Pyloricidins, novel anti-Helicobacter pylori antibiotics produced by Bacillus sp.: II.: Isolation and structure elucidation

被引：18

作者：

Nagano, Y

Ikedo, K

Fujishima, A

Izawa, M

Tsubotani, S

Nishimura, O

Fujino, M

机构：

[1] Takeda Chem Ind Ltd, Div Pharmaceut Res, Pharmaceut Discovery Ctr, Yodogawa Ku, Osaka 5328686, Japan

[2] Takeda Chem Ind Ltd, Div Pharmaceut Res, Med Chem Res Labs 1, Yodogawa Ku, Osaka 5328686, Japan

[3] Takeda Chem Ind Ltd, Div Pharmaceut Res, Tsukuba, Ibaraki 3004293, Japan

[4] Takeda Chem Ind Ltd, Chuo Ku, Osaka 5408645, Japan

来源：

JOURNAL OF ANTIBIOTICS | 2001年 / 54卷 / 11期

关键词：

D O I：

10.7164/antibiotics.54.934

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：

Novel anti-Helicobacter pylori antibiotics, pyloricidins A, A(1), A(2), B, C and D were isolated from Bacillus sp. HC-70 and Bacillus sp. HC-72 by column chromatographies using adsorption and ion exchange resins. Their structures have been elucidated based on spectroscopic and degradation studies and shown to be peptide-like compounds. These compounds contained two unusual amino acids, viz.. 5-amino-2,3,4,6-tetrahydroxyhexanoic acid and 3-amino-3-phenylpropionic acid (beta -phenylalanine). The structure-activity relationship studies suggested that 3-(5-amino-2,3,4,6-tetrahydroxyhexanoyl)amino-3-phenylpropionic acid moiety was essential for anti-H. pylori activity.

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收藏

页码：934 / 947

页数：14

相关论文

共 16 条

[1] SIR92 - a program for automatic solution of crystal structures by direct methods [J].

ALTOMARE, A ;

CASCARANO, G ;

GIACOVAZZO, G ;

GUAGLIARDI, A ;

BURLA, MC ;

POLIDORI, G ;

CAMALLI, M .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1994, 27 :435-435

[2]

CHIBA N, 1997, Patent No. 9157168

[3] HYDROLYSIS OF D(-)-ETHYL BETA-PHENYL-BETA-HYDROXYPROPIONATE + D)-)-ETHYL BETA-PHENYL-BETA-ACETAMIDOPROPIONATE BY ALPHA-CHYMOTRYPSIN [J].

COHEN, SG ;

WEINSTEIN, SY .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (04) :725-&

[4] CJ-12,954 and its congeners, new anti-Helicobacter pylori compounds produced by Phanerochaete velutina: Fermentation, isolation, structural elucidation and biological activities [J].

Dekker, KA ;

Inagaki, T ;

Gootz, TD ;

Kaneda, K ;

Nomura, E ;

Sakakibara, T ;

Sakemi, S ;

Sugie, Y ;

Yamauchi, Y ;

Yoshikawa, N ;

Kojima, N .

JOURNAL OF ANTIBIOTICS, 1997, 50 (10) :833-839

[5] New quinolone compounds from Pseudonocardia sp. with selective and potent anti-Helicobacter pylori activity:: Taxonomy of producing strain, fermentation, isolation, structural elucidation and biological activities [J].

Dekker, KA ;

Inagaki, T ;

Gootz, TD ;

Huang, LH ;

Kojima, Y ;

Kohlbrenner, WE ;

Matsunaga, Y ;

McGuirk, PR ;

Nomura, E ;

Sakakibara, T ;

Sakemi, S ;

Suzuki, Y ;

Yamauchi, Y ;

Kojima, N .

JOURNAL OF ANTIBIOTICS, 1998, 51 (02) :145-152

[6] ON ENANTIOMORPH-POLARITY ESTIMATION [J].

FLACK, HD .

ACTA CRYSTALLOGRAPHICA SECTION A, 1983, 39 (NOV) :876-881

[7] EFFECT OF TREATMENT OF HELICOBACTER-PYLORI INFECTION ON THE LONG-TERM RECURRENCE OF GASTRIC OR DUODENAL-ULCER - A RANDOMIZED, CONTROLLED-STUDY [J].

GRAHAM, DY ;

LEW, GM ;

KLEIN, PD ;

EVANS, DG ;

EVANS, DJ ;

SAEED, ZA ;

MALATY, HM .

ANNALS OF INTERNAL MEDICINE, 1992, 116 (09) :705-708

[8]

Malfertheiner P, 1997, GUT, V41, P8

[9]

*MOL STRUCT CORP, 1999, TEXS SINGL CRYST STR

[10] Pyloricidins, novel anti-Helicobacter pylori antibiotics produced by Bacillus sp.: I.: Taxonomy, fermentation and biological activity [J].

Nakao, M ;

Miyagawa, K ;

Nakano, Y ;

Sakane, T ;

Tada, M ;

Nishimura, O ;

Fujino, M .

JOURNAL OF ANTIBIOTICS, 2001, 54 (11) :926-933