深山含笑次級代謝產(chǎn)物中化感物質(zhì)的研究
發(fā)布時間:2018-05-01 12:14
本文選題:木蘭科 + 含笑屬。 參考:《中央民族大學(xué)》2017年碩士論文
【摘要】:化學(xué)合成除草劑存在高毒性、高殘留性和植物抗藥性的缺點(diǎn),而天然植物源除草劑來源于植物自身合成化感物質(zhì),是未來綠色高效除草劑開發(fā)的趨勢。本論文在抑制種子萌發(fā)活性實(shí)驗(yàn)的指導(dǎo)下,對含笑屬(Michelia L.)植物深山含笑(Michelia maudiae Dunn)的樹皮進(jìn)行了化學(xué)成分研究,并對部分所得次級代謝產(chǎn)物進(jìn)行了抑制種子萌發(fā)活性測試。深山含笑(Michelia maudiae Dunn)為木蘭科(Magnoliaceae)含笑屬(Michelia L.)植物,常綠喬木,為我國特有植物,主要分布在我國南方地區(qū)。本論文選擇深山含笑樹皮的有抑制種子萌發(fā)活性的洗脫物,采用硅膠柱色譜、凝膠柱色譜、薄層制備色譜等色譜方法進(jìn)行了化學(xué)成分的提取分離。通過核磁共振波譜、紫外、紅外、高分辨質(zhì)譜等光譜數(shù)據(jù)解析,結(jié)合物理常數(shù)測定,以及與文獻(xiàn)數(shù)據(jù)進(jìn)行對比的方法,鑒定了 19個次級代謝產(chǎn)物結(jié)構(gòu)。所得19個化合物包括3個吉馬烷型倍半萜:2,8-二羥基二氫小白菊內(nèi)酯(1),小白菊內(nèi)酯(2),二氫小白菊內(nèi)酯(3);3個香木蘭烷型倍半萜:aromadendrane-4β,10α,15-triol(4),alloaromadendrane-4β,10α-diol(5),桉油烯醇(6);1個石竹烷型倍半萜:氧化石竹烯(7);1個法呢烷型倍半萜:橙花叔醇(8);1個累積二烯烴降碳倍半萜:LyratolF(9);5個莰烷型單萜:望春玉蘭脂素C(10),咖啡酸龍腦酯(11),乙酸龍腦酯(12),2-exo-3-exo-camphane-2,3-diol(13),龍腦(14);1 個薄荷烷型單萜類化合物:α-松油醇(15);2個酚酸類:香草酸(16)和對羥基苯甲醛(17);2個甾醇類:β-谷甾醇(18)和7α-羥基甾醇(19)。其中化合物(1)為未見文獻(xiàn)報道的新化合物,化合物(9)為首次從含笑屬(Michelia L.)植物中發(fā)現(xiàn)。進(jìn)一步選擇質(zhì)量較多的化合物3、5、10、11、16和19進(jìn)行種子萌發(fā)活性初步測試。通過分析受試物在1.0×10-3 M時對黑麥草(Lolium perenne L.)、蘇丹草(Sorghum sudanense(Piper)Stapf)、萵筍(Lactuca sativa L.var.angustana Irish ex Bremer)種子萌發(fā)的抑制效果,發(fā)現(xiàn)化合物3對蘇丹草種子的萌發(fā)抑制作用較強(qiáng),化合物10對黑麥草的萌發(fā)抑制作用較強(qiáng),化合物16對蘇丹草種子的萌發(fā)抑制作用較強(qiáng),化合物19對黑麥草種子的萌發(fā)抑制作用較強(qiáng)。進(jìn)一步的濃度梯度抑制實(shí)驗(yàn)發(fā)現(xiàn),化合物3對蘇丹草的萌發(fā)EC50值為4.05× 10-4 M、化合物10對黑麥草的萌發(fā)EC50值為4.51×10-5 M、化合物16對蘇丹草的萌發(fā)EC50值為1.49×10-5 M、化合物19對黑麥草種子的萌發(fā)EC50值為2.18 X 1 0-4 M。論文所得實(shí)驗(yàn)結(jié)果支持了文獻(xiàn)關(guān)于萜類、酚酸類、甾醇類化合物是天然植物激素重要來源的報道,更為從深山含笑中尋找和開發(fā)新型植物源除草劑的化感物質(zhì)提供了深入研究的先導(dǎo)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 偽, 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: 偽 -terpinol 15C; two phenolic acids: vanillic acid 16) and p-hydroxybenzaldehyde 17m; two sterols: 尾 -sitosterol 18) and 7 偽 -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.
【學(xué)位授予單位】:中央民族大學(xué)
【學(xué)位級別】:碩士
【學(xué)位授予年份】:2017
【分類號】:Q946
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