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研究生:許恩翎
研究生(外文):Hsu,En Ling
論文名稱:樟芝菌絲體之定量分析與抗發炎活性成分
論文名稱(外文):Quantitative analysis and anti-inflammatory compounds of Antrodia cinnamomea mycelia
指導教授:陳立耿博士
指導教授(外文):Chen,Lih Geeng
學位類別:碩士
校院名稱:國立嘉義大學
系所名稱:微生物免疫與生物藥學系研究所
學門:生命科學學門
學類:生物科技學類
論文種類:學術論文
畢業學年度:100
語文別:中文
論文頁數:230
中文關鍵詞:樟芝菌絲體真菌antroquinonol定量分析市售品
外文關鍵詞:Antrodia cinnamomeamyceliafungiantroquinonolquantitative analysiscommercial product
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樟芝(Antrodia cinnamomea Chang & Chou) 為多孔菌科
(Polyporaceae) 寄生於樟科 (Lauraceae) 植物牛樟 (Cinnamomum
kanehirai Hay) 心材之真菌,為台灣特有種之保育類藥材。樟芝常用於
養肝治肝,民間流傳樟芝可解毒消腫、鎮靜止痛、抗菌及抗腫瘤,由
於樟芝昂貴且稀有,素有「森林中的紅寶石」之美稱;現今樟芝之生
理活性及成分都已被發表及證實,具有抗腫瘤、抗發炎、調節免疫等
活性。
本研究取液態發酵之樟芝菌絲體及樟芝多醣體為實驗材料,以不
同溶劑進行萃取,針對各劃分部利用不同性質之管柱分離,共純化十
七種成分,其中有固醇類:ergosterol,antcin B,三萜類:sulphurenic acid,
2 種泛醌類衍生物:antroquinonol,4-acetyl antroquinonol B,琥珀酸衍
生物:antrodin D, trans-1-hydroxy-4-hydroxyphenyl)-4-isobutyl
pyrrolidine-2,5-dione, trans-3-isobutyl-4-[4-(3-methyl-2-butenyloxy)
phenyl]pyrrolidine-2,5-dione,馬來酸衍生物:antrocinnamomin B, antrodin
A, antrodin B, 3-(4-hydroxyphenyl)-4-isobutyl-1H-pyrrole-2,5-dione
以及維生素riboflavin,而有四個未鑑定出。
將樟芝分離出之化學成分進行定量及定性的分析,由HPLC 檢測
11 家市售品之含有成分及量之多寡,針對其標榜具有的成分和含量探
討,可發現全市售品中,其中五家符合標榜其成分但含量有些差距,
而有四家相對應的成分僅有一兩種,含量上只具有微量的成分,還有
兩家市售品無對應到相同的成分,另外每家產品建議用量幾乎大不相
同。樟芝菌絲體經由加熱迴流及均質之不同萃取方式,觀察萃取物之
層析圖譜,可得知所含成分種類多相同,但含量上有所差異,若以同
材料來源對溶劑的選擇性作探討,樟芝菌絲體粉末以乙醇萃取其產率
達12.8 %,而以甲醇萃取其產率只有6.7 %,對照同成分之含量顯示兩
II
批次之品質變化與特性。
以LPS 誘導小鼠巨噬細胞RAW264.7 產生NO 試驗,結果顯示在
濃度10 μg/ ml 下,得知antcin B,antrodin B,antrodin D,
antrocinnamomin B 及 riboflavin 初步評估具有抗發炎活性。
樟芝菌絲體之培育分為固態發酵及液態發酵兩種方式,其培養溫
度和環境之不同型態,使得品質和控管之標準無規格化,凸顯出各家
產品之優缺性。本研究建立樟芝之HPLC 分析方法,其結果顯示檢量
線之相關係數 (r2) 均大於0.999,表示線性關係良好,樟芝成分之最小
偵測濃度0.77 μg/ ml 及最小定量濃度2.33 μg/ ml;成分分析方面不論
是同日內或異日間結果,樟芝之antroquinonol, 4-acetyl antroquinonol B
主成分之變異係數皆小於4 %;而利用antrodin B 標準品測定添加回收
率之結果,回收率皆大於97 %,確認本研究的分析方法之準確度、穩
定性佳且具有再現性。以上在未來可針對國人對樟芝保健食品之食用
的確效和安全,並提供樟芝指標成分建立與品管之所需。
Antrodia cinnamomea Chang & Chou is a native fungi to Taiwan. It is
rare and expensive because it grows only on the heart wood of
Cinnamomum kanehirai Hay (Lauraceae). The biological activities of the
mycelia and the fruiting body of A. cinnamomea have been studied. It
contains a variety of phenyl derivatives, steroids, sesquiterpenes,
triterpenoids, lignans, maleic acid and succinic acid derivatives.
