五种中国南海海绵的化学成分及生物活性研究
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摘要
次生代谢产物具有结构复杂和生物活性多样的特点,长期以来在新药和新药先导化合物的发现中起着重要的作用。在寻找具有生物活性的次级代谢产物过程中,我们对采自于中国南海海域的5种海绵动物进行了系统的化学成分研究,同时对这些化合物进行了生物活性评价和化学生态学方面的研究。
综合运用多种柱层析方法,从这些生物样品中共分离得到55个化合物,包括：21个倍半萜,4个二萜,6个甾体,11个3-烷基吡啶生物碱,2个多聚不饱和胺酮类化合物,4个长链类化合物,3个核苷类化合物和4个其它类型的化合物；其中有1个新骨架化合物、12个新化合物和1个新天然产物。化合物的结构及其相对构型是在分析1D、2D NMR、UV、IR、旋光等波谱学数据、化学沟通以及与报道的已知化合物数据比较的基础上确定的。对分离得到的化合物进行了广泛的生物活性筛选,发现了一些具有较好生物活性的化学成分,不仅加深了对上述生物材料化学成分的了解,而且为它们的进一步研究和利用提供了依据。
在对海绵LS-340(Axinyssa属)和YAL-64(Acanthella属)的研究中,不仅分离得到常共存的含有异腈、异硫氰和甲酰胺等基团的含氮倍半萜(共21个),我们还得到了含有异腈、异硫氰和甲酰胺等基团的kalihinane型二帖化合物(共4个),其中4个新化合物。我们小组曾在上述海绵的同一海域采集的海洋软体动物血红六鳃(Hexabranchus sangueneus)和丘凸叶海牛(Phyllidiella pustulosa)中分离得到过一些与上述结构相同或类似的含氮倍半萜,软体动物常常通过富集食物中的活性物质以建立自身的化学防御体系,我们初步推测这些倍半萜可能来源于它们捕食的海绵,这也间接证明了这两类无脊椎动物间的关系是捕食。
在对海绵LS-58 (Topsentia属)、WZ-33 (Fasciospongia属)和海绵WZ-9(Haliclona属)的研究中发现了13个长链的生物碱化合物,其中1个新骨架、8个新化合物和1个新天然产物。含有醛基末端的3-烷基吡啶生物碱在软体动物中曾经被分离得到过,但是新天然产物4-4是首次从海绵中分离得到的含有醛基末端的3-烷基吡啶生物碱。新骨架化合物6-5是由3-亚甲基吡啶与一个倍半萜连接而成,结构十分新奇。
生物活性研究显示,含氮的倍半萜及二萜化合物表现出较好的对肿瘤细胞的抑制活性如：2-6,2-11,3-3,3-4,3-9和3-10对人肺腺癌细胞株A-549表现出一定的抑制作用。3-烷基吡啶生物碱也表现出了较好的生物活性如：4-1,4-3,4-7,4-8和4-10对电压门控离子通道有较好的调控作用。
Natural materials are prolific source of secondary metabolites with diverse structures and biological properties. In the processes of our searching for bioactive compounds, we have chemically investigated five species of marine sponges collected along the coast of South China Sea. All the compounds have been evaluated for biological activities and studied on the roles in chemecology.
From these marine sponges,55 compounds were isolated, including 21 sesquiterpenoids,4 diterpenoids,6 steroids,11 3-alkylpyridines,2 polyunsaturated amino ketones,4 long-chain compounds and 7 compounds with other type of skeletons, were isolated by repeated chromatography. Their structure and relative stereochemistry were elucidated on the basis of extensive spectroscopic analysis and chemical methods, and by comparison of the data with those reported data in the literature. In these compounds,13 new compounds were identified. Some of them were found to show significant bioactivities on specific bioassay models.
From the acetone extracts of sponge LS-340 and YAL-64, we obtained 21 sesquiterpenes containing unusual nitrogenous functional groups, such as isothiocyanate, formamide, isonitrile, and thiocyanate and 4 kalihinol diterpenes. In these compounds,4 new compounds were identified. It is interesting to note that a series of N-containing sesquiterpenes were isolated, from Hainan nudibranches Hexabranchus sangueneus and Phyllidiella pustulosa implied that the nudibranche might acquire the metabolites by dietary transfer from these sponges.
From the acetone extracts of sponge LS-58, WZ-33 and WZ-9 we obtained 13 long-chain alkaloids. In these compounds,11 3-alkylpyridines and 2 polyunsaturated amino ketones were identified. Although 3-alkylpyridine alkaloids with side chains terminating in an aldehyde group have been reported from opisthobranch mollusks, compound 4-4 is the first report from a sponge.
