两种中国南海软珊瑚二萜类化学成分及其生物活性研究
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摘要
生长环境是生物产生特异性次生代谢产物的重要决定性因素之一,特殊的生态环境往往影响生物体产生化学结构及生物活性特殊性和多样性的因素。由于海洋生物所处的特殊生境,导致其与陆生生物有着不同的代谢途径,因此有可能产生一系列特殊的次生代谢产物。
本论文分为三个部分,第一部分是对软珊瑚中Casbane二萜和Sarcophyton属来源的Cembranoids二萜及其生物活性研究进行综述。总体来看,Casbane二萜在海洋生物中报道极为罕见,且来源集中在中国南海海域,而Cembranoid作为Sarcophyton属软珊瑚的特征代谢产物,化学结构研究已经相当丰富,但生物活性研究并未取得突出成果。
本论文第二部分是对短指软珊瑚Sinularia gibberosa次生代谢产物化学多样性和生物活性多样性进行了研究。从该种软珊瑚乙酸乙酯部位中分离得到了23个化合物,应用现代多种分析手段(IR, UV, ESIMS, NMR, XRD)鉴定了它们的结构,其中二萜17个,包括新化合物16个。化合物类型包括Casbane型二萜(1-12,16,17),西松烷型二萜(15),倍半萜(18,19),多羟基甾体(20-22),胸腺嘧啶(23)。化合物13,14为新骨架二萜化合物。目前,已知的Casbane型二萜共39个,仅有三篇文献报道了海洋来源的16个该类型化合物,属于极为罕见的化合物。本文不仅分离得到了数量较多的此类化合物,首次运用单晶X-Ray衍射手段确定了其中三个化合物的绝对构型：其余二萜的绝对构型通过CD光谱、改良Mosher法以及四醋酸钼试剂诱导的ICD光谱等多种手段确立,还对这类二萜进行了多种活性研究。化合物13,14为新骨架化合物,由一个5-11-3三环结构组成。
论文的第三部分是对肉芝软珊瑚Sarcophyton ehrenbergi次生代谢产物及其活性的研究。以细胞毒活性指导分离,通过多种色谱手段,得到了27个化合物。应用核磁共振谱(1D、2D NMR),质谱(ESIMS、LC-MS), CD光谱等现代波谱技术确定了它们的化学结构,其中包括24个西松烷二萜(Cembranoids),其中七个为新化合物(24-30)。
Ecological condition had been proven to be one of the most significant influence factors for the secondary metabolites, the marine organisms endow with unique chemical diversity and distinct bioactivities, due to the inhabitation in special ecological environment. Two soft coral species, collected in South China Sea, were selected for the investigation of chemical constitution and bioactivities, resulting in the isolation of50compounds with mainly two types of diterpenoids.
The dissertation is designed into three parts. The first part, as a review, focuses on the novel casbane-type diterpenoids from marine organisms together with the cembrane-type diterpenoids from the genes of Sarcophyton. The date is up to2012.
In the second part, the EtOAC soluble fraction from soft coral Sinularia gibberosa is taken into chemical examination, with23compounds isolated as a result,16of them are new compounds. They can be classified into casbane-type diterpenoids (1-12,16), cembrane-type diterpenoids (15), sesquiterpenoids (18,19), steroids (20-22), thymine (23); two compounds (13,14) shared a new scaffold, in addition. The casbane-type diterpenoids are isolated from the genus of Sinularia gibberosa for the first time. The absolute configuration of two casbane-type diterpenoids are determined by using the X-ray single crystal diffract meter. The congfiguration of the other diterpenoids were determined by modified Mosher's method or CD spectra. The new scaffold is formed with a5-11-3tricyclie system. The bioactive of these compounds are tested.
In the second part, the secondary metabolites and their bioactivities from the soft coral Sarcophyton ehrenbergi are reported. From the EtOAc soluble fraction,27pure compounds are isolated, as a result of bio-guide isolation. The structures of these compounds are determined with the using of modern spectroscopy (NMR,2D NMR, ESIMS, LC-MS), CD spectra.23out of27are cembranoids, together with seven new compounds. These compounds are tested the cytotoxity to several leukemia cell lines.
