海洋放线菌Streptomyces novaecaesareae次生代谢产物
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摘要
对南海来源链霉菌Streptomyces novaecaesareae的次级代谢产物进行研究,经多种柱色谱技术分离得到10个化合物,通过波谱学方法并结合文献数据比对鉴定其结构分别为:环(4-羟基-L-脯-D-苯丙)二肽(1)、环(4-羟基-L-脯-L-苯丙)二肽(2)、环(4-羟基-L-脯-D-脯)二肽(3)、环(4-羟基-L-脯-L-亮)二肽(4)、环(L-脯-L苯丙)二肽(5)、环(L-亮-L-脯)二肽(6)、环(D-脯-L-亮)二肽(7)、环(8-羟基-L-脯-D-异亮)二肽(8)、N-(4-氧代戊基)-乙酰胺(9)和邻苯二甲酸二丁酯(10)。化合物1-9为叶立德类化合物,且1、3和7含有自然界中不常见的D构型氨基酸。所有化合物均首次从Streptomyces novaecaesareae中分离得。
By using various sorts of column chromatography, ten compounds were isolated from Streptomyces novaecaesareae which was isolated from the South China Sea. Based on the spectrum of NMR, MS and comparing the data with references, their structures were identified as cyclo-(L-4-Hypro-D-phe)(1), cyclo-(4-hydroxy-L-pro-L-phe)(2), cyclo(L-Pro-D-trans-Hyp)(3), cyclo(4-hydroxy-L-pro-L-leu)(4), cyclo-(L-Pro-L-Phe)(5), cyclo-(L-leu-L-pro)(6), cyclo(D-Pro-L-Leu)(7), callyspongidipeptide A(8), N-(4-oxopentyl)-acetamide(9) and dibutylphthalate(10). Compounds 1-9 were Ylide compounds which were composed of naturally rare D-configured amino acids. All Compounds were isolated from S. novaecaesareae for the first time.
By using various sorts of column chromatography, ten compounds were isolated from Streptomyces novaecaesareae which was isolated from the South China Sea. Based on the spectrum of NMR, MS and comparing the data with references, their structures were identified as cyclo-(L-4-Hypro-D-phe)(1), cyclo-(4-hydroxy-L-pro-L-phe)(2), cyclo(L-Pro-D-trans-Hyp)(3), cyclo(4-hydroxy-L-pro-L-leu)(4), cyclo-(L-Pro-L-Phe)(5), cyclo-(L-leu-L-pro)(6), cyclo(D-Pro-L-Leu)(7), callyspongidipeptide A(8), N-(4-oxopentyl)-acetamide(9) and dibutylphthalate(10). Compounds 1-9 were Ylide compounds which were composed of naturally rare D-configured amino acids. All Compounds were isolated from S. novaecaesareae for the first time.
引文
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[2] BLUT J W,CARROLL A R,COPP B R,et al.Marine natural products [J].Natural Product Reports,2017,34:235-294.
[3] BLUT J W,COPP B R,KEYZERS R A,et al.Marine natural products [J].Natural Product Reports,2016,33:382-431.
[4] BLUT J W,COPP B R,KEYZERS R A,et al.Marine natural products [J].Natural Product Reports,2015,32:116-211.
[5] BLUT J W,COPP B R,KEYZERS R A,et al.Marine natural products [J].Natural Product Reports,2014,31:160-258.
[6] BLUT J W,COPP B R,KEYZERS R A,et al.Marine natural products [J].Natural Product Reports,2013,30:237-323.
[7] BLUT J W,COPP B R,KEYZERS R A,et al.Marine natural products [J].Natural Product Reports,2012,29:144-222.
[8] LEI L F,CHEN M F,WANG T,et al.Novel cytotoxic nine-membered macrocyclic polysulfur cembranoid lactones from the soft coral Sinularia sp.[J].Tetrahedron,2015,46(7):6851-6858.
[9] HE X X,CHEN X J,PENG G T,et al.Pelopuradazole,a new imidazole derivative alkaloid from the marine bacteria Pelomonas puraquae sp.nov[J].Natural Product Research,2014,28(9):680-682.
[10] LIU B X,GUO Q,PENG G T,et al.New cyclic tetrapeptide from the coral-derived endophytic bacteria Brevibacterium sp.L-4 collected from the South China Sea[J].Natural Product Research,2016,30(1):7-12.
[11] CHEN X Q,MOU Y H,LING J H,et al.Cyclic dipeptides produced by fungus Eupenicillium brefeldianum HMP-F96 induced extracellular alkalinization and H2O2 production in tobacco cell suspensions[J].World Journal of Microbiology & Biotechnology,2015,31(1):247-253.
[12] FURTADO N J C,PUPO M T,CARVALHO I,et al.Diketopiperazines produced by an Aspergillus fumigatus Brazilian strain[J].Journal of the Brazilian Chemical society,2005,16(6):1448-1453.
