메뉴 건너뛰기




Volumn 53, Issue 20, 2014, Pages 3287-3293

Direct and stereospecific interaction of amphidinol 3 with sterol in lipid bilayers

Author keywords

[No Author keywords available]

Indexed keywords

CHOLESTEROL; LIPID BILAYERS; MEMBRANES; MOLECULAR RECOGNITION; PHOSPHOLIPIDS;

EID: 84901389268     PISSN: 00062960     EISSN: 15204995     Source Type: Journal    
DOI: 10.1021/bi5002932     Document Type: Article
Times cited : (36)

References (39)
  • 1
    • 84879172856 scopus 로고    scopus 로고
    • Tetrahydrofuran-containing macrolides: A fascinating gift from the deep sea
    • Lorente, A., Lamariano-Merketegi, J., Albericio, F., and álvarez, M. (2013) Tetrahydrofuran-containing macrolides: a fascinating gift from the deep sea Chem. Rev. 113, 4567-4610
    • (2013) Chem. Rev. , vol.113 , pp. 4567-4610
    • Lorente, A.1    Lamariano-Merketegi, J.2    Albericio, F.3    Álvarez, M.4
  • 2
    • 54049094020 scopus 로고    scopus 로고
    • Amphidinolides and its related macrolides from marine dinoflagellates
    • Kobayashi, J. (2008) Amphidinolides and its related macrolides from marine dinoflagellates J. Antibiot. 61, 271-284
    • (2008) J. Antibiot. , vol.61 , pp. 271-284
    • Kobayashi, J.1
  • 3
    • 34547843710 scopus 로고    scopus 로고
    • Amphidinolactone A, a new 13-membered macrolide from dinoflagellate Amphidinium sp
    • Takahasi, Y., Kubota, T., and Kobayashi, J. (2007) Amphidinolactone A, a new 13-membered macrolide from dinoflagellate Amphidinium sp Heterocycles 72, 567-572
    • (2007) Heterocycles , vol.72 , pp. 567-572
    • Takahasi, Y.1    Kubota, T.2    Kobayashi, J.3
  • 6
    • 0026322293 scopus 로고
    • Amphidinol, a polyhydroxy-polyene antifungal agent with an unprecedented structure, from a marine dinoflagellate Amphidinium klebsii
    • Satake, M., Murata, M., Yasumoto, T., Fujita, T., and Naoki, H. (1991) Amphidinol, a polyhydroxy-polyene antifungal agent with an unprecedented structure, from a marine dinoflagellate Amphidinium klebsii J. Am. Chem. Soc. 113, 9859-9861
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 9859-9861
    • Satake, M.1    Murata, M.2    Yasumoto, T.3    Fujita, T.4    Naoki, H.5
  • 7
    • 0029153948 scopus 로고
    • Isolation and chemical structure of amphidinol 2, a potent hemolytic compound from marine dinoflagellate Amphidinium klebsii
    • Paul, G. K., Matsumori, N., Murata, M., and Tachibana, K. (1995) Isolation and chemical structure of amphidinol 2, a potent hemolytic compound from marine dinoflagellate Amphidinium klebsii Tetrahedron Lett. 36, 6279-6282
    • (1995) Tetrahedron Lett. , vol.36 , pp. 6279-6282
    • Paul, G.K.1    Matsumori, N.2    Murata, M.3    Tachibana, K.4
  • 8
    • 0001569209 scopus 로고    scopus 로고
    • Chemical structures of amphidinols 5 and 6 isolated from marine dinoflagellate Amphidinium klebsii and their cholesterol-dependent membrane disruption
    • Paul, G. K., Matsumori, N., Konoki, K., Murata, M., and Tachibana, K. (1997) Chemical structures of amphidinols 5 and 6 isolated from marine dinoflagellate Amphidinium klebsii and their cholesterol-dependent membrane disruption J. Mar. Biotechnol. 5, 124-128
    • (1997) J. Mar. Biotechnol. , vol.5 , pp. 124-128
    • Paul, G.K.1    Matsumori, N.2    Konoki, K.3    Murata, M.4    Tachibana, K.5
  • 9
    • 0004605946 scopus 로고    scopus 로고
    • Structure of amphidinol 3 and its cholesterol-dependent membrane perturbation: A strong antifungal metabolite produced by dinoflagellate Amphidinium klebsii
    • (Yasumoto, T. Oshima, Y. and Fukuyo, Y. Eds.), Intergovernmental Oceanographic Commission of UNESCO, Paris
    • Paul, G. K., Matsumori, N., Konoki, K., Sasaki, M., Murata, M., and Tachibana, K. (1996) Structure of amphidinol 3 and its cholesterol-dependent membrane perturbation: A strong antifungal metabolite produced by dinoflagellate Amphidinium klebsii, in Harmful and Toxic Algal Blooms (Yasumoto, T., Oshima, Y., and Fukuyo, Y., Eds.) pp 503-506, Intergovernmental Oceanographic Commission of UNESCO, Paris.
