网柄细胞状黏菌的化学成分及药理作用研究进展
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摘要
文中综述了从网柄细胞状黏菌中分离得到的DIF-1及其衍生物、氯代苯并呋喃、三联苯化合物等芳香族化合物,脂肪酸和磷酸化合物、酶以及糖类等,并介绍了各成分的药理或生理作用等。表明网柄细胞状黏菌可以成为某些活性成分及药物的新来源。
Chemical components,such as DIF-1 and its derivatives including chlorinated benzofurans,dictyobiphenyl,dictyoterphenyl,fatty acid and phospholipid composition,enzyme and saccharide were extracted from dictyostelid cellular slime molds. The pharmacological and physiological activities of these chemical components were introduced. It is shown that dictyostelid cellular slime molds are new resources for chemical components and medicines.
Chemical components,such as DIF-1 and its derivatives including chlorinated benzofurans,dictyobiphenyl,dictyoterphenyl,fatty acid and phospholipid composition,enzyme and saccharide were extracted from dictyostelid cellular slime molds. The pharmacological and physiological activities of these chemical components were introduced. It is shown that dictyostelid cellular slime molds are new resources for chemical components and medicines.
引文
[1]姚一建,李玉(主译).菌物学概论[M].北京:中国农业出版社,2002.
[2]Singh B N.Studies on Soil Acrasieae:1.Distribution of species of Dictyostelium in soils of Great Britain and the effect of bacteria on their development[J].Microbiology,1947,1(1):11-21.
[3]Cavender J C,Raper K B.The Acrasieae in nature.II.Forest soil as a primary habitat[J].American Journal of Botany,1965:297-302.
[4]Cavender J C,Raper K B.The Acrasieae in nature.III.Occurrence and distributionin forests of eastern North America[J].American Journal of Botany,1965:302-308.
[5]Gokan Naomi,Haruhisa Kikuchi,Koji Nakamura,et al.Structural requirements of Dictyostelium differentiation-inducing factors for their stalk-cell-inducing activity in Dictyostelium cells and anti-proliferative activity in K562 human leukemic cells[J].Biochemical Pharmacology,2005,70(5):676-685.
[6]Kikuchi Haruhisa,Shinya Ishiko,Yoshiteru Oshima,et al.Biological activities of novel derivatives of DIF-1 isolated from Dictyostelium[J].Biochemical and Biophysical Research Communications,2008,377(3):1012-1017.
[7]Ritsuko Kawaharada,Akio Nakamura,Katsunori Takahashi,et al.Oral administration of Dictyostelium differentiation-inducing factor 1 lowers blood glucoselevels in streptozotocin-induced diabetic rats[J].Life Sciences,2016,155:56-62.
[8]Masashi K anai,Yoshitaka Konda,Toshio Nakajima,et al.Differentiation-inducing factor-1(DIF-1)inhibits STAT3 activity involved in gastric cancer cell proliferation via MEK-ERK-dependent pathway[J].Oncogene,2003,22(4):548-554.
[9]Kubohara Yuzuru,Haruhisa Kikuchi,Yoshiteru Oshima.Exploitation of the derivatives of Dictyostelium differentiation-inducing factor-1,which promote glucose consumption in mammalian cells[J].Life Sciences,2008,83(17/18):608-612.
[10]Yuzuru Kubohara,Haruhisa Kikuchi,Yusuke Matsuo,et al.Mitochondria are the target organelle of differentiationinducing factor-3,an anti-tumor agent isolated from Dictyostelium discoideum corrected[J].PloS One,2013,8(8):e72118-e72118.
[11]Nakajima-Shimada Junko,Hatabu Toshimitsu,Hosoi Yukari.Derivatives of Dictyostelium discoideum differentiation-inducing factor-3 suppress the activities of Trypanosoma cruzi in vitro and in vivo[J].Biochemical Pharmacology,2013,85(11):1603-1610.
[12]Alix Dubois,Clemence Ginet,Nathan Furstoss,et al.Differentiation inducing factor 3 mediates its anti-leukemic effect through ROS-dependent DRP1-mediated mitochondrial fission and induction of caspase-independent cell death[J].Oncotarget,2016,7(18):26120-26136.
