Pyloricidins, novel anti-Helicobacter pylori antibiotics produced by bacillus sp. II. Isolation and structure elucidation.
Novel anti-Helicobacter pylori antibiotics, pyloricidins A, A1, A2, 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.
Nagano
Y
Y
Pharmaceutical Discovery Center, Pharmaceutical Research Division, Takeda Chemical Industries, Ltd., Osaka, Japan.
Ikedo
K
K
Fujishima
A
A
Izawa
M
M
Tsubotani
S
S
Nishimura
O
O
Fujino
M
M
D000596:Amino Acids / Q000032:analysis; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D001407:Bacillus / Q000737:chemistry*; D018360:Crystallography, X-Ray; D005285:Fermentation; D008401:Gas Chromatography-Mass Spectrometry; D016481:Helicobacter Infections / Q000188:drug therapy; D016480:Helicobacter pylori / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D009904:Optical Rotation; D010455:Peptides; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013329:Structure-Activity Relationship
D000596:Amino Acids; D000900:Anti-Bacterial Agents; D010455:Peptides