臺灣博碩士論文加值系統

中文摘要
牛樟芝多孔菌科(Polyporaceae)植物 Antrodia camphorata.固態栽培子實體以70%丙酮萃取，經由各種層析管柱及不同溶媒系統層析後，共分離出十二個化合物。根據物理數據、核磁共振光譜判定，其結構分為六類：三個酚類化合物2,4-Dihydroxy-3,5-dimethoxytoluene (1)、2,3,6-Trimethoxy-4-methylphenol (2)、2-Hydroxyl-3,4,5-trimethoxytoluene(3)；一個苯環類化合物4,7-Dimethoxy-5-methyl-1,3-benzodioxole (4)；三個固醇類化合物Ergosta-7,22-dien-3β-ol (5)、Ergosterol peroxide (6)、Ergosterol-4,6,8(14),22-trtraen-3-one) (7)；三個三萜類化合物Granoderic acid (8)、3β-Hydroxylanosta-7,9(11)24-trien-21-oic acid (9)、Eburicoic acid (10)；一個脂肪酸化合物Methyl oleate (11)；一個雜項類化合物Bis-(2-ethylhexyl)phthaiate (12)。
關鍵字：固態栽培，牛樟芝。

英文摘要
Antrodia camphorata by solid culture were extracted with 70%
aqueous acetone. By means of column chromatographies, Twelve
compounds were isolation and purified. The structures of these
compounds were elucidated. According to the data and the NMR ,
their structures are divided to six types. Including three phenyl
methanoids ： 2,4-Dihydroxy-3,5-dimethoxytoluene (1)、2,3,6-Trimethoxy-4-methylphenol (2)、2-Hydroxyl-3,4,5-trimethoxytoluene (3)；a Ben-zenoid ： 4,7-Dimethoxy-5-methyl-1,3-benzodioxole (4)；three
Steroids： Ergosta-7,22-dien-3β-ol (5)、Ergosterol peroxide (6)、 Ergosterol-4,6,8(14),22-trtraen-3-one (7)；three Triterpenoids：Granoder-ic acid (8)、3β-Hydroxylanosta-7,9(11)24-trien-21-oic acid (9)、 Eburico-ic acid (10)；a Fatty compound： Methyl oleate (11) and the other： Bis-(2-ethylhexyl)phthaiate (12)。

Key words：Solid culture，Antrodia camphorata

總目錄
中文摘要 I
英文摘要 II
總目錄 III
圖目錄 V
表目錄 IX
縮寫表 XI
第一章 緒論 1
第二章 結果與討論 16
第三章 實驗方法與材料 106
文獻參考 115


第一章 緒論 1
1.1 研究背景 1
1.2 牛樟芝介紹 4
1.2.1 命名緣由 4
1.2.2 牛樟芝特徵 4
1.3 文獻回顧 6
1.3.1 化學成分研究之文獻回顧： 6
1.3.2 活性研究之文獻回顧： 16
第二章 結果與討論 17
2.1 抽取及分離 17
2.2 化合物之構造鑑定 19
2.2.1 2,4-Dihydroxy-3,5-dimethoxytoluene (1) 之結構解析 19
2.2.2 2,3,6-Trimethoxy-4-methylphenol (2) 之結構解析 26
2.2.3 2-Hydroxy-3,4,5-trimethoxytoluene (3) 之結構解析 32
2.2.4 4,7-Dimethoxy-5-methyl-1,3-benzodioxole (4) 之結構解
析. 38
2.2.5 Eergosta-7,22E-diene-3β-o1 (5) 之結構解析 46
2.2.6 Ergosterol peroxide (6) 之結構解析 60
2.2.7 Ergosta-4,6,8(14),22-tetraen-3-one (7) 之結構解析 66
2.2.8 Ganoderic acid (8) 之結構式解析 75
2.2.9 3β-Hydroxyhanosta-7,9(11),24-trien-21-oic acid (9) 之結
構解析 83
2.2.10 Eburicoic acid (24-Methyenelanosta-8-en-3β-ol-21-oic acid) (10) 之結構解析 90
2.2.11 Methyl oleate (11) 之結構解析 96
2.2.12 Bis-(2-ethklhexyl)phthalate (12) 之結構解析 100
2.3 結果與討論 104
2.3.1 結果與討論 104


第三章 實驗方法與材料 105
3.1 實驗材料 106
3.1.1 儀器與材料 106
3.2 實驗方法 106
3.2.1 溶媒及試藥 106
3.2.2 層析法 106
3.2.3 TLC檢測法 107
3.3 各化合物之物裡數據 107