In this study, three different solvents were used to extract the mycelia
of A. cinnamomea. Each fraction was separated and purified by silica gel
column or ODS-80 Ts column.
Seventeen compounds were isolated from the mycelia powder and
polysaccharides-enrich powder of A.cinnamomea, including ergosterol,
antcin B, sulphurenic acid, antroquinonol, 4-acetyl antroquinonol B,
ant rodin A, ant rodin B, ant rodin D, ant roc innamomin B,
t r a n s - 3 - i s o b u t y l - 4 - [ 4 - ( 3 - m e t h y l - 2 - b u t e n y l o x y )
phenyl]pyrrolidine-2,5-dione, trans-1-hydroxy-3-(4-hydoxyphenyl)-4-
isobutylpyrrolidine-2,5-dione, cis-3-(4-hydroxyphenyl)-4-isobutyldi
hydrofuran-2,5-dione and riboflavin.The chemical structures were
identified by nuclear magnetic resonance spectroscopy (NMR).
Eleven commercial products of A. cinnamomea were analyzed by
HPLC. The content of antroquinonol and 4-acetyl antroquinonol B have
significant different between commercial products.
Compounds of the mycelia of A. cinnamomea inhibited nitric oxide
(NO) production from lipopolysaccharide (LPS)-stimulated RAW 264.7
IV
cells to assess the in vitro anti-inflammatory activity. Antcin B, antrodin B,
antrodin D, antrocinnamomin B and riboflavin showed anti-inflammatory
activity at concentration of 10 μg/ ml.
In conclusion, we established a HPLC quantitative analysis method
and demonstrated that the results of the interday or intraday, antroquinonol
composition of the coefficient of variation were less than 4 %, and the
results of recovery were greater than 97%. On the aspect of quantitative
analysis, the calibration curve of the correlation coefficient (r2) was greater
than 0.999-indicating a good linear relationship, and the limit of detection
concentration of antrodin B components was as low as 0.77 μg / ml. This
method was suitable for the determination of antroquinonol and its
structural related derivatives in commercial product of A. cinnamomea
contained indicator compounds extract.
