海燕和中华疣海星的化学成分及其生物活性研究
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摘要
近年来,随着我国水产养殖业的发展和环境的变化,为海星的生长繁殖创造了条件,出现了海星泛滥的事件,给贝类养殖户带来了严重损失,因此,海星被认为是一种有害无益的动物,大部分海星均被抛弃。
为了开发我国海星生物资源,本论文以资源丰富的黄海海燕和南海中华疣海星为原料,首先通过基本营养成分、皂苷和抗卤虫活性来评价其营养、药用价值,然后利用硅胶柱色谱、大孔树脂吸附柱色谱、Sephadex LH-20分子排阻色谱、制备薄层色谱和HPLC等技术对两种海星乙醇提取物的化学成分进行分离纯化,并通过NMR、IR、MS、化学降解和文献比对等多种方法对得到的单体化合物进行结构鉴定,接着对部分化合物进行抗癌、抗病毒和抗菌活性测试,并对化合物的活性和结构进行分析,主要结果如下:
1、海燕含有较高的蛋白质(29.37%)和脂肪(10.18%),具有较高的营养价值,同时体内还含有皂苷(48 mg/100g),乙醇提取物对卤虫幼体的24小时LC50为587.8μg/ml,海燕具有一定的药用价值;中华疣海星也具有较高的营养价值,体内含有较高的蛋白质(12.08%)和较低的脂肪(1.66%),还含有皂苷(105 mg/100g),乙醇提取物对卤虫幼体的24小时LC50为124.1μg/ml,中华疣海星也具有一定的药用价值。
2、从海燕体内分离得到40个单体化合物,鉴定了其中29个(A1~A29),包括6个核苷,7个甾醇,1个甾醇硫酸盐,1个多羟基甾醇脂肪酸酯,2个皂苷,1个环二肽,1个豆甾醇糖苷和10个其它类型化合物。其中化合物A13为新化合物,化合物A3、A5、A11、A17、A18和A23~A28为首次从海燕体内分离得到。
3、利用MTT法、CPE法和纸片琼脂扩散法对从海燕体内分离得到的部分化合物进行活性测试,结果表明化合物A11、A16和A18对HepG2细胞表现出不同的毒性,毒性浓度为50~100μg/ml,A11、A15、A16、A18、A19和A21在50~100μg/ml时对HSV-1致细胞病变作用表现出不同程度的抑制活性,A3、A10、A12、A13、A20、A22、A24和A29对大肠杆菌或金黄色葡萄球菌的生长表现出明显的抑制活性。
4、从中华疣海星体内分离得到22个单体化合物,鉴定了其中13个(PC1~PC13),包括4个环二肽,2个甾醇硫酸盐,1个麦角甾醇,1个吲哚酸,2个甘油酯糖苷和3个其它类型化合物。其中化合物PC1~PC12为首次从该物种分离得到。
5、对从中华疣海星体内分离得到的部分化合物进行体外抗癌、抗病毒和抗菌活性测试,结果表明化合物PC7和PC8对HepG_2细胞具有一定的毒性,毒性浓度为50~100μg/ml,PC1、PC2、PC3、PC4、PC5、PC6、PC7、PC8、PC9和PC10对大肠杆菌或金黄色葡萄球菌的生长显示出明显的抑制活性。
6、通过对比分析化合物的活性与结构之间的关系,发现化合物对HepG2显示细胞毒活性可能与结构中的甘氨酸、甾体母核上的硫酸盐、15β-OH、甾醇侧链上的24-OH和△22(23)双键等基团相关,抑制HSV-1活性可能与甾体母核上的15-OH及硫酸盐、甾体侧链上C-24位上的阿拉伯糖、24-OH和△22(23)双键等基团有关,抑菌活性可能与结构的核糖、羟基、NH、环二肽中的氢键给体或受体、硫酸盐、甾体母核、双键、半乳糖、甘油和脯氨酸等基团相关。
The sea star, feeding on oyster, abalone and other echinoderms, were widely distributed in the Seas all over the world. In recent years, they have attracted much attention due to their large scale outbreak in Chinese coastal areas, which led to severe economy damage to fishery and aquaculutral grounds for benthic shellfish. In fisher’s opinion, they were animals without any value, thus they were usually thrown away when appearing in aquacultural grounds for benthic shellfish.
