碩士 / 國立中山大學 / 海洋生物科技暨資源學系研究所 / 102 / 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.
| Identifer | oai:union.ndltd.org:TW/102NSYS5277009 |
| Date | January 2014 |
| Creators | Kai-hsun Chen, 陳楷勛 |
| Contributors | Chih-Chuang Liaw, 廖志中 |
| Source Sets | National Digital Library of Theses and Dissertations in Taiwan |
| Language | zh-TW |
| Detected Language | English |
| Type | 學位論文 ; thesis |
| Format | 379 |
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