目錄
中文摘要 ........................................................................................................... I
英文摘要 ........................................................................................................ III
目錄 ................................................................................................................. V
附表目錄 .................................................................................................. XXIV
縮寫表 ........................................................................................................ XXV
第一章 介紹 ............................................................................................ 1
一、 引序 ........................................................................................... 1
二、 樟芝簡介 ................................................................................... 1
三、 樟芝活性評估 ........................................................................... 6
(一) 發炎反應 ................................................................................... 6
四、 文獻回顧 ................................................................................... 9
(一) 樟芝已知成分 ........................................................................... 9
(二) 樟芝之生理活性回顧 ............................................................. 14
1. 活性成分 ................................................................................. 14
2. 不同溶劑萃取之活性 ............................................................. 18
第二章 實驗材料與方法 ...................................................................... 20
VI
一、 材料 ..................................................................................... 20
二、 試驗細胞 ................................................................................. 21
三、 分離管柱及管柱填充劑 ......................................................... 21
四、 溶媒及化學試劑 ..................................................................... 22
五、 儀器設備 ................................................................................. 23
六、 實驗架構 ................................................................................. 24
七、 樟芝活性成分之分離 ............................................................. 25
(一) 樟芝菌絲體成分之分離 ......................................................... 25
(二) 樟芝多醣體成分之分離 ......................................................... 41
八、 樟芝之抗發炎活性評估 ......................................................... 44
(一) 實驗樣品製備 .......................................................................... 44
(二) RAW 264.7 細胞培養 ............................................................. 44
(1) 細胞株 ...................................................................................... 44
(2) 溶液配製 .................................................................................. 44
(3) RAW 264.7 細胞培養 ............................................................. 44
1. 細胞解凍 ............................................................................... 44
2. 細胞繼代培養 ....................................................................... 45
VII
3. 細胞計數 .................................................................................. 45
(三) 細胞毒性測試 .......................................................................... 45
(四) 抑制NO 活性測試法 ............................................................ 47
九、 樟芝成分之HPLC 分析 ........................................................ 48
(一) 層析條件 ................................................................................. 48
(二) 化合物檢量線之製作 ............................................................. 50
(三) 樟芝萃取物成分之含量分析 ................................................. 50
(四) 同、異日間之分析方法 ......................................................... 51
(五) 添加回收率試驗 ..................................................................... 51
