A new isocoumarin antibiotic, Y-05460M-A.

Sato, Tutomu; Nagai, Koji; Suzuki, Kenichi; Morioka, Moto; Saito, Takeshi; Nohara, Chieko; Susaki, Kiyoshi; Takebayashi, Yukihiro

doi:10.7164/antibiotics.45.1949

Cited by 28 publications

(12 citation statements)

References 4 publications

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“…This is the first report of the isolation of C-8Ј modified amicoumacin derivatives and their evaluation for antibacterial activity, though some studies of structure-activity relationships have been reported in these compounds. 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].…”

Section: Resultsmentioning

confidence: 66%

“…Preparative HPLC was performed using a Waters 600E system fitted with diode array detector. 1 H-NMR (400 MHz), 13 C-NMR (100 MHz) and 31 P-NMR (162 MHz) spectra were recorded on a JEOL JNM-ECX400 spectrometer. Liquid chromatography timeof-flight mass spectrometry (LC TOF-MS) data were obtained under electron spray ionization (ESI) on a Waters LCT Premier TM .…”

Section: Generalmentioning

confidence: 99%

“…1) of the dihydroisocoumarin with a hydroxy amino acid side chain have attention from synthetic chemists, and there are a number of total syntheses and synthetic approaches, represented by Cappiello et al [11] and references cited therein. The structurally related antibiotics with different hydroxy amino acid side chains, baciphelacin [12], Y-05460M-A [13], PM-94128 [14], xenocoumacins [15], and Sg17-1-4 [16], all with significant activities, represent a growing number of antibiotics in this class.…”

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confidence: 99%

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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: Resultsmentioning

confidence: 66%

Section: Generalmentioning

confidence: 99%

mentioning

confidence: 99%

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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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“…secrete antibiotics. These antibiotics usually belong to the peptide and lipopeptide groups, the aminoglycoside group, and sometimes, groups of antibiotics with various original chemical structures (11,18,24).…”

Section: Discussionmentioning

confidence: 99%

In Vitro Anti- Helicobacter pylori Activity of the Probiotic Strain Bacillus subtilis 3 Is Due to Secretion of Antibiotics

Pinchuk

Bressollier²,

Verneuil³

et al. 2001

Antimicrob Agents Chemother

212

132

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A limited number of antibiotics can be used against Helicobacter pylori infection, and resistance jeopardizes the success of treatment. Therefore, a search for new agents is warranted. The use of probiotics to enhance gastrointestinal health has been proposed for many years, but the scientific basis of the prophylactic and therapeutic actions of probiotics has not yet been clearly delineated. Probiotic strain Bacillus subtilis 3, whose safety has previously been demonstrated, is known to have antagonistic properties against species of the family Enterobacteriaceae. In the present study, it was also found to inhibit H. pylori. The anti-H. pylori activity present in the cell-free supernatant was not related to pH or organic acid concentration. It was heat stable and protease insensitive. At least two antibiotics, detected by thin-layer chromatography (R f values, 0.47 and 0.85, respectively) and confirmed by high-performance liquid chromatographic analysis, were found to be responsible for this anti-H. pylori activity. All H. pylori strains tested were sensitive to both compounds. One of these compounds was identified as amicoumacin A, an antibiotic with anti-inflammatory properties. MICs for H. pylori determined in solid and liquid media ranged between 1.7 and 6.8 g/ml and 0.75 and 2.5 g/ml, respectively. The underestimation of MICs determined in solid medium may be due to physicochemical instability of the antibiotic under these test conditions. An additive effect between amicoumacin A and the nonamicoumacin antibiotic against H. pylori was demonstrated.

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“…NA-4803 was determined to be 6,8-dihydroxy-7-methoxy-3-methylisocoumarin (reticulol) by spectroscopic analysis (data not shown). Many isocoumarin derivatives from bacteria [16] and fungi [17] have been reported as Fig. 4.…”

Section: Discussionmentioning

confidence: 99%

Antitumor Efficacy of Reticulol from <i>Streptoverticillium</i> against the Lung Metastasis Model B16F10 Melanoma

et al. 2003

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Reticulol was isolated from the culture broth of the strain Streptoverticillium sp. NA-4803. Recticulol (M.W. 222.2) exhibited a potent in vitro cytotoxicity against A427, a human lung tumor cell line, and B16F10, a mouse melanoma cell line. In the trypan blue staining assay for B16F10 cells, the cell viability by reticulol treatment was significantly decreased in a dose-dependent manner. The in vivo assay for the lung metastasis-blocking effect showed that reticulol injected intravenously suppressed the increase in colonies on the lung in a dose-dependent manner. In addition, the survival rate of tumor-implanted mice treated with reticulol was closely associated with its antitumoral efficacy. Reticulol administered via the peritoneum of mice showed less metastasis inhibition than that injected intravenously. To demonstrate the mechanism for inhibition of metastasis, the inhibitory effect of reticulol for matrix metalloproteinase-2 or -9 involved in melanoma metastasis was investigated; however, they were not observed on zymogram gel. In addition, the antitumor efficacy of reticulol was not associated with cell cycle arrest or apoptosis. Therefore, it was inferred that reticulol known as a phosphodiesterase inhibitor directly inhibited the growth of B16F10 melanoma, showing necrotic response. These results suggest that reticulol protects its lung metastasis via the bloodstream by inhibiting the growth of B16F10 melanoma at the cellular level.

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A new isocoumarin antibiotic, Y-05460M-A.

Cited by 28 publications

References 4 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

In Vitro Anti- Helicobacter pylori Activity of the Probiotic Strain Bacillus subtilis 3 Is Due to Secretion of Antibiotics

Antitumor Efficacy of Reticulol from <i>Streptoverticillium</i> against the Lung Metastasis Model B16F10 Melanoma

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