八株海洋微生物次级代谢产物的研究
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摘要
本论文选取4株胶州湾海洋放线菌和4株条斑紫菜丝状体相关丝状真菌,进行了次级代谢产物的分离纯化与鉴定,共得到78个单体化合物,其中10个为新颖结构。对部分纯化合物进行了抑菌,抗肿瘤活性测试,并对菌株进行了菌种鉴定。具体结果如下:
从胶州湾放线菌M491,M097,M361和M353得到40个单体化合物,其中6个为新颖结构化合物。从M491分离到14个单体化合物,包括2个新结构倍半萜15-hydroxy-T-muurolol (1a)和11,15-dihydroxy-T-muurolol (1b),2个首次报道的微生物来源的倍半萜T-muurolol (2b)和3α-hydroxy-T-muurolol (2c),2个新颖结构大环内酯chalcomycin C (7)和chalcomycin D (8)。制备了3-oxo-T-muurolol (2a)单晶体,纠正了前人发表的错误结构。从M353分离得到10个化合物,包括2个新颖倍半萜5-hydroxy-epi-isozizaene (28)和5,14-dihydroxy-isozizaene (30)。自M097和M361分别分离得到12个,4个已知结构化合物。
从健康条斑紫菜丝状体分离得到了12株真菌。从优势附生菌N5分离得到了12个化合物,包括phenylacetic acid (42),p-hydroxyphenylethyl alcohol (43)和L-β-phenyllactic acid (49)等广谱抗生素和紫菜生长调节剂。
对分离自白斑病条斑紫菜丝状体真菌N27,EF8,GA4进行了次级代谢产物研究,分离得到38个单体化合物。从GA4分离得到了16个化合物,4个为新结构化合物,包括1个酰脲类化合物hualyzin (62)和3个phenalenone族新化合物7-methyl isonorherqueinone (69) , 7,8-dimethyl atrovenetin (70)和8-methyl-deoxyherqueinone (73)。从真菌N27和EF8分别分离得到12个和2个已知结构化合物。
采用MTT法,对37株人体肿瘤细胞株活性表明:chalcomycin C (7)和chalcomycin D (8)具有非常强的细胞毒活性,其平均IC50分别为0.027μg/mL和0.007μg/mL。7,8-Dimethyl atrovenetin (71)和8-methyl deoxyherqueinone (73)具有中等细胞毒活性,其平均IC50分别为5.1μg/mL和0.7μg/mL。
此外,本文首次报道了几个已知化合物的细胞毒活性,分别是chalcomycin (0.015μg/mL),kalamycin (0.06μg/mL),(+)-homononactic acid(1.9μg/mL),(+)-nonactic acid(2.3μg/mL),griseoviridin(3.9μg/mL),cyclo(L-Trp-L-Phe)(3.3μg/mL),WIN 64821(5.8μg/mL)和3,5-dihydroxy-2-methyl-4-pyrone(3.3μg/mL)。
菌种鉴定结果表明:M353归属链霉菌,GA4,N27归属青霉属,EF8归属曲霉属,N5为枝孢霉属。
This thesis reports the secondary metabolites isolated from eight marine-derived microbes including four actinomycetes isolated from Jiaozhou Bay and four fungi isolated from Porphyra yezoensis. Seventy-eight pure compounds among which ten are novel ones, have been obtained. Some of the pure compounds have been tested of their biological activities. And, some strains have been identified through morphological observation and phylogenetic analysis.
Fourty compounds including six novel secondary metabolites have been separated from actinomycetes M491, M097, M361 and M353. Fourteen compounds including two novel sesquiterpenes 15-hydroxy-T-muurolol (1a) and 11,15-dihydroxy-T-muurolol (1b), two novel microbial metabolites T-muurolol (2b) and 3α-hydroxy-T-muurolol (2c), and two novel macrolides chalcomycin C (7) and chalcomycin D (8) have been obtained from M491. 3-Oxo-T-muurolol (2a) was re-isolated and crystalized. The absolute configuration was solved by X-ray spectroscopy and the previously reported structures were corrected. Two novel sesquiterpenes 5-hydroxy-epi-isozizaene (28) and 5,14-dihydroxy-isozizaene (30) and another eight known compounds have been separated from M353. Twelve and three known compounds have been isolated from M097 and M361, respectively.
