Fractionation of lentil seeds (Lens culinaris Medik.) for insecticidal and flavonol tetraglycoside components
Fractionation of lentil seeds (Lens culinaris Medik.) for insecticidal and flavonol tetraglycoside components
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DOI：
10.1021/jf0705062
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发表时间：
2007-07-11
影响因子：
6.1
通讯作者：
Sutherland, Daniel H.
中科院分区：
文献类型：
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作者：
Taylor, Wesley G.;Fields, Paul G.;Sutherland, Daniel H.
对4个栽培品种的成熟扁豆（透镜culinaris Medik.）在实验室试验中发现具有拒食和杀虫特性，储藏物的害虫。用硅胶对活性Diaion HP-20甲醇提取物进行快速色谱，得到黄酮醇、来苏糖醇、大豆皂苷和肽级分，通过高分辨率NMR实验显示黄酮醇级分含有山奈酚3-O-β-吡喃葡萄糖基（1 -> 2）-O-[α-吡喃鼠李糖基（1 -> 6）]-β-吡喃半乳糖苷-7-O-α-鼠李吡喃糖苷和暂时的山奈酚3-O-β-吡喃葡萄糖基（1 -> 2）-O-[α-吡喃鼠李糖基（1 -> 6）]-β-吡喃葡萄糖苷-7-O-α-吡喃鼠李糖苷。这些无活性的四糖苷，虽然在报道的HPLC条件下不可分离，但通过NMR光谱法以几乎相等的比例检测到。三种溶血卵磷脂与先前在豌豆提取物中鉴定的溶血卵磷脂相同。在Diaion HP-20甲醇提取物中发现了大豆皂苷I（大豆皂苷Bb）和大豆皂苷VI（大豆皂苷β g）。杀虫扁豆肽与质量为3881 Da，分离出少量的埃斯顿品种阴离子交换色谱法，与富含半胱氨酸的豌豆白蛋白1b类植物杀虫剂。杀虫扁豆肽和大豆皂甙I的二元混合物在与S.米。
Crude methanol extracts from four cultivated varieties of mature lentil seeds (Lens culinaris Medik.) were found to possess antifeedant and insecticidal properties in laboratory tests with the rice weevil (Sitophilus oryzae L.), an insect pest of stored products. Flash chromatography with silica gel on active Diaion HP-20 methanol extracts gave flavonol, lysolecithin, soyasaponin, and peptide fractions, as determined by HPLC and electrospray ionization LC/MS. The flavonol fraction was shown by high-resolution NMR experiments to contain a mixture of kaempferol 3-O-beta-glucopyranosyl(1 -> 2)-O-[alpha-rhamnopyranosyl(1 -> 6)]-beta-galactopyranoside-7-O-alpha-rhamnopyranoside and, tentatively, kaempferol 3-O-beta-glucopyranosyl(1 -> 2)-O-[alpha-rhamnopyranosyl(1 -> 6)]-beta-glucopyranoside-7-O-alpha-rhamnopyranoside. These inactive tetraglycosides, although inseparable under the reported HPLC conditions, were detected by NMR spectroscopy in nearly equal proportions. Three lysolecithins were identical to those previously identified in pea extracts. Soyasaponin I (soyasaponin Bb) and soyasaponin VI (soyasaponin beta g) were found in Diaion HP-20 methanol extracts. An insecticidal lentil peptide with a mass of 3881 Da, isolated from an Eston variety in small quantities by anion exchange chromatography, was related to the cysteine-rich pea albumin 1b class of botanical insecticides. Binary mixtures of the insecticidal lentil peptide and soybean soyasaponin I were synergistic in tests with S. oryzae.