To exploit the resource of starfish, the sea star Asterina pectinifera and Pectaceraster chinensis, collected from the Yellow Sea and Southern Sea, respectively, were studied in this paper. The main contents included the nutritional and pharmacology evaluation by the contents of nutritional composition and saponin from starfish A. pectinifera and P. chinensis and the acute toxicity of crude extract against larvae, the isolation and purification of chemical constituents from sea star A. pectinifera and P. chinensis by chromatographic and recrystallization methods, structural identification of compounds on basis of analysis of extensive spectra analysis ( NMR, IR, and MS), chemical degradation, and comparison with known compounds in literatures, and biological activities of compounds against HepG2, HSV-1, CVB3 and bacteria by MTT, CPE and disk agar diffusion methods. The main results were as follows:
(1)The sea star A. pectinifera has high nutritional value due to its high protein content (29.37%)and high lipid content (10.18%), and it has moderate pharmacology value because of saponin(48 mg/100g)and the weak activity of its ethanol extracts against larvae with LC50 value of 587.8μg/ml in twenty-four hours. The starfish P. chinensis has also high nutritional and moderate pharmacology value due to its high protein content(12.08%), low lipid content(1.66%), saponin(105 mg/100g)and the activity of its ethanol extract against larvae with LC50 value of 124.1μg/ml in twenty-four hours.
(2)Forty compounds were isolated from the ethanol extract of starfish A. pectinifera by chromatographic and recrystallization methods. On the basis of analysis of extensive spectra data and chemical degradation, twenty-nine compounds (named A1~A29, respectively) of them were identified, including six nucleosides, seven sterols, one steroid sulfate, one fatty acid ester of polyhydroxyl steroid, two asterosaponins, one glycoside of stigmasterol, one cyclodipeptide, and ten other type compounds. Furthermore, compound A13 was one new compound first isolated from the natural resource, compounds A3, A5, A11, A17, A18 and A23~A28 were first isolated from the sea star A. pectinifera.
(3) In the essays of biological activities of compounds from starfish A. pectinifera, the compounds were evaluated for their cytotoxicity against human liver carcinoma HepG2 cell line by MTT method, their antiviral activities against herpes simplex virus type 1(HSV-1) and coxsachie virus B3 (CVB3) by the cytopathic effect (CPE) inhibitory assay, and their antibacterial activities against some bacteria by disk agar diffusion method in vitro. The results showed that compounds A11, A16, A18 and A19 exhibited weak cytotoxicity against HepG2 cell line with concentration of 50~100μg/ml, compounds A11, A15, A16, A18, A19 and A21 exhibited different antiviral activity against HSV-1 virus with concentration of 50~100μg/ml, and compounds A3, A10, A12, A13, A20, A22, A24 and A29 showed certain activities against Escherichia coli or Staphylococcus aureus in vitro.
(4)twenty-two compounds were isolated from the ethanol extract of sea star P. chinensis by chromatographic and recrystallization methods. On the basis of analysis of extensive spectra data, thirteen compounds (named PC1~PC13, respectively) of them were identified, including four cyclodipeptides, two steroid sulfates, one ergosterol, one indole derivative, two glyceryl ether glycoside derivatives, and three other type compounds. Furthermore, compounds PC1~PC12 were first isolated from the starfish P. chinensis.
(5)Most compounds from sea star P. chinensis were evaluated for their antibacterial activities against six bacteria by disk agar diffusion method in vitro, while only two compounds were evaluated for their cytotoxicity against HepG2 cell line by MTT method and their antiviral activities against HSV-1 and CVB3 in vitro. The resulted showed that compound PC7 and PC8 showed weak cytotoxicity against HepG2 cell line in vitro with the concentration value of 50~100μg/ml, compounds PC1、PC2、PC3、PC4、PC5、PC6、PC7、PC8、PC9 and PC10 displayed certain activities against Escherichia coli or Staphylococcus aureus in vitro.
(6)By analyzing activities of compounds and their structures, there a possible structure–activity relationship among some compounds from A. pectinifera and P. chinensis. The residue of glycine, sulfate group at C-3 in steroid nucleus,βconfiguration of hydroxyl group at C-15 in steroid nucleus, the hydroxyl group at C-24 in steroid side chain, and double bond at C-22 and C-23 in steroid side chain may be necessary for anti-HepG2 activity. The hydroxyl group at C-15 and sulfate at C-3 in steroid, the residue of arabinose and hydroxyl group at C-24 in steroid side chain, sulfate in steroid nucleus, and double bond at C-22 and C-23 in steroid side chain may be necessary for anti-HSV-1 activity. In addition, the residue of ribose, NH group, proton donor and recipient, sulfate, and double bond may be essential for antibacterial activities against Escherichia coli and Staphylococcus aureus, which would be proved by more experiments in future.