Twelve fungal isolates have been isolated from the Concocelis of Porphyra yezoensis. The dorminant strain N5 produced fifteen compounds including wide-spectrum antibiotics and plant growth-regulators phenylacetic acid (42), p-hydroxyphenylethyl alcohol (43), L-β-phenyllactic acid (49).
Fungal strains N27, EF8 and GA4 have been isolated from Porphyra yezoensis with white-spot syndrome. Sixteen compounds including one new urea-derivative hualyzin (62) and three new phenalenones 7-methyl isonorherqueinone (69), 7,8-dimethyl atrovenetin (71) and 8-methyl-deoxyherqueinone (73) have been purified from GA4. Twelve and two known compounds have been separated from N27 and EF8, respectively.
Some of the compounds have been tested of their cytotoxicity against thirty-seven human cell tumor lines using MTT method. Chalcomycin C (7) and chalcomycin D (8) exhibited high cytoxicity with the average IC50 of 0.027μg/ml and 0.007μg/mL, respectively. 7,8-Dimethyl atrovenetin (71) and 8-methyl deoxyherqueinone (73) showed moderate cytotoxicity with the IC50 of 5.1μg/mL and 0.7μg/mL, respectively.
Besides, some known compounds have been firstly reported for their cytotoxicity: chalcomycin (0.015μg/mL), kalamycin (0.06μg/mL), (+)-homononactic acid (1.9μg/mL), (+)-nonactic acid (2.3μg/mL), griseoviridin (3.9μg/mL), cyclo (L-Trp-L-Phe) (3.3μg/mL), WIN 64821 (5.8μg/mL) and 3,5-dihydroxy-2-methyl-4-pyrone (3.3μg/mL).
M353 was identified as Streptomyces sp. N5 belongs to Cladosporium. EF8 belongs to Aspergillus. GA4 and N27 belong to Penicillium.
从胶州湾放线菌M491,M097,M361和M353得到40个单体化合物,其中6个为新颖结构化合物。从M491分离到14个单体化合物,包括2个新结构倍半萜15-hydroxy-T-muurolol (1a)和11,15-dihydroxy-T-muurolol (1b),2个首次报道的微生物来源的倍半萜T-muurolol (2b)和3α-hydroxy-T-muurolol (2c),2个新颖结构大环内酯chalcomycin C (7)和chalcomycin D (8)。制备了3-oxo-T-muurolol (2a)单晶体,纠正了前人发表的错误结构。从M353分离得到10个化合物,包括2个新颖倍半萜5-hydroxy-epi-isozizaene (28)和5,14-dihydroxy-isozizaene (30)。自M097和M361分别分离得到12个,4个已知结构化合物。
从健康条斑紫菜丝状体分离得到了12株真菌。从优势附生菌N5分离得到了12个化合物,包括phenylacetic acid (42),p-hydroxyphenylethyl alcohol (43)和L-β-phenyllactic acid (49)等广谱抗生素和紫菜生长调节剂。
对分离自白斑病条斑紫菜丝状体真菌N27,EF8,GA4进行了次级代谢产物研究,分离得到38个单体化合物。从GA4分离得到了16个化合物,4个为新结构化合物,包括1个酰脲类化合物hualyzin (62)和3个phenalenone族新化合物7-methyl isonorherqueinone (69) , 7,8-dimethyl atrovenetin (70)和8-methyl-deoxyherqueinone (73)。从真菌N27和EF8分别分离得到12个和2个已知结构化合物。
采用MTT法,对37株人体肿瘤细胞株活性表明:chalcomycin C (7)和chalcomycin D (8)具有非常强的细胞毒活性,其平均IC50分别为0.027μg/mL和0.007μg/mL。7,8-Dimethyl atrovenetin (71)和8-methyl deoxyherqueinone (73)具有中等细胞毒活性,其平均IC50分别为5.1μg/mL和0.7μg/mL。
此外,本文首次报道了几个已知化合物的细胞毒活性,分别是chalcomycin (0.015μg/mL),kalamycin (0.06μg/mL),(+)-homononactic acid(1.9μg/mL),(+)-nonactic acid(2.3μg/mL),griseoviridin(3.9μg/mL),cyclo(L-Trp-L-Phe)(3.3μg/mL),WIN 64821(5.8μg/mL)和3,5-dihydroxy-2-methyl-4-pyrone(3.3μg/mL)。
菌种鉴定结果表明:M353归属链霉菌,GA4,N27归属青霉属,EF8归属曲霉属,N5为枝孢霉属。
