植物美登木素类化合物生物合成起源的初步的研究
其他题名The Primary Studies on the Biosynthesis of Plant Maytansinoids
鲁春华
学位类型博士
导师郝小江
2003
学位授予单位中国科学院昆明植物研究所
学位授予地点中国科学院昆明植物研究所
学位专业植物学
关键词美登木素 美登木素类化合物 生物合成 云南美登木 共生菌
摘要本论文以探讨“植物美登木素的生物合成起源”为切入点,以云南美登木为实验材料,从植物细胞培养及其化学成分、共生微生物的分离及其化学成分和饲喂或植物-共生微生物共培养三个方面开展了研究,取得了一些有意义的结果。从云南美登木愈伤组织和悬浮细胞培养中分别分离鉴定了6个化合物和9个化合物,大部分化合物与同属植物中分离到的成分相同l相似,其中有一个新二降木栓烷型三萜(Fig.A)。从云南美登木的不同部位共分离了21株放线菌、6株真菌和2株细菌,活性结果表明,其中5株菌株的发酵提取物表现较好的抗真菌活性;从菌株CS、IBI、3C的发酵提取物中共分离鉴定了19个化合物包括10个新化合物,分别属于bafilomycins、naphthomycins、angucycline和I型二酮等(Fig.A)。从橙色束丝放线菌的固体发酵培养物中分离鉴定了绊环丝裂霉素酰胺氮甙,该化合物是次生代谢产物中的第一个酰胺N-苷以及5个非常见碳水化合物包括4个C-2位去氧己糖和1个呋喃衍生物,它们都是首次从该菌中分离得到(Fig.A)。从美登木细胞与共生放线菌7B的共培养实验中分离鉴定了一个新二降三萜CE3(Fig.A);在植物细胞一微生物共培养、水杨酸、几丁质和茉莉酮酸甲酯诱导实验中均没有分离和用LC-ESI-MS检测到美登木素类化合物,但是发现共培养系和水杨酸诱导实验都产生相同的三羟基脂肪酸9,12,13-三羟基十八碳-10-烯酸,提示云南美登木植物细胞对伤信号和放线菌可能有相似的反应-防御机制。对”部分化合物的抗菌和抗肿瘤活性进行了测试,发现了一些活性较好的化合物。其中最为突出的是,大环内酯CSN3具有广谱抗菌和强抗肿瘤细胞活性;萘霉素A和绊环丝裂霉素酰胺氮甙P-2有较好的抗真菌和抗肿瘤细胞活性。还通过,13C-标记的桂皮酸、莽草酸和乙酸钠饲喂实验对部分化合物的生物合成途径进行了研究,初步结果表明化合物L-3是通过I型多酮途径合成的最小聚酮-二酮。综合本学位论文的实验结果和前人的有关研究成果得出以下结论:①云南美登木组织培养和悬浮细胞培养系不能独立产生美登木素类化合物,“植物美登木素可能是共生微生物来源”并应当强调是“植物-微生物相互作用的结果”,并认为基于植物-微生物相互作用机制所设计的植物共生菌的培养或植物-共生微生物的共培养实验并能够从中分离得到植物美登木素类化合物将是回答“植物美登木素生物合成起源”的关键。;②植物共生菌是产生结构新颖活性化合物的重要来源;③植物-微生物共培养将可能是产生活性化合物的有效途径之一。
其他摘要To explore the biosynthetic origins of plant maytansinoids, Maytenus hookeri was used as experimental material, and researches illustrated in this thesis were carried out, which was consisted of three aspects including plant cell cultures and their chemical components of Maytenus hookeri, isolation and chemical components of commensal microbes of M. hookeri and further investigation on the biosynthetic origins of plant maytansinoids through feeding and co-culture experiments. Some interesting results were obtained during the progress of investigating onto the biosynthetic origin of plant maytansinoids. Five and nine compounds were isolated from the calli and suspension cell cultures of M. hookeri, respectively, and among those one was new triterpene of dinorfriedooleane type (Fig. A). From different parts of M. hookeri, 21 strains of actinomycetes, 6 strains of fungi and 2 bacteria were isolated. Chemical "studies on the strains CS, 1B1 and 3C afforded ten novel compounds belonging to bafilomycins, naphthomycins, angucycline and type I diketide, respectively (Fig. A). One unusual amide N/glycoside and five carbohydrates including four 2-deoxyhexoses and one furan derivative were isolated from the solid state fermentation of Actinosynnema pretiosum ssp. aurantium ATCC31565 (Fig. A). A new triterpene, CE3 was isolated from the co-culture of suspension culture cells of M. hookeri and the strain 7B (Fig. A). No maytansinoids were isolated or detected by LC-ESI-MS in the extracts of this co-cultures, and elicitations with salicylic acid, chitosan and methyl jasmonate on suspension cell cultures of M. hookeri. However, the production of 9,12,13-trihydroxy-10-octadecenoic acid was observed in the elicitation experiment with salicylic acid, which implied that the plant cells of M. hookeri may have similar responsive and defensive mechanisms to wounding signals and actinomycetes. The antimicrobial and antitumor activities of some compounds were analyzed, indicating that several compounds have prominent bioactivities. Among those compounds, the most striking examples were that the macrolide CSN3 showed broad spectral antimicrobial activities and very strong antitumor activities, and that naphthomycin A and the novel amide N-glycoside of ansamitocin P-2 showed evident antifungal and antitumor activities. The feeding experiments with 13C-labeled cinnamic acid, shikimic acid and sodium acetate indicated that compound L-3 was the smallest diketide synthesized through type I polyketide pathway. On the basis of the results described in this thesis and reported previously, the following conclusions were put forward: 1. plant cells of M. hookeri could not produce maytansinoids independently, and we suggested that plant maytansinoids may be commensal microbial origin, and the isolation of maytansinoids from the culture of commensal microbe or the co-culture of plant-commensal microbe designed based on the mechanisms of plant-microbe interactions will be the key to the question of biosynthetic origin of plant maytansinoids; 2. plant commensal microbes are important sources of novel bioactive compounds, and 3. co-cultures of plant and microbe will be one of the efficient approaches to producing bioactive compounds.
页数223
语种中文
文献类型学位论文
条目标识符http://ir.kib.ac.cn/handle/151853/716
专题昆明植物所硕博研究生毕业学位论文
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鲁春华. 植物美登木素类化合物生物合成起源的初步的研究[D]. 中国科学院昆明植物研究所. 中国科学院昆明植物研究所,2003.
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