title: Paleic acid, a fatty acid from Paenibacillus sp.: taxonomy, fermentation, isolation, structure determination, and anti-Mannheimia and -Pasteurella activity.
abstract: 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).
authors.affiliation: Institute of Microbial Chemistry, Tokyo, Shinagawa-ku, Tokyo, Japan.
authors.forename: Ikuko
authors.initials: I
authors.lastname: Kurata
authors.forename: Maya
authors.initials: M
authors.lastname: Umekita
authors.forename: Tsutomu
authors.initials: T
authors.lastname: Sawa
authors.forename: Seiko
authors.initials: S
authors.lastname: Hattori
authors.forename: Chigusa
authors.initials: C
authors.lastname: Hayashi
authors.forename: Naoko
authors.initials: N
authors.lastname: Kinoshita
authors.forename: Yoshiko
authors.initials: Y
authors.lastname: Homma
authors.forename: Masayuki
authors.initials: M
authors.lastname: Igarashi
authors.forename: Masa
authors.initials: M
authors.lastname: Hamada
authors.forename: Takumi
authors.initials: T
authors.lastname: Watanabe
authors.forename: Ryuichi
authors.initials: R
authors.lastname: Sawa
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Naganawa
authors.forename: Yoshikazu
authors.initials: Y
authors.lastname: Takahashi
authors.forename: Yuzuru
authors.initials: Y
authors.lastname: Akamatsu
mesh_terms: 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
chemical_list: D000900:Anti-Bacterial Agents; D004269:DNA, Bacterial; D004275:DNA, Ribosomal; D005227:Fatty Acids; D009829:Oleic Acids; D012336:RNA, Ribosomal, 16S; C556099:paleic acid