第三章 結果與討論 .............................................................................. 52
第一節 樟芝成分之結構鑑定 .............................................................. 52
一、 樟芝菌絲體純化之成分 ......................................................... 52
(一) Terpenoids ............................................................................... 52
(1) AC-A 之圖譜解析 .................................................................. 52
(2) AC-I 之圖譜解析 ................................................................... 56
(3) AC-R 之圖譜解析 .................................................................. 59
(二) Succinic and maleic derivatives .............................................. 62
VIII
(1) AC-C 之圖譜解析 .................................................................. 62
(2) AC-D 之圖譜解析 .................................................................. 63
(3) AC-O 之圖譜解析 ................................................................. 66
(4) AC-H 之圖譜解析 ................................................................. 68
(5) AC-Q 之圖譜解析 ................................................................. 69
(6) AC-J 之圖譜解析 ................................................................... 71
(7) AC-N 之圖譜解析 .................................................................. 73
(三) Ubiquinone derivatives ........................................................... 75
(1) AC-E 之圖譜解析 .................................................................. 75
(2) AC-K 之圖譜解析 ................................................................. 76
二、 樟芝polysaccharides-enrich 純化之成分 .............................. 79
(1) AC-P 之圖譜解析 .................................................................. 79
第二節 樟芝成分之抗發炎活性 .......................................................... 81
一、 樟芝成分之細胞毒性 ............................................................. 81
二、 樟芝成分抑制NO 含量測定 ................................................. 81
三、 抗發炎活性評估 ..................................................................... 81
第三節 樟芝成分之定量分析 .............................................................. 84
IX
一、 樟芝成分HPLC...................................................................... 84
二、 樟芝各成分之定量 ................................................................. 95
(一) 樟芝各成分之檢量線 ............................................................. 95
(二) 同、異日間及回收率分析 ..................................................... 96
(三) LOD/LOQ 之分析 .................................................................. 98
(四) 樟芝市售品成分之含量分析 ................................................. 99
第四章 結論 ................................................................................. 102
一、 樟芝之不同溶劑萃取比較 ................................................... 102
二、 樟芝之市售品成分含量總整理 ........................................... 102
參考文獻 .............................................................................................. 107
附表 ....................................................................................................... S1
附圖 ..................................................................................................... S21
X
圖目錄
圖一 牛樟樹及樟芝型態 ................................................................................ 2
圖二 本實驗所使用之樟芝市售品 ................................................................ 5
圖三 LPS 誘導發炎反應分泌相關細胞激素 ................................................ 8
圖四 萜類之生合成途徑 .............................................................................. 13
圖五 本實驗所使用的子實體樣品 ............................................................ 21
圖六 樟芝菌絲體實驗架構 .......................................................................... 24
圖七 樟芝菌絲體乙醇萃取流程圖 .............................................................. 25
圖八 AC-H 之HPLC 層析圖及滯留時間7.3 分鐘 .................................... 27
圖九 AC-J 之HPLC 層析圖及滯留時間6.2 分鐘 ..................................... 27
