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目的研究番荔枝Annona squamosa种子的化学成分。方法利用常压硅胶柱、中压制备液相与高压制备液相色谱等现代仪器方法进行分离纯化,结合化合物的理化性质和紫外、核磁、质谱数据鉴定化合物结构。结果从番荔枝种子超临界CO2提取物中分得10个邻双四氢呋喃型番荔枝内酯类化合物,分别鉴定为3-[(13R)-13-[(2R,2’R,5R,5’R)-5’-[(1S)-1,5-二羟基壬基]八氢[2,2’-双呋喃]-5-基]13-羟基十三烷基]-5-甲基-2(5H)-呋喃酮(1)、3-[(2R,9R)-2,9-二羟基-9-[(2R,2’R,5R,5’R)-八氢-5’-[(1S)-1-羟基十五烷基][2,2’-双呋喃]-5-基]壬基]-5-甲基-2(5H)-呋喃酮(2)、6-羟基-去乙酰紫玉盘辛素(3)、6-羟基-4-去氧-番荔枝太辛(4)、bullanin(5)、10-羟基-巴婆双呋内酯(6)、刺叶番荔枝素A(7)、多鳞番荔枝辛素I(8)、多鳞番荔枝辛素C(9)、番荔辛I(10)。结论化合物1和2为新化合物,分别命名为28-羟基-番荔枝素L和4-羟基-番荔枝素Y,化合物3~7为首次从番荔枝中分离得到。
Objective To study the chemical constituents of annona squamosa seeds. Methods The compounds were isolated and purified by using conventional instruments such as pressure silica gel column, medium pressure liquid chromatography and high pressure liquid chromatography. The structures of compounds were identified by physicochemical properties and UV, NMR and MS data. Results Ten ortho-tetrahydrofurandonanoside compounds were isolated from the supercritical carbon dioxide (CO2) extract of Annona Sulzer seeds and identified as 3 - [(13R) -13 - [(2R, 2’R, 5R, ) -5 ’- [(1S) -1,5-dihydroxynonyl] octahydro [2,2’-biran] -5-yl] 13-hydroxytridecyl] (5H) -furanone (1), 3 - [(2R, 9R) -2,9- dihydroxy-9 - [(2R, 2’R, 5R, (1S) -1-hydroxypentadecyl] [2,2’-bifuran] -5-yl] nonyl] (4), bullanin (5), 10-hydroxy-paraparevulinide (6), pricklyash Litchi A (7), Squamosteen Ⅰ (8), Squamosteen C (9), Picein I (10). Conclusions Compounds 1 and 2 are new compounds named as 28-hydroxy-o-tolunidine L and 4-hydroxy-oicin Y, respectively. Compounds 3 to 7 were isolated from annona for the first time.