黏菌代谢产物及其生物活性的研究进展
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摘要
黏菌代谢产物的研究显示出其较高的应用价值,并取得了较大的进展。本文综述了从黏菌中分离得到的100余个代谢产物,主要包括:脂肪酸、氨基酸、生物碱、萘醌、芳香族化合物、萜类化合物以及酯或其衍生品等。阐述了其抑菌、抗肿瘤、细胞毒及抗氧化活性,简要介绍了化合物的构效关系,同时对黏菌生物活性的研究方法及生物化学特征进行了总结,分析了不同黏菌类群代谢产物的异同。最后对黏菌代谢产物的研究提出了问题与展望。
Research on the metabolites of myxomycetes has previously demonstrated the high potential for practical applications and has made great progress. In this paper, we reviewed more than 100 metabolites isolated from myxomycetes, including fatty acids, amino acids, alkaloids, naphthoquinones, aromatic compounds, terpenoids, esters or derivatives thereof. We also introduced their antimicrobial, antitumor, cytotoxic and antioxidant activities. In addition, the structure-activity relationship of these compounds has been briefly introduced. Furthermore, the biological activity research methods and biochemical characteristics of myxomycetes were also summarized, whilst the differences between the metabolites of various myxomycetes were analyzed. Finally, the problems and prospects of myxomycetes metabolites research have been discussed.
Research on the metabolites of myxomycetes has previously demonstrated the high potential for practical applications and has made great progress. In this paper, we reviewed more than 100 metabolites isolated from myxomycetes, including fatty acids, amino acids, alkaloids, naphthoquinones, aromatic compounds, terpenoids, esters or derivatives thereof. We also introduced their antimicrobial, antitumor, cytotoxic and antioxidant activities. In addition, the structure-activity relationship of these compounds has been briefly introduced. Furthermore, the biological activity research methods and biochemical characteristics of myxomycetes were also summarized, whilst the differences between the metabolites of various myxomycetes were analyzed. Finally, the problems and prospects of myxomycetes metabolites research have been discussed.
引文
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[2]Ishibashi M.Isolation of bioactive natural products from myxomycetes.Medicinal Chemistry,2005,1(6):575–590.
[3]Tran HTM,Stephenson SL,Chen Z,Pollock ED,Goggin FL.Evaluating the potential use of myxomycetes as a source of lipids for biodiesel production.Bioresource Technology,2012,123:386–389.
[4]Watanabe S,Tero A,Takamatsu A,Nakagaki T.Traffic optimization in railroad networks using an algorithm mimicking an amoeba-like organism,Physarum plasmodium.Biosystems,2011,105(3):225–232.
[5]Tran HTM,Stephenson SL,Pollock ED.Evaluation of Physarum polycephalum plasmodial growth and lipid production using rice bran as a carbon source.BMC Biotechnology,2015,15:67.
[6]Steglich W.Slime moulds(myxomycetes)as a source of new biologically active metabolites.Pure and Applied Chemistry,1989,61(3):281–288.
[7]Misono Y,Ishibashi M,Ito A.Bahiensol,a new glycerolipid from a cultured myxomycete Didymium bahiense var.bahiense.Chemical and Pharmaceutical Bulletin,2003,51(5):612–613.
[8]Ishibashi M,Iwasaki T,Imai S,Sakamoto S,Yamaguchi K,Ito A.Laboratory culture of the myxomycetes:formation of fruiting bodies of Didymium bahiense and its plasmodial production of makaluvamine A.Journal of Natural Products,2001,64(1):108–110.
[9]Masami I,Mitamura M,Ito A.Laboratory culture of the myxomycete Didymium squamulosum and its production of clionasterol.Natural Medicines,1999,53(6):316–318.
[10]Nakatani S,Kiyota M,Matsumoto J,Ishibashi M.Pyrroloiminoquinone pigments from Didymium iridis.Biochemical Systematics and Ecology,2005,33(3):323–325.
[11]朱鹤.中国北方代表地区黏菌主要类群的个体发育及化学成分研究.吉林农业大学博士学位论文,2012.
[12]Casser I,Steffan B,Steglich W.The chemistry of the plasmodial pigments of the slime mold Fuligo septica(Myxomycetes).Angewandte Chemie International Edition in Endlish,1987,26(6):586–587.
[13]姜宁.绒泡菌目黏菌主要代表种化学成分及活性研究.吉林农业大学硕士学位论文,2013.
[14]Nakatani S,Yamamoto Y,Hayashi M,Komiyama K,Ishibashi M.Cycloanthranilylproline-derived constituents from a myxomycete Fuligo candida.Chemical and Pharmaceutical Bulletin,2004,52(3):368–370.
