Isolation and characterization of structurally novel antimutagenic flavonoids from spinach (Spinacia oleracea)
Isolation and characterization of structurally novel antimutagenic flavonoids from spinach (Spinacia oleracea)
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DOI：
10.1021/jf0013712
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发表时间：
2001-06-01
影响因子：
6.1
通讯作者：
Unger, KK
中科院分区：
文献类型：
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作者：
Edenharder, R;Keller, G;Unger, KK
从菠菜中分离得到13个化合物，对小鼠伤寒沙门氏菌TA 98中的膳食致癌物质2-氨基-3-甲基咪唑[4，5-f]喹啉具有抗突变作用。用制备型和微制备型高效液相色谱分离菠菜干品(商品)的甲醇/水(70：30，v/v)萃取物，再用固相萃取(SPE)去除脂类化合物，得到抗诱变物质。通过仪器分析，包括FT-IR、H-1和C-13核磁共振谱、UV-Vis光谱和质谱图，对活性物质进行了鉴定。化合物1，5，2‘，3’-三羟基-4‘-甲氧基-6，7-亚甲基二氧基黄酮醇-3-O-β-葡萄糖醛酸苷(化合物1)，5，2’，3‘-三羟基-4’-甲氧基-6，7-亚甲基二氧基黄酮醇3-O-β-葡萄糖醛酸苷(化合物2)，5-羟基-3‘，4’-二甲氧基-6，7-二甲氧基-3-O-β-葡萄糖醛酸苷(化合物3)；化合物5，6，3‘-三羟基-7，4’-二甲氧基黄酮醇3-O-β-葡萄糖醛酸苷(化合物4)，5，6-二羟基-7，3‘，4’-三甲氧基黄酮醇3-O-β-葡萄糖醛酸苷(化合物5)；(C)黄酮醇二糖)5，6，4‘-三羟基-7，3’-二甲氧基黄酮醇3-O-二糖(化合物6)，5，6，3‘，4’-四羟基-7-甲氧基黄酮醇3-O-二糖(化合物7和8)；(D，黄烷酮)5，8，4‘-三羟基黄烷酮(化合物9)，7，8，4’-三羟基黄烷酮(化合物10)，(E，黄酮类化合物)化合物11，12，13，结构不完全明确。化合物1的产率与干重相关，为0.3%，而化合物2-13的产率在0.017%~0.069%之间。黄酮醇葡萄糖醛酸类化合物的IC50值在24.2~58.2微米之间，而黄酮醇二糖(化合物7和8)、黄烷酮(化合物9和10)以及与黄酮类相关的糖苷化合物11-13只有微弱的活性。而化合物7和8的苷元具有较强的抗诱变作用(IC50分别为104和13.0um)。
Thirteen compounds, isolated from spinach (Spinacia oleracea), acted as antimutagens against the dietary carcinogen 2-amino-3-methylimidazo [4,5-f]quinoline in Salmonella typhimurium TA 98. The antimutagens were purified by preparative and micropreparative HPLC from a methanol/water (70:30, v/v) extract of dry spinach (commercial product) after removal of lipophilic compounds such as chlorophylls and carotenoids by solid-phase extraction (SPE). Pure active compounds were identified by instrumental analysis including FT-IR, H-1 and C-13 NMR, UV-vis spectroscopy, and mass spectrometry. All of these compounds were flavonoids and related compounds that could be attributed to five groups: (A, methylenedioxyflavonal glucuronides) 5,3 ' -dihydroxy-4 ' -methoxy-6,7-methylenedioxyflavonol 3-O-beta -glucuronide (compound 1), 5,2 ' ,3 ' -trihydroxy-4 ' -methoxy-6,7-methylenedioxyflavonol 3-O-beta -glucuronide (compound 2), 5-hydroxy-3 ' ,4 ' -dimethoxy-6,7-methylenedioxyflavonol 3-O-beta -glucuronide (compound 3); (B, flavonol glucuronides) 5,6,3 ' -trihydroxy-7,4 ' -dimethoxyflavonol 3-O-beta -glucuronide (compound 4), 5,6-dihydroxy-7,3 ' ,4 ' -trimethoxyflavonol 3-O-beta -glucuronide (compound 5); (C, flavonol disaccharides) 5,6,4 ' -trihydroxy-7,3 ' -dimethoxyflavonol 3-O-disaccharide (compound 6), 5,6,3 ' ,4 ' -tetrahydroxy-7-methoxyflavonol 3-O-disaccharide (compounds 7 and 8); (D, flavanones) 5,8,4 ' -trihydroxyflavanone (compound 9), 7,8,4 ' -trihydroxyflavanone (compound 10); (E, flavonoid-related compounds) compounds 11, 12, and 13 with incompletely elucidated structures. The yield of compound 1 was 0.3%, related to dry weight, whereas the yields of compounds 2-13 ranged between 0.017 and 0.069%. IC50 values (antimutagenic potencies) of the flavonol glucuronides ranged between 24.2 and 58.2 muM, whereas the flavonol disaccharides (compounds 7 and 8), the flavanones (compounds 9 and 10), and the flavonoid-related glycosidic compounds 11-13 were only weakly active. The aglycons of compounds 7 and 8, however, were potent antimutagens (IC50 = 10 4 and 13.0 muM, respectively).