鷹爪桃化學成分及生物活性之研究

番荔枝科鷹爪桃 [Artabotrys uncinatus (Lam.) Merr. (Annonaceae)] 為一觀賞植物，亦是優良的香花植物。本研究採集其莖部，以甲醇萃取並震盪分配為n-Hexane、EtOAc、MeOH/H2O三層；在DPPH assay中，發現其甲醇粗萃物具有抗氧化活性，並由此植物中分離得到33個化合物，分別為7個sesquiterpenes : clovan-2β,9α-diol (1) 、caryolane-1,9β-diol (2)、 spathulenol (3)、β-caryophyllene-8R,9R-oxide (4)、(-)-ent-4β-hydroxy-10α-methoxyaromadendrane (5)、4β-hydroxy-10α-methoxyaromadendrane (6)、1-methoxy-9-caryolanol (7) ; 2個triterpenes : 24-methylenelanosta-7,9(11)-dien- 3β-ol (8)、24-methylenelanosta-7,9(11)-diene-3-one (9)* ; 6個flavonoids : artabotryside A (10)、artabotryside B (11)、apigenin (12)、 luteolin (13)、5-hydroxy-7,4’-dimethoxyflavone (14)、 catechin (15) ; 7個alkaloids : liriodenine (16)、 atherospermidine (17)、 artacinatine (18)、 asimilobine (19)、artavenustine (20)、 4,5-dioxoartacinatine (21)*、N-P-coumaroyltyramine (22); 1個lignan : (+)-syringaresinol (23) ; 2個butyrolactones : (2R,3R)-3-hydroxyl-2-methylbutyrolactone (24)、 tetrahydrofuran-4-methylidene-3-ol (25) ; 1個diterpene : phytol (26); 1個glyceryl ester : phosphoric acid mono-(1-hydroxy-3-palmitoyloxypropyl) ester (27) ; 6個steroids : (24R)-stigmasta-5-en-3β,7α-diol (28)、(22E,24S)-stigmasta-5,22- dien-3β,7α-diol (29)、 β-sitosteryl-3-O-β-D-glucoside (30)、stigmasteryl-3-O-β-D-glucoside (31)、 β-stigmasterol (32)、 β-sitosterol (33)。此外，並利用GC-MS分析比對出15個油狀化合物，分別為化合物34~48。其中化合物9及21為新化合物，而化合物1-3、5-7、14-15、22、25-29首次分離自鷹爪花屬( Artabotrys )植物。所有化合物都經由光譜及質譜分析加以證明。上述化合物在生物活性試驗中，化合物13、16、17及23具有細胞毒殺效果；化合物10、11、13、15在DPPH , SOD, and Hydroxy radical scavenging assays中具有抗氧化活性。

關鍵字

番荔枝科；抗氧化；鷹爪桃

並列摘要

Artabotrys uncinatus (Lam.) Merr. (Annonaceae) is a landscape plant (known as Eagle’s Claw) and an excellent resource of fragrant flowers. In this study, the stems of this plant were collected and extracted by MeOH. In DPPH antioxidant assay, it showed that the MeOH extract was active. The extract was then partitioned between H2O-MeOH/n-Hexane, H2O-MeOH/EtOAc to give three layers (n-Hexane, EtOAc, MeOH/H2O). Chromatographic separation of the n-Hexane and EtOAc layers yielded 33 compounds, including 7 sesquiterpenes: clovan-2β,9α-diol (1), caryolane-1,9β-diol (2), spathulenol (3), β-caryophyllene- 8R,9R-oxide (4), (-)-ent-4β-hydroxy-10α-methoxyaromadendrane (5), 4β-hydroxy-10α-methoxyaromadendrane (6), and 1-methoxy-9-caryolanol (7), 2 triterpenes: 24-methylene-lanosta-7,9(11)-dien-3β-ol (8) and 24-methylenelanosta-7,9(11)-diene-3-one (9)*, 6 flavonoids: artabotryside A (10), artabotryside B (11), apigenin (12), luteolin (13), 5-hydroxy-7,4’-dimethoxyflavone (14), and catechin (15), 7 alkaloids: liriodenine (16), atherospermidine (17), artacinatine (18), aisimilobine (19), artavenustine (20), 4,5-dioxoartacinatine (21)*, and N-P-coumaroyltyramine (22), 1 lignan: (+)-syringaresinol (23), 2 butyrolactones: (2R,3R)-3-hydroxyl-2-methylbutyrolactone (24) and tetrahydrofuran-4-methylidene-3-ol (25), 1 diterpene : phytol (26), 1 glyceryl ester : phosphoric acid mono-(1-hydroxy-3- palmitoyloxypropyl) ester (27), 6 steroids: (24R)-stigmasta-5-en- 3β,7α-diol (28), (22E,24S)-stigmasta-5,22-dien-3β,7α- diol (29), β-sitostery-3-O-β-D-glucoside (30), stigmasteryl-3-O-β-D- glucoside (31), β-stigmasterol (32), and β-sitosterol (33). Besides, compounds 34 - 48 were identified by GC-MS. The structures of these compounds were identified by spectral and mass data. Among them, 9 & 21 ars new compounds. 1-3、5-7、14-15、22、25-29 are isolated for the first time from genus Artabotrys. In addition, compounds 13, 16, 17, 23 had different cytotoxicity in MTT assay. Compounds 10, 11, 13, 15 showed different anti-oxidant ability in DPPH , SOD, and Hydroxy radical scavenging assays.