Biosynthesis of bacillomycin D by <i>Bacillus subtilis</i> Evidence for amino acid‐activating enzymes by the use of affinity chromatography

Besson, Françoise; Michel, Georges

doi:10.1016/0014-5793(92)81040-s

Cited by 20 publications

(9 citation statements)

References 14 publications

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“…B. subtilis was grown at 35°C for 150 h in a Landy medium [20], modified for the nitrogen source, containing 20 g of D ‐glucose, 1.82 g of 15 NH 4 Cl (Isotec Inc.; instead of glutamic acid), 0.5 g of MgSO 4 , 0.5 g of KCl, 6.8 g of KH 2 PO 4 , 1.2 mg of Fe 2 (SO 4 ) 3 , 0.4 mg of MnSO 4 , and 1.6 mg of CuSO 4 per liter. The pH was adjusted to 7.7 with 10 N NaOH before autoclaving (the solution of D ‐glucose was sterilised separately) [21,22]. The lipopeptides were then isolated and purified as reported before for bacillomycin L [17].…”

Section: Methodsmentioning

confidence: 99%

NMR structure of antibiotics plipastatins A and B from Bacillus subtilis inhibitors of phospholipase A₂

2000

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Plipastatins A and B are antifungal antibiotics belonging to a family of lipopeptides capable of inhibiting phospholipase A 2 (PLA 2 ) and are biosynthesised under certain circumstances by Bacillus subtilis. U-15 N plipastatins A and B were obtained from cultures of the strain NCIB 8872 on a Landy medium modified for stable-isotope labelling by the substitution of the L-glutamic acid used as the sole nitrogen source, by 15 NH 4 Cl. These two lipo-decapeptides, lactonised by esterification of the Ile10 C-terminus with the phenolic hydroxyl of Tyr3, differ only by a D-Ala (plipastatin A)/D-Val (plipastatin B) substitution at the position 6. The 1 H-and 15 N-nuclear magnetic resonance (NMR) signals of a 4:6 mixture of plipastatins A and B were unambiguously assigned and their structures in dimethylsulfoxide solution were calculated on the basis of a set of NMRderived restraints. Plipastatins A and B are well-defined structures in solution stabilised by a type 1 L L-turn comprising residues 6^9 and several other specific hydrogen bonds. The structures afford a first molecular basis for the future studies of their biological activities both in lipidic layers or on PLA 2 . ß

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Section: Methodsmentioning

confidence: 99%

NMR structure of antibiotics plipastatins A and B from Bacillus subtilis inhibitors of phospholipase A₂

2000

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“…tritici (de Souza et al 2003 ). Several strains of Bacillus subtilis produce iturin (Yu et al 2002 ;Chitarra et al 2003 ) bacillomycin D (Besson and Michel 1992 ), plipastatins, surfactin, and aminopolyol that exert strong antimicrobial action against Pythium ultimum , Rhizoctonia solani , Fusarium oxysporum , Sclerotinia sclerotiorum , and M. phaseolina (Constantinescu 2001 ).…”

Section: Antibioticsmentioning

confidence: 99%

Role of Plant Growth-Promoting Rhizobacteria and Their Formulation in Biocontrol of Plant Diseases

Shaikh

Sayyed

2014

Plant Microbes Symbiosis: Applied Facets

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Fungal phytopathogens are a major threat to crop plants. More than 60 fungal phytopathogens are known to cause various plant diseases. These diseases lead to the loss of 30 % crop yield that accounts to about 20,000 crore rupees per year in the global market. Different methods of chemotherapy have been used to control these diseases. However, uncontrolled use of chemical fungicides has severely affected the agroecosystem, leading to the development of pesticide-resistant pests and emergence of new species of pests. Increased dependence on chemicals is inevitably associated with environmental and health hazards. In this regard, plant growth-promoting rhizobacteria (PGPR) have been found as an effective, eco-friendly, and sustainable replacement to the chemical fungicides. The present chapter focuses on antifungal traits such as siderophores, lytic enzymes, hydrogen cyanide, and antibiotics of PGPR, development of effective formulation of PGPR for longer shelf life and competitiveness with the natural environment, obstacles in formulation development, and characteristics of bioformulation. Biotechnological attributes of PGPR with respect to plant growth promotion, disease resistance, and iron nutrition are also discussed.

