Cytotoxic activity of secondary metabolites from co-culture of Eurotium cristatum with Staphylococcus aureus

YANG Juanjuan; ZOU Xianwei; HUANG Yun; LI Qian; CHEN Benke; TANG Jintian

doi:10.3981/j.issn.1000-7857.2016.09.012

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Science & Technology Review ›› 2016, Vol. 34 ›› Issue (9) : 96-101. DOI: 10.3981/j.issn.1000-7857.2016.09.012

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Cytotoxic activity of secondary metabolites from co-culture of Eurotium cristatum with Staphylococcus aureus

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1. Xinjiang Production & Construction Corps Key Laboratory of Protection and Utilization of Biological Resources in Tarim Basin;College of Life Sciences, Tarim University, Alar 843300, China;
2. Key Laboratory of Particle & Radiation Imaging, Ministry of Education;Department of Engineering Physics, Tsinghua University, Beijing 100084, China

Abstract

To evaluate the cytotoxic activity of secondary metabolites from co-culture of Eurotium cristatum with Staphylococcus aureus, seven known compounds, including echinulin(1), cristatumin F(2), neoechinulin A(3), preechinulin (4), flvoglaucin (5), tetrahydroauroglaucine (6), and epiheveadride (7) are isolated from the solid culture of the co-culture of Eurotiumcristatum with Staphylococcus aureus. The structures are checked on the basis of spectroscopic analysis NMR experiments and by mass spectrometric measurements. These metabolites are evaluated in vitro for cytotoxicity activities against four tumor cell lines such as A549, MCF-7, Bel-7402, and Colo205. Compounds 3, 5 and 7 are found to show moderate cytotoxicity against the Bel-7402 cancer cell line.

Key words

Eurotium cristatum / co-culture / secondary metabolites / cytotoxic activity

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YANG Juanjuan, ZOU Xianwei, HUANG Yun, LI Qian, CHEN Benke, TANG Jintian. Cytotoxic activity of secondary metabolites from co-culture of Eurotium cristatum with Staphylococcus aureus[J]. Science & Technology Review, 2016, 34(9): 96-101 https://doi.org/10.3981/j.issn.1000-7857.2016.09.012

