Determination of Fatty Acid in Surfactin and Elucidation of the Total Structure of Surfactin

Kakinuma, Atsushi; Sugino, Hiromu; Isono, Masao; Tamura, Gakuzo; Arima, Kei

doi:10.1271/bbb1961.33.973

Cited by 66 publications

(32 citation statements)

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“…The mass gain of 19 Da observed for each product was assigned to hydrolysis of a lactone. This result indicated that each molecule contained a cyclic peptide domain, analogous to previously characterized microbial lipopeptides 8–12. In addition, one mass unit was hypothesized to be added by conversion of Gln or Asn to Glu or Asp.…”

Section: Resultsmentioning

confidence: 56%

Structural characterization of lipopeptide biomarkers isolated from Bacillus globigii

2002

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Spectra obtained using matrix-assisted laser desorption/ionization (MALDI) mass spectrometry of Bacillus globigii (Bacillus subtilis niger) spores, vegetative cells and the culture supernatant show a cluster of biomarkers centered at a molecular mass of 1478 Da. Three biomarkers were isolated from the cell-free culture supernatant by solid-phase extraction and reversed-phase high-performance liquid chromatography, and characterized using various kinds of mass spectrometry. A Fourier transform mass spectrometer with a MALDI source was used to determine the monoisotopic protonated masses at 1463.8, 1477.8, and 1505.8 Da in order of elution. The mass differences of 14 and 28 Da suggest that they are homologous molecules. Alkaline hydrolysis of each species showed that it contained a lactone linkage. Strong acid hydrolysis released a fatty acid from an amide bond, consistent with a lipopeptide. A quadrupole time-of-flight instrument with a nanospray source was used to sequence the hydrolyzed forms of the three biomarkers. The cyclic lipopeptides were found to have amino acid sequences identical with those in fengycins and plipastatins, antimicrobial compounds with phospholipase inhibitor activity, previously identified in related species of Bacillus subtilis and Bacillus cereus.

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Section: Resultsmentioning

confidence: 56%

Structural characterization of lipopeptide biomarkers isolated from Bacillus globigii

2002

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“…Its structure was demonstrated by Kakinuma et al (1969)i It consists of a heptapeptide sequence linked to a fl-hydroxy fatty acid in a cyclic structure. In a previous paper we reported that B. subtilis S 449 produced two related surfactins, differing by their peptide moiety (Peypoux et al 1991).…”

Section: Introductionmentioning

confidence: 99%

Controlled biosynthesis of Val7- and Leu7-surfactins

Peypoux

Michel

1992

Appl Microbiol Biotechnol

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Surfactin was found to consist of a mixture of two groups of homologous lipopeptides differing by their peptide sequence; ValT-surfactin was recently characterized as a minor companion of the previously described Leu7-surfactin. The addition of various aamino acids to the culture media led to variations in the production ratios of the two congeners. The supplementation of L-valine or L-isoleucine to the culture medium resulted in a selective enhancement of the production of the Val7-surfactin whereas this production was very low when L-leucine was the nitrogen source in the culture medium.

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“…We isolated the active substance, named it subtilysin, and found that it contained a heptapeptide and probably also a lipid [20]. It turned out that the year before, Kakinuma and co-workers [21] published papers in which they identified a product of B. subtilis that inhibits fibrin clot formation and contained the same seven amino acids as subtilysin. They appropriately named their substance "surfactin", and showed as well (Fig.…”

Section: Comparative Toxinologymentioning

confidence: 99%

Some aspects of the history of membrane-damaging toxins

Bernheimer

1996

Medical Microbiology and Immunology

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In this review the following topics are considered: (a) the character of biomedical research and how it has changed during the last six decades; (b) the early history of membrane-damaging toxins; (c) comparative toxinology as illustrated by similarity of the toxins of the brown recluse spider and the bacterial agent of peudotuberculosis, and by similarity of a toxin of a sea anemone and the thiol-activated membrane-damaging agents of bacteria; (d) examples of the diversity of membrane-damaging toxins; (e) cooperative or synergistic lytic systems; and (f) the outlook for the future.

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Determination of Fatty Acid in Surfactin and Elucidation of the Total Structure of Surfactin

Cited by 66 publications

References 0 publications

Structural characterization of lipopeptide biomarkers isolated from Bacillus globigii

Structural characterization of lipopeptide biomarkers isolated from Bacillus globigii

Controlled biosynthesis of Val7- and Leu7-surfactins

Some aspects of the history of membrane-damaging toxins

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