Chemical structures of amicoumacins produced by Bacillus pumilus.

Itoh, Jiro; Omoto, Shoji; Nishizawa, Naoyuki; Kodama, Yoshio; Inouye, Shigeharu

doi:10.1271/bbb1961.46.2659

Cited by 26 publications

(27 citation statements)

References 2 publications

(1 reference statement)

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“…In this study, we showed 754 Table 2 1 H-, 13 C-and 31 P-NMR chemical shifts of 3 and 4 3 4 that C-8Ј hydroxyl and C-12Ј amide group of 1 play a critical role for anti-MRSA activity. The importance of the C-12Ј amide group for anti-MRSA activity agrees with the structural requirements for other biological activities [6]. This study has shown that the antibacterial activity of amicoumacin A is a dramatically decreased by phosphorylation at the C-8Ј hydroxyl group.…”

Section: Resultssupporting

confidence: 77%

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Isolation of 8′-Phosphate Ester Derivatives of Amicoumacins: Structure-activity Relationship of Hydroxy Amino Acid Moiety

et al. 2007

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Two new compounds, 8Ј-phospho derivatives of amicoumacins A and B, were isolated from the culture broth of a strain of Bacillus pumilus together with amicoumacins A and B. Their structures were elucidated on the basis of spectroscopic methods and alkaline phosphatase treatments. Comparison of the antibacterial activities against methicillin-resistant Staphylococcus aureus (MRSA) of these compounds suggested that C-8Ј hydroxyl and C-12Ј amide group of amicoumacin A played a critical role for anti-MRSA activity.

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Section: Resultssupporting

confidence: 77%

“…2 to 4 were purified by the same procedure for 1. The physico-chemical properties and NMR spectral data of 4 and 3 were very similar to those of amicoumacin A and B [6], respectively (Tables 1 and 2). The molecular formula of 4 was revealed to be C 20 H 30 N 3 O 10 P by HR-ESI-MS analysis.…”

Section: Resultsmentioning

confidence: 57%

Isolation of 8′-Phosphate Ester Derivatives of Amicoumacins: Structure-activity Relationship of Hydroxy Amino Acid Moiety

et al. 2007

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“…Mass spectrometric analysis of the fraction F5-P3 showed molecular mass clusters [M + H] + at m/z ratios of 485.36 (Figure 4(b)), 569.31 (Figure 4(c)), 441.18 (Figure 4(d)) and 409.16 (Figure 4(e)) relative to peaks A, B, C and D, respectively. These compounds were identified as 7-O-malonyl (Kang et al, 2012), N-acetylated amicoumacin B (Itoh, Omoto, Nishizawa, Kodama, & Inouye, 1982) and amicoumacin C (Pinchuk, Bressollier, Sorokulova, Verneuil, & Urdaci, 2002), respectively (Table 2). In addition, the five major peaks in the LC chromatogram for fraction F5-P4 ( (Nagao, Adachi, Sakai, Nishijima, & Sano, 2001), macrolactin B or C and, macrolactin D (Kang et al, 2012, respectively (Table 2).…”

Section: Nanoflow-lc-q-tof-ms Analysis Of Purified Antimicrobial Compmentioning

confidence: 99%

“…Thus, macrolactin is assumed to restrict the growth of bacteria (bacteriostatic action) rather than to effect direct killing (bactericidal action) (Yuan et al, 2012). Amicoumacin has been classified as a group of six compounds sharing the same backbone, termed amicoumacin A, B, C, D, E and F (Itoh et al, 1982;Shimojima, Hayashi, Ooka, Shibukawa, & Iitaka, 1982, 1984. Among these, amicoumacin A and B are considered the major Figura 3.…”

Section: Scanning Electron Microscopymentioning

confidence: 99%

Purification and characterization of macrolactins and amicoumacins from Bacillus licheniformis BFP011: a new source of food antimicrobial substances

Arbsuwan

Payoungkiattikun

Sirithorn

et al. 2017

CyTA - Journal of Food

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In this study, Bacillus licheniformis BFP011 has been cultivated for producing antimicrobial compounds, which were concentrated from the crude supernatant and purified using thin-layer chromatography. The antimicrobial activity was investigated in the presence of several organic solvents and detergents, and inhibiting effects to various Gram-negative and Gram-positive human pathogenic and food spoilage bacteria were observed. Three bands (F4, F5 and F6) showing antimicrobial activity against Salmonella typhi ATCC 5784 were subjected to reversed-phase high-performance liquid chromatography purification. Two peaks of fraction F5, F5-P3 and F5-P4, showed 100% inhibition against S. typhi ATCC 5784. The contained mixture of antimicrobial compounds consists of macrolactins and amicoumacins, which induced the collapse and breaking of S. typhi ATCC 5784 cell membranes in a time-dependent manner. Taken collectively, the results indicate that these compounds may represent promising candidates for the development of food preservative agents of natural origin, as well as novel antimicrobial drug candidates against multiresistant bacterial strains.Purificación y caracterización de macrolactinas y amicoumacinas procedentes de Bacillus licheniformis BFP011: una nueva fuente de sustancias antimicrobianas para los alimentos RESUMEN En el presente estudio, se cultivó Bacillus licheniformis BFP011 para producir compuestos antimicrobianos; estos fueron concentrados del sobrenadante crudo y purificado empleando cromatografía en capa fina (CCF). En presencia de varios solventes y detergentes orgánicos se analizó la actividad antimicrobiana, observándose, además, los efectos inhibidores de varias bacterias gram-negativas y gram-positivas, patógenas para los seres humanos y causantes del deterioro de los alimentos. Mediante RP-HPLC se purificaron tres franjas (F4, F5 y F6) que mostraron actividad antimicrobiana contra la Salmonella typhi ATCC 5784, comprobándose que los dos picos de la fracción F5 (F5-P3 y F5-P4) provocan una inhibición del 100% contra la S. typhi ATCC 5784. La mezcla de compuestos antimicrobianos contiene macrolactinas y amicoumacinas; estas produjeron el colapso y el rompimiento de las membranas celulares de S. typhi ATCC 5784 a medida que fue transcurriendo el tiempo. Considerados en su conjunto, estos resultados indican que es posible que dichos compuestos sean sustancias prometedoras para la creación de agentes conservantes de alimentos de origen natural, y para el desarrollo de medicamentos antimicrobianas novedosas contra cepas bacterianas multirresistentes. ARTICLE HISTORY

