Cyclodepsipeptides from Beauveria bassiana Bals. Part 1. Beauverolides H and I

Elsworth, John F.; Grove, John Frederick

doi:10.1039/p19770000270

Cited by 51 publications

(25 citation statements)

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“…The comparison of HPLC-UV-vis profiles showed that in C. javanica, glycoasperfuran (3), and beauverolides I (5) [22] and J b (6) were present in all isolates, with the exceptions of the isolates BCC01857 and BCC29254, from which only glycoasperfuran (3) could be detected, while beauverolide N (4) [15] was produced in trace amounts and only seen in four out of eight isolates ( Figure 6). Beauveria and Cordyceps (Isaria) have been found to be phylogenetically close to each other [23], and they produce the same secondary metabolites according to the evidence from Kadlec and co-workers [24], Jegorov and co-workers [25], and Luangsa-ard and co-workers [26].…”

Section: Chemotaxonomic Investigationmentioning

confidence: 99%

Pigmentosins from Gibellula sp. as antibiofilm agents and a new glycosylated asperfuran from Cordyceps javanica

Helaly¹,

Kuephadungphan²,

Phainuphong³

et al. 2019

Beilstein J. Org. Chem.

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In the course of our exploration of the Thai invertebrate-pathogenic fungi for biologically active metabolites, pigmentosin A (1) and a new bis(naphtho-α-pyrone) derivative, pigmentosin B (2), were isolated from the spider-associated fungus Gibellula sp. Furthermore, a new glycosylated asperfuran 3, together with one new (6) and two known (4 and 5) cyclodepsipeptides, was isolated from Cordyceps javanica. The pigmentosins 1 and 2 showed to be active against biofilm formation of Staphylococcus aureus DSM1104. The lack of toxicity toward the studied microorganism and cell lines of pigmentosin B (2), as well as the antimicrobial effect of pigmentosin A (1), made them good candidates for further development for use in combination therapy of infections involving biofilm-forming S. aureus. The structure elucidation and determination of the absolute configuration were accomplished using a combination of spectroscopy, including 1D and 2D NMR, HRMS, Mosher ester analysis, and comparison of calculated/experimental ECD spectra. A chemotaxonomic investigation of the secondary metabolite profiles using analytical HPLC coupled with diode array detection and mass spectrometry (HPLC–DAD–MS) revealed that the production of pigmentosin B (2) was apparently specific for Gibellula sp., while the glycoasperfuran 3 was specific for C. javanica.

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Section: Chemotaxonomic Investigationmentioning

confidence: 99%

Pigmentosins from Gibellula sp. as antibiofilm agents and a new glycosylated asperfuran from Cordyceps javanica

Helaly¹,

Kuephadungphan²,

Phainuphong³

et al. 2019

Beilstein J. Org. Chem.

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“…Up to now, only electron ionization (EI) mass spectra of beauverolides have been reported 1,18,19 (Table 1). Although the accurate EI mass spectral data have revealed detailed information on structures of pure substances, no useful information can be obtained with this technique when applied in complex mixture analysis.…”

Section: Introductionmentioning

confidence: 99%

Sequencing of new beauverolides by high‐performance liquid chromatography and mass spectrometry

Kuzma

Jegorov²,

Kačer

et al. 2001

J. Mass Spectrom.

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Mass spectrometry (MS) and tandem mass spectrometry (MS(n)) were used for the identification of beauverolides in the fermentation broth of Beauveria bassiana and for evaluation of the purified fraction obtained by sublimation of beauverolides. Besides being a new efficient route for purification of beauverolides, sublimation provided an enrichment of new minor lipophilic beauverolides of lower molecular weight from the original complex mycelial extract. The product ion collision-induced dissociation (CID) spectra obtained on an ion trap (electrospray ionization), the in-source CID mass spectra on a sector instrument (atmospheric-pressure chemical ionization) and the post-source decay matrix-assisted laser desorption/ionization mass spectra of beauverolides were compared and evaluated. All MS(n) experiments started with singly charged precursor ions. The following two new representatives of this group of compounds were identified by high-performance liquid chromatography and MS (HPLC/MS): cyclo-(3-hydroxy-4-methyloctanoyl-valyl-alanyl-leucyl) and cyclo-(3-hydroxy-4-methyloctanoyl-tyrosyl-alanyl-leucyl). Individual structures were confirmed by preparative isolation and nuclear magnetic resonance spectroscopy. The structure of a third novel and minor beauverolide was tentatively assigned by HPLC/MS only as cyclo-(3-hydroxy-4-methyldecanoyl-valyl-alanyl-Lxx), Lxx = leucyl, isoleucyl, or allo-isoleucyl.

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“…Many cyanobacterial macrocycles are peptides and depsipeptides [ 11 ] derived from NRPS or mixed NRPS-PKS genetic architecture and encode proteins with the ability to incorporate l - and d - α -amino acids as well as β -hydroxy fatty acids [ 12 , 13 ]. β -hydroxyacyl incorporation has been observed in several microbial depsipeptides including the beauverolides [ 14 , 15 , 16 ] (3 and 4 residue macrocycles); the unnarmicins [ 17 ], the solonamides [ 18 ], the arthroamides [ 19 ], the turnagainolides [ 20 ], and ngercheumicin C, D and E [ 21 ] (five residue macrocycles); and scytonemide B [ 22 ] and kailuin A-H (six residue macrocycles) [ 23 , 24 ]. These macrocycles have generally displayed antibiotic activity [ 17 ], quorum sensing interference [ 18 ] and weak cytotoxicity [ 24 ].…”

Section: Introductionmentioning

confidence: 99%

Tricholides A and B and Unnarmicin D: New Hybrid PKS-NRPS Macrocycles Isolated from an Environmental Collection of Trichodesmium thiebautii

et al. 2017

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Bioassay-guided isolation of the lipophilic extract of Trichodesmium thiebautii bloom material led to the purification and structure characterization of two new hybrid polyketide-non-ribosomal peptide (PKS-NRPS) macrocyclic compounds, tricholides A and B (1 and 2). A third macrocyclic compound, unnarmicin D (3), was identified as a new depsipeptide in the unnarmicin family, given its structural similarity to the existing compounds in this group. The planar structures of 1–3 were determined using 1D and 2D NMR spectra and complementary spectroscopic and spectrometric procedures. The absolute configurations of the amino acid components of 1–3 were determined via acid hydrolysis, derivitization with Marfey’s reagent and HPLC-UV comparison to authentic amino acid standards. The absolute configuration of the 3-hydroxydodecanoic acid moiety in 3 was determined using a modified Mosher’s esterification procedure on a linear derivative of tricharmicin (4) and additionally by a comparison of 13C NMR shifts of 3 to known depsipeptides with β-hydroxy acid subunits. Tricholide B (2) showed moderate cytotoxicity to Neuro-2A murine neuroblastoma cells (EC50: 14.5 ± 6.2 μM).

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Cyclodepsipeptides from Beauveria bassiana Bals. Part 1. Beauverolides H and I

Cited by 51 publications

References 0 publications

Pigmentosins from Gibellula sp. as antibiofilm agents and a new glycosylated asperfuran from Cordyceps javanica

Pigmentosins from Gibellula sp. as antibiofilm agents and a new glycosylated asperfuran from Cordyceps javanica

Sequencing of new beauverolides by high‐performance liquid chromatography and mass spectrometry

Tricholides A and B and Unnarmicin D: New Hybrid PKS-NRPS Macrocycles Isolated from an Environmental Collection of Trichodesmium thiebautii

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