[13]Oladimeji Peter,Yuzuru Kubohara,Haruhisa Kikuchi,et al.Aderivative of differentiation-Inducing factor-3 inhibits PAK1activity and breast cancer cell proliferation[J].International Journal of Cancerand Clinical Research,2015,2(3):1-6.
[14]Van Hai Nguyen,Haruhisa Kikuchi,Yuzuru Kubohara,et al.Development of novel DIF-1 derivatives that selectively suppress innate immune responses[J].Bioorganic&Medicinal Chemistry,2015,23(15):4311-4315.
[15]Yuzuru Kubohara,Mayumi Komachi,Yoshimi Homma,et al.Derivatives of Dictyostelium differentiation-inducing factors inhibit lysophosphatidic acid-stimulated migration of murine osteosarcoma LM8 cells[J].Biochem Biophys Res Commun,2015,463(4):800-805.
[16]Kuwayama Hidekazu,Yuzuru Kubohara.Differentiationinducing factor 2 modulates chemotaxis via the histidine kinase Dhk C-dependent pathway in Dictyostelium discoideum[J].FEBS Letters,2016,590(6):760-768.
[17]Haruhisa Kikuchi,Yoshinori Saito,Yumiko Okano,et al.Isolation and synthesis of a new aromatic compound,brefelamide,from Dictyostelium cellular slime molds and its inhibitory effect on the proliferation of astrocytoma cells[J].The Journal of Organic Chemistry,2005,70(22):8854-8858.
[18]Shigeyoshi Honma,Sachina Takasaka,Takahiro Ishikawa,et al.Effect of brefelamide on HGF-induced survival of 1321N1human astrocytoma cells[J].In Vitro Cellular&Developmental Biology Animal,2016,52(6):705-711.
[19]Shigeyoshi Honma,Masaki Saito,Haruhisa Kikuchi,et al.Areduction of epidermal growth factor receptor is involved in brefelamide-induced inhibition of phosphorylation of ERK in human astrocytoma cells[J].European Journal of Pharmacology,2009,616(1-3):38-42.
[20]Jing-Zhang,Osamu Yamada,Shinya Kida,et al.Identification of brefelamide as a novel inhibitor of osteopontin that suppresses invasion of A549 lung cancer cells[J].Oncology Reports,2016,36(4):2357-2364.
[21]Haruhisa Kikuchi.Novel biologically active compounds isolated from unexploited organisms,cellular sime molds[J].Journal of the Pharmaceutical Society of Japan,2007,127(9):1431-1439.
[22]Haruhisa Kikuchi,Yuzuru Kubohara,Van Hai Nguyen,et al.Novel chlorinated dibenzofurans isolated from the cellular slime mold,Polysphondylium filamentosum,and their biological activities[J].Bioorganic&Medicinal Chemistry,2013,21(15):4628-4633.
[23]Haruhisa Kikuchi,Matsuo Yusuke,Katou Yasuhiro,et al.Isolation,synthesis,and biological activity of biphenyl and m-terphenyl-type compounds from Dictyostelium cellular slime molds[J].Tetrahedron,2012,68(43):8884-8889.
[24]Haruhisa Kikuchi,Yoshiteru Oshima,Aya Ichimura,et al.Anti-leukemic activities of Dictyostelium secondary metabolites:Anovel aromatic metabolite,4-methyl-5-n-pentylbenzene-1,3-diol,isolated from Dictyostelium mucoroides suppresses cell growth in human leukemia K562 and HL-60 cells[J].Life Sciences,2006,80(2):160-165.
[25]Murata Chihiro,Ogura Tetsuhiro,Narita Shuhei,et al.Synthesis and SAR of 4-methyl-5-pentylbenzene-1,3-diol(MPBD),produced by Dictyostelium discoideum[J].Bioorganic&Medicinal Chemistry Letters,2016,26(5):1428-1433.