为了开发我国海星生物资源,本论文以资源丰富的黄海海燕和南海中华疣海星为原料,首先通过基本营养成分、皂苷和抗卤虫活性来评价其营养、药用价值,然后利用硅胶柱色谱、大孔树脂吸附柱色谱、Sephadex LH-20分子排阻色谱、制备薄层色谱和HPLC等技术对两种海星乙醇提取物的化学成分进行分离纯化,并通过NMR、IR、MS、化学降解和文献比对等多种方法对得到的单体化合物进行结构鉴定,接着对部分化合物进行抗癌、抗病毒和抗菌活性测试,并对化合物的活性和结构进行分析,主要结果如下:
1、海燕含有较高的蛋白质(29.37%)和脂肪(10.18%),具有较高的营养价值,同时体内还含有皂苷(48 mg/100g),乙醇提取物对卤虫幼体的24小时LC50为587.8μg/ml,海燕具有一定的药用价值;中华疣海星也具有较高的营养价值,体内含有较高的蛋白质(12.08%)和较低的脂肪(1.66%),还含有皂苷(105 mg/100g),乙醇提取物对卤虫幼体的24小时LC50为124.1μg/ml,中华疣海星也具有一定的药用价值。
2、从海燕体内分离得到40个单体化合物,鉴定了其中29个(A1~A29),包括6个核苷,7个甾醇,1个甾醇硫酸盐,1个多羟基甾醇脂肪酸酯,2个皂苷,1个环二肽,1个豆甾醇糖苷和10个其它类型化合物。其中化合物A13为新化合物,化合物A3、A5、A11、A17、A18和A23~A28为首次从海燕体内分离得到。
3、利用MTT法、CPE法和纸片琼脂扩散法对从海燕体内分离得到的部分化合物进行活性测试,结果表明化合物A11、A16和A18对HepG2细胞表现出不同的毒性,毒性浓度为50~100μg/ml,A11、A15、A16、A18、A19和A21在50~100μg/ml时对HSV-1致细胞病变作用表现出不同程度的抑制活性,A3、A10、A12、A13、A20、A22、A24和A29对大肠杆菌或金黄色葡萄球菌的生长表现出明显的抑制活性。
4、从中华疣海星体内分离得到22个单体化合物,鉴定了其中13个(PC1~PC13),包括4个环二肽,2个甾醇硫酸盐,1个麦角甾醇,1个吲哚酸,2个甘油酯糖苷和3个其它类型化合物。其中化合物PC1~PC12为首次从该物种分离得到。
5、对从中华疣海星体内分离得到的部分化合物进行体外抗癌、抗病毒和抗菌活性测试,结果表明化合物PC7和PC8对HepG_2细胞具有一定的毒性,毒性浓度为50~100μg/ml,PC1、PC2、PC3、PC4、PC5、PC6、PC7、PC8、PC9和PC10对大肠杆菌或金黄色葡萄球菌的生长显示出明显的抑制活性。
6、通过对比分析化合物的活性与结构之间的关系,发现化合物对HepG2显示细胞毒活性可能与结构中的甘氨酸、甾体母核上的硫酸盐、15β-OH、甾醇侧链上的24-OH和△22(23)双键等基团相关,抑制HSV-1活性可能与甾体母核上的15-OH及硫酸盐、甾体侧链上C-24位上的阿拉伯糖、24-OH和△22(23)双键等基团有关,抑菌活性可能与结构的核糖、羟基、NH、环二肽中的氢键给体或受体、硫酸盐、甾体母核、双键、半乳糖、甘油和脯氨酸等基团相关。
The sea star, feeding on oyster, abalone and other echinoderms, were widely distributed in the Seas all over the world. In recent years, they have attracted much attention due to their large scale outbreak in Chinese coastal areas, which led to severe economy damage to fishery and aquaculutral grounds for benthic shellfish. In fisher’s opinion, they were animals without any value, thus they were usually thrown away when appearing in aquacultural grounds for benthic shellfish.
