Structure-activity studies of irumamycin type macrolides from Streptomyces sp. INA-Ac-5812 |
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| Authors: | Vera A Alferova Maxim V Shuvalov Roman A Novikov Alexey S Trenin Lubov G Dezhenkova Elena G Gladkikh Olda A Lapchinskaya Valeriya V Kulyaeva Olga P Bychkova Elena P Mirchink Pavel N Solyev Gulnara Kh Kudryakova Vladimir A Korshun Anton P Tyurin |
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| Institution: | 1. Gause Institute of New Antibiotics, B. Pirogovskaya 11, Moscow 119021, Russia;2. Department of Chemistry, Lomonosov Moscow State University, 1-3 Leninskiye Gory, Moscow 119992, Russia;3. Engelhardt Institute of Molecular Biology, Vavilova 32, Moscow 119991, Russia;4. Zelinsky Institute of Organic Chemistry, Leninsky Prospect 47, Moscow 119991, Russia;5. Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Miklukho-Maklaya 16/10, Moscow 117997, Russia |
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| Abstract: | Three natural glycosylated macrolide compounds, known irumamycin 1 and X-14952B 2, as well as new isoirumamycin 3, were isolated from ethyl acetate mycelium extract of Streptomyces sp. INA-Ac-5812. Structures of the compounds were elucidated using 1D and 2D NMR. Isoirumamycin 3 was found to be an isomer of irumamycin with an 18-membered macrolactone ring instead of 20-membered macrolide in irumamycin. A previously unknown stereo configuration of irumamycin epoxide (C23, C24) and hemiketal (C3, C7) fragments was deduced from NMR data (ROESY/NOESY and HSQMBC). Cytotoxic, antifungal and antibacterial activities were studied for all isolated compounds. Comparison of the collected data showed crucial importance of 20-membered macrolactone ring for antimicrobial properties of this antibiotic family. |
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| Keywords: | Corresponding author Macrolide antibiotics Irumamycin Antifungal activity |
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