[26]Azelmat Jabrane,Fiorito Serena,Genovese Salvator,et al.Antibacterial and anti-inflammatory activities of Ppc-1,active principle of the cellular slime mold Polysphondylium pseudocandidum[J].Medicinal Chemistry(Shariqah(United Arab Emirates)),2015,11(7):666-669.
[27]Haruhisa Kikuchi,Toshiyuki Suzuki,Masato Ogura,et al.Synthesis of prenylated quinolinecarboxylic acid derivatives and their anti-obesity activities[J].Bioorganic&Medicinal Chemistry,2015,23(1):66-72.
[28]Toshiyuki Suzuki,Haruhisa Kikuchi,Masato Ogura,et al.Weight Loss by Ppc-1,a novel small molecule mitochondrial uncoupler derived from slime mold[J].PLoS One,2015,10(2):e0117088.
[29]Davidoff F,Korn E D.The Conversion of Long Chain Saturated Fatty Acids to Theirα,β-Unsaturated,β,γ-Unsaturated,andβ-Hydroxy Derivatives by Enzymes from the Cellular Slime Mold,Dictyostelium discoideum[J].The Journal of Biological Chemistry,1964,239:2496-2506.
[30]Davidoff F,Korn E D.The biosynthesis of fatty acids in the cellular slime mold,Dictyostelium discoideum[J].The Journal of Biological Chemistry,1963,238:3210-3215.
[31]Davidoff F,Korn E D.Fatty acid and phospholipid composition of the cellular slime mold,Dictyostelium discoideum[J].The Journal of Biological Chemistry,1963,238:3199-3209.
[32]Valérie E.Paquet,RenéLessire,Frédéric Domergue,et al.Lipid composition of multilamellar bodies secreted by Dictyostelium discoideum reveals their amoebal origin[J].Eukaryotic cell,2013,12(10):1326-1334.
[33]Xiaoli-Du,Caroline Barisch,Peggy Paschke,et al.Dictyostelium lipid droplets host novel proteins[J].Eukaryotic cell,2013,12(11):1517-1529.
[34]Saito T,Ochiai H.Fatty acid composition of the cellular slime mold Polysphondylium pallidum[J].Lipids,1998,33(3):327-332.
[35]安颖.网柄细胞状黏菌中脂肪酸的测定及其分类学意义的初步研究[D].长春:吉林农业大学,2012.
[36]RenéJ W,Theo M Konijn.Identification of the acrasin of Dictyostelium minutum as a derivative of folic acid[J].Cell Differentiation,1983,12(4):205-210.
[37]Peter J M,Haastert V,RenéJ W,et al.Identification of a pterin as the acrasin of the cellular slime mold Dictyostelium lacteum[J].Proceedings of the National Academy of Sciences of the United States of America,1982,79(20):6270-6274.
[38]Bonner J T.Observations on polarity in the slime mold Dictyostelium discoideum[J].The Biological Bulletin,1950,99(2):143-151.
[39]Earle J P,Stephen L B.A cell surface-localizedacetylcholinesterase in the cellular slime mold Polysphondylium violaceum[J].FEMS Microbiology Letters,1986,35(1):83-87.
[40]Freeze H H,Etchison J R.Presence of a nonlysosomal endo-β-N-acetylglucosaminidase in the cellular slime mold Dictyostelium discoideum[J].Archives of Biochemistry and Biophysics,1984,232(1):414-421.
[41]Kazunori Motohashi,Naoki Morita,Atsushi Kato,et al.Identification of des-methyl-DIF-1 methyltransferase in Dictyostelium purpureum[J].Bioscience Biotechnology Biochemical,2012.76(9):1672-1676.
[42]Hobdey S E,Knott B C,Majid Haddad Momeni,et al.Biochemical and structural characterizations of two Dictyostelium cellobiohydrolases from the amoebozoa kingdom reveal a high level of conservation between distant phylogenetic trees of life[J].Applied and Environmental Microbiology,2016,82(11):3395-3409.
[43]Ceccarini C,Filosa M.Carbohydrate content during development of the slime mold,Dictyostelium discoideum[J].Journal of Cellular Physiology,1965,66(2):135-140.
