冈村凹顶藻中的倍半萜和C15-多聚乙酰类成分研究

IOCAS-IR > 海洋环流与波动重点实验室

	冈村凹顶藻中的倍半萜和C15-多聚乙酰类成分研究
其他题名	Studies on sesquiterpenes and C15-acetogenins from Laurencia okamurai
	梁毅
学位类型	博士
	2009-05-26
学位授予单位	中国科学院海洋研究所
学位授予地点	海洋研究所
关键词	海藻松节藻科冈村凹顶藻次级代谢产物倍半萜 C15-多聚乙酰
摘要	凹顶藻属(Laurencia)海藻在分类学上属于红藻门(Rhodophyta)、红藻纲(Rhodophyceae)、仙菜目(Ceramiales)、松节藻科(Rhodomalaceae)，主要分布于热带、亚热带和温带海域的低潮线附近及深海部分，约135种，中国有20种以上。凹顶藻次级代谢产物的结构类型主要包括倍半萜、二萜、三萜/聚醚和C15-多聚乙酰等，冈村凹顶藻中，倍半萜和C15-多聚乙酰最为常见，且以卤代著称。本文对凹顶藻卤代机制的研究进行了总结，并对最近10年来从凹顶藻中分离到的倍半萜、C15-多聚乙酰类成分及其合成研究进行了综述，同时对采自山东和广东的两种冈村凹顶藻(Laurencia okamurai Yamada)的化学成分进行了比较研究，发现生长在不同地理位置的同种凹顶藻化学成分有很大差异。干燥并粉碎的冈村凹顶藻(L. okamurai)分别进行有机溶剂提取，粗提物通过硅胶柱层析、凝胶Sephadex LH-20柱层析、反相硅胶柱层析、制备薄层层析等方法分离纯化得单体化合物，利用超导核磁共振、质谱和红外光谱等现代波谱技术鉴定化合物的结构。从上述采自不同地点的冈村凹顶藻中分离鉴定的化合物共计30个，包括新化合物8个，依次是laurenokamurenes A-E (LA1-LA5)，laurenokamurin (LA6)，laurenokaldehyde (LA7)和isochlorolaurenol (LB1)，新天然产物1个 (LA12)和已知化合物21个。其中，采自山东的冈村凹顶藻次级代谢产物结构类型相对复杂多样，从中分离到的化合物包括bisabolane型倍半萜4个，chamigrane型倍半萜5个，laurane型倍半萜6个，C15-多聚乙酰类化合物5个，其他类型化合物1个（见第III页）；从采自广东的冈村凹顶藻中分离鉴定的化合物主要为7个laurane型倍半萜和2个其他类型的化合物（见第IV页）。对分离鉴定的部分单体化合物进行了抗细菌（金黄色葡萄球菌）活性筛选，结果表明所有的测试样品都不具有抗金黄色葡萄球菌活性。
其他摘要	The marine red algal species of the genus Laurencia (family Rhodomalaceae, order Ceramiales, class Rhodophyceae, and phylum Rhodophyta) are consisted of 135 species in the world and over 20 of them distributed in China. They mainly spread along tropical, subtropical, and temperate coasts. The secondary metabolites of the genus Laurencia are mainly sesquiterpenes, diterpenes, triterpenes/polyethers, and C15-acetogenins. Sesquiterpenes and C15-acetogenins with the majority bonding to halogen are quite common in the species of Laurencia okamurai. In this thesis, the halogenation mechanism of Laurencia sp. was summarized and sesquiterpenes and C15-acetogenins isolated from the species as well as their synthetic approachs in the last 10 years were reviewed. Chemical investigation of Laurencia okamurai collected respectively from Shandong (northern China) and Guangdong (southern China) was conducted. The results showed that geographic settings exerted remarkable influence on the chemical components of the red alga Laurencia okamurai. Dried and powdered algal material was extracted with organic solvents. The extract was purified by repeated silica gel and Sephadex LH-20 and RP-18 column chromatography and by preparative thin layer chromatography (PTLC) to yield pure compounds, their structures were elucidated mainly by 1D and 2D NMR, mass, and infrared spectroscopic techniques. As results, a total of 30 compounds were isolated and identified. Among them, there were 8 new compounds, which were determined and named as laurenokamurenes A-E (LA1-LA5)，laurenokamurin (LA6)，laurenokaldehyde (LA7) and isochlorolaurenol (LB1), and 1 new natural product (LA12) together with 21 known compounds. Secondary metabolites of the species from Shandong province comprising 4 bisabolane-type, 5 chamigrane-type, and 6 laurane-type sesquiterpenes, 5 C15-acetogenins, and 1 other compound, were more diversified in comparison with those from Guangdong province, which included 7 laurane-type sesquiterpenes and 2 other compounds. Antibacterial bioassay against Staphylococcus showed that the tested compounds didn’t possess antibacterial activities.
页数	68
语种	中文
文献类型	学位论文
条目标识符	http://ir.qdio.ac.cn/handle/337002/717
专题	海洋环流与波动重点实验室
推荐引用方式 GB/T 7714	梁毅. 冈村凹顶藻中的倍半萜和C15-多聚乙酰类成分研究[D]. 海洋研究所. 中国科学院海洋研究所,2009.

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