This thesis reports the secondary metabolites isolated from eight marine-derived microbes including four actinomycetes isolated from Jiaozhou Bay and four fungi isolated from Porphyra yezoensis. Seventy-eight pure compounds among which ten are novel ones, have been obtained. Some of the pure compounds have been tested of their biological activities. And, some strains have been identified through morphological observation and phylogenetic analysis.
Fourty compounds including six novel secondary metabolites have been separated from actinomycetes M491, M097, M361 and M353. Fourteen compounds including two novel sesquiterpenes 15-hydroxy-T-muurolol (1a) and 11,15-dihydroxy-T-muurolol (1b), two novel microbial metabolites T-muurolol (2b) and 3α-hydroxy-T-muurolol (2c), and two novel macrolides chalcomycin C (7) and chalcomycin D (8) have been obtained from M491. 3-Oxo-T-muurolol (2a) was re-isolated and crystalized. The absolute configuration was solved by X-ray spectroscopy and the previously reported structures were corrected. Two novel sesquiterpenes 5-hydroxy-epi-isozizaene (28) and 5,14-dihydroxy-isozizaene (30) and another eight known compounds have been separated from M353. Twelve and three known compounds have been isolated from M097 and M361, respectively.
Twelve fungal isolates have been isolated from the Concocelis of Porphyra yezoensis. The dorminant strain N5 produced fifteen compounds including wide-spectrum antibiotics and plant growth-regulators phenylacetic acid (42), p-hydroxyphenylethyl alcohol (43), L-β-phenyllactic acid (49).
Fungal strains N27, EF8 and GA4 have been isolated from Porphyra yezoensis with white-spot syndrome. Sixteen compounds including one new urea-derivative hualyzin (62) and three new phenalenones 7-methyl isonorherqueinone (69), 7,8-dimethyl atrovenetin (71) and 8-methyl-deoxyherqueinone (73) have been purified from GA4. Twelve and two known compounds have been separated from N27 and EF8, respectively.
Some of the compounds have been tested of their cytotoxicity against thirty-seven human cell tumor lines using MTT method. Chalcomycin C (7) and chalcomycin D (8) exhibited high cytoxicity with the average IC50 of 0.027μg/ml and 0.007μg/mL, respectively. 7,8-Dimethyl atrovenetin (71) and 8-methyl deoxyherqueinone (73) showed moderate cytotoxicity with the IC50 of 5.1μg/mL and 0.7μg/mL, respectively.
Besides, some known compounds have been firstly reported for their cytotoxicity: chalcomycin (0.015μg/mL), kalamycin (0.06μg/mL), (+)-homononactic acid (1.9μg/mL), (+)-nonactic acid (2.3μg/mL), griseoviridin (3.9μg/mL), cyclo (L-Trp-L-Phe) (3.3μg/mL), WIN 64821 (5.8μg/mL) and 3,5-dihydroxy-2-methyl-4-pyrone (3.3μg/mL).
M353 was identified as Streptomyces sp. N5 belongs to Cladosporium. EF8 belongs to Aspergillus. GA4 and N27 belong to Penicillium.
引文
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