[44]Haruhisa Kikuchi,Yoshinori Saito,Jun Komiya,et al.Furanodictine A and B:amino sugar analogues produced by cellular slime mold Dictyostelium discoideum showing neuronal differentiation activity[J].The Journal of Organic Chemistry,2001,66(21):6982-6987.
[45]Mereyala Hari Babu,Mohd Baseeruddin,Sreenivasulu Reddy Koduru.Formal synthesis of furanodictine B from d-glucose[J].Tetrahedron:Asymmetry,2004,15(21):3457-3460.
[46]Freeze H,Loomis W F.Chemical analysis of stalk components of Dictostelium discoideum[J].Biochimica et Biophysica Acta,1978,539(4):529-537.
[2]Singh B N.Studies on Soil Acrasieae:1.Distribution of species of Dictyostelium in soils of Great Britain and the effect of bacteria on their development[J].Microbiology,1947,1(1):11-21.
[3]Cavender J C,Raper K B.The Acrasieae in nature.II.Forest soil as a primary habitat[J].American Journal of Botany,1965:297-302.
[4]Cavender J C,Raper K B.The Acrasieae in nature.III.Occurrence and distributionin forests of eastern North America[J].American Journal of Botany,1965:302-308.
[5]Gokan Naomi,Haruhisa Kikuchi,Koji Nakamura,et al.Structural requirements of Dictyostelium differentiation-inducing factors for their stalk-cell-inducing activity in Dictyostelium cells and anti-proliferative activity in K562 human leukemic cells[J].Biochemical Pharmacology,2005,70(5):676-685.
[6]Kikuchi Haruhisa,Shinya Ishiko,Yoshiteru Oshima,et al.Biological activities of novel derivatives of DIF-1 isolated from Dictyostelium[J].Biochemical and Biophysical Research Communications,2008,377(3):1012-1017.
[7]Ritsuko Kawaharada,Akio Nakamura,Katsunori Takahashi,et al.Oral administration of Dictyostelium differentiation-inducing factor 1 lowers blood glucoselevels in streptozotocin-induced diabetic rats[J].Life Sciences,2016,155:56-62.
[8]Masashi K anai,Yoshitaka Konda,Toshio Nakajima,et al.Differentiation-inducing factor-1(DIF-1)inhibits STAT3 activity involved in gastric cancer cell proliferation via MEK-ERK-dependent pathway[J].Oncogene,2003,22(4):548-554.
[9]Kubohara Yuzuru,Haruhisa Kikuchi,Yoshiteru Oshima.Exploitation of the derivatives of Dictyostelium differentiation-inducing factor-1,which promote glucose consumption in mammalian cells[J].Life Sciences,2008,83(17/18):608-612.
[10]Yuzuru Kubohara,Haruhisa Kikuchi,Yusuke Matsuo,et al.Mitochondria are the target organelle of differentiationinducing factor-3,an anti-tumor agent isolated from Dictyostelium discoideum corrected[J].PloS One,2013,8(8):e72118-e72118.
[11]Nakajima-Shimada Junko,Hatabu Toshimitsu,Hosoi Yukari.Derivatives of Dictyostelium discoideum differentiation-inducing factor-3 suppress the activities of Trypanosoma cruzi in vitro and in vivo[J].Biochemical Pharmacology,2013,85(11):1603-1610.
[12]Alix Dubois,Clemence Ginet,Nathan Furstoss,et al.Differentiation inducing factor 3 mediates its anti-leukemic effect through ROS-dependent DRP1-mediated mitochondrial fission and induction of caspase-independent cell death[J].Oncotarget,2016,7(18):26120-26136.
[13]Oladimeji Peter,Yuzuru Kubohara,Haruhisa Kikuchi,et al.Aderivative of differentiation-Inducing factor-3 inhibits PAK1activity and breast cancer cell proliferation[J].International Journal of Cancerand Clinical Research,2015,2(3):1-6.
[14]Van Hai Nguyen,Haruhisa Kikuchi,Yuzuru Kubohara,et al.Development of novel DIF-1 derivatives that selectively suppress innate immune responses[J].Bioorganic&Medicinal Chemistry,2015,23(15):4311-4315.