    • (1996) Harmful and Toxic Algal Blooms , pp. 503-506
    • Paul, G.K.1    Matsumori, N.2    Konoki, K.3    Sasaki, M.4    Murata, M.5    Tachibana, K.6
  • 10
    • 0033518615 scopus 로고    scopus 로고
    • Absolute configuration of amphidinol 3, the first complete structure determination from amphidinol homologues: Application of a new configuration analysis based on carbon-hydrogen spin-coupling constants
    • Murata, M., Matsuoka, S., Matsumori, N., Paul, G. K., and Tachibana, K. (1999) Absolute configuration of amphidinol 3, the first complete structure determination from amphidinol homologues: Application of a new configuration analysis based on carbon-hydrogen spin-coupling constants J. Am. Chem. Soc. 121, 870-871
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 870-871
    • Murata, M.1    Matsuoka, S.2    Matsumori, N.3    Paul, G.K.4    Tachibana, K.5
  • 11
    • 23444434915 scopus 로고    scopus 로고
    • Isolation and structure elucidation of a new amphidinol with a truncated polyhydroxyl chain from Amphidinium klebsii
    • Morsy, N., Matsuoka, S., Houdai, T., Matsumori, N., Adachi, S., Murata, M., Iwashita, T., and Fujita, T. (2005) Isolation and structure elucidation of a new amphidinol with a truncated polyhydroxyl chain from Amphidinium klebsii Tetrahedron 61, 8606-8610
    • (2005) Tetrahedron , vol.61 , pp. 8606-8610
    • Morsy, N.1    Matsuoka, S.2    Houdai, T.3    Matsumori, N.4    Adachi, S.5    Murata, M.6    Iwashita, T.7    Fujita, T.8
  • 12
    • 10944231361 scopus 로고    scopus 로고
    • The structures of five new antifungal and hemolytic amphidinol analogs from Amphidinium carterae collected in New Zealand
    • Echigoya, R., Rhodes, L., Oshima, Y., and Satake, M. (2005) The structures of five new antifungal and hemolytic amphidinol analogs from Amphidinium carterae collected in New Zealand Harmful Algae 4, 383-389
    • (2005) Harmful Algae , vol.4 , pp. 383-389
    • Echigoya, R.1    Rhodes, L.2    Oshima, Y.3    Satake, M.4
  • 14
    • 77950394308 scopus 로고    scopus 로고
    • Structure and biosynthesis of amphidinol 17, a hemolytic compound from Amphidinium carterae
    • Meng, Y., Van Wagoner, R. M., Misner, I., Tomas, C., and Wright, J. L. C. (2010) Structure and biosynthesis of amphidinol 17, a hemolytic compound from Amphidinium carterae J. Nat. Prod. 73, 409-415
    • (2010) J. Nat. Prod. , vol.73 , pp. 409-415
    • Meng, Y.1    Van Wagoner, R.M.2    Misner, I.3    Tomas, C.4    Wright, J.L.C.5
  • 15
    • 29844435631 scopus 로고    scopus 로고
    • Luteophanol D, new polyhydroxyl metabolite from marine dinoflagellate Amphidinium sp
    • Kubota, T., Takahashi, A., Tsuda, M., and Kobayashi, J. (2005) Luteophanol D, new polyhydroxyl metabolite from marine dinoflagellate Amphidinium sp Mar. Drugs 3, 113-118
    • (2005) Mar. Drugs , vol.3 , pp. 113-118
    • Kubota, T.1    Takahashi, A.2    Tsuda, M.3    Kobayashi, J.4
  • 16
    • 2942696172 scopus 로고    scopus 로고
    • Lingshuiols A and B, two new polyhydroxy compounds from the Chinese marine dinoflagellate Amphidinium sp
