-MS spectrum of machilupin A (122*) 76 Fig. 8-2 IR spectrum of machilupin A (122*) 77 Fig. 8-3 1H-NMR spectrum of machilupin A (122*) 77 Fig. 8-4 13C-NMR spectrum of machilupin A (122*) 78 Fig. 8-5 NOESY spectrum of machilupin A (122*) 78 Fig. 8-6 HMBC spectrum of machilupin A (122*) 79 Fig. 9-1 EI-MS spectrum of machilupin B (123*) 81 Fig. 9-2 IR spectrum of machilupinB (123*) 82 Fig. 9-3 1H-NMR spectrum of machilupin B (123*) 82 Fig. 9-4 13C-NMR spetrum of machilupin B (123*) 83 Fig. 9-5 NOESY spectrum of machilupin B (123*) 84 Fig. 9-6 HMBC spectrum of machilupin B (123*) 83 Fig. 10-1 EI-MS spectrum of machiphilin A (124*) 86 Fig. 10-2 IR spectrum of machiphilin A (124*) 86 Fig. 10-3 1H-NMR spectrum of machiphilin A (124*) 87 Fig. 10-4 13C-NMR spectrum of machiphilin A (124*) 87 Fig. 10-5 COSY spectrum of machiphilin A (124*) 88 Fig. 10-6 NOESY spectrum of machiphilin A (124*) 88 Fig. 10-7 HMBC spectrum of machiphilin A (124*) 89 Fig. 11-1 EI-MS spectrum of machilutone A (125*) 91 Fig. 11-2 IR spectrum of machilutone A (125*) 91 Fig. 11-3 1H-NMR spectrum of machilutone A (125*) 92 Fig. 11-4 13C-NMR spectrum of machilutone A (125*) 92 Fig. 11-5 NOESY spectrum of machilutone A (125*) 93 Fig. 11-6 HMBC spectrum of machilutone A (125*) 93 Fig. 12-1 IR spectrum of machilutone B (126*) 95 Fig. 12-2 1H-NMR spectrum of machilutone B (126*) 95 Fig. 12-3 13C-NMR spectrum of machilutone B (126*) 96 Fig. 12-4 HMQC spectrum of machilutone B (126*) 96 Fig. 12-5 NOESY spectrum of machilutone B (126*) 97 Fig. 12-6 HMBC spectrum of machilutone B (126*) 97 Fig. 13-1 FAB-MS spectrum of sesquichamaenol (140) 99 Fig. 13-2 IR spectrum of sesquichamaenol (140) 99 Fig. 13-3 1H-NMR spectrum of sesquichamaenol (140) 100 Fig. 13-4 13C-NMR spectrum of sesquichamaenol (140) 100 Fig. 13-5 COSY spectrum of sesquichamaenol (140) 101 Fig. 13-6 NOESY spectrum of sesquichamaenol (140) 101 Fig. 13-7 HMBC spectrum of sesquichamaenol (140) 102 Fig. 14-1 IR spectrum of machilusoxide A (141*) 104 Fig. 14-2 1H-NMR spectrum of machilusoxide A (141*) 104 Fig. 14-3 13C-NMR spectrum of machilusoxide A (141*) 105 Fig. 14-4 COSY spectrum of machilusoxide A (141*) 105 Fig. 14-5 NOESY spectrum of machilusoxide A (141*) 106 Fig. 14-6 HMBC spectrum of machilusoxide A (141*) 106 Fig. 15-1 IR spectrum of machilusoxide B (142*) 108 Fig. 15-2 1H-NMR spectrum of machilusoxide B (142*) 108 Fig. 15-3 13C-NMR spectrum of machilusoxide B (142*) 109 Fig. 15-4 HMBC spectrum of machilusoxide B (142*) 109 Fig. 15-5 NOESY spectrum of machilusoxide B (142*) 110 Fig. 15-6 CD spectrum of machilusoxide B (142*) 110

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