文獻參考 114



圖目錄
Fig.1 Extraction and Isolation of Antrodia camphorata 18
Fig. 2 1H-NMR spectrum of 2,4-Dihydroxy-3,5-dimethoxytoluene (1) (CDCl3, 400 MHz) 21
Fig. 3 13C-NMR spectrum of 2,4-Dihydroxy-3,5-dimethoxytoluene (1) ( CDCl3, 100 MHz) 22
Fig. 4 DEPT spectrum of 2,4-Dihydroxy-3,5-dimethoxytoluene (1) (CDCl3, 100 MHz) 23
Fig. 5 HMQC spectrum of 2,4-Dihydroxy-3,5-dimethoxytoluene (1) (CDCl3, 400 MHz) 24
Fig. 6 HMBC spectrum of 2,4-Dihydroxy-3,5-dimethoxytoluene (1) (CDCl3, 400 MHz) 25
Fig. 7 1H-NMR spectrum of 2,3,6-Trimethoxy-4-methylphenol (2) (CDCl3, 400 MHz ) 28
Fig. 8 13C-NMR spectrum of 2,3,6-Trimethoxy-4-methylphenol (2) ( CDCl3, 100 MHz) 29
Fig. 9 HMQC spectrum of 2,3,6-Trimethoxy-4-methylphenol (2) (CDCl3, 400 MHz) 30
Fig. 10 HMBC spectrum of 2,3,6-Trimethoxy-4-methoxyphenol (2) (CDCl3, 400 MHz) 31
Fig.11 1H-NMR spectrum of 2-Hydroxy-3,4,5-trimethoxytoluene (3) (CDCl3, 400 MHz ) 34
Fig.12 13C-NMR spectrum of 2-Hydroxy-3,4,5-trimethoxytoluene (3) (CDCl3, 400 MHz 35
Fig.13 HMQC spectrum of 2-Hydroxy-3,4,5-trimethoxytoluene (3) (CDCl3, 400 MHz) 36
Fig 14. HMBC spectrum of 2-Hydroxy-3,4,5-trimethoxytoluene (3) (CDCl3, 400 MHz) 37
Fig.15 1H-NMR spectrum of 4,7-Dimethoxy-5-methyl-1,3-benzodioxole (4) (CDCl3, 500 MHz ) 41
Fig.16 13C-NMR spectrum of 4,7-Dimethoxy-5-methyl-1,3-benzodioxole (4) ( CDCl3, 125 MHz) 42
Fig.17 13C-NMR spectrum of 4,7-Dimethoxy-5-methyl-1,3-benzodioxole (4) (CDCl3, 500 MHz) 43
Fig.18 HMQC spectrum of 4,7-Dimethoxy-5-methyl-1,3-benzodioxole (4) (CDCl3, 500 MHz) 44
Fig.19 HMBC spectrum of 4,7-Dimethoxy-5-methyl-1,3-benzodioxole (4) (CDCl3, 500 MHz) 45
Fig. 20 1H-NMR spectrum of Ergosta-7,22E-dien-3β-o1 (5) (CDCl3, 400 MHz) 50
Fig.21 1H-NMR spectrum of Ergosta-7,22E-dien-3β-o1 (5) (CDCl3, 400 MHz) 51
Fig.22 13CNMR spectrum of Ergosta-7,22E-dien-3β-o1 (5) ( CDCl3, 100 MHz) 52
Fig.23 DEPT spectrum of Ergosta-7,22E-dien-3β-o1 (5) ( CDCl3, 100 MHz) 53
Fig.24 HMQC spectrum of Ergosta-7,22E-dien-3β-o1 (5) (CDCl3, 400 MHz) 54
Fig.25 HMBC spectrum of Ergosta-7,22E-dien-3β-o1 (5) (CDCl3, 400 MHz) 55
Fig.26 HMBC spectrum of Ergosta-7,22E-dien-3β-o1 (5) (CDCl3, 400 MHz) 56
Fig.27 HMBC spectrum of Ergosta-7,22E-dien-3β-o1 (5) (CDCl3, 400 MHz) 57
Fig.28 HMBC spectrum of Ergosta-7,22E-dien-3β-o1 (5) (CDCl3, 400 MHz) 58
Fig.29 HMBC spectrum of Ergosta-7,22E-dien-3β-o1 (5) (CDCl3, 400 MHz) 59
Fig. 30 1H-NMR spectrum of Ergosterol peroxide (6) (MeOH-d4, 600 MHz ) 63
Fig. 31 13C NMR spectrum of Ergosterol peroxide (6) (MeOH-d4 , 150 MHz) 64
Fig. 32. 13C NMR spectrum of Ergosterol peroxide (6) (MeOH-d4, 150 MHz) 65
Fig. 33 1H-NMR spectrum of Ergosta-4,6,8(14),22-tetraen-3-one (7) (MeOH-d4 , 600 MHz) 69
Fig. 34 1H-NMR spectrum of Ergosta-4,6,8(14),22-tetraen-3-one (7) (MeOH-d4 , 600 MHz) 70
Fig. 35 1H-NMR spectrum of Ergosta-4,6,8(14),22-tetraen-3-one (7) (MeOH-d4 , 600 MHz) 71
Fig.36. 13C NMR spectrum of Ergosta-4,6,8(14),22-tetraen-3-one (7) (MeOH-d4 , 150 MHz) 72
Fig.37. 13C NMR spectrum of Ergosta-4,6,8(14),22-tetraen-3-one (7) (MeOH-d4 , 150 MHz) 73
Fig.38 13C NMR spectrum of Ergosta-4,6,8(14),22-tetraen-3-one (7) (MeOH-d4 , 150 MHz) 74
Fig.39 1H-NMR spectrum of Granodric acid (8) (MeOH-d4 , 600 Mz) 78
Fig.40 1H-NMR spectrum of Granodric acid (8 ) (MeOH-d4 , 600 Mz) 79
Fig.41 13C NMR spectrum of of Granodric acid (8) (MeOH-d4 , 150 MHz) 80
Fig.42 13C NMR spectrum of of Granodric acid (8) (MeOH-d4 , 150 MHz) 81
Fig.43 13C NMR spectrum of of Granodric acid (8) (MeOH-d4, 150 MHz) 82
Fig.44. 1H-NMR spectrum of 3β-Hydroxyhanosta-7,9(11),24-trien-21-oic acid (9) (MeOH-d4 , 600 MHz) 87
Fig.45. 13C NMR spectrum of 3β-Hydroxyhanosta-7,9(11),24-trien-21-oic acid (9) (MeOH-d4, 150 MHz) 88
Fig.46.13C NMR spectrum of 3β-Hydroxyhanosta-7,9(11),24-trien-21-oic acid (9) (MeOH-d4, 150 MHz) 89
Fig.47.13C NMR spectrum of 3β-Hydroxyhanosta-7,9(11),24-trien-21-oic acid (9) (MeOH-d4, 150 MHz) 90
Fig.48 1H-NMR spectrum of Eburicoic acid (10) (MeOH-d4, 600 MHz) 93
Fig.49 1H-NMR spectrum of Eburicoic acid (10) (MeOH-d4, 600 MHz) 94
Fig.50 13C NMR spectrum of Eburicoic acid (10) (MeOH-d4, 150 MHz) 95
Fig.51 13C NMR spectrum of Eburicoic acid (10) (MeOH-d4, 150 MHz) 96
Fig.52 1H-NMR spectrum of Methyl oleate (11) (CDCl3, 500 MHz ) 99
Fig.53 1H-NMR spectrum of Methyl oleate (11) (CDCl3, 500 MHz ) 100
Fig.54 1H-NMR spectrum Bis-(2-ethklhexyl)phthalatef (12) (CDCl3, 500 MHz ) 103
Fig.55.13C NMR spectrum of Bis-(2-ethklhexyl)phthalate (12) (CDCl3, 125 MHz) 104