    • Huang, X. C., Zhao, D., Guo, Y. W., Wu, H. M., Trivellone, E., and Cimino, G. (2004) Lingshuiols A and B, two new polyhydroxy compounds from the Chinese marine dinoflagellate Amphidinium sp Tetrahedron Lett. 45, 5501-5504
    • (2004) Tetrahedron Lett. , vol.45 , pp. 5501-5504
    • Huang, X.C.1    Zhao, D.2    Guo, Y.W.3    Wu, H.M.4    Trivellone, E.5    Cimino, G.6
  • 17
    • 77954904171 scopus 로고    scopus 로고
    • Symbiopolyol, a VCAM-1 inhibitor from a symbiotic dinoflagellate of the jellyfish Mastigias papua
    • Hanif, N., Ohno, O., Kitamura, M., Yamada, K., and Uemura, D. (2010) Symbiopolyol, a VCAM-1 inhibitor from a symbiotic dinoflagellate of the jellyfish Mastigias papua J. Nat. Prod. 73, 1318-1322
    • (2010) J. Nat. Prod. , vol.73 , pp. 1318-1322
    • Hanif, N.1    Ohno, O.2    Kitamura, M.3    Yamada, K.4    Uemura, D.5
  • 18
    • 33644889899 scopus 로고    scopus 로고
    • Karatungiols A and B, two novel antimicrobial polyol compounds, from the symbiotic marine dinoflagellate Amphidinium sp
    • Washida, K., Koyama, T., Yamada, K., Kita, M., and Uemura, D. (2006) Karatungiols A and B, two novel antimicrobial polyol compounds, from the symbiotic marine dinoflagellate Amphidinium sp Tetrahedron Lett. 47, 2521-2525
    • (2006) Tetrahedron Lett. , vol.47 , pp. 2521-2525
    • Washida, K.1    Koyama, T.2    Yamada, K.3    Kita, M.4    Uemura, D.5
  • 19
    • 77950487360 scopus 로고    scopus 로고
    • Structure and absolute configuration of karlotoxin-2, an ichthyotoxin from the marine dinoflagellate Karlodinium veneficum
    • Peng, J., Place, A. R., Yoshida, W., Anklin, C., and Hamann, M. T. (2010) Structure and absolute configuration of karlotoxin-2, an ichthyotoxin from the marine dinoflagellate Karlodinium veneficum J. Am. Chem. Soc. 132, 3277-3279
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 3277-3279
    • Peng, J.1    Place, A.R.2    Yoshida, W.3    Anklin, C.4    Hamann, M.T.5
  • 20
    • 79955551060 scopus 로고    scopus 로고
    • Prorocentrol, a polyoxy linear carbon chain compound isolated from the toxic dinoflagellate Prorocentrum hoffmannianum
    • Sugahara, K., Kitamura, Y., Murata, M., Satake, M., and Tachibana, K. (2011) Prorocentrol, a polyoxy linear carbon chain compound isolated from the toxic dinoflagellate Prorocentrum hoffmannianum J. Org. Chem. 76, 3131-3138
    • (2011) J. Org. Chem. , vol.76 , pp. 3131-3138
    • Sugahara, K.1    Kitamura, Y.2    Murata, M.3    Satake, M.4    Tachibana, K.5
  • 22
    • 40949144025 scopus 로고    scopus 로고
    • Effects of lipid constituents on membrane-permeabilizing activity of amphidinols
    • Morsy, N., Houdai, T., Konoki, K., Matsumori, N., Oishi, T., and Murata, M. (2008) Effects of lipid constituents on membrane-permeabilizing activity of amphidinols Bioorg. Med. Chem. 16, 3084-3090
    • (2008) Bioorg. Med. Chem. , vol.16 , pp. 3084-3090
    • Morsy, N.1    Houdai, T.2    Konoki, K.3    Matsumori, N.4    Oishi, T.5    Murata, M.6
  • 23
    • 77949490838 scopus 로고    scopus 로고
