FUNGAL METABOLITES. PART 14†. NOVEL POTENT IMMUNOSUPPRESSANTS, MYCESTERICINS, PRODUCED BY Mycelia sterilia
Mycestericins A, B, C, D and E were isolated from the culture broth of Mycelia sterilia ATCC 20349 along with thermozymocidin (= myriocin). Their structures were elucidated on the basis of spectroscopic studies and chemical evidence. The acetate of mycestericin C was identical with the acetate of 6,...
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| Published in | Journal of antibiotics Vol. 47; no. 4; pp. 420 - 433 |
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| Main Authors | , , , , , , , , , |
| Format | Journal Article |
| Language | English |
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Japan
JAPAN ANTIBIOTICS RESEARCH ASSOCIATION
1994
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| Abstract | Mycestericins A, B, C, D and E were isolated from the culture broth of Mycelia sterilia ATCC 20349 along with thermozymocidin (= myriocin). Their structures were elucidated on the basis of spectroscopic studies and chemical evidence. The acetate of mycestericin C was identical with the acetate of 6, 7-dihydromyriocin. Mycestericins suppressed the proliferation of lymphocytes in the mouse allogeneic mixed lymphocyte reaction, with a potency similar to that of myriocin. |
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| AbstractList | Mycestericins A, B, C, D and E were isolated from the culture broth of Mycelia sterilia ATCC 20349 along with thermozymocidin (= myriocin). Their structures were elucidated on the basis of spectroscopic studies and chemical evidence. The acetate of mycestericin C was identical with the acetate of 6,7-dihydromyriocin. Mycestericins suppressed the proliferation of lymphocytes in the mouse allogeneic mixed lymphocyte reaction, with a potency similar to that of myriocin. Mycestericine A, B, C, D and E were isolated from the culture broth of Mycelia sterilia ATCC 20349 along with thermozymocidin (= myriocin). Their structures were elucidated on the basis of spectroscopic studies and chemical evidence. The acetate of mycestericin C was identical with the acetate of 6,7-dihydromyriocin. Mycestericines suppressed the proliferation of lymphocytes in the mouse allogeneic mixed lymphocyte reaction, with a potency similar to that of myriocin. |
| Author | INOUE, KENICHIRO FUJITA, TETSURO SASAKI, SHGEO HASHIMOTO, RYOUTA HIROSE, RYOJI OKUMOTO, TAKEKI IKUMOTO, TAKESHI CHIBA, KENJI KIUCHI, MASATOSHI HOSHINO, YUKIO |
| Author_xml | – sequence: 1 fullname: SASAKI, SHGEO organization: Research Laboratory, Taito Company, Ltd – sequence: 2 fullname: HASHIMOTO, RYOUTA organization: Faculty of Pharmaceutical Sciences, Kyoto University – sequence: 3 fullname: KIUCHI, MASATOSHI organization: Faculty of Pharmaceutical Sciences, Kyoto University – sequence: 4 fullname: INOUE, KENICHIRO organization: Faculty of Pharmaceutical Sciences, Kyoto University – sequence: 5 fullname: IKUMOTO, TAKESHI organization: Research Laboratory, Taito Company, Ltd – sequence: 6 fullname: HIROSE, RYOJI organization: Research Laboratory, Taito Company, Ltd – sequence: 7 fullname: CHIBA, KENJI organization: Tokyo Research Laboratories, Yoshitomi Pharmaceutical Industries, Ltd – sequence: 8 fullname: HOSHINO, YUKIO organization: Tokyo Research Laboratories, Yoshitomi Pharmaceutical Industries, Ltd – sequence: 9 fullname: OKUMOTO, TAKEKI organization: Tokyo Research Laboratories, Yoshitomi Pharmaceutical Industries, Ltd – sequence: 10 fullname: FUJITA, TETSURO organization: Faculty of Pharmaceutical Sciences, Kyoto University |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/8195042$$D View this record in MEDLINE/PubMed |