表目錄
Table 1 野生牛樟芝子實體、固體培養牛樟芝子實體及液體發酵牛樟 芝 菌 絲體比較 2
Table 2 液態培養菌絲體及固體栽培子實體方式比較 2
Table 3 NMR spectral data of 2,4-Dihydroxy-3,5-dimethoxytoluene (1) (δ values, in CDCl3, J in Hz) 20
Table 4 NMR spectral data of 2,3,6-Trimethoxy-4-methylphenol (2) (δ values, in CDCl3, J in Hz) 27
Table 5 NMR spectral data of 2-Hydroxy-3,4,5-trimethoxytoluene (3) 33
Table 6 NMR spectral data of 4,7-dimethoxy-5-methyl-1,3- benzodioxole (4) (δ values, in CDCl3, J in Hz) 40
Table 7 NMR spectral data of Ergosta-7,22E-diene-3β-o1 (5) (δ values, in CDCl3, J in Hz) 49
Table 8 NMR spectral data of Ergosterol peroxide (6) (δ values, in MeOH -d4, J in Hz)。 62
Table 9 NMR spectral data of Ergosta-4,6,8(14),22-tetraen- 3-one (7) (δ values, in MeOH-d4, J in Hz) 68
Table 10 NMR spectral data of Ganodenic acid (8) (δ values, in MeOH-d4, J in Hz) 77
Table 11 NMR spectral data of 3β-Hydroxyhanosta-7,9(11), 24-trien--21-oic acid (9) (δ values, in MeOH-d4, J in Hz) 85
Table 12 NMR spectral data of Eburicoic acid (10) (δ values, in CDCl3, J in Hz) 92
Table 13 NMR spectral data of Methyl oleate (11) (δ values, in CDCl3, J in Hz) : 97
Table 14 NMR spectral data of Bis-(2-ethklhexyl)phthalate (12) (δ values, in CDCl3, J in Hz) 102




縮寫表

Fr. Fraction
C. C. Column Chromatography
1H-NMR Proton nuclear resonance spectrum
13C-NMR Carbon-13 nuclear magnetic resonance spectrum
DEPT Distortionless enhancement via polarization transfer
HMQC Heteronuclear multiple quantum coherence
HMBC Heteronuclear multiple bond coherence

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