    • Sterol effect on interaction between amphidinol 3 and liposomal membrane as evidenced by surface plasmon resonance
    • Swasono, R. T., Mouri, R., Morsy, N., Matsumori, N., Oishi, T., and Murata, M. (2010) Sterol effect on interaction between amphidinol 3 and liposomal membrane as evidenced by surface plasmon resonance Bioorg. Med. Chem. Lett. 20, 2215-2218
    • (2010) Bioorg. Med. Chem. Lett. , vol.20 , pp. 2215-2218
    • Swasono, R.T.1    Mouri, R.2    Morsy, N.3    Matsumori, N.4    Oishi, T.5    Murata, M.6
  • 25
    • 0023046610 scopus 로고
    • Sterol orientations in phosphatidylcholine liposomes as determined by deuterium NMR
    • Murari, R., Murari, M. P., and Baumann, W. J. (1986) Sterol orientations in phosphatidylcholine liposomes as determined by deuterium NMR Biochemistry 25, 1062-1067
    • (1986) Biochemistry , vol.25 , pp. 1062-1067
    • Murari, R.1    Murari, M.P.2    Baumann, W.J.3
  • 28
    • 48249090423 scopus 로고    scopus 로고
    • Complex formation of amphotericin B in sterol-containing membranes as evidenced by surface plasmon resonance
    • Mouri, R., Konoki, K., Matsumori, N., Oishi, T., and Murata, M. (2008) Complex formation of amphotericin B in sterol-containing membranes as evidenced by surface plasmon resonance Biochemistry 47, 7807-7815
    • (2008) Biochemistry , vol.47 , pp. 7807-7815
    • Mouri, R.1    Konoki, K.2    Matsumori, N.3    Oishi, T.4    Murata, M.5
  • 29
    • 80052266413 scopus 로고    scopus 로고
    • Membranes and Fluorescence Microscopy
    • (Geddes, C. D. Ed.) pp, Springer, New York
    • Bagatolli, L. A. (2009) Membranes and Fluorescence Microscopy, in Reviews in Fluorescence (Geddes, C. D., Ed.) pp 33-51, Springer, New York.
    • (2009) Reviews in Fluorescence , pp. 33-51
    • Bagatolli, L.A.1
  • 30
    • 67249136866 scopus 로고    scopus 로고
    • Giant unilamellar vesicles - A perfect tool to visualize phase separation and lipid rafts in model systems
    • Wesolowska, O., Michalak, K., Maniewska, J., and Hendrich, A. B. (2009) Giant unilamellar vesicles-a perfect tool to visualize phase separation and lipid rafts in model systems Acta Biochim. Polym. 56, 33-39
    • (2009) Acta Biochim. Polym. , vol.56 , pp. 33-39
    • Wesolowska, O.1    Michalak, K.2    Maniewska, J.3    Hendrich, A.B.4
  • 31
    • 0034902235 scopus 로고    scopus 로고
    • Interaction of cholesterol with lipid bilayers: The preferred configurations and fluctuations
    • Kessel, A., Ben-Tal, N., and May, S. (2001) Interaction of cholesterol with lipid bilayers: The preferred configurations and fluctuations Biophys. J. 81, 643-658
    • (2001) Biophys. J. , vol.81 , pp. 643-658
    • Kessel, A.1    Ben-Tal, N.2    May, S.3
  • 32
    • 0037340913 scopus 로고    scopus 로고
    • Effects of epicholesterol on the phosphatidylcholine bilayer: A molecular simulation study
    • Róg, T. and Pasenkiewicz-Gierula, M. (2003) Effects of epicholesterol on the phosphatidylcholine bilayer: A molecular simulation study Biophys. J. 84, 1818-1826
    • (2003) Biophys. J. , vol.84 , pp. 1818-1826
    • Róg, T.1    Pasenkiewicz-Gierula, M.2
  • 34