[15]Yuzuru Kubohara,Mayumi Komachi,Yoshimi Homma,et al.Derivatives of Dictyostelium differentiation-inducing factors inhibit lysophosphatidic acid-stimulated migration of murine osteosarcoma LM8 cells[J].Biochem Biophys Res Commun,2015,463(4):800-805.
[16]Kuwayama Hidekazu,Yuzuru Kubohara.Differentiationinducing factor 2 modulates chemotaxis via the histidine kinase Dhk C-dependent pathway in Dictyostelium discoideum[J].FEBS Letters,2016,590(6):760-768.
[17]Haruhisa Kikuchi,Yoshinori Saito,Yumiko Okano,et al.Isolation and synthesis of a new aromatic compound,brefelamide,from Dictyostelium cellular slime molds and its inhibitory effect on the proliferation of astrocytoma cells[J].The Journal of Organic Chemistry,2005,70(22):8854-8858.
[18]Shigeyoshi Honma,Sachina Takasaka,Takahiro Ishikawa,et al.Effect of brefelamide on HGF-induced survival of 1321N1human astrocytoma cells[J].In Vitro Cellular&Developmental Biology Animal,2016,52(6):705-711.
[19]Shigeyoshi Honma,Masaki Saito,Haruhisa Kikuchi,et al.Areduction of epidermal growth factor receptor is involved in brefelamide-induced inhibition of phosphorylation of ERK in human astrocytoma cells[J].European Journal of Pharmacology,2009,616(1-3):38-42.
[20]Jing-Zhang,Osamu Yamada,Shinya Kida,et al.Identification of brefelamide as a novel inhibitor of osteopontin that suppresses invasion of A549 lung cancer cells[J].Oncology Reports,2016,36(4):2357-2364.
[21]Haruhisa Kikuchi.Novel biologically active compounds isolated from unexploited organisms,cellular sime molds[J].Journal of the Pharmaceutical Society of Japan,2007,127(9):1431-1439.
[22]Haruhisa Kikuchi,Yuzuru Kubohara,Van Hai Nguyen,et al.Novel chlorinated dibenzofurans isolated from the cellular slime mold,Polysphondylium filamentosum,and their biological activities[J].Bioorganic&Medicinal Chemistry,2013,21(15):4628-4633.
[23]Haruhisa Kikuchi,Matsuo Yusuke,Katou Yasuhiro,et al.Isolation,synthesis,and biological activity of biphenyl and m-terphenyl-type compounds from Dictyostelium cellular slime molds[J].Tetrahedron,2012,68(43):8884-8889.
[24]Haruhisa Kikuchi,Yoshiteru Oshima,Aya Ichimura,et al.Anti-leukemic activities of Dictyostelium secondary metabolites:Anovel aromatic metabolite,4-methyl-5-n-pentylbenzene-1,3-diol,isolated from Dictyostelium mucoroides suppresses cell growth in human leukemia K562 and HL-60 cells[J].Life Sciences,2006,80(2):160-165.
[25]Murata Chihiro,Ogura Tetsuhiro,Narita Shuhei,et al.Synthesis and SAR of 4-methyl-5-pentylbenzene-1,3-diol(MPBD),produced by Dictyostelium discoideum[J].Bioorganic&Medicinal Chemistry Letters,2016,26(5):1428-1433.
[26]Azelmat Jabrane,Fiorito Serena,Genovese Salvator,et al.Antibacterial and anti-inflammatory activities of Ppc-1,active principle of the cellular slime mold Polysphondylium pseudocandidum[J].Medicinal Chemistry(Shariqah(United Arab Emirates)),2015,11(7):666-669.
[27]Haruhisa Kikuchi,Toshiyuki Suzuki,Masato Ogura,et al.Synthesis of prenylated quinolinecarboxylic acid derivatives and their anti-obesity activities[J].Bioorganic&Medicinal Chemistry,2015,23(1):66-72.
[28]Toshiyuki Suzuki,Haruhisa Kikuchi,Masato Ogura,et al.Weight Loss by Ppc-1,a novel small molecule mitochondrial uncoupler derived from slime mold[J].PLoS One,2015,10(2):e0117088.
