Paleic acid, a fatty acid from Paenibacillus sp.: taxonomy, fermentation, isolation, structure determination, and anti-Mannheimia and -Pasteurella activity.
Paleic acid (1), an antibiotic, was obtained from a fermentation broth of Paenibacillus sp. BMK771-AF3. The compound is a fatty acid (9Z,16R)-16-hydroxy-9-octadecenoic acid ((R)-16-hydroxyoleic acid), whose isolation required protection of its polar functional groups. Mosher esters of paleic acid yielded information on the absolute configuration of secondary alcohol, and well-resolved (1)H NMR peaks around the double bond suggested that olefin adopted a Z geometry. Paleic acid showed potent antibacterial activity and narrow spectrum against Mannheimia haemolytica with MIC values ranging between 0.78 and 1.56 microg ml(-1).
Kurata
Ikuko
I
Institute of Microbial Chemistry, Tokyo, Shinagawa-ku, Tokyo, Japan.
Umekita
Maya
M
Sawa
Tsutomu
T
Hattori
Seiko
S
Hayashi
Chigusa
C
Kinoshita
Naoko
N
Homma
Yoshiko
Y
Igarashi
Masayuki
M
Hamada
Masa
M
Watanabe
Takumi
T
Sawa
Ryuichi
R
Naganawa
Hiroshi
H
Takahashi
Yoshikazu
Y
Akamatsu
Yuzuru
Y
D000900:Anti-Bacterial Agents / Q000302:isolation & purification / Q000494:pharmacology*; D004269:DNA, Bacterial / Q000737:chemistry / Q000235:genetics; D004275:DNA, Ribosomal / Q000737:chemistry / Q000235:genetics; D005227:Fatty Acids / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism / Q000494:pharmacology*; D005285:Fermentation; D009682:Magnetic Resonance Spectroscopy; D016978:Mannheimia haemolytica / Q000187:drug effects*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009829:Oleic Acids / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism / Q000494:pharmacology*; D056507:Paenibacillus / Q000737:chemistry* / Q000145:classification / Q000235:genetics / Q000378:metabolism; D010325:Pasteurella / Q000187:drug effects*; D010802:Phylogeny; D012336:RNA, Ribosomal, 16S / Q000235:genetics; D017422:Sequence Analysis, DNA; D012988:Soil Microbiology
D000900:Anti-Bacterial Agents; D004269:DNA, Bacterial; D004275:DNA, Ribosomal; D005227:Fatty Acids; D009829:Oleic Acids; D012336:RNA, Ribosomal, 16S; C556099:paleic acid