FREE AND BOUND C-13 NORISOPRENOIDS IN QUINCE (CYDONIA-OBLONGA, MILL) FRUIT
FREE AND BOUND C-13 NORISOPRENOIDS IN QUINCE (CYDONIA-OBLONGA, MILL) FRUIT
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DOI：
10.1021/jf00084a031
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发表时间：
1988-11-01
影响因子：
6.1
通讯作者：
SCHREIER, P
中科院分区：
文献类型：
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作者：
WINTERHALTER, P;SCHREIER, P
木瓜(Cydonia obonga，Mill.)果汁用溶剂萃取法(戊烷-二氯甲烷，2：1)提取。经硅胶高效液相色谱分离得到的极性组分中，毛细管气相色谱(HRGC)和毛细管气相色谱-质谱联用(HRGC-MS)首次在木瓜果实中鉴定出C13去异戊二烯类化合物：4-羟基-β-紫罗兰醇、3-羟基-β-紫罗兰醇、4-羟基-β-紫罗兰酮、4-氧代-β-紫罗兰醇、3-羟基-β-紫罗兰酮、5，6-二羟基-β-紫罗兰酮和去氢香草酚。木瓜果汁中的糖苷提取物经Amberlite XAD-2树脂吸附和甲醇洗脱后，经酶解，确定主要产物为3-羟基-β-紫罗兰醇。此外，还发现了以下苷元：3-羟基-β-紫罗兰酮、3-羟基-7，8-二氢-β-紫罗兰醇、呕吐叶醇、3-ONO-α-紫罗兰醇和7，8-二氢香草酚。在这些结果的基础上，讨论了具有工业吸引力的木瓜果实成分的潜在前体，如维替螺烷、双环[4.3.0]壬烷衍生物、3，4-二氢-β-紫罗兰醇、巨型-4，6，8-三烯-3-酮和阿司匹酮。
The constituents of quince fruit (Cydonia oblonga, Mill.) juice were isolated by solvent extraction (pentane-dichloromethane, 2:1). In the polar fractions obtained by liquid chromatography of the extract on silica gel, capillary gas chromatography (HRGC) and capillary gas chromatography-mass spectrometry (HRGC-MS) revealed the occurrence of C13 norisoprenoids identified in quince fruit for the first time: 4-hydroxy-.beta.-ionol, 3-hydroxy-.beta.-ionol, 4-hydroxy-.beta.-ionone, 4-oxo-.beta.-ionol, 3-hydroxy-.beta.-ionone, 5,6-dihydroxy-.beta.-ionone, and dehydrovomifoliol. Enzymatic hydrolysis of a glycosidic extract obtained from quince fruit juice by adsorption on Amberlite XAD-2 resin and subsequent methanol elution led to the identification of 3-hydroxy-.beta.-ionol as major product. Additionally, the following aglycons were found: 3-hydroxy-.beta.-ionone, 3-hydroxy-7,8-dihydro-.beta.-ionol, vomifoliol, 3-ono-.alpha.-ionol, and 7,8-dihydrovomifoliol. On the basis of these results, the potential precursors of industrially attractive quince fruit constituents such as vitispiranes, bicyclo[4.3.0]nonane derivatives, 3,4-didehydro-.beta.-ionol, megastigma-4,6,8-trien-3-ones, and theaspirones are discussed.