圖十 AC-N 之HPLC 層析圖及滯留時間8.0 分鐘 .................................... 28
圖十一 樟芝菌絲體乙醇萃取之乙酸乙酯層分離流程圖 .......................... 29
圖十二 樟芝菌絲體甲醇萃取流程圖 .......................................................... 30
圖十三 AC-C 之HPLC 層析圖及滯留時間4.1 分鐘 ................................ 31
圖十四 AC-D 之HPLC 層析圖及滯留時間7.4 分鐘 ................................ 32
圖十五 AC-E 之HPLC 層析圖及滯留時間8.6 分鐘 ................................ 32
圖十六 樟芝菌絲體甲醇萃取之乙酸乙酯層分離流程圖 .......................... 33
圖十七 AC-K 之HPLC 層析圖及滯留時間9.0 分鐘 ................................ 34
圖十八 AC-L 之HPLC 層析圖及滯留時間3.0 分鐘 ................................ 35
XI
圖十九 AC-M 之HPLC 層析圖及滯留時間5.8 分鐘 ............................... 35
圖二十AC-O 之HPLC 層析圖及滯留時間9.1 分鐘 ................................. 35
圖二十一 AC-Q 之HPLC 層析圖及滯留時間5.5 分鐘 ............................ 36
圖二十二 AC-R 之HPLC 層析圖及滯留時間7.4 分鐘 ............................ 36
圖二十三 AC-S 之HPLC 層析圖及滯留時間6.5 分鐘 ............................ 37
圖二十四 樟芝菌絲體甲醇萃取之MH 劃分部流程圖 ............................. 37
圖二十五 樟芝菌絲體甲醇均質萃取流程圖 .............................................. 38
圖二十六 AC-B 之HPLC 層析圖及滯留時間4.0 分鐘 ............................ 39
圖二十七 樟芝菌絲體甲醇均質萃取之乙酸乙酯分離流程圖 .................. 40
圖二十八 AC-P 之HPLC 層析圖及滯留時間18.7 分鐘 .......................... 41
圖二十九 樟芝多醣體十公斤乙醇萃取流程圖 .......................................... 42
圖三十 樟芝多醣體三公斤乙醇萃取流程圖 .............................................. 43
圖三十一 MTT 反應原理示意圖 ................................................................ 46
圖三十二 AC-A 之GC-MS 層析圖 ........................................................... 53
圖三十三 ergosterol 之結構 ......................................................................... 53
圖三十四 sulphurenic acid 之結構 .............................................................. 57
圖三十五antcin B 之結構 ............................................................................ 60
圖三十六 antrodin A 之結構........................................................................ 63
圖三十七 antrodin B 之結構 ........................................................................ 64
XII
圖三十八 antrocinnamomin B 之結構 ......................................................... 67
圖三十九 antrodin D 之結構........................................................................ 69
圖四十 AC-Q 之結構 ................................................................................... 70
圖四十一AC-J 之結構 ................................................................................. 72
圖四十二 AC-N 之結構 ............................................................................... 74
圖四十三 4-acetyl antroquinonol B 之結構 ................................................. 76
圖四十四antroquinonol 之結構 ................................................................... 77
圖四十五 riboflavin 之結構 ......................................................................... 79
圖四十六 樟芝之各成分HPLC 層析圖譜 ................................................. 86
圖四十七 樟芝之不同溶劑粗萃物及市售品1-4 層析圖譜 .................... 87
圖四十八 樟芝之不同溶劑粗萃物及市售品5-11 層析圖譜 .................... 88
圖四十九 樟芝之不同溶劑粗萃物及市售品1-4 層析圖譜 (265 nm) ..... 89
圖五十 樟芝之不同溶劑粗萃物及市售品5-11 層析圖譜 (265 nm) ........ 90
圖五十一 乙醇萃取物純化出的琥珀酸衍生物結構 .................................. 92
圖五十二 甲醇萃取物純化出的琥珀酸衍生物及馬來酸衍生物結構...... 93
圖五十三 樟芝各萃取物之純化出ergostane 及lanostane 結構 ............... 94
XIII
表目錄
表一 樟芝市售品及原藥材之成分來源 .................................................... 20
表二 GC/MS 條件 ...................................................................................... 49
表三 ergosterol 之1H-NMR 及 13C-NMR 整理數據 ............................... 55
表四 ulphurenic acid 之1H-NMR 及13C-NMR 整理數據 ......................... 58
表五 antcin B 之1H-NMR 及 13C-NMR 整理數據..................................... 61
表六 antrodin A 及antrodin B 之1H-NMR 及 13C-NMR 整理數據 .......... 65
表七 antrocinnamomin B 之1H-NMR 及 13C-NMR 整理數據 ................ 67
表八 antrodin D 及AC-Q 之1H-NMR 及 13C-NMR 整理數據 ................. 71