References

[1] Bu'Lock J D. Intermediary metabolism and antibiotic synthesis[J]. Ad-vances in Applied Microbiology, 1961(3):293-342.
[2] Demain A L, Adrio J L. Contributions of microorganisms to industrial biology[J]. Molecular Biotechnology, 2008, 38(1):41-55.
[3] Fajardo A, Martinez J L. Antibiotics as signals that trigger specific bac-terial responses[J]. Current Opinion in Microbiology, 2008, 11(2):161-167.
[4] Challis G L, Hopwood D A. Synergy and contingency as driving forces for the evolution of multiply secondary metabolite production by Strepto-myces species[J]. Colloquium, 2003, 100(2):14555-14561.
[5] Zazopoulos E, Huang K, Staffa A, et al. A genomics-guided approach for discovering and expressing cryptic metabolic pathways[J]. Nature Biotechnology, 2003, 21(2):187-190.
[6] Bérdy J. Bioactive microbial metabolites[J]. Journal of Antibiotics (To-kyo), 2005, 58(1):1-26.
[7] Pachapur V L, Sarma S J, Brar S K, et al. Biohydrogen production by co-fermentation of crude glycerol and apple pomacehydrolysate using co-culture of Enterobacteraerogenes and Clostridium butyricum[J]. Biore-source Technology, 2015, 193:297-306.
[8] Xiong T, Peng F, Liu Y Y, et al. Fermentation of Chinese sauerkraut in pure culture and binary co-culture with Leuconostocmesenteroides and Lactobacillus plantarum[J]. LWT-Food Science and Technology, 2014, 59:713-717.
[9] Wang H K, Ng Y K, Koh E, et al. RNA-Seq reveals transcriptomic in-teractions of Bacillus subtilisnatto and Bifidobacteriumanimalis subsp. lactis in whole soybean solid-state co-fermentation[J]. Food Microbiolo-gy, 2015, 51:5-32.
[10] 齐祖同, 孙曾美. 茯砖茶中优势菌群的鉴定[J]. 真菌学报, 1990, 9(3):176-179. Qi Zutong, Sun Zengmei. Identification of fu brick dominant flora[J]. Mycosystema, 1990, 9(3):176-179.
[11] Zou X W, Li Y, Zhang X N, et al. A new prenylatedindolediketopiper-azine alkaloid from Eurotium cristatum[J]. Molecules, 2014, 19(11):17839-17847.
[12] 李玉婷, 吕嘉枥. 金花菌黄色素的稳定性及其抗氧化活性研究[J]. 微生物学通报, 2013, 40(11):2030-2036. Li Yuting, Lü Jiali. Study on stability and antioxidant activity of the yellow pigments from Eurotium cristatum[J]. Microbiology China, 2013, 40(11):2030-2036.
[13] 黄群, 陈林杰, 李彦坡, 等. 冠突散囊菌黑茶发酵液对消化酶活性影响的研究[J]. 微生物学通报, 2007, 34(5):917-920. Huang Qun, Chen Linjie, Li Yanpo, et al. Study of Eurotium cristatum black tea broth to digestive enzyme activity[J]. Microbiology China, 2007, 34(5):917-920.
[14] 李莹, 邹先伟, 张小娜, 等. 突散囊菌不同溶剂提取物体外抗氧化活性研究[J]. 中国实验方剂学杂志, 2014, 20(7):143-146. Li Ying, Zou Xianwei, Zhang Xiaona, et al. Antioxidant activity of dif-ferent extracts from Eurotium cristatum in vitro[J]. Chinese Journal of Experimental Traditional Medical Formulae, 2014, 20(7):143-146.
[15] 彭晓赟, 梁法亮, 李冬利, 等. 茯砖茶中冠突散囊菌的次级代谢产物及其生物活性研究[J]. 中草药, 2013, 44(14):1881-1886. Peng Xiaozan, Liang Faliang, Li Dongli, et al. Secondary metabolites of Eurotium cristatum from fu brick tea and their biological activities[J]. Chinese Traditional and Herbal Drugs, 2013, 44(14):1881-1886.
[16] Mosmann T. Rapid colorimetric assay for cellular growth and survival:Application to proliferation and cytotoxicity[J]. Journal of Immunologi-cal Methods, 1983, 65(1-2):55-63.
[17] Chen X, Si L, Liu D, et al. Neoechinulin B and its analogues as poten-tial entry inhibitors of influenza viruses, targeting viral hemagglutinin[J]. European journal of Medicinal Chemistry, 2015, 93:182-195.
[18] 郭志勇, 黄忠京, 温露, 等. 三种红树林内生真菌的环肽类次级代谢产物的研究[J]. 中药材, 2007, 30(12):1526-1529. Guo Zhiyong, Huang Zhongjing, Wen Lu, et al. The metabolites of cy-clic peptides from three endophytic mangrove fungi[J]. Journal of Chi-nese Medicinal Materials, 2007, 30(12):1526-1529.
[19] Kim K S, Cui X, Lee D S, et al. Anti-inflammatory effect of neoechi-nulin A from the marine fungus Eurotium sp. SF-5989 through the suppression of NF-кB and p38 MAPK pathways in lipopolysaccha-ride-stimulated RAW264. 7 macrophages[J]. Molecules, 2013, 18(11):13245-13259.
[20] Chen X, Si L, Liu D, et al. Neoechinulin B and its analogues as poten-tial entry inhibitors of influenza viruses, targeting viral hemagglutinin[J]. European Journal of Medicinal Chemistry, 2015, 93:182-195.
[21] Miyake Y, Ito C, Itoigawa M, et al. Antioxidants produced by Euro-tium herbariorum of filamentous fungi used for the manufacture of Karebushi, dried bonito (Katsuobushi)[J]. Bioscience, Biotechnology, and Biochemistry, 2009, 73(6):1323-1327.
[22] Hosoe T, Fukushima K, Itabashi T, et al. A new nonadride derivative, dihydroepiheveadride, as characteristic antifungal agent against fila-mentous fungi, isolated from unidentified fungus IFM 52672[J]. The Journal of Antibiotics, 2004, 57(9):573-578.
[23] Ishikawa Y, Morimoto K, Hamasaki T. Flavoglaucin, a metabolite of Eurotium chevalieri, its antioxidation and synergism with tocopherol[J]. Journal of the American Oil Chemists' Society, 1984, 61(12):1864-1868.
[24] Du F Y, Li X M, Song J Y, et al. Anthraquinone Derivatives and an Orsellinic Acid Ester from the Marine Alga-Derived Endophytic Fun-gus Eurotium cristatum EN-220[J]. Helvetica Chimica Acta, 2014, 97(7):973-978.
[25] Slack G J, Puniani E, Frisvad J C, et al. Secondary metabolites from Eurotium species, Aspergillus calidoustus and A. insuetus common in Canadian homes with a review of their chemistry and biological activi-ties[J]. Mycological Research, 2009, 113(4):480-490.
[26] Nazar M, Afzal M, Mirza J H, et al. Aspergillus chevalieri contamina-tion of barley[J]. Journal of the University of Kuwait(science). Kuwait, 1987, 14(1):121-126.
[27] Chen L, Gu Q Q. Study on the Antitumor Metabolites of a Sponge-De-rived Fungus, Aspergillus repens[J]. Periodical of Ocean University of China, 2010, 40(5):69-71.
[28] Oh D C, Jensen P R, Kauffman C A, et al. Libertellenones A-D:in-duction of cytotoxic diterpenoid biosynthesis by marine microbial com-petition[J]. Bioorganic & Medicinal Chemistry, 2005, 13(51):5267-5273.
[29] Kohn H, Widger W. The molecular basis for the mode of action of bi-cyclomycin[J]. Current Drug Targets-Infectious Disorders, 2005, 5(3):273-295.
[30] Musetti R, Polizzotto R, Vecchione A, et al. Antifungal activity of dike-topiperazines extracted from Alternaria alternata against Plasmopara viticola:An ultrastructural study[J]. Micron, 2007, 38(6):643-650.
[31] Rodriguez P L, Carrasco L. Gliotoxin:Inhibitor of poliovirus RNA syn-thesis that blocks the viral RNA polymerase 3Dpol[J]. Journal of Virol-ogy, 1992, 66(4):1971-1976.
[32] Kanzaki H, Yanagisawa S, Nitoda T. Enzymatic synthesis of dehydro cyclo(His-Phe)s, analogs of the potent cell cycle inhibitor, dehydro-phenylahistin, and their inhibitory activities toward cell division[J]. Bioscience, Biotechnology and Biochemistry, 2004, 68(11):2341-2345.
[33] Perez-Picaso L, Olivo H F, Argotte-Ramos R, et al. Linear and cyclic dipeptides with antimalarial activity[J]. Bioorganic and Medical Chem-istry Letters, 2012, 22(23):7048-7051.