New Macrolactins from a Marine <i>Bacillus </i>sp. Sc026

Jaruchoktaweechai, Chutima; Suwanborirux, Khanit; Tanasupawatt, Somboon; Kittakoop, Prasat; Menasveta, Piamsak

doi:10.1021/np990605c

Cited by 91 publications

(84 citation statements)

References 11 publications

(24 reference statements)

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“…Six macrolactins were first described in 1989 by Gustafson (22,33,34). Macrolactins are considered to be potent antiviral and cytotoxic agents that also have antibacterial activity (10,16). Macrolactin A inhibits murine melanoma cancer cells in in vitro assays, replication of Herpes simplex viruses, and the enzyme squalene synthase, (4) and protects T lymphoblast cells against human immunodeficiency virus replication (10).…”

Section: Discussionmentioning

confidence: 99%

7- O -Malonyl Macrolactin A, a New Macrolactin Antibiotic from Bacillus subtilis Active against Methicillin-Resistant Staphylococcus aureus , Vancomycin-Resistant Enterococci, and a Small-Colony Variant of Burkholderia cepacia

Romero-Tabarez

Jansen

Sylla

et al. 2006

Antimicrob Agents Chemother

128

115

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We report here the discovery, isolation, and chemical and preliminary biological characterization of a new antibiotic compound, 7-O-malonyl macrolactin A (MMA), produced by a Bacillus subtilis soil isolate. MMA is a bacteriostatic antibiotic that inhibits a number of multidrug-resistant gram-positive bacterial pathogens, including methicillin-resistant Staphylococcus aureus, vancomycin-resistant enterococci, and a small-colony variant of Burkholderia cepacia. MMA-treated staphylococci and enterococci were pseudomulticellular and exhibited multiple asymmetric initiation points of septum formation, indicating that MMA may inhibit a cell division function.The spread of resistance to antibiotics undermines the therapeutic utility of anti-infective drugs in current clinical use (1). For example, Staphylococcus aureus, a major cause of community-and hospital-acquired infections, has developed resistance to most classes of antibiotics. Methicillin-resistant S. aureus (MRSA) strains appeared in the hospital environment after introduction of the semisynthetic penicillin methicillin, leaving vancomycin as the last line of defense for MRSA treatment (7). S. aureus organisms intermediately susceptible to vancomycin were first isolated in 1997 in Japan (15) and later in other countries (8). With the recent appearance of vancomycin-resistant clinical isolates (32,36,38), no antibiotic class is effective against multiresistant S. aureus infections. The increase in vancomycin-resistant enterococci (VRE), important agents of nosocomial infections, is another cause of great concern (2,3,19,27). Therapy options for multiresistant gramnegative opportunistic bacterial pathogens are also diminishing. Such bacteria, like Pseudomonas aeruginosa and Burkholderia cepacia (6), are common environmental organisms and opportunistic pathogens having the capacity to infect essentially all tissues of patients with compromised host defenses (21).Compounding the problem of genetically determined transmissible antibiotic resistance is the development of phenotypically resistant, often slow-growing, forms in chronic bacterial infections. These may take the form of biofilm microbes or small-colony variants (SCV) (12; reviewed in reference 14), are known to include both gram-positive and gram-negative pathogens, and are usually associated with a worsening of the disease prognosis.Thus, new antibiotics and therapy options are urgently needed to improve the management of bacterial infections (29, 35), and a major challenge is to find drugs that act against SCV and/or bacteria growing in biofilms.In this study, we report the discovery and preliminary characterization of 7-O-malonyl macrolactin A (MMA), a new antibiotic having bacteriostatic activity against clinical strains of MRSA, VRE, and a SCV of Burkholderia cepacia. The parental wild-type (WT) and SCV pairs of P. aeruginosa and B. cepacia, as well as Stenotrophomonas maltophilia strain 1124, were isolated from cystic fibrosis patients in the Department of Medical Microbiology at the Medical School...

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Section: Discussionmentioning

confidence: 99%

7- O -Malonyl Macrolactin A, a New Macrolactin Antibiotic from Bacillus subtilis Active against Methicillin-Resistant Staphylococcus aureus , Vancomycin-Resistant Enterococci, and a Small-Colony Variant of Burkholderia cepacia

Romero-Tabarez

Jansen

Sylla

et al. 2006

Antimicrob Agents Chemother

128

115

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“…1. The ROESY correlations between H-7/H-9, H-7/H-5, H-20/H- Table 1 Comparison of 1 H-and 13 C-NMR data between 1 and macrolactin A in DMSO-d 6 No. 18, and a weak NOE between H-13/H-15 (Fig.…”

Section: Original Articlementioning

confidence: 99%

A New 24-membered Lactone and a New Polyene δ-Lactone from the Marine Bacterium Bacillus marinus

Xue

Tian

et al. 2008

J Antibiot

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A new 24-membered macrolide macrolactin T (1), and a new polyene d-lactone macrolactin U (2), along with macrolactins A, B, D, O, and S, were isolated from the cultured broth of the bacterium Bacillus marinus, which was isolated from Suaeda salsa collected in the coastline of Bohai Sea of China. The structures of 1 and 2 were elucidated on the basis of extensive spectroscopic data analyses. The inhibitory activity of macrolactins T, B and D against fungi Pyricularia oryzae and Alternaria solani, and bacteria Staphylococcus aureus is reported.

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“…The IR absorptions at 3374 and 1733 cm À1 indicated the presence of hydroxy (OH) and ester carbonyl (C ¼ O) groups, respectively. 1D and 2D NMR spectra of 3 were identical to those of 7-O-succinyl macrolactin A, 17 except for the presence of an additional methoxy group, which was located at C-4 0 (Figure 1) Structure elucidation of linieodolide A (5) The molecular formula of 5, C 17 H 30 O 6 with three degrees of unsaturation, was deduced from its HRESIMS, which showed an [M þ Na] þ ion at m/z 353.1935. The IR spectrum of 5 showed absorption bands at 1650 and 3317 cm À1 , indicating the presence of an ester carbonyl and hydroxy groups, respectively.…”

Section: Structure Elucidation Of Macrolactin Z (3)mentioning

confidence: 74%

New antimicrobial compounds from a marine-derived Bacillus sp.

et al. 2012

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In the course of our ongoing research for antimicrobial agents, we isolated five new compounds, three 24-membered macrolactones, macrolactins X-Z (1-3) and two hydroxy unsaturated fatty acids, linieodolides A (5) and B (6), together with a known metabolite, macrolactinic acid (4), from the culture broth of a marine Bacillus sp. The structures of these metabolites were determined on the basis of their spectroscopic data interpretation. Their absolute configurations were addressed by modified Mosher's method and literature data review. Compounds 1-6 showed moderate to potent inhibitory activities (8B128 mg ml À1 ) against selected pathogenic microorganisms.

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New Macrolactins from a Marine Bacillus sp. Sc026

Cited by 91 publications

References 11 publications

7- O -Malonyl Macrolactin A, a New Macrolactin Antibiotic from Bacillus subtilis Active against Methicillin-Resistant Staphylococcus aureus , Vancomycin-Resistant Enterococci, and a Small-Colony Variant of Burkholderia cepacia

7- O -Malonyl Macrolactin A, a New Macrolactin Antibiotic from Bacillus subtilis Active against Methicillin-Resistant Staphylococcus aureus , Vancomycin-Resistant Enterococci, and a Small-Colony Variant of Burkholderia cepacia

A New 24-membered Lactone and a New Polyene δ-Lactone from the Marine Bacterium Bacillus marinus

New antimicrobial compounds from a marine-derived Bacillus sp.

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