表九 AC-J 及AC-N 之1H-NMR 及 13C-NMR 整理數據 .......................... 74
表十 AC-E 及antroquinonol 之1H-NMR 及 13C-NMR 整理數據 ............ 78
表十二 樟芝各成分之產率 ........................................................................ 80
表十三 樟芝各成分在10 μg/ ml RAW264.7 細胞之細胞存活率及NO
抑制率 .......................................................................................... 82
表十四 分離自樟芝菌絲體之成分活性 .................................................... 83
表十五 各化合物在管柱內的滯留時間以及各成分之ClogP 值 ............ 91
表十六 各成分之檢量線 ............................................................................ 95
表十七 樟芝成分之intra-day 及inter-day 之含量及變異係數 ............... 96
表十八 antrodin B 之添加回收率試驗 ...................................................... 97
XIV
表十九 樟芝十五種成分之LOD 及LOQ ................................................ 98
表二十 樟芝各市售品之成分含量分析 .................................................. 101
表二十一 樟芝各市售品之總整理 ............................................................ 105
XV
附圖目錄
附圖一 樟芝菌絲體各成分之UV 全波長吸收圖,劑為甲醇 .............. S21
附圖二 樟芝菌絲體成分之檢量線及ESI-MS 質譜圖 .......................... S22
附圖三 ergosterol 之1H 圖譜 .................................................................. S26
附圖四 ergosterol 之COSY 圖譜 ............................................................ S26
附圖五 ergosterol 之13C 圖譜 ................................................................. S27
附圖六 ergosterol 之HSQC 圖譜 ............................................................ S27
附圖七 sulphurenic acid 之1H 圖譜 ........................................................ S28
附圖八 sulphurenic acid 之COSY 圖譜 ................................................. S28
附圖九 sulphurenic acid 之13C 圖譜 ....................................................... S29
附圖十 sulphurenic acid 之DEPT 圖譜 .................................................. S29
附圖十一 sulphurenic acid 之HSQC 圖譜 ............................................. S30
附圖十二 sulphurenic acid 之HMBC 圖譜 ............................................ S30
附圖十三 antcin B 之1H 圖譜 ................................................................. S31
附圖十四 antcin B 之COSY 圖譜 .......................................................... S31
附圖十五 antcin B 之13C 圖譜 ................................................................ S32
附圖十六 antcin B 之DEPT 圖譜 ........................................................... S32
附圖十七 antcin B 之HSQC 圖譜 ........................................................ S33
附圖十八 antcin B 之HMBC 圖譜 ......................................................... S33
XVI
附圖十九 methyl antcinate H 之1H 圖譜 ................................................ S33
附圖二十 antrodin A 之1H 圖譜 ............................................................. S34
附圖二十一 antrodin A 之COSY 圖譜 ................................................... S34
附圖二十二 antrodin A 之13C 圖譜 ........................................................ S35
附圖二十三 antrodin A 之DEPT 圖譜 ................................................. S35
附圖二十四 antrodin A 之HSQC 圖譜 ................................................. S36
附圖二十五 antrodin A 之HMBC 圖譜 .................................................. S36
附圖二十六 antrodin B 之1H 圖譜 ......................................................... S37
附圖二十七 antrodin B 之COSY 圖譜 ................................................... S37
附圖二十八 antrodin B 之13C 圖譜 ........................................................ S38
附圖二十九 antrodin B 之DEPT 圖譜 ................................................. S38
附圖三十 antrodin B 之HSQC 圖譜 ..................................................... S39
附圖三十一 antrodin B 之HMBC 圖譜 .................................................. S39
附圖三十二 antrocinnamomin B 之1H 圖譜 .......................................... S40
附圖三十三 antrocinnamomin B 之COSY 圖譜 .................................... S40
附圖三十四 antrocinnamomin B 之13C 圖譜 ......................................... S41
附圖三十五 antrocinnamomin B 之DEPT 圖譜 ..................................... S41