本论文分为三个部分,第一部分是对软珊瑚中Casbane二萜和Sarcophyton属来源的Cembranoids二萜及其生物活性研究进行综述。总体来看,Casbane二萜在海洋生物中报道极为罕见,且来源集中在中国南海海域,而Cembranoid作为Sarcophyton属软珊瑚的特征代谢产物,化学结构研究已经相当丰富,但生物活性研究并未取得突出成果。
本论文第二部分是对短指软珊瑚Sinularia gibberosa次生代谢产物化学多样性和生物活性多样性进行了研究。从该种软珊瑚乙酸乙酯部位中分离得到了23个化合物,应用现代多种分析手段(IR, UV, ESIMS, NMR, XRD)鉴定了它们的结构,其中二萜17个,包括新化合物16个。化合物类型包括Casbane型二萜(1-12,16,17),西松烷型二萜(15),倍半萜(18,19),多羟基甾体(20-22),胸腺嘧啶(23)。化合物13,14为新骨架二萜化合物。目前,已知的Casbane型二萜共39个,仅有三篇文献报道了海洋来源的16个该类型化合物,属于极为罕见的化合物。本文不仅分离得到了数量较多的此类化合物,首次运用单晶X-Ray衍射手段确定了其中三个化合物的绝对构型：其余二萜的绝对构型通过CD光谱、改良Mosher法以及四醋酸钼试剂诱导的ICD光谱等多种手段确立,还对这类二萜进行了多种活性研究。化合物13,14为新骨架化合物,由一个5-11-3三环结构组成。
论文的第三部分是对肉芝软珊瑚Sarcophyton ehrenbergi次生代谢产物及其活性的研究。以细胞毒活性指导分离,通过多种色谱手段,得到了27个化合物。应用核磁共振谱(1D、2D NMR),质谱(ESIMS、LC-MS), CD光谱等现代波谱技术确定了它们的化学结构,其中包括24个西松烷二萜(Cembranoids),其中七个为新化合物(24-30)。
Ecological condition had been proven to be one of the most significant influence factors for the secondary metabolites, the marine organisms endow with unique chemical diversity and distinct bioactivities, due to the inhabitation in special ecological environment. Two soft coral species, collected in South China Sea, were selected for the investigation of chemical constitution and bioactivities, resulting in the isolation of50compounds with mainly two types of diterpenoids.
The dissertation is designed into three parts. The first part, as a review, focuses on the novel casbane-type diterpenoids from marine organisms together with the cembrane-type diterpenoids from the genes of Sarcophyton. The date is up to2012.
In the second part, the EtOAC soluble fraction from soft coral Sinularia gibberosa is taken into chemical examination, with23compounds isolated as a result,16of them are new compounds. They can be classified into casbane-type diterpenoids (1-12,16), cembrane-type diterpenoids (15), sesquiterpenoids (18,19), steroids (20-22), thymine (23); two compounds (13,14) shared a new scaffold, in addition. The casbane-type diterpenoids are isolated from the genus of Sinularia gibberosa for the first time. The absolute configuration of two casbane-type diterpenoids are determined by using the X-ray single crystal diffract meter. The congfiguration of the other diterpenoids were determined by modified Mosher's method or CD spectra. The new scaffold is formed with a5-11-3tricyclie system. The bioactive of these compounds are tested.
In the second part, the secondary metabolites and their bioactivities from the soft coral Sarcophyton ehrenbergi are reported. From the EtOAc soluble fraction,27pure compounds are isolated, as a result of bio-guide isolation. The structures of these compounds are determined with the using of modern spectroscopy (NMR,2D NMR, ESIMS, LC-MS), CD spectra.23out of27are cembranoids, together with seven new compounds. These compounds are tested the cytotoxity to several leukemia cell lines.
引文
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