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“…In the course of screening micro-organisms for new anti-osteoporosis agents targeting bone morphogenetic protein-2 (BMP-2), an active compound (5195A) with the potential to increase expression of the BMP-2 gene was found in fermentation broth of a nocardioform actinomycete, strain 04-5195 T , that had been isolated from soil. The compound 5195A was identified as amicoumacin B (Yang et al, 2007), which has been reported previously to be produced by Bacillus pumilus (Itoh et al, 1982). A polyphasic taxonomic investigation based on genotypic and phenotypic characteristics revealed that isolate T represents a novel species of the genus Nocardia.…”

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confidence: 89%

Nocardia jinanensis sp. nov., an amicoumacin B-producing actinomycete

Sun

Zhang

Huang

et al. 2009

INTERNATIONAL JOURNAL OF SYSTEMATIC AND EVOLUTIONARY MICROBIOLO

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A novel actinomycete, strain 04-5195 T , that produces amicoumacin B, which targets bone morphogenetic protein-2, was isolated from a soil sample collected in Jinan, Shandong Province, China. Strain 04-5195 T had morphological, biochemical, physiological and chemotaxonomic properties that were consistent with its classification in the genus Nocardia and it formed a phyletic line in the Nocardia 16S rRNA gene tree. It was evident from the phylogenetic data that strain 04-5195 T was most closely associated with Nocardia speluncae N2-11 T . However, the two organisms were distinguishable from one another using DNA-DNA relatedness and phenotypic data. The isolate was readily differentiated from other related Nocardia strains by a set of phenotypic properties and by its phylogenetic position. Therefore, it is proposed that the isolate represents a novel species in the genus Nocardia, Nocardia jinanensis sp. nov.; the type strain is 04-5195 T (5CGMCC 4.3508 T 5DSM 45048 T ).The genus Nocardia was proposed by Trevisan (1889) with Nocardia farcinica as the original type species (the type species is now Nocardia asteroides). The genus belongs to the mycolic-acid-containing group of actinomycetes, members of which form extensively branched mycelia and substrate hyphae that fragment into rod-shaped, nonmotile elements (Goodfellow & Lechevalier, 1989). The application of chemotaxonomic, numerical phenetic and molecular systematic methods has led to improved classification of members of the genus Nocardia (Goodfellow, 1998;Goodfellow et al., 1999). At the time of writing, the genus contained 71 species with validly published names. Many Nocardia species have been shown to be agents of human disease, such as N. asteroides, N. farcinica and Nocardia nova (Schaal & Lee, 1992;Wallace et al., 1991), although it has also been shown that some species produce secondary metabolites of potential industrial value Kinoshita et al., 2001), e.g. Nocardia uniformis, which can produce nocardicin. In the course of screening micro-organisms for new anti-osteoporosis agents targeting bone morphogenetic protein-2 (BMP-2), an active compound (5195A) with the potential to increase expression of the BMP-2 gene was found in fermentation broth of a nocardioform actinomycete, strain 04-5195 T , that had been isolated from soil. The compound 5195A was identified as amicoumacin B (Yang et al., 2007), which has been reported previously to be produced by Bacillus pumilus (Itoh et al., 1982). A polyphasic taxonomic investigation based on genotypic and phenotypic characteristics revealed that isolate T represents a novel species of the genus Nocardia. Strain 04-5195T was isolated on a modified Sauton's agar plate (Mordarska et al., 1972) that had been incubated at 28 u C for 2 weeks following inoculation with a suspension of a soil sample collected from Jinan, Shandong Province, China. The isolate was maintained on yeast extract-malt extract agar (ISP 2;Shirling & Gottlieb, 1966) slopes at 4 u C and as glycerol suspensions (20 %, v/v) at 220 u C. All...

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Chemical structures of amicoumacins produced by Bacillus pumilus.

Cited by 26 publications

References 2 publications

Isolation of 8′-Phosphate Ester Derivatives of Amicoumacins: Structure-activity Relationship of Hydroxy Amino Acid Moiety

Isolation of 8′-Phosphate Ester Derivatives of Amicoumacins: Structure-activity Relationship of Hydroxy Amino Acid Moiety

Purification and characterization of macrolactins and amicoumacins from Bacillus licheniformis BFP011: a new source of food antimicrobial substances

Nocardia jinanensis sp. nov., an amicoumacin B-producing actinomycete

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