Fungal metabolites. 22. Determination of absolute configuration and biological activity of new immunosuppressants, mycestericins D, E, F and G

被引:59
作者
Fujita, T
Hamamichi, N
Kiuchi, M
Matsuzaki, T
Kitao, Y
Inoue, K
Hirose, R
Yoneta, M
Sasaki, S
Chiba, K
机构
[1] KYOTO UNIV, FAC PHARMACEUT SCI, SAKYO KU, KYOTO 60601, JAPAN
[2] TAITO CO LTD, RES LAB, NAGATA KU, KOBE 653, JAPAN
[3] YOSHITOMI PHARMACEUT IND LTD, RES LABS, IRUMA, SAITAMA 358, JAPAN
关键词
D O I
10.7164/antibiotics.49.846
中图分类号
Q81 [生物工程学(生物技术)]; Q93 [微生物学];
学科分类号
071005 ; 0836 ; 090102 ; 100705 ;
摘要
Mycestericins D, E, F and G were isolated from the culture broth of Mycelia sterilia ATCC 20349 as potent immunosuppressants. Mycestericins F and G were identical with dihydromycestericins D and E, respectively. Their absolute configurations were determined by use of the modified MOSHER's method and by comparison of the CD spectra of their benzoate derivatives with those of synthetic analogs. Mycestericins D, E, F and G suppressed the proliferation of lymphocytes in the mouse allogeneic mixed lymphocyte reaction.
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页码:846 / 853
页数:8
相关论文
共 12 条
[1]   DESIGN, SYNTHESIS, AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF 2-SUBSTITUTED-2-AMINO-1,3-PROPANEDIOLS - DISCOVERY OF A NOVEL IMMUNOSUPPRESSANT, FTY720 [J].
ADACHI, K ;
KOHARA, T ;
NAKAO, N ;
ARITA, M ;
CHIBA, K ;
MISHINA, T ;
SASAKI, S ;
FUJITA, T .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (08) :853-856
[2]   ISOLATION AND STRUCTURE DETERMINATION OF A NEW ANTIFUNGAL ALPHA-HYDROXYMHTHYL-ALPHA-AMINO ACID [J].
ARAGOZZINI, F ;
CRAVERI, R ;
SCOLASTICO, C ;
RINDONE, B ;
MANACHINI, PL .
TETRAHEDRON, 1972, 28 (21) :5493-+
[3]   ELUCIDATION OF STRUCTURE AND STEREOCHEMISTRY OF MYRIOCIN - NOVEL ANTIFUNGAL ANTIBIOTIC [J].
BAGLI, JF ;
KLUEPFEL, D ;
STJACQUE.M .
JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (07) :1253-1260
[4]  
FUJITA T, 1995, TETRAHEDRON LETT, V36, P8599
[5]   SIMPLE COMPOUNDS, 2-ALKYL-2-AMINO-1,3-PROPANEDIOLS HAVE POTENT IMMUNOSUPPRESSIVE ACTIVITY [J].
FUJITA, T ;
YONETA, M ;
HIROSE, R ;
SASAKI, S ;
INOUE, K ;
KIUCHI, M ;
HIRASE, S ;
ADACHI, K ;
ARITA, M ;
CHIBA, K .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (08) :847-852
[6]   FUNGAL METABOLITES .11. A POTENT IMMUNOSUPPRESSIVE ACTIVITY FOUND IN ISARIA-SINCLAIRII METABOLITE [J].
FUJITA, T ;
INOUE, K ;
YAMAMOTO, S ;
IKUMOTO, T ;
SASAKI, S ;
TOYAMA, R ;
CHIBA, K ;
HOSHINO, Y ;
OKUMOTO, T .
JOURNAL OF ANTIBIOTICS, 1994, 47 (02) :208-215
[7]  
KANAI M, 1966, J MASS SPECTROM, V31, P177
[8]   MYRIOCIN, A NEW ANTIFUNGAL ANTIBIOTIC FROM MYRIOCOCCUM-ALBOMYCES [J].
KLUEPFEL, D ;
VEZINA, C ;
SEHGAL, SN ;
KUDELSKI, A ;
CHAREST, MP ;
BAGLI, J .
JOURNAL OF ANTIBIOTICS, 1972, 25 (02) :109-+
[9]   ANOMALY IN THE MODIFIED MOSHER METHOD - ABSOLUTE-CONFIGURATIONS OF SOME MARINE CEMBRANOLIDES [J].
KUSUMI, T ;
FUJITA, Y ;
OHTANI, I ;
KAKISAWA, H .
TETRAHEDRON LETTERS, 1991, 32 (25) :2923-2926
[10]   FUNGAL METABOLITES .14. NOVEL POTENT IMMUNOSUPPRESSANTS, MYCESTERICINS, PRODUCED BY MYCELIA-STERILIA [J].
SASAKI, S ;
HASHIMOTO, R ;
KIUCHI, M ;
INOUE, K ;
IKUMOTO, T ;
HIROSE, R ;
CHIBA, K ;
HOSHINO, Y ;
OKUMOTO, T ;
FUJITA, T .
JOURNAL OF ANTIBIOTICS, 1994, 47 (04) :420-433