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| References | 2) FUJITA, T.; K. INOUE, S. YAMAMOTO, T. IKUMOTO, S. SASAKI, R. TOYAMA, K. CHIBA, Y. HOSHINO & T. OKUMOTO: Fungal metabolites. Part 11. A potent immunosuppressive activity found in Isaria sinclairii metabolite. J. Antibiotics 47: 208 - 215, 1994 8) GENELLA, N. C; K. NAKANISHI, V. S. MARTIN & K. B. SHARPLESS: General method for determining absolute configurations of acyclic allylic alcohols. J. Am. Chem. Soc. 104: 3775 - 3776, 1982 4) KLUEPFEL, D.; J. BAGLI, H. BAKER, M.-P. CHAREST, A. KUDELSKI, S. N. SEHGAL & C. VÉZINA: Myriocin, a new antifungal antibiotic from Myriococcum albomyces. J. Antibiotics 25: 109 - 115, 1972 3) FUJITA, T.; K. INOUE, S. YAMAMOTO, T. IKUMOTO, S. SASAKI, R. TOYAMA, K. CHIBA, Y. HOSHINO & T. OKUMOTO: Isolation of ISP-I, a novel immunosuppressant produced by Isaria sinclairii. Abstracts of papers of 17th IUPAC International Symposium on the Chemistry of Natural Products, p. 68, New Delhi, Feb. 4 - 9, 1990 5) BAGLI, J. F.; D. KLUEPFEL & M. ST-JACQUES: Elucidation of structure and stereochemistry of myriocin. A novel antifungal antibiotic. J. Org. Chem. 38: 1253-1260, 1973 9) KOSHINO, H.; S. TOGIYA, S. SAKAMURA, T. SHIMANUKI, T. SATO & A. TAJIMA: Four fungitoxic C-18 hydroxy unsaturated fatty acids from stromata of Epichloe typhina. Tetrahedron Lett. 28: 73 - 76, 1987 7) FUJITA, T.; K. INOUE, S. YAMAMOTO, T. IKUMOTO, S. SASAKI, R. TOYAMA, M. YONETA, K. CHIBA, Y. HOSHINO & T. OKUMOTO: Fungal metabolites. Part 12. Potent immunosuppressant, 14-deoxomyriocin, (2S,3R,4R)-(E)-2-amino-3,4-dihydroxy-2-hydroxymethyleicos-6-enoic acid and structure-activity relationships of myriocin derivatives. J. Antibiotics 47: 216-224, 1994 1) FUJITA, T.; S. WADA, A. IIDA, T. NISHIMURA, M. KANAI & N. TOYAMA: Fungal metabolites. Part 13. Isolation and structural elucidation of new peptaibols, trichodecenins-I and -II, from Trichoderma viride. Chem. Pharm. Bull. 42: 489-494, 1994 6) ARAGOZZINI, F.; P. L. MANACHINI, R. CRAVERI, B. RINDONE & C. SCOLASTICO: Isolation and structure determination of a new antifungal α-hydroxymethyl-α-amino acid. Tetrahedron 28: 5493 - 5498, 1972 |
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| SubjectTerms | Animals Antifungal Agents - chemistry Antifungal Agents - isolation & purification Antifungal Agents - pharmacology Cell Division - drug effects Chromatography, High Pressure Liquid Eicosanoic Acids - chemistry Eicosanoic Acids - isolation & purification Eicosanoic Acids - pharmacology Fatty Acids, Monounsaturated - chemistry Fatty Acids, Monounsaturated - isolation & purification Fatty Acids, Monounsaturated - pharmacology Fatty Acids, Unsaturated - biosynthesis Fatty Acids, Unsaturated - chemistry Fatty Acids, Unsaturated - isolation & purification Fatty Acids, Unsaturated - pharmacology Immunosuppressive Agents - chemistry Immunosuppressive Agents - isolation & purification Immunosuppressive Agents - pharmacology Lymphocyte Culture Test, Mixed Lymphocytes - drug effects Lymphocytes - immunology Magnetic Resonance Spectroscopy Mice Mitosporic Fungi - metabolism Mycelia sterilia Stereoisomerism |
| Title | FUNGAL METABOLITES. PART 14†. NOVEL POTENT IMMUNOSUPPRESSANTS, MYCESTERICINS, PRODUCED BY Mycelia sterilia |
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