深山含笑次级代谢产物中化感物质的研究

发布时间：2018-05-01 12:14

本文选题：木兰科 + 含笑属　；参考：《中央民族大学》2017年硕士论文

【摘要】：化学合成除草剂存在高毒性、高残留性和植物抗药性的缺点,而天然植物源除草剂来源于植物自身合成化感物质,是未来绿色高效除草剂开发的趋势。本论文在抑制种子萌发活性实验的指导下,对含笑属(Michelia L.)植物深山含笑(Michelia maudiae Dunn)的树皮进行了化学成分研究,并对部分所得次级代谢产物进行了抑制种子萌发活性测试。深山含笑(Michelia maudiae Dunn)为木兰科(Magnoliaceae)含笑属(Michelia L.)植物,常绿乔木,为我国特有植物,主要分布在我国南方地区。本论文选择深山含笑树皮的有抑制种子萌发活性的洗脱物,采用硅胶柱色谱、凝胶柱色谱、薄层制备色谱等色谱方法进行了化学成分的提取分离。通过核磁共振波谱、紫外、红外、高分辨质谱等光谱数据解析,结合物理常数测定,以及与文献数据进行对比的方法,鉴定了 19个次级代谢产物结构。所得19个化合物包括3个吉马烷型倍半萜:2,8-二羟基二氢小白菊内酯(1),小白菊内酯(2),二氢小白菊内酯(3);3个香木兰烷型倍半萜:aromadendrane-4β,10α,15-triol(4),alloaromadendrane-4β,10α-diol(5),桉油烯醇(6);1个石竹烷型倍半萜:氧化石竹烯(7);1个法呢烷型倍半萜:橙花叔醇(8);1个累积二烯烃降碳倍半萜:LyratolF(9);5个莰烷型单萜:望春玉兰脂素C(10),咖啡酸龙脑酯(11),乙酸龙脑酯(12),2-exo-3-exo-camphane-2,3-diol(13),龙脑(14);1 个薄荷烷型单萜类化合物:α-松油醇(15);2个酚酸类:香草酸(16)和对羟基苯甲醛(17);2个甾醇类:β-谷甾醇(18)和7α-羟基甾醇(19)。其中化合物(1)为未见文献报道的新化合物,化合物(9)为首次从含笑属(Michelia L.)植物中发现。进一步选择质量较多的化合物3、5、10、11、16和19进行种子萌发活性初步测试。通过分析受试物在1.0×10-3 M时对黑麦草(Lolium perenne L.)、苏丹草(Sorghum sudanense(Piper)Stapf)、莴笋(Lactuca sativa L.var.angustana Irish ex Bremer)种子萌发的抑制效果,发现化合物3对苏丹草种子的萌发抑制作用较强,化合物10对黑麦草的萌发抑制作用较强,化合物16对苏丹草种子的萌发抑制作用较强,化合物19对黑麦草种子的萌发抑制作用较强。进一步的浓度梯度抑制实验发现,化合物3对苏丹草的萌发EC50值为4.05× 10-4 M、化合物10对黑麦草的萌发EC50值为4.51×10-5 M、化合物16对苏丹草的萌发EC50值为1.49×10-5 M、化合物19对黑麦草种子的萌发EC50值为2.18 X 1 0-4 M。论文所得实验结果支持了文献关于萜类、酚酸类、甾醇类化合物是天然植物激素重要来源的报道,更为从深山含笑中寻找和开发新型植物源除草剂的化感物质提供了深入研究的先导化合物。
[Abstract]:Chemical synthetic herbicides have the disadvantages of high toxicity, high residue and plant resistance, while natural plant-derived herbicides come from plant synthetic allelochemicals, which is the trend of the development of green and efficient herbicides in the future. In this paper, under the guidance of the experiment of inhibiting seed germination activity, Michelia L. The bark of Michelia maudiae Dunn was studied and some secondary metabolites were tested for inhibiting seed germination. Michelia maudiae Dunnus (Magnoliaceaeae) is Michelia L. Plants, evergreen trees, endemic to China, mainly distributed in southern China. In this paper, the extracts from the bark of Hedysticum sinensis were extracted and separated by silica gel column chromatography, gel column chromatography and thin-layer preparation chromatography. The structures of 19 secondary metabolites were identified by means of NMR, UV, IR, high resolution mass spectrometry, physical constant determination and comparison with literature data. 19 compounds were obtained, including three sesquiterpenes of the jimane type: 2, 8-dihydroxy, dihydrohalobalide, 1, 2, 3, 3, 3 sesquiterpenes: aromadendrane-4 尾 10 伪, 15-triol4alloaromadendrane-4 尾 10, eucalyptenol 5, and eucalyptenol 6, respectively. Caryophyllene 7e; 1 sesquiterpene: nerolflower tertiary alcohol 8; 1 cumulative diolefins decarbonate sesquiterpene 9; 5 camphene type monoterpenes: Magnolipin C10, caffeic acid borneol 11, borneol acetate 122-exo-camphane-2e 3-diolanine 13, borneol 1414 terpene 1 monoterpene type, monoterpene type monopterpene, 1 monoterpene, 122-exo-3-exo-camphane-2, 3-diolanine, 1 monoterpene, 1 monophyllethene monoterpene, 1 monoterpenoid. Products: 伪 -terpinol 15C; two phenolic acids: vanillic acid 16) and p-hydroxybenzaldehyde 17m; two sterols: 尾 -sitosterol 18) and 7 伪 -hydroxysterol 19. Compound 1) is a new compound that has not been reported in the literature, and compound 9) is the first one from Michelia L. Found in plants. The seed germination activity was determined by further selection of the higher quality compounds, 3O5A10, 10A11, 16, and 19, respectively. By analyzing the inhibitory effects of 1. 0 脳 10 ~ (-3) M on seed germination of Lolium perenne L., Sorghum Sudanensei Pipera Stapfus and Lactuca sativa L.var.angustana Irish ex Bremer) at 1.0 脳 10 ~ (-3) M, it was found that compound 3 had a strong inhibitory effect on seed germination of Sudan grass. Compound 10 had a strong inhibitory effect on the germination of ryegrass, compound 16 on the seed germination of Sudan grass, and compound 19 on the germination of ryegrass seeds. Further concentration gradient inhibition experiments showed that, The germination EC50 value of compound 3 to Sudan grass was 4.05 脳 10 ~ (-4) M, the germination EC50 value of compound 10 to ryegrass was 4.51 脳 10 ~ (-5) M, the germination EC50 value of compound 16 to Sudan grass was 1.49 脳 10 ~ (-5) M, the EC50 value of compound 19 to ryegrass seed germination was 2.18 X 10 ~ (-4) M. The experimental results support the reports that terpenoids, phenolic acids and sterols are important sources of natural plant hormones. Finding and developing the allelochemicals of new plant herbicides from the deep mountain provide a leading compound for further study.
【学位授予单位】：中央民族大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：Q946

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