附圖三十六 antrocinnamomin B 之HSQC 圖譜 .................................... S42
附圖三十七 antrocinnamomin B 之HMBC 圖譜 ................................. S42
XVII
附圖三十八 antrodin D 之1H 圖譜 ....................................................... S43
附圖三十九 antrodin D 之COSY 圖譜 ................................................... S43
附圖四十 antrodin D 之13C 圖譜 ............................................................ S44
附圖四十一 antrodin D 之DEPT 圖譜 ................................................... S44
附圖四十二 antrodin D 之HSQC 圖譜 ................................................... S45
附圖四十三 antrodin D 之HMBC 圖譜 ................................................. S45
附圖四十四
trans-3-Isobutyl-4-[4-(3-methyl-2-butenyloxy)phenyl]pyrrolid
ine-2,5-dione 之1H 圖譜 ........................................................ S46
附圖四十五 trans-3-Isobutyl-4-[4-(3-methyl-2-butenyloxy)
phenyl]pyrrolidine-2,5-dione 之COSY 圖譜 ........................ S46
附圖四十六
trans-3-Isobutyl-4-[4-(3-methyl-2-butenyloxy)phenyl]pyrrolid
ine-2,5-dione 之13C 圖譜 ....................................................... S47
附圖四十七
trans-3-Isobutyl-4-[4-(3-methyl-2-butenyloxy)phenyl]pyrrolid
ine-2,5-dione 之DEPT 圖譜 .................................................. S47
附圖四十八
trans-3-Isobutyl-4-[4-(3-methyl-2-butenyloxy)phenyl]pyrrolid
XVIII
ine-2,5-dione 之HSQC 圖譜 ................................................. S48
附圖四十九
trans-3-Isobutyl-4-[4-(3-methyl-2-butenyloxy)phenyl]pyrrolid
ine-2,5-dione 之HMBC 圖譜 ................................................ S48
附圖五十
trans-1-Hydroxy-3-(4-hydroxyphenyl)-4-isobutylpyrrolidine-
2,5- dione 之1H 圖譜 ............................................................. S49
附圖五十一
trans-1-Hydroxy-3-(4-hydroxyphenyl)-4-isobutylpyrrolidine-
2,5- dione 之COSY 圖譜 ....................................................... S49
附圖五十二
trans-1-Hydroxy-3-(4-hydroxyphenyl)-4-isobutylpyrrolidine-
2,5- dione 之13C 圖譜 ............................................................ S50
附圖五十三
trans-1-Hydroxy-3-(4-hydroxyphenyl)-4-isobutylpyrrolidine-
2,5- dione 之DEPT 圖譜 ....................................................... S50
附圖五十四
trans-1-Hydroxy-3-(4-hydroxyphenyl)-4-isobutylpyrrolidine-
2,5- dione 之HSQC 圖譜 ....................................................... S51
XIX
附圖五十五
trans-1-Hydroxy-3-(4-hydroxyphenyl)-4-isobutylpyrrolidine-
2,5- dione 之HMBC 圖譜 ..................................................... S51
附圖五十六 cis-3-(4-Hydroxyphenyl)-4-isobutyldihydrofuran-2,5-dione
之1H 圖譜 .............................................................................. S52
附圖五十七 cis-3-(4-Hydroxyphenyl)-4-isobutyldihydrofuran-2,5-dione
之COSY 圖譜 ........................................................................ S52
附圖五十八 cis-3-(4-Hydroxyphenyl)-4-isobutyldihydrofuran-2,5-dione
之13C 圖譜 ............................................................................. S53
附圖五十九 cis-3-(4-Hydroxyphenyl)-4-isobutyldihydrofuran-2,5-dione
之DEPT 圖譜......................................................................... S53
附圖六十 cis-3-(4-Hydroxyphenyl)-4-isobutyldihydrofuran-2,5-dione 之
HSQC 圖譜 ............................................................................. S54
附圖六十一 cis-3-(4-Hydroxyphenyl)-4-isobutyldihydrofuran-2,5-dione
之HMBC 圖譜 ....................................................................... S54
附圖六十二 4-acetyl antroquinonol B 之1H 圖譜 .................................. S55
附圖六十三 4-acetyl-antroquinonol B 之COSY 圖譜 ........................... S55
附圖六十四 4-acetyl-antroquinonol B 之13C 圖譜 ................................. S56
附圖六十五 4-acetyl-antroquinonol B 之DEPT 圖譜 ............................ S56
XX
附圖六十六 4-acetyl-antroquinonol B 之HSQC 圖譜 ........................... S57
附圖六十七 4-acetyl-antroquinonol B 之HMBC 圖譜 .......................... S57
附圖六十八 antroquinonol 之1H 圖譜 .................................................... S58
