Isolation, physicochemical properties and biological activities of amicoumacins produced by Bacillus pumilus.

Itoh, Jiro; Shomura, Takashi; Omoto, Shoji; Miyado, Shinji; YUDA, Yasukatsu; Shibata, Uichi; Inouye, Shigeharu

doi:10.1271/bbb1961.46.1255

Cited by 39 publications

(31 citation statements)

References 1 publication

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“…These two compounds did not have significant antibacterial activities. The production of amicoumacin A as a major component of a mixture of amicoumacins A, B, and C has already been described in another Bacillus species: B. pumilus AI-77 (10).…”

Section: Discussionmentioning

confidence: 83%

“…Furthermore, it has been reported that amicoumacin A also exhibits anti-inflammatory properties, as well as anti-stress ulcer properties, both of which were detected in a rat model (10). However, its activity against H. pylori, which causes inflammation of the gastric epithelium in humans, was not previously bacterial viability (Fig.…”

Section: Discussionmentioning

confidence: 95%

“…They also show that this activity is due to the production of at least two antibiotics with additive activity, including amicoumacin A. This compound, which belongs to the isocoumarin group of antibiotics, may also exert other properties such as anti-inflammatory and antitumoral activities (4,10) and is therefore very promising because of its potential for use in the treatment of H. pylori infection. Determination of the structure of the nonamicoumacin antibiotic produced by probiotic B. subtilis 3 is in progress.…”

Section: Discussionmentioning

confidence: 99%

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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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Section: Discussionmentioning

confidence: 83%

Section: Discussionmentioning

confidence: 95%

Section: Discussionmentioning

confidence: 99%

See 1 more Smart Citation

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

View full text Add to dashboard Cite

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“…Some are toxic to man, such as ochratoxin A and B, which are nephrotoxic and hepatotoxic, respectively [5,6]. On the other hand, several isocoumarins are extremely beneficial: duclauxin has antitumor effects [7], baciphelacin is an antiviral [8], amicoumacins are antibacterial and antiulcer [9,10], while others are diuretics, antihypertensives, and used in the treatment of lymphoedema [11,12].…”

Section: Introductionmentioning

confidence: 99%

Mutagenic and cytotoxic activity of an isocoumarin (paepalantine) isolated fromPaepalanthus vellozioides

Varanda

Raddi

Dias

et al. 1997

Teratog. Carcinog. Mutagen.

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“…For example, the heterocyclic isocoumarin ring can be found in glycosides [homalicin (1) and dihydrohomalicin (2)] and as amino-acid derivatives of active functional groups such as ochratoxin A (3) [3] and amicoumacin B (4) [4]. The antibacterial and gastric-protection activities of a group of amicoumacins isolated from plant material were especially high [4,5]. This confirmed that research on the design of natural compound analogs that combine an isocoumarin core with an amino acid was important and urgent.…”

mentioning

confidence: 99%

3-Arylisocoumarins with Amino-Acid Fragments

Shilin¹,

Shablykina²,

Ishchenko³

et al. 2014

Chem Nat Compd

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New amino-acid derivatives of 3-arylisocoumarins were prepared via acylation of the amine groups of natural amino acids by phenoxyacetic acids containing an isocoumarin substituent on the benzene ring.Keywords: [4-(1-oxo-1H-isochromen-3-yl)phenoxy]acetic acid, [2-(1-oxo-1H-isochromen-3-yl)-4-methylphenoxy]acetic acid, N-hydroxysuccinimide, activated ester, amino acid.Interest in isocoumarins has risen consistently since the first mention of natural [1] and synthetic [2] compounds with this core because they are widely distributed in nature and possess high biological activity. The variety of modifications of this heterocyclic system was apparent after the isolation and identification of natural isocoumarins and dihydroisocoumarins from plants and microorganisms.Plant isocoumarins can include both simple molecules and complicated polycyclic structures in both the free and bound state. For example, the heterocyclic isocoumarin ring can be found in glycosides [homalicin (1) and dihydrohomalicin (2)] and as amino-acid derivatives of active functional groups such as ochratoxin A (3) [3] and amicoumacin B (4) [4]. The antibacterial and gastric-protection activities of a group of amicoumacins isolated from plant material were especially high [4,5]. This confirmed that research on the design of natural compound analogs that combine an isocoumarin core with an amino acid was important and urgent.Herein we present results from modification of homalicin aglycon analogs, i.e., 3-(4-hydroxyphenyl)isocoumarin (5) and 3-(2-hydroxy-5-methylphenyl)isocoumarin (6), at the active hydroxyl by various natural amino acids. The linker was hydroxyacetic acid.Isocoumarin derivatives 5 and 6 were alkylated by chloroacetic acid ester with subsequent hydrolysis of the ester [6] to obtain 7 and 8 with a carboxylic acid that was capable of reacting with the amino-acid NH 2 group.

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Isolation, physicochemical properties and biological activities of amicoumacins produced by Bacillus pumilus.

Cited by 39 publications

References 1 publication

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

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

Mutagenic and cytotoxic activity of an isocoumarin (paepalantine) isolated fromPaepalanthus vellozioides

3-Arylisocoumarins with Amino-Acid Fragments

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