[13] LEE S,TAMAYO-CASTILLO G,PANG C,et al.Diketopiperazines from costa rican endolichenic fungus Colpoma sp.CR1465A.[J].Bioorganic & Medicinal Chemistry Letters,2016,26(10):2438-2441.
[14] CRONAN Jr J M,DAVIDSON T R,SINGLETON F L,et al.Plant growth promoters isolated from a marine bacterium associated with Palythoa sp.[J].Natural Product Letters,1998,11(4):271-278.
[15] DIGN L,YUAN W,PENG Q,et al.Secondary metabolites isolated from the sponge-associated fungus Nigrospora oryzae[J].Chemistry of Natural Compounds,2016,52(5):1-2.
[16] LI T,WANG G C,HUANG X J,et al.Whitmanoside A,a new α-pyrone glycoside from the leech Whitmania pigra [J].Heterocycles,2013,87(7):1537-1543.
[17] LI Z Y,PENG C S,SHEN Y,et al.L,L-diketopiperazines from Alcaligenes faecalis A72 associated with South China Sea sponge Stelletta tenuis[J].Biochemical Systematics and Ecology,2008,36(3):230-234.
[18] KUMAR N,MOHANDAS C,NAMBISAN B,et al.Isolation of proline-based cyclic dipeptides from Bacillus sp.N strain associated with rhabditid entomopathogenic nematode and its antimicrobial properties[J].World Journal of Microbiology & Biotechnology,2013,29(2):355-364.
[19] YANG B,DONG J D,ZHOU X F,et al.Proline-containing dipeptides from a marine sponge of a Callyspongia species[J].Helv Chim Acta,2010,92(6):1112-1117.
[20] NENAJDENKO V G,ZAKURDAEV E P,PRUSOV E V,et al.Convenient synthesis of melatonin analogues:2-and 3-substituted-N-acetylindolylalkylamines[J].Tetrahedron,2004,60(51):11719-11724.
[21] 曲新颜,顾谦群,崔承彬,等.海洋来源的放线菌3295代谢产物的结构鉴定及抗肿瘤活性(Ⅰ)[J].中国海洋药物,2004,23(6):1-4.QU X Y,GU Q Q,CUI C B,et al.Structural identification and antitumor activity of secondary metabolites of marine-derived actinomycete 3295[J].Chinese Journal of Marine Drugs,2004,23(6):1-4.
[22] FDHILA F,VAZQUEZ V,SANCHEZ J L,et al.DD-diketopiperazines:antibiotics active against Vibrio anguillarum is olated from marine bacteria associated with cultures of Pecten maximus[J].Journal of Natural Products,2003,66(10):1299-1301.
[23] 彭坤,苏瑞强,张改云,等.深海放线菌Micrococcus sp.R21的次生代谢产物研究[J].中国中药杂志,2015,40(12):2367-2371.PENG K,SU R Q,ZHANG G Y,et al.Secondary metabolites from a deep-sea-derived actinomycete Micrococcus sp.R21[J].China Journal of Chinese Materia Medica,2015,40(12):2367-2371.
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[25] CHEN J H,LAN X P,LIU Y,et al.The effects of diketopiperazines from Callyspongia sp.on release of cytokines and chemokines in cultured J774A.1 macrophages[J].Bioorganic & Medicinal Chemistry Letters,2012,22(9):3177-3180.
[26] 罗小卫,林秀萍,雪峰,等.中国南海深海真菌Penicillium brocae SCSIO 05793的次级代谢产物研究[J].中国海洋药物,2017,36(3):23-28.LUO X W,LIN X P,XUE F,et al.Study on the secondary metabolites from South China Sea deep-water-derived fungus Penicillium brocae SCSIO 05793[J].Chinese Journal of Marine Drugs,2017,36(3):23-28.
[27] 王鸿,冯宇美,吴祺豪,等.海洋真菌Mucor circinelloides MNP12010102的次级代谢产物研究[J].浙江工业大学学报,2014,42(5):487-490.WANG H,FENG Y M,WU Q H,et al.Researches on the secondary metabolites of marine-derived fungus Mucor circinelloides MNP 12010102[J].Journal of Zhejiang University of Technology,2014,42(5):487-490.
[28] KLOSE K E.Increased chatter:cyclic dipeptides as molecules of chemical communication in Vibrio spp.[J].Journal of Bacteriology,2006,188(6):2025-2026.
[29] LI J R,WANG W L,XU S X,et al.Lactobacillus reuteri-produced cyclic dipeptides quench agr-mediated expression of toxic shock syndrome toxin-1 in staphylococci[J].Proceedings of the National Academy of Sciences of the United States of America,2011,108(8):3360-3365.
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