A Strong Antifungal Activity of 7- O -Succinyl Macrolactin A vs Macrolactin A from Bacillus amyloliquefaciens ELI149
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A Strong Antifungal Activity of 7‑O‑Succinyl Macrolactin A vs Macrolactin A from Bacillus amyloliquefaciens ELI149 Francisco Salazar1 · Aurelio Ortiz1 · Estibaliz Sansinenea1 Received: 13 May 2020 / Accepted: 3 September 2020 / Published online: 17 September 2020 © Springer Science+Business Media, LLC, part of Springer Nature 2020
Abstract Chemical analysis of the crude extract of bacterial strain Bacillus amyloliquefaciens ELI149, which had been previously isolated from soil, resulted in the isolation and characterization of two known macrolactin derivatives, macrolactin A (1) and 7-O-succinyl macrolactin A (2). The structures of two compounds were assigned by 1D/2D NMR techniques. The two compounds were demonstrated antifungal activity against some important phytopathogens. However, the presence of the succinyl moiety at C-7 gives to the molecule more activity being the second compound more active than the first, showing for the first time, a structure/activity relationship. The cellular damage was also studied in two important phytopathogen fungi.
Introduction Phytopathogens have devastating effects on crops yield producing economic losses worldwide. Chemical fungicides have been the solution during many years resulting in severe damages to the environment and human health [1]. Currently, biocontrol using microorganisms has become an effective alternative against plant pathogens being antibiosis as the main mechanism for this purpose. Many of antifungal compounds have been identified that suppress plant pathogens [2]. In this context there are several Bacillus-based products active against fungi. On the market, several Bacillus-based biofungicide commercial products are available. They are employed to control fungal diseases, like root diseases, foliar diseases and postharvest diseases. B. amyloliquefaciens has been described as a plant suppressing microorganism due to its ability to synthesize a huge spectrum of different secondary metabolites, many of them with antibacterial and/or antifungal action [3]. Electronic supplementary material The online version of this article (https://doi.org/10.1007/s00284-020-02200-2) contains supplementary material, which is available to authorized users. * Estibaliz Sansinenea [email protected]; [email protected] 1
Facultad de Ciencias químicas, Benemérita Universidad Autónoma de Puebla, Ciudad Universitaria, 14 sur y Av. San Claudio, Col. San Manuel, CP. 72570 Puebla, Pue, Mexico
In this sense, macrolactins have been described as an important group of 24 membered macrolides [4] mainly produced by B. subtilis and having the most of them principally antibacterial activity. For example, 7-O-methyl-5-hydroxy-3-heptenoate macrolactin showed broad spectrum activity against human opportunistic clinical pathogens [5]. Furthermore, 7-O-malonyl macrolactin A exhibited antibacterial activity against methicillin-resistant Staphylococcus aureus [6] and macrolactin A showed antibacterial activity against Gram-positive bacteria S. aureus [7]. Li et al. eva
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