[15]Shintani A,Ohtsuki T,Yamamoto Y,Hakamatsuka T,Kawahara N,Goda Y,Ishibashi M.Fuligoic acid,a new yellow pigment with a chlorinated polyene-pyrone acid structure isolated from the myxomycete Fuligo septica f.flava.Tetrahedron Letters,2009,50(26):3189–3190.
[16]?ezanka T,Hanu?LO,Kujan P,Dembitsky VM.Fulicineroside,an unusual glycosidic dibenzofuran metabolite from the slime mold Fuligo cinerea(Schwein.)Morgan.European Journal of Organic Chemistry,2005,2005(13):2708–2714.
[17]Hasegawa H,Yamada Y,Komiyama K,Hayashi M,Ishibashi M,Sunazuka T,Izuhara T,Sugahara K,Tsuruda K,Masuda M,Takasu N,Tsukasaki K,Tomonaga M,Kamihira S.A novel natural compound,a cycloanthranilylproline derivative(Fuligocandin B),sensitizes leukemia cells to apoptosis induced by tumor necrosis factor–related apoptosis-inducing ligand(TRAIL)through 15–deoxy-△12,14 prostaglandin J2production.Blood,2007,110:1664–1674.
[18]Bullock E,Dawson CJ.Sterol content of the myxomycetes Physarum polycephalum and P.flavicomum.Journal of Lipid Research,1976,17(6):565–571.
[19]Simon HL,Henney HR.Chemical composition of slime from three species of myxomycetes.FEBS Letters,1970,7(1):80–82.
[20]Korn ED,Greenblatt CL,Lees AM.Synthesis of unsaturated fatty acids in the slime mold Physarum polycephalum and the zooflagellates Leishmania tarentolae,Trypanosoma lewisi,and Crithidia sp.:a comparative study.Journal of Lipid Research,1965,6:43–50.
[21]Lenfant M,Lecompte MF,Farrugia G.Identification des stérols de Physarum polycephalum.Phytochemistry,1970,9(12):2529–2535.
[22]Comes P,Kleinig H.Phospholipids and phospholipase D in the true slime mold Physarum polycephalum.Biochimica et Biophysica Acta(BBA)-Lipids and Lipid Metabolism,1973,316(1):13–18.
[23]Murakami–Murofushi K,Uchiyama A,Fujiwara Y,Kobayashi T,Kobayashi S,Mukai M,Murofushi H,Tigyi G.Biological functions of a novel lipid mediator,cyclic phosphatidic acid.Biochimica et Biophysica Acta(BBA)-Lipids and Lipid Metabolism,2002,1582(1/3):1–7.
[24]Eisenbarth S,Steffan B.Structure and biosynthesis of chrysophysarin A,a plasmodial pigment from the slime mould Physarum polycephalum(Myxomycetes).Tetrahedron,2000,56(3):363–365.
[25]Steffan B,Praemassing M,Steglich W.Physarochrome A,a plasmodial pigment from the slime mould Physarum polycephalum(myxomycetes).Tetrahedron Letters,1987,28(32):3667–3670.
[26]Nowak A,Steffan B.Polycephalin B and C:unusual tetramic acids from plasmodia of the slime mold Physarum polycephalum(Myxomycetes).Angewandte Chemie International Edition,1998,37(22):3139–3141.
[27]Hamana K,Matsuzaki S.Unusual polyamines in slime molds Physarum polycephalum and Dictyostelium discoideum.Journal of Biochemistry,1984,95(4):1105–1110.
[28]Furuhashi K.Alkaline phosphatase of Physarum polycephalum is insoluble.Archives of Microbiology,2008,189(2):151–156.
[29]Kouno T,Watanabe N,Sakai N,Nakamura T,Nabeshima Y,Morita M,Mizuguchi M,Aizawa T,Demura M,Imanaka T,Tanaka I,Kawano K.The structure of Physarum polycephalum Hemagglutinin I suggests a minimal carbohydrate recognition domain of legume lectin fold.Journal of Molecular Biology,2011,405(2):560–569.
[30]Misono Y,Ito A,Matsumoto J,Sakamoto S,Yamaguchi K,Ishibashi M.Physarigins A–C,three new yellow pigments from a cultured myxomycete Physarum rigidum.Tetrahedron Letters,2003,44(24):4479–4481.
[31]Shintani A,Yamazaki H,Yamamoto Y,Ahmed F,Ishibashi M.Cribrarione C,a naphthoquinone pigment from the myxomycete Cribraria meylanii.Chemical&Pharmaceutical Bulletin,2009,57(8):894–895.
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