To exploit the resource of starfish, the sea star Asterina pectinifera and Pectaceraster chinensis, collected from the Yellow Sea and Southern Sea, respectively, were studied in this paper. The main contents included the nutritional and pharmacology evaluation by the contents of nutritional composition and saponin from starfish A. pectinifera and P. chinensis and the acute toxicity of crude extract against larvae, the isolation and purification of chemical constituents from sea star A. pectinifera and P. chinensis by chromatographic and recrystallization methods, structural identification of compounds on basis of analysis of extensive spectra analysis ( NMR, IR, and MS), chemical degradation, and comparison with known compounds in literatures, and biological activities of compounds against HepG2, HSV-1, CVB3 and bacteria by MTT, CPE and disk agar diffusion methods. The main results were as follows:
(1)The sea star A. pectinifera has high nutritional value due to its high protein content (29.37%)and high lipid content (10.18%), and it has moderate pharmacology value because of saponin(48 mg/100g)and the weak activity of its ethanol extracts against larvae with LC50 value of 587.8μg/ml in twenty-four hours. The starfish P. chinensis has also high nutritional and moderate pharmacology value due to its high protein content(12.08%), low lipid content(1.66%), saponin(105 mg/100g)and the activity of its ethanol extract against larvae with LC50 value of 124.1μg/ml in twenty-four hours.
(2)Forty compounds were isolated from the ethanol extract of starfish A. pectinifera by chromatographic and recrystallization methods. On the basis of analysis of extensive spectra data and chemical degradation, twenty-nine compounds (named A1~A29, respectively) of them were identified, including six nucleosides, seven sterols, one steroid sulfate, one fatty acid ester of polyhydroxyl steroid, two asterosaponins, one glycoside of stigmasterol, one cyclodipeptide, and ten other type compounds. Furthermore, compound A13 was one new compound first isolated from the natural resource, compounds A3, A5, A11, A17, A18 and A23~A28 were first isolated from the sea star A. pectinifera.
(3) In the essays of biological activities of compounds from starfish A. pectinifera, the compounds were evaluated for their cytotoxicity against human liver carcinoma HepG2 cell line by MTT method, their antiviral activities against herpes simplex virus type 1(HSV-1) and coxsachie virus B3 (CVB3) by the cytopathic effect (CPE) inhibitory assay, and their antibacterial activities against some bacteria by disk agar diffusion method in vitro. The results showed that compounds A11, A16, A18 and A19 exhibited weak cytotoxicity against HepG2 cell line with concentration of 50~100μg/ml, compounds A11, A15, A16, A18, A19 and A21 exhibited different antiviral activity against HSV-1 virus with concentration of 50~100μg/ml, and compounds A3, A10, A12, A13, A20, A22, A24 and A29 showed certain activities against Escherichia coli or Staphylococcus aureus in vitro.
(4)twenty-two compounds were isolated from the ethanol extract of sea star P. chinensis by chromatographic and recrystallization methods. On the basis of analysis of extensive spectra data, thirteen compounds (named PC1~PC13, respectively) of them were identified, including four cyclodipeptides, two steroid sulfates, one ergosterol, one indole derivative, two glyceryl ether glycoside derivatives, and three other type compounds. Furthermore, compounds PC1~PC12 were first isolated from the starfish P. chinensis.
(5)Most compounds from sea star P. chinensis were evaluated for their antibacterial activities against six bacteria by disk agar diffusion method in vitro, while only two compounds were evaluated for their cytotoxicity against HepG2 cell line by MTT method and their antiviral activities against HSV-1 and CVB3 in vitro. The resulted showed that compound PC7 and PC8 showed weak cytotoxicity against HepG2 cell line in vitro with the concentration value of 50~100μg/ml, compounds PC1、PC2、PC3、PC4、PC5、PC6、PC7、PC8、PC9 and PC10 displayed certain activities against Escherichia coli or Staphylococcus aureus in vitro.
(6)By analyzing activities of compounds and their structures, there a possible structure–activity relationship among some compounds from A. pectinifera and P. chinensis. The residue of glycine, sulfate group at C-3 in steroid nucleus,βconfiguration of hydroxyl group at C-15 in steroid nucleus, the hydroxyl group at C-24 in steroid side chain, and double bond at C-22 and C-23 in steroid side chain may be necessary for anti-HepG2 activity. The hydroxyl group at C-15 and sulfate at C-3 in steroid, the residue of arabinose and hydroxyl group at C-24 in steroid side chain, sulfate in steroid nucleus, and double bond at C-22 and C-23 in steroid side chain may be necessary for anti-HSV-1 activity. In addition, the residue of ribose, NH group, proton donor and recipient, sulfate, and double bond may be essential for antibacterial activities against Escherichia coli and Staphylococcus aureus, which would be proved by more experiments in future.
引文
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