网肺衣和硬指叶苔内生真菌活性代谢产物的研究

发布时间：2018-01-25 02:26

本文关键词： 内生真菌网肺衣杂色曲霉硬指叶苔 Penicillium sp.SD1617 蒽醌氧杂蒽酮生物碱　出处：《山东大学》2014年硕士论文　论文类型：学位论文

【摘要】：内生菌是指其生命周期的一定阶段或全部阶段生活于健康植物组织或器官内部而对宿主没有明显负面影响的细菌、真菌或放线菌。与大量有关植物内生真菌代谢产物的研究相比,目前对地衣和苔藓内生真菌的研究较少,但近年来取得的研究成果表明,这些微生物也是结构新颖并且生物活性多样的次生代谢产物的来源。本文对一株地衣内生真菌杂色曲霉(Aspergillus versicolor)和一株苔藓内生真菌(Penicillium sp. SD1617)的次生代谢产物进行了系统的化学成分研究。运用硅胶柱层析、凝胶柱层析、反相键合硅胶柱层析以及高效液相色谱等技术共分离获得36个化合物,包括15个蒽醌类化合物,3个氧杂葸酮类化合物,7个生物碱类化合物,5个简单的芳香化合物,3个甾体类化合物,2个曲酸衍生物以及1个混源萜类化合物。采用一维和二维核磁共振谱(NMR)、质谱(MS)、红外光谱(IR)和紫外光谱(UV)等技术鉴定了以上化合物的结构。对从网肺衣(Lobaria retigera)中分离获得的杂色曲霉(Aspergillus versicolor)在大米和PDB两种培养基中产生的次生代谢产物进行了研究。共分离获得14个蒽醌类化合物：8-O-methylversicolorin A和B(1和2),8-O-methylaverythin (3),1'-O-ethyl-6,8-di-O-methylaverantin (4),6,8,1'-tri-O-methylaverantin (5),6,8-di-O-methylaverufin (6), aversin (7),6,8-di-O-methylversicolorin A (8),1'-O-methylaverantin(9),6,8-di-O-methylnidurufin (10), averythin(11),6,8-di-O-mrthyl averufanin (21), questin (22)和1-O-methylparirtin (23);3个氧杂葸酮类化合物：sterigmatocystin (12),5-methoxysterigmatocystin (13)和dihydrosterigmatocystin(14)；5个生物碱类化合物：notoamide C (15), dehydronotoamide C (16),(-)-cyclopenol (17), phomopsin A (18)和3-formylindole (26);2个简单的芳香化合物：dibutyl phthalate (24)和dimethyl phthalate (25);3个甾体类化合物：stigmasterol (19), ergosterol-5,7-dien-3β-ol (27)和dankasterone A (28)以及1个混源萜类化合物asperdemin (20)。对新化合物1-4进行了细胞毒活性筛选,结果表明只有化合物1和2对PC-3和H460细胞株有弱的细胞毒活性。对硬指叶苔(Lepidozia vitrea Steph.)的内生真菌Penicillium sp. SD1617的次生代谢产物进行了研究,从中分离获得8个已知化合物,包括1个蒽醌类化合物：citreorosein (33);2个生物碱类化合物：ditryptophenaline (29)和brevianamide F(30)；3个简单的芳香化合物：4-hydroxybenzaldehyde (34), flemingipanic acid (35)和4-hydroxy-2-methoxy-3,6-dimethylbenzoic acid (36);以及2个曲酸衍生物：kojic acid (31)和7-O-acetylkojic acid(32)。
[Abstract]:Endophytic bacteria are bacteria that live in healthy plant tissues or organs at a certain or all stages of their life cycle without significant negative effects on their hosts. Fungi or actinomycetes. Compared with a large number of studies on plant endophytic fungi metabolites, there is less research on lichen and lichen endophytic fungi, but recent research results show that. These microorganisms are also sources of secondary metabolites with novel structures and diverse biological activities. A strain of endophytic fungi Aspergillus versicolor and a strain of endophytic fungi from lichens were studied in this paper. The secondary metabolites of Penicillium sp. SD1617) were systematically studied by silica gel column chromatography. A total of 36 compounds, including 15 anthraquinones and 3 oxyanthracanones, were isolated by gel column chromatography, reverse phase bonded silica gel chromatography and high performance liquid chromatography. Seven alkaloids, five simple aromatic compounds, three steroids, two kojic acid derivatives and one mixed terpene were studied by 1D and 2D NMR. The structures of the compounds were identified by MS, IR and UV). Aspergillus versicolor was isolated from Lobaria retigera. The secondary metabolites produced in rice and PDB medium were studied. Fourteen anthraquinones: 8-O-methylversicolorin A and B _ (2) were isolated. 1 and 2). 8-O-methylaverythin (8-O-methylaverythin), 8-di-O-methylaverantin (8-O-methylaverantin), 8-O-methylaverantin (8-O-methylaverantin). (1) tri-O-methylaverantin (68-di-O-methylaverufin, aversin 7). 6-di-O-methylversicolorin A (1: 1) -O-methylaverantin (6). 8-di-O-methylnidurufin 10, averythinan111. 8-di-O-mrthyl averufanin, questin 22) and 1-O-methylparirtin; Three oxazanone compounds: sterigmatocystin 12). 5-methoxysterigmatocystin 13) and dihydrosterigmatocystin14; Five alkaloids, dehydronotoamide C ~ (15) and dehydronotoamide C ~ (16). Phomopsin A (18) and 3-formylindole (26); Two simple aromatic compounds: dibutyl phthalate (24) and dimethyl phthalate (25); Three steroidal compounds: stigmasterol, ergosterol-5. 7-dien-3 尾 -ol (27) and dankasterone A (28)) and a mixed terpene compound asperdemin 20). The cytotoxic activity of new compound 1-4 was screened. The results showed that only compounds 1 and 2 had weak cytotoxic activity against PC-3 and H460 cell lines. Lepidozia vitrea Steph. The secondary metabolites of endophytic fungi Penicillium sp. SD1617 were studied. Eight known compounds were isolated, including one anthraquinone compound: 1: citreorosein 33; Two alkaloids, 1: ditryptophenaline (29) and brevianamide (30); Three simple aromatic compounds: 4-hydroxybenzaldehyde 34). Flemingipanic acid 35) and 4-hydroxy-2-methoxy-3. 6-dimethylbenzoic acid; And two kojic acid derivatives: kojic acid31and 7-O-acetylkojic acid32.
【学位授予单位】：山东大学
【学位级别】：硕士
【学位授予年份】：2014
【分类号】：R915

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