Antibacterial Ilicicolinic Acids C and D and Ilicicolinal from <i>Neonectria discophora</i> SNB-CN63 Isolated from a Termite Nest

Nirma, Charlotte; Éparvier, Véronique; Stien, Didier

doi:10.1021/np500080m

Cited by 36 publications

(37 citation statements)

References 16 publications

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“…The HMBCs of H-C(15 0 ) to C(2 0 ) and C(4 0 ), H-C(14 0 ) to C(6 0 ) and C(8 0 ), and from H-C(12 0 ) and H-C(13 0 ) to C(10 0 ), revealed the sesquiterpene from C(1 0 ) to C(15 0 ) ( Figure 2). Further, the 1 H-and 13 C-NMR spectral data ( Table 2) of 3 were very similar to those reported for ilicicolinic acid D, [8] and only difference was that a hydroxy group was located at C(10 0 ) in 3. On the basis of its optical rotations ([a] D = À3.0 (c = 0.13, MeOH)), the absolute configuration at C(10 0 ) in 3 was assigned to be (S) by comparing those of dihydroxyneogrifolic acid ([a] D = À4.0 (c = 0.2, MeOH)).…”

Section: Resultssupporting

confidence: 76%

“…The related compound to 3 , ilicicolinic acid D was reported to show the antimicrobial activity against Candida albicans , C . parapsilosis , and Staphylococcus aureus .…”

Section: Resultsmentioning

confidence: 99%

“…Furthermore, the relative configuration of 5 was supported by the fact that 13 C-NMR chemical shifts of 5 were similar to those of 4-O-acetyl-3-dehydroxycephalosporolide C (6) ( Table 4). [10] The related compound to 3, ilicicolinic acid D [8] was reported to show the antimicrobial activity against Candida albicans, C. parapsilosis, and Staphylococcus aureus. We examined the biological activity of isolated compounds using an antimicrobial activity assay against S. aureus NBRC 13276, Pseudomonas aeruginosa ATCC 15442, Aspergillus clavatus F318a, and C. albicans ATCC 2019.…”

Section: Resultsmentioning

confidence: 99%

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New Metabolites Produced by Cylindrocarpon sp. SY‐39 from a Driftwood

Suzuki

Yoshida

Koseki

et al. 2018

Chemistry & Biodiversity

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Four novel compounds, cylindropyrone A (1), 10'-hydroxyilicicolinic acid D (3), cylindrolactones A (4) and B (5), together with known dihydroinfectopyrone (2) were isolated from the culture of Cylindrocarpon sp. SY-39 from a driftwood. Their structures were elucidated using 1D- and 2D-NMR spectroscopy. Compound 3 showed antimicrobial activity against Staphylococcus aureus with MIC value of 5.0 μg/mL.

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Section: Resultssupporting

confidence: 76%

“…The related compound to 3 , ilicicolinic acid D was reported to show the antimicrobial activity against Candida albicans , C . parapsilosis , and Staphylococcus aureus .…”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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New Metabolites Produced by Cylindrocarpon sp. SY‐39 from a Driftwood

Suzuki

Yoshida

Koseki

et al. 2018

Chemistry & Biodiversity

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“…Some of the most recent demonstrations of this kind of defensive mutualism include: i) antibiotic (+)-scleroderolide production by the mycangial fungus Penicillium herquei associated with the leaf-rolling weevil Euops chinensis , 48 ii) production of antibacterial ilicicolinic NPs by a putative fungal symbiont Neonectria discophora SNB-CN63 isolated from termite ( Nasutitermes corniger ) nests in French Guiana, 49 and similarly, iii) production of the antifungal agents tyroscherin and N -methyltyroscherin by the termite-associated fungus Pseudallescheria boydii . 50 …”

Section: Animal-microbe Symbiosesmentioning

confidence: 99%

Symbiosis-inspired approaches to antibiotic discovery

2017

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Life on Earth is characterized by a remarkable abundance of symbiotic and highly refined relationships among life forms. Defined as any kind of close, long-term association between two organisms, symbioses can be mutualistic, commensalistic or parasitic. Historically speaking, selective pressures have shaped symbioses in which one organism (typically a bacterium or fungus) generates bioactive small molecules that impact the host (and possibly other symbionts); the symbiosis is driven fundamentally by the genetic machineries available to the small molecule producer. The human microbiome is now integral to the most recent chapter in animal-microbe symbiosis studies and plant-microbe symbioses have significantly advanced our understanding of natural products biosynthesis; this also is the case for studies of fungal-microbe symbioses. However, much less is known about microbe-microbe systems involving interspecies interactions. Microbe-derived small molecules (i.e. antibiotics and quorum sensing molecules, etc.) have been shown to regulate transcription in microbes within the same environmental niche, suggesting interspecies interactions whereas, intraspecies interactions, such as those that exploit autoinducing small molecules, also modulate gene expression based on environmental cues. We, and others, contend that symbioses provide almost unlimited opportunities for the discovery of new bioactive compounds whose activities and applications have been evolutionarily optimized. Particularly intriguing is the possibility that environmental effectors can guide laboratory expression of secondary metabolites from “orphan”, or silent, biosynthetic gene clusters (BGCs). Notably, many of the studies summarized here result from advances in “omics” technologies and highlight how symbioses have given rise to new anti-bacterial and antifungal natural products now being discovered.

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“…The Gram-negative bacterial strain P. aeruginosa CIP 82118, the Gram-positive bacterial strains S. aureus ATCC 29213 and S. aureus ATCC 33591 (methicillinresistant S. aureus (MRSA)), the yeast C. albicans ATCC 10231, and clinical isolates of dermatophytic fungi, including T. rubrum SNB-TR1, Tricophyton mentagrophytes SNB-TM1, Tricophyton soudanense SNB-TS1, Tricophyton violaceum SNB-TV1, and Tricophyton tonsurans SNB-TT1 [31], were the microorganisms tested for EO sensitivity in this study. EO Antimicrobial activity was measured using a broth microdilution method according to guidelines from the Clinical and Laboratory Standards Institute (CLSI) [32 -36].…”

Section: Antimicrobial Activitymentioning

confidence: 99%

Chemical Diversity and Antimicrobial Activity of Salvia multicaulis Vahl Essential Oils

Fahed

Stien

Ouaini

et al. 2016

Chemistry & Biodiversity

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The chemical compositions and antimicrobial activities of