Tauramamide, a Lipopeptide Antibiotic Produced in Culture by Brevibacillus laterosporus Isolated from a Marine Habitat: Structure Elucidation and Synthesis

Abstract

Tauramamide (1), a new lipopeptide antibiotic, is produced by cultures of the marine bacterial isolate Brevibacillus laterosporus PNG276 obtained from Papua New Guinea. Tauramamide was isolated as its methyl and ethyl esters 2 and 3, whose structures were elucidated by analysis of NMR, MS, and chemical degradation data. A total synthesis of tauramamide (1) and tauramamide ethyl ester (3) confirmed the structure proposed from spectroscopic analysis and provided the natural product for antimicrobial testing. Tauramamide (1) and ethyl ester 3 show potent and relatively selective inhibition of pathogenic Enterococcus sp.

PeBL1, a Novel Protein Elicitor from Brevibacillus laterosporus Strain A60, Activates Defense Responses and Systemic Resistance in Nicotiana benthamiana

“…The B. laterosporus strain A60 has a well-known ability to act as a biocontrol agent, to induce systemic resistance in plants, and to produce various antagonistic factors, such as a parasporal crystal, an extracellular protease, a lipopeptide antibiotic, and a pseudopeptide (35,(54)(55)(56). However, the molecular mechanisms involved in the activation of systemic resistance by strain A60 have not yet been completely elucidated.…”

Isolation and Structural Elucidation of Brevibacillin, an Antimicrobial Lipopeptide from Brevibacillus laterosporus That Combats Drug-Resistant Gram-Positive Bacteria

“…Experiments were conducted at 298 K on Bruker Avance-III HD-600 and -700 spectrometers (Bruker, Karlsruhe, Germany). Both spectrometers were equipped with a 5-mm ( 1 H, 13 C, 15 N) triple-resonance cryoprobe (TXI and TXO, respectively) and a z-axis gradient. The following data sets were recorded: one-dimensional (1D) 1 H NMR, 1D 13 C NMR, 1D 13 C distortionless enhancement by polarization transfer (DEPT)-90 and DEPT-135, two-dimensional (2D) 1 H-homonuclear double-quantum filtered correlation spectroscopy (DQF-COSY), total correlation spectroscopy (TOCSY; 60-ms DIPSI2 [decoupling in the presence of scalar interactions-2] mixing time), nuclear Overhauser effect spectroscopy (NOESY; 200-and 400-ms mixing times), 2D heteronuclear 1 H- 13 C heteronuclear single quantum coherence (spectroscopy) (HSQC), multiplicity-edited HSQC, heteronuclear multiple-bond correlations (HMBC), HSQC-NOESY (350-ms mixing time), HSQC-TOCSY (60-ms DIPSI2), heteronuclear multiple-quantum correlation (HMQC)-COSY (21), and 2D heteronuclear 1 H-15 N HSQC.…”

“…(10); a Brevibacillus laterosporus strain was reported to inhibit the growth of a number of fungi, including Fusarium, Aspergillus, and Alternaria (11); and a B. laterosporus strain, A60, was found to be active against Gram-negative bacteria of the genus Pseudomonas and the Gram-positive bacterium Bacillus subtilis (12). Recently, a lipopeptide antibiotic, designated tauramamide, was discovered in a culture of a B. laterosporus strain (13). A lipopeptide is generally composed of a specific lipophilic moiety attached to a peptide chain.…”

A Cytotoxic Fellutamide Analogue from the Sponge-Derived Fungus Aspergillus versicolor

“…These lipopeptides were found to have interesting bioactivities, including, anti-inflammatory, antimalarial properties, antimicrobial, antileishmanial, cytotoxic and neurotoxic activities. [1][2][3][4][5][6][7][8][9] Fellutamides A and B are lipopeptides first isolated from the fish-derived fungus Penicillium fellutanum. Fellutamides exhibit cytotoxic properties, 10 and fellutamide A has been shown to stimulate the synthesis and secretion of nerve growth factor (NGF) in vitro.…”