All the compounds have been evaluated for biological activities, some of them exhibited broad bioactivities such as 2-6,2-11,3-3,3-4,3-9 and 3-10 showed inhibitory activity to A-549 and 4-1,4-3,4-7,4-8 and 4-10 exhibited moderate inhibitions of voltage gated potassium channels.
综合运用多种柱层析方法,从这些生物样品中共分离得到55个化合物,包括：21个倍半萜,4个二萜,6个甾体,11个3-烷基吡啶生物碱,2个多聚不饱和胺酮类化合物,4个长链类化合物,3个核苷类化合物和4个其它类型的化合物；其中有1个新骨架化合物、12个新化合物和1个新天然产物。化合物的结构及其相对构型是在分析1D、2D NMR、UV、IR、旋光等波谱学数据、化学沟通以及与报道的已知化合物数据比较的基础上确定的。对分离得到的化合物进行了广泛的生物活性筛选,发现了一些具有较好生物活性的化学成分,不仅加深了对上述生物材料化学成分的了解,而且为它们的进一步研究和利用提供了依据。
在对海绵LS-340(Axinyssa属)和YAL-64(Acanthella属)的研究中,不仅分离得到常共存的含有异腈、异硫氰和甲酰胺等基团的含氮倍半萜(共21个),我们还得到了含有异腈、异硫氰和甲酰胺等基团的kalihinane型二帖化合物(共4个),其中4个新化合物。我们小组曾在上述海绵的同一海域采集的海洋软体动物血红六鳃(Hexabranchus sangueneus)和丘凸叶海牛(Phyllidiella pustulosa)中分离得到过一些与上述结构相同或类似的含氮倍半萜,软体动物常常通过富集食物中的活性物质以建立自身的化学防御体系,我们初步推测这些倍半萜可能来源于它们捕食的海绵,这也间接证明了这两类无脊椎动物间的关系是捕食。
在对海绵LS-58 (Topsentia属)、WZ-33 (Fasciospongia属)和海绵WZ-9(Haliclona属)的研究中发现了13个长链的生物碱化合物,其中1个新骨架、8个新化合物和1个新天然产物。含有醛基末端的3-烷基吡啶生物碱在软体动物中曾经被分离得到过,但是新天然产物4-4是首次从海绵中分离得到的含有醛基末端的3-烷基吡啶生物碱。新骨架化合物6-5是由3-亚甲基吡啶与一个倍半萜连接而成,结构十分新奇。
生物活性研究显示,含氮的倍半萜及二萜化合物表现出较好的对肿瘤细胞的抑制活性如：2-6,2-11,3-3,3-4,3-9和3-10对人肺腺癌细胞株A-549表现出一定的抑制作用。3-烷基吡啶生物碱也表现出了较好的生物活性如：4-1,4-3,4-7,4-8和4-10对电压门控离子通道有较好的调控作用。
Natural materials are prolific source of secondary metabolites with diverse structures and biological properties. In the processes of our searching for bioactive compounds, we have chemically investigated five species of marine sponges collected along the coast of South China Sea. All the compounds have been evaluated for biological activities and studied on the roles in chemecology.
From these marine sponges,55 compounds were isolated, including 21 sesquiterpenoids,4 diterpenoids,6 steroids,11 3-alkylpyridines,2 polyunsaturated amino ketones,4 long-chain compounds and 7 compounds with other type of skeletons, were isolated by repeated chromatography. Their structure and relative stereochemistry were elucidated on the basis of extensive spectroscopic analysis and chemical methods, and by comparison of the data with those reported data in the literature. In these compounds,13 new compounds were identified. Some of them were found to show significant bioactivities on specific bioassay models.
From the acetone extracts of sponge LS-340 and YAL-64, we obtained 21 sesquiterpenes containing unusual nitrogenous functional groups, such as isothiocyanate, formamide, isonitrile, and thiocyanate and 4 kalihinol diterpenes. In these compounds,4 new compounds were identified. It is interesting to note that a series of N-containing sesquiterpenes were isolated, from Hainan nudibranches Hexabranchus sangueneus and Phyllidiella pustulosa implied that the nudibranche might acquire the metabolites by dietary transfer from these sponges.
From the acetone extracts of sponge LS-58, WZ-33 and WZ-9 we obtained 13 long-chain alkaloids. In these compounds,11 3-alkylpyridines and 2 polyunsaturated amino ketones were identified. Although 3-alkylpyridine alkaloids with side chains terminating in an aldehyde group have been reported from opisthobranch mollusks, compound 4-4 is the first report from a sponge.
All the compounds have been evaluated for biological activities, some of them exhibited broad bioactivities such as 2-6,2-11,3-3,3-4,3-9 and 3-10 showed inhibitory activity to A-549 and 4-1,4-3,4-7,4-8 and 4-10 exhibited moderate inhibitions of voltage gated potassium channels.
引文
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