海茄苳[Avicennia marina (Forsk.) Vierh.]為國際性的紅樹林植物，廣泛分佈於熱帶及亞熱帶地區。在埃及海茄苳被視為民間用藥(folk medicine)，其樹皮、樹葉、果實，被用於治療風濕、潰瘍、天花等皮膚疾病。為了尋找更具有生物活性的新化合物，本研究針對海茄苳氣根(呼吸根)進行化學成分之分離與純化，得到8個新三萜皂苷類(triterpenoid glycosides)化合物：avimarsosides A-H (4-11)，以及19個已知化合物，包括：4個三萜皂苷類：ilekudinoside B (1)、ilexasoside C (2)、19α,23-dihydroxyurs-12-en-28-oic acid 3β-O-[β-D-glucuronopyranoside-6-O-methyl ester]-28-O-β-D-glucopyranosyl ester (3)、ilexoside XLVII (12)；3個苯乙醇糖甙類(phenylethanoid glycosides)：acteoside (13)、isoacteoside (14)、orobanchoside (15)；4個酚類(phenolic compounds)：trans-caffeic acid (16)、(E)-3,4-dimethoxycinnamic acid (17)、methyl chlorogenate (18)、chlorogenic acid (19)；1個木酚素類(lignan)：(－)-(7′S,8S,8′R)-4,4′-dihydroxy-3,3′,5,5′-tetramethoxy-7′,9-epoxylignan-9′-ol-7-one (20)；2個木酚素苷類(lignan glucosides)：(2R,3S,4R)-lyoniresinol 3α-O-β-D-glucopyranoside (21)、(2R,3R,4S)-lyoniresinol 3α-O-β-D-glucopyranoside (22)；2個環烯醚萜苷類(iridoid glucosides)：marinoid D (23)、geniposidic acid (24)；3個三萜類(triterpenoids)：betulinic acid (25)、betulin (26)、lupeol (27)。此外，將化合物3-11進行水解反應，並獲得7個反應產物HD-01-HD-07。
化合物1-3、12、15-22和24為首次自該屬植物中分離得到，所有化合物都經由光譜分析、質譜及化學方法加以證明。在生物活性試驗中，化合物3、4、8、25和26對人類口腔癌細胞(Ca9-22)具有細胞毒殺作用；化合物25和26具有抑制C型肝炎病毒(HCV)複製作用；化合物13具有抑制C型肝炎病毒(HCV)進入細胞作用。
關鍵詞：海茄苳、氣根(呼吸根)、三萜皂苷類、人類口腔癌細胞、C型肝炎病毒

Avicennia marina (Forsk.) Vierh. is a cosmopolitan mangrove plant and widely distributed in tropical and subtropical regions. The barks, leaves, and fruits of A. marina have been used as traditional medicine in Egypt to treat rheumatism, ulcers, smallpox and other skin diseases. In order to search for novel bioactive compounds from A. marina, eight new compounds avimarsosides A-H (4-11) were isolated from the aerial root of this plant, along with nineteen known compounds, including four triterpenoid glycosides: ilekudinoside B (1), ilexasoside C (2), 19α,23-dihydroxyurs-12-en-28-oic acid 3β-O-[β-D-glucuronopyranoside-6-O-methyl ester]-28-O-β-D-glucopyranosyl ester (3), ilexoside XLVII (12); three phenylethanoid glycosides: acteoside (13), isoacteoside (14), orobanchoside (15); four phenolic compounds: trans-caffeic acid (16), (E)-3,4-dimethoxycinnamic acid (17), methyl chlorogenate (18), chlorogenic acid (19); one lignan: (－)-(7′S,8S,8′R)-4,4′-dihydroxy-3,3′,5,5′-tetramethoxy-7′,9-epoxylignan-9′-ol-7-one (20); two lignan glucosides: (2R,3S,4R)-lyoniresinol 3α-O-β-D-glucopyranoside (21), (2R,3R,4S)-lyoniresinol 3α-O-β-D-glucopyranoside (22); two iridoid glucosides: marinoid D (23), geniposidic acid (24); three triterpenoids: betulinic acid (25), betulin (26), lupeol (27). Besides, we further hydrolyzed compounds 3-11 to give seven products HD-01-HD-07 for the structure elucidation.
Compounds 1-3, 12, 15-22 and 24 were found for the first time from the genus of Avicennia. The structures of these compounds were identified by spectroscopic analysis, mass data and chemical methods. In biological activity test, compounds 3, 4, 8, 25 and 26 had cytotoxicity toward human oral cancer cells (Ca9-22). Compounds 25 and 26 could inhibit HCV replication in Ava5 cells. Compound 13 obviously inhibited HCV entry toward Huh7.5 cells.
Keywords: Avicennia marina, aerial root, triterpenoid glycolsides, human oral cancer cells, hepatitis C virus.