[29]Davidoff F,Korn E D.The Conversion of Long Chain Saturated Fatty Acids to Theirα,β-Unsaturated,β,γ-Unsaturated,andβ-Hydroxy Derivatives by Enzymes from the Cellular Slime Mold,Dictyostelium discoideum[J].The Journal of Biological Chemistry,1964,239:2496-2506.
[30]Davidoff F,Korn E D.The biosynthesis of fatty acids in the cellular slime mold,Dictyostelium discoideum[J].The Journal of Biological Chemistry,1963,238:3210-3215.
[31]Davidoff F,Korn E D.Fatty acid and phospholipid composition of the cellular slime mold,Dictyostelium discoideum[J].The Journal of Biological Chemistry,1963,238:3199-3209.
[32]Valérie E.Paquet,RenéLessire,Frédéric Domergue,et al.Lipid composition of multilamellar bodies secreted by Dictyostelium discoideum reveals their amoebal origin[J].Eukaryotic cell,2013,12(10):1326-1334.
[33]Xiaoli-Du,Caroline Barisch,Peggy Paschke,et al.Dictyostelium lipid droplets host novel proteins[J].Eukaryotic cell,2013,12(11):1517-1529.
[34]Saito T,Ochiai H.Fatty acid composition of the cellular slime mold Polysphondylium pallidum[J].Lipids,1998,33(3):327-332.
[35]安颖.网柄细胞状黏菌中脂肪酸的测定及其分类学意义的初步研究[D].长春:吉林农业大学,2012.
[36]RenéJ W,Theo M Konijn.Identification of the acrasin of Dictyostelium minutum as a derivative of folic acid[J].Cell Differentiation,1983,12(4):205-210.
[37]Peter J M,Haastert V,RenéJ W,et al.Identification of a pterin as the acrasin of the cellular slime mold Dictyostelium lacteum[J].Proceedings of the National Academy of Sciences of the United States of America,1982,79(20):6270-6274.
[38]Bonner J T.Observations on polarity in the slime mold Dictyostelium discoideum[J].The Biological Bulletin,1950,99(2):143-151.
[39]Earle J P,Stephen L B.A cell surface-localizedacetylcholinesterase in the cellular slime mold Polysphondylium violaceum[J].FEMS Microbiology Letters,1986,35(1):83-87.
[40]Freeze H H,Etchison J R.Presence of a nonlysosomal endo-β-N-acetylglucosaminidase in the cellular slime mold Dictyostelium discoideum[J].Archives of Biochemistry and Biophysics,1984,232(1):414-421.
[41]Kazunori Motohashi,Naoki Morita,Atsushi Kato,et al.Identification of des-methyl-DIF-1 methyltransferase in Dictyostelium purpureum[J].Bioscience Biotechnology Biochemical,2012.76(9):1672-1676.
[42]Hobdey S E,Knott B C,Majid Haddad Momeni,et al.Biochemical and structural characterizations of two Dictyostelium cellobiohydrolases from the amoebozoa kingdom reveal a high level of conservation between distant phylogenetic trees of life[J].Applied and Environmental Microbiology,2016,82(11):3395-3409.
[43]Ceccarini C,Filosa M.Carbohydrate content during development of the slime mold,Dictyostelium discoideum[J].Journal of Cellular Physiology,1965,66(2):135-140.
[44]Haruhisa Kikuchi,Yoshinori Saito,Jun Komiya,et al.Furanodictine A and B:amino sugar analogues produced by cellular slime mold Dictyostelium discoideum showing neuronal differentiation activity[J].The Journal of Organic Chemistry,2001,66(21):6982-6987.
[45]Mereyala Hari Babu,Mohd Baseeruddin,Sreenivasulu Reddy Koduru.Formal synthesis of furanodictine B from d-glucose[J].Tetrahedron:Asymmetry,2004,15(21):3457-3460.
[46]Freeze H,Loomis W F.Chemical analysis of stalk components of Dictostelium discoideum[J].Biochimica et Biophysica Acta,1978,539(4):529-537.