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Dihydromaniwamycin E, a Heat-Shock Metabolite from Thermotolerant Streptomyces sp. JA74, Exhibiting Antiviral Activity against Influenza and SARS-CoV-2 Viruses.
Saito, Shun; Funayama, Kayo; Kato, Wataru; Okuda, Mayu; Kawamoto, Meiko; Matsubara, Teruhiko; Sato, Toshinori; Sato, Akihiko; Otsuguro, Satoko; Sasaki, Michihito; Orba, Yasuko; Sawa, Hirofumi; Maenaka, Katsumi; Shindo, Kazutoshi; Imoto, Masaya; Arai, Midori A.
  • Saito S; Department of Biosciences and Informatics, Faculty of Science and Technology, Keio University, Yokohama 223-8522, Japan.
  • Funayama K; Department of Biosciences and Informatics, Faculty of Science and Technology, Keio University, Yokohama 223-8522, Japan.
  • Kato W; Department of Biosciences and Informatics, Faculty of Science and Technology, Keio University, Yokohama 223-8522, Japan.
  • Okuda M; Department of Biosciences and Informatics, Faculty of Science and Technology, Keio University, Yokohama 223-8522, Japan.
  • Kawamoto M; Department of Biosciences and Informatics, Faculty of Science and Technology, Keio University, Yokohama 223-8522, Japan.
  • Matsubara T; Department of Biosciences and Informatics, Faculty of Science and Technology, Keio University, Yokohama 223-8522, Japan.
  • Sato T; Department of Biosciences and Informatics, Faculty of Science and Technology, Keio University, Yokohama 223-8522, Japan.
  • Sato A; Drug Discovery and Disease Research Laboratory, Shionogi & Co., Ltd., Osaka 541-0045, Japan.
  • Otsuguro S; Division of Molecular Pathobiology, International Institute for Zoonosis Control, Hokkaido University, Sapporo 001-0020, Japan.
  • Sasaki M; Laboratory of Biomolecular Science, Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan.
  • Orba Y; Division of Molecular Pathobiology, International Institute for Zoonosis Control, Hokkaido University, Sapporo 001-0020, Japan.
  • Sawa H; Division of Molecular Pathobiology, International Institute for Zoonosis Control, Hokkaido University, Sapporo 001-0020, Japan.
  • Maenaka K; International Collaboration Unit, International Institute for Zoonosis Control, Hokkaido University, Sapporo 001-0020, Japan.
  • Shindo K; Division of Molecular Pathobiology, International Institute for Zoonosis Control, Hokkaido University, Sapporo 001-0020, Japan.
  • Imoto M; International Collaboration Unit, International Institute for Zoonosis Control, Hokkaido University, Sapporo 001-0020, Japan.
  • Arai MA; One Health Research Center, Hokkaido University, Sapporo 060-0818, Japan.
J Nat Prod ; 85(11): 2583-2591, 2022 Nov 25.
Статья в английский | MEDLINE | ID: covidwho-2062146
ABSTRACT
Dihydromaniwamycin E (1), a new maniwamycin derivative featuring an azoxy moiety, has been isolated from the culture extract of thermotolerant Streptomyces sp. JA74 along with the known analogue maniwamycin E (2). Compound 1 is produced only by cultivation of strain JA74 at 45 °C, and this type of compound has been previously designated a "heat shock metabolite (HSM)" by our research group. Compound 2 is detected as a production-enhanced metabolite at high temperature. Structures of 1 and 2 are elucidated by NMR and MS spectroscopic analyses. The absolute structure of 1 is determined after the total synthesis of four stereoisomers. Though the absolute structure of 2 has been proposed to be the same as the structure of maniwamycin D, the NMR and the optical rotation value of 2 are in agreement with those of maniwamycin E. Therefore, this study proposes a structural revision of maniwamycins D and E. Compounds 1 and 2 show inhibitory activity against the influenza (H1N1) virus infection of MDCK cells, demonstrating IC50 values of 25.7 and 63.2 µM, respectively. Notably, 1 and 2 display antiviral activity against SARS-CoV-2, the causative agent of COVID-19, when used to infect 293TA and VeroE6T cells, with 1 and 2 showing IC50 values (for infection of 293TA cells) of 19.7 and 9.7 µM, respectively. The two compounds do not exhibit cytotoxicity in these cell lines at those IC50 concentrations.
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Полный текст: Имеется в наличии Коллекция: Международные базы данных база данных: MEDLINE Основная тема: Antiviral Agents / Streptomyces / Azo Compounds / Influenza A Virus, H1N1 Subtype / SARS-CoV-2 / COVID-19 Пределы темы: Животные / Люди Язык: английский Журнал: J Nat Prod Год: 2022 Тип: Статья Аффилированная страна: Acs.jnatprod.2c00550

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Полный текст: Имеется в наличии Коллекция: Международные базы данных база данных: MEDLINE Основная тема: Antiviral Agents / Streptomyces / Azo Compounds / Influenza A Virus, H1N1 Subtype / SARS-CoV-2 / COVID-19 Пределы темы: Животные / Люди Язык: английский Журнал: J Nat Prod Год: 2022 Тип: Статья Аффилированная страна: Acs.jnatprod.2c00550