附圖六十九 antroquinonol 之COSY 圖譜 ............................................. S58
附圖七十 antroquinonol 之13C 圖譜 ................................................... S59
附圖七十一 antroquinonol 之DEPT 圖譜 .............................................. S59
附圖七十二 antroquinonol 之HSQC 圖譜 ............................................. S60
附圖七十三 antroquinonol 之HMBC 圖譜 ............................................ S60
附圖 七十四 riboflavin 之1H 圖譜......................................................... S61
附圖七十五 riboflavin 之COSY 圖譜 .................................................... S61
附圖七十六 riboflavin 之13C 圖譜 ......................................................... S62
附圖七十七 riboflavin 之DEPT 圖譜 ..................................................... S62
附圖七十八 riboflavin 之HSQC 圖譜 .................................................... S63
附圖七十九 樟芝乙醇萃取波長230 nm 層析圖 ................................... S64
附圖八十 樟芝乙醇萃取波長265 nm 層析圖 ................................... S64
附圖八十一 樟芝甲醇萃取波長230 nm 層析圖 ................................... S65
附圖八十二 樟芝甲醇萃取波長265 nm 層析圖 ................................... S65
附圖八十三 樟芝甲醇均質萃取波長230 nm 層析圖 ........................... S66
附圖八十四 樟芝甲醇均質萃取波長265 nm 層析圖 ........................... S66
XXI
附圖八十五 樟芝多醣體10 kg 波長230 nm 層析圖 ........................... S67
附圖八十六 樟芝多醣體10 kg 波長265 nm 層析圖 ........................... S67
附圖八十七 樟芝多醣體3 kg 波長230 nm 層析圖 ............................. S68
附圖八十八 樟芝多醣體3 kg 波長265 nm 層析圖 ............................. S68
附圖八十九 樟芝編號1 市售品波長230 nm 層析圖 ........................... S69
附圖九十 樟芝編號1 市售品波長265 nm 層析圖 ............................... S69
附圖九十一 樟芝編號2 市售品波長230 nm 層析圖 ........................... S70
附圖九十二 樟芝編號2 市售品波長265 nm 層析圖 ........................... S70
附圖九十三 樟芝編號3 市售品波長230 nm 層析圖 ........................... S71
附圖九十四 樟芝編號3 市售品波長265 nm 層析圖 ........................... S71
附圖九十五 樟芝編號4 市售品波長230 nm 層析圖 ........................... S72
附圖九十六 樟芝編號4 市售品波長265 nm 層析圖 ........................... S72
附圖九十七 樟芝編號5 市售品波長230 nm 層析圖 ........................... S73
附圖九十八 樟芝編號5 市售品波長265 nm 層析圖 ........................... S73
附圖九十九 樟芝編號6 市售品波長230 nm 層析圖 ........................... S74
附圖一百 樟芝編號6 市售品波長265 nm 層析圖 ............................... S74
附圖一百零一 樟芝編號7 市售品波長230 nm 層析圖 ....................... S75
附圖一百零二 樟芝編號7 市售品波長265 nm 層析圖 ....................... S75
附圖一百零三 樟芝編號8 市售品波長230 nm 層析圖 ....................... S76
XXII
附圖一百零四 樟芝編號8 市售品波長265 nm 層析圖 ....................... S76
附圖一百零五 樟芝編號9 市售品波長230 nm 層析圖 ....................... S77
附圖一百零六 樟芝編號9 市售品波長265 nm 層析圖 ....................... S77
附圖一百零七 樟芝編號10 市售品波長230 nm 層析圖 ..................... S78
附圖一百零八 樟芝編號10 市售品波長265 nm 層析圖 ..................... S78
附圖一百零九 樟芝編號11 市售品波長230 nm 層析圖 ..................... S79
附圖一百一十 樟芝編號11 市售品波長265 nm 層析圖 ..................... S79
附圖一百一十一 子實體樣品1 波長230 nm 層析圖 ........................... S80
附圖一百一十二 子實體樣品1 波長265 nm 層析圖 ........................... S80
附圖一百一十三 子實體樣品2 波長230 nm 層析圖 ........................... S81
附圖一百一十四 子實體樣品2 波長265 nm 層析圖 ........................... S81
附圖一百一十五 antrodin A 之LOD 及LOQ ........................................ S82
附圖一百一十六 antrodin B 之LOD 及LOQ ........................................ S82
附圖一百一十七 4-acetyl antroquinonol B 之LOD 及LOQ ................. S83
附圖一百一十八 antrodin D 之LOD 及LOQ ........................................ S83
附圖一百一十九 trans-1-hydroxy-3-(4-hydoxyphenyl)- ........................ S84
附圖一百二十 antroquinonol 之LOD 及LOQ.................................. S84
附圖一百二十一 antrocinnamomin B 之LOD 及LOQ ........................ S85
附圖一百二十二 trans-3-isobutyl-4-[4-(3-methyl-2-butenyloxy) ........ S85
XXIII
附圖一百二十三 antcin B 之LOD 及LOQ ......................................... S86
附圖一百二十四
cis-3-(4-hydroxyphenyl)-4-isobutyldihydrofuran-2,5-dione .. S86
附圖一百二十五 riboflavin 之LOD 及LOQ ....................................... S87
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