論文審定書 i
謝誌 ii
中文摘要 iii
英文摘要 iv
化合物1-27之化學結構 v
目錄 x
圖次 xii
表次 xx
縮寫對照表 xxii
第一章 緒論 1
第一節 前言 1
第二節 研究背景 2
第三節 海茄苳型態分佈及應用 5
第四節 文獻回顧 9
第五節 研究目的 19
第二章 研究材料與方法 22
第三章 化合物之結構證明 27
第一節 Ilekudinoside B (1)之結構證明 27
第二節 Ilexasoside C (2)之結構證明 38
第三節 19α,23-Dihydroxyurs-12-en-28-oic acid 3β-O-[β-D-glucuronopyranoside-6-O-methyl ester]-28-O-β-D-glucopyranosyl ester (3)之結構證明 50
第四節 Avimarsoside A (4)之結構證明 63
第五節 Avimarsoside B (5)之結構證明 76
第六節 Avimarsoside C (6)之結構證明 89
第七節 Avimarsoside D (7)之結構證明 101
第八節 Avimarsoside E (8)之結構證明 114
第九節 Avimarsoside F (9)之結構證明 127
第十節 Avimarsoside G (10)之結構證明 139
第十一節 Avimarsoside H (11)之結構證明 151
第十二節 Ilexoside XLVII (12)之結構證明 163
第十三節 Acteoside (13)之結構證明 181
第十四節 Isoacteoside (14)之結構證明 188
第十五節 Orobanchoside (15)之結構證明 195
第十六節 trans-Caffeic acid (16)之結構證明 203
第十七節 (E)-3,4-Dimethoxycinnamic acid (17)之結構證明 208
第十八節 Methyl chlorogenate (18)之結構證明 213
第十九節 Chlorogenic acid (19)之結構證明 222
第二十節 (－)-(7′S,8S,8′R)-4,4′-Dihydroxy-3,3′,5,5′-tetramethoxy-7′,9-epoxylignan-9′-ol-7-one (20)之結構證明 234
第二十一節 (2R,3S,4R)-Lyoniresinol 3α-O-β-D-glucopyranoside (21)之結構證明 241
第二十二節 (2R,3R,4S)-Lyoniresinol 3α-O-β-D-glucopyranoside (22)之結構證明 250
第二十三節 Marinoid D (23)之結構證明 262
第二十四節 Geniposidic acid (24)之結構證明 270
第二十五節 Betulinic acid (25)之結構證明 279
第二十六節 Betulin (26)之結構證明 284
第二十七節 Lupeol (27)之結構證明 290
第四章 醣水解試驗 297
第五章 生物活性試驗 299
第六章 結論 309
第七章 相關實驗部分 314
第一節 儀器與材料 314
第二節 植物材料與分離純化 317
第三節 醣水解試驗之實驗方法 321
第四節 生物活性試驗之實驗方法 322
第五節 各化合物之物理與光譜數據總整理 326
第八章 參考文獻 350
論文公開授權書 356

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