本文關(guān)鍵詞： 內(nèi)生真菌 網(wǎng)肺衣 雜色曲霉 硬指葉苔 Penicillium sp.SD1617 蒽醌 氧雜蒽酮 生物堿　出處：《山東大學(xué)》2014年碩士論文　論文類型：學(xué)位論文

【摘要】：內(nèi)生菌是指其生命周期的一定階段或全部階段生活于健康植物組織或器官內(nèi)部而對宿主沒有明顯負(fù)面影響的細(xì)菌、真菌或放線菌。與大量有關(guān)植物內(nèi)生真菌代謝產(chǎn)物的研究相比,目前對地衣和苔蘚內(nèi)生真菌的研究較少,但近年來取得的研究成果表明,這些微生物也是結(jié)構(gòu)新穎并且生物活性多樣的次生代謝產(chǎn)物的來源。 本文對一株地衣內(nèi)生真菌雜色曲霉(Aspergillus versicolor)和一株苔蘚內(nèi)生真菌(Penicillium sp. SD1617)的次生代謝產(chǎn)物進(jìn)行了系統(tǒng)的化學(xué)成分研究。運(yùn)用硅膠柱層析、凝膠柱層析、反相鍵合硅膠柱層析以及高效液相色譜等技術(shù)共分離獲得36個化合物,包括15個蒽醌類化合物,3個氧雜葸酮類化合物,7個生物堿類化合物,5個簡單的芳香化合物,3個甾體類化合物,2個曲酸衍生物以及1個混源萜類化合物。采用一維和二維核磁共振譜(NMR)、質(zhì)譜(MS)、紅外光譜(IR)和紫外光譜(UV)等技術(shù)鑒定了以上化合物的結(jié)構(gòu)。 對從網(wǎng)肺衣(Lobaria retigera)中分離獲得的雜色曲霉(Aspergillus versicolor)在大米和PDB兩種培養(yǎng)基中產(chǎn)生的次生代謝產(chǎn)物進(jìn)行了研究。共分離獲得14個蒽醌類化合物：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個氧雜葸酮類化合物：sterigmatocystin (12),5-methoxysterigmatocystin (13)和dihydrosterigmatocystin(14)；5個生物堿類化合物：notoamide C (15), dehydronotoamide C (16),(-)-cyclopenol (17), phomopsin A (18)和3-formylindole (26);2個簡單的芳香化合物：dibutyl phthalate (24)和dimethyl phthalate (25);3個甾體類化合物：stigmasterol (19), ergosterol-5,7-dien-3β-ol (27)和dankasterone A (28)以及1個混源萜類化合物asperdemin (20)。對新化合物1-4進(jìn)行了細(xì)胞毒活性篩選,結(jié)果表明只有化合物1和2對PC-3和H460細(xì)胞株有弱的細(xì)胞毒活性。 對硬指葉苔(Lepidozia vitrea Steph.)的內(nèi)生真菌Penicillium sp. SD1617的次生代謝產(chǎn)物進(jìn)行了研究,從中分離獲得8個已知化合物,包括1個蒽醌類化合物：citreorosein (33);2個生物堿類化合物：ditryptophenaline (29)和brevianamide F(30)；3個簡單的芳香化合物：4-hydroxybenzaldehyde (34), flemingipanic acid (35)和4-hydroxy-2-methoxy-3,6-dimethylbenzoic acid (36);以及2個曲酸衍生物：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.
【學(xué)位授予單位】：山東大學(xué)
【學(xué)位級別】：碩士
【學(xué)位授予年份】：2014
【分類號】：R915

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