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“…It was grown in a basal medium containing 10 g of d ‐glucose, 5 g of l ‐glutamic acid, 0.5 g of MgSO 4 , 0.5 g of KCl, 1 g of KH 2 PO 4 , 1.2 mg of Fe 2 (SO 4 ) 3 , 0.4 mg of MnSO 4 and 1.6 mg of CuSO 4 per litre. The pH was adjusted to 7.7 with 10 m NaOH before being autoclaved [37,38]. The culture was shaken at 35 °C in an incubator for 150 h. The culture was centrifuged for 30 min at 10 000 g and 10 °C; the pellets were lyophilized and the supernatant acidified to pH 2 using 1 m HCl.…”

Section: Methodsmentioning

confidence: 99%

NMR structure of active and inactive forms of the sterol‐dependent antifungal antibiotic bacillomycin L

Volpon

Besson

Lancelin

1999

European Journal of Biochemistry

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The antifungal antibiotic lipopeptide bacillomycin L [cyclo-(l-Asp1-d-Tyr2-d-Asn3-l-Ser4-l-Gln5-d-Ser6-lThr7-b-amino fatty acid)] from Bacillus subtilis belongs to the iturinic family of antifungal agents and acts with a strict sterol-phospholipid dependence on biomembranes. This antibiotic has been analysed using solution NMR spectroscopy in its native active form and its inactive (l-Asp1, d-Tyr2) di-O-methylated form. The structures were calculated under NMR-derived restraints using molecular-dynamic simulated-annealing protocols starting from a random array of atoms. The structure of the native antibiotic is spread over different conformers in which two families are recognized. It was found that most structures have dihedral f and c angles defining a type-II H b-turn including amino acids 5±8, in certain cases stabilized by a 8H N -5CO hydrogen bond, whereas a minority of structures adopt an inverse g-turn including amino acids 6±8, stabilized in all cases by an 8H N -6CO hydrogen bond. The di-O-methylation of l-Asp1 and d-Tyr2, an amino acid strictly conserved within the iturinic group of antibiotics, does not induce major differences in the NMR spectra and in the NMR structures. The results are discussed in relation to the specific loss of interaction with sterols when the native antifungal bacillomycin L is methylated on the conserved d-Tyr2 position.Keywords: antibiotics; antifungals; bacillomycin L; NMR.Among the antifungal antibiotic substances, there is a specific family of molecules that acts on the biomembrane of infectious agents with an established sterol dependency. This family comprises very different molecules including the polyene macrolides as the widely used nystatins or amphotericins in pharmacotherapy (for reviews see [1,2]). The antifungal activity is believed to rely on a better interaction with ergosterol, which is more abundant in the lipid composition of fungal membranes, than cholesterol present in other organisms. However, the fine nature of the molecular interaction and the origin of this selectivity at atomic resolution remain unknown [3±6]. Lipidic cyclopeptides (lipopeptides) isolated from cultures of bacterial strains of Bacillus subtilis also exhibit such a general property. Their peptidic nature potentially makes them more adapted for a drug-design approach or a combinatorial-chemistry search for more active or more suitable molecules. These peptides include iturins [7±9], bacillomycins [10±14] and mycosubtilin [15]. All antibiotics of the iturinic group (Fig. 1) are characterized by an invariant lddlldl amino acid sequence alternation with a conserved tyrosine residue at position 2, and variable hydrophobic tails [16] with the R absolute configuration at C 3 [17] linked into the cyclic peptide through a b-peptide bond. The molecular structure of two members, mycosubtilin [18] and iturin A [19,20], have already been studied mainly using solution NMR spectroscopy.All these lipopeptides are also haemolytic [21±23], very potent against fungi [24] and different yeasts [25±27], but...

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Biosynthesis of bacillomycin D by Bacillus subtilis Evidence for amino acid‐activating enzymes by the use of affinity chromatography

Cited by 20 publications

References 14 publications

NMR structure of antibiotics plipastatins A and B from Bacillus subtilis inhibitors of phospholipase A₂

NMR structure of antibiotics plipastatins A and B from Bacillus subtilis inhibitors of phospholipase A₂

Role of Plant Growth-Promoting Rhizobacteria and Their Formulation in Biocontrol of Plant Diseases

NMR structure of active and inactive forms of the sterol‐dependent antifungal antibiotic bacillomycin L

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Biosynthesis of bacillomycin D by Bacillus subtilis Evidence for amino acid‐activating enzymes by the use of affinity chromatography

Cited by 20 publications

References 14 publications

NMR structure of antibiotics plipastatins A and B from Bacillus subtilis inhibitors of phospholipase A2

NMR structure of antibiotics plipastatins A and B from Bacillus subtilis inhibitors of phospholipase A2

Role of Plant Growth-Promoting Rhizobacteria and Their Formulation in Biocontrol of Plant Diseases

NMR structure of active and inactive forms of the sterol‐dependent antifungal antibiotic bacillomycin L

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NMR structure of antibiotics plipastatins A and B from Bacillus subtilis inhibitors of phospholipase A₂

NMR structure of antibiotics plipastatins A and B from Bacillus subtilis inhibitors of phospholipase A₂