    • 52049103819 scopus 로고    scopus 로고
    • Comparative calorimetric and spectroscopic studies of the effects of cholesterol and epicholesterol on the thermotropic phase behavior of dipalmytoylphosphatidylcholine bilayer membranes
    • Mannock, D. A., Lee, M. Y. T., Lewis, R. N. A. H., and McElhaney, R. N. (2008) Comparative calorimetric and spectroscopic studies of the effects of cholesterol and epicholesterol on the thermotropic phase behavior of dipalmytoylphosphatidylcholine bilayer membranes Biochim. Biophys. Acta 1778, 2191-2202
    • (2008) Biochim. Biophys. Acta , vol.1778 , pp. 2191-2202
    • Mannock, D.A.1    Lee, M.Y.T.2    Lewis, R.N.A.H.3    McElhaney, R.N.4
  • 35
    • 14244268422 scopus 로고    scopus 로고
    • Hairpin conformation of amphidinols possibly accounting for potent membrane permeabilizing activities
    • Houdai, T., Matsuoka, S., Morsy, S., Matsumori, N., Satake, M., and Murata, M. (2005) Hairpin conformation of amphidinols possibly accounting for potent membrane permeabilizing activities Tetrahedron 61, 2795-2802
    • (2005) Tetrahedron , vol.61 , pp. 2795-2802
    • Houdai, T.1    Matsuoka, S.2    Morsy, S.3    Matsumori, N.4    Satake, M.5    Murata, M.6
  • 36
    • 55449119778 scopus 로고    scopus 로고
    • Structure of membrane-bound amphidinol 3 in isotropic small bicelles
    • Houdai, T., Matsumori, N., and Murata, M. (2008) Structure of membrane-bound amphidinol 3 in isotropic small bicelles Org. Lett. 10, 4191-4194
    • (2008) Org. Lett. , vol.10 , pp. 4191-4194
    • Houdai, T.1    Matsumori, N.2    Murata, M.3
  • 37
    • 84871591508 scopus 로고    scopus 로고
    • The lipid dependence of antimicrobial peptide activity is an unreliable experimental test for different pore models
    • Bobone, S., Roversi, D., Giordano, L., De Zotti, M., Formaggio, F., Toniolo, C., Park, Y., and Stella, L. (2012) The lipid dependence of antimicrobial peptide activity is an unreliable experimental test for different pore models Biochemistry 51, 10124-10126
    • (2012) Biochemistry , vol.51 , pp. 10124-10126
    • Bobone, S.1    Roversi, D.2    Giordano, L.3    De Zotti, M.4    Formaggio, F.5    Toniolo, C.6    Park, Y.7    Stella, L.8
  • 38
    • 33745747109 scopus 로고    scopus 로고
    • Solid-state NMR investigation of the membrane-disrupting mechanism of antimicrobial peptides MSI-78 and MSI-594 derived from magainin 2 and melittin
    • Ramamoorthy, A., Thennarasu, S., Lee, D.-K., Tan, A., and Maloy, L. (2006) Solid-state NMR investigation of the membrane-disrupting mechanism of antimicrobial peptides MSI-78 and MSI-594 derived from magainin 2 and melittin Biophys. J. 91, 206-216
    • (2006) Biophys. J. , vol.91 , pp. 206-216
    • Ramamoorthy, A.1    Thennarasu, S.2    Lee, D.-K.3    Tan, A.4    Maloy, L.5
  • 39
    • 20444400818 scopus 로고    scopus 로고
    • 31P solid-state NMR spectroscopy study
    • 31P solid-state NMR spectroscopy study Biochim. Biophys. Acta 1712, 101-108
    • (2005) Biochim. Biophys. Acta , vol.1712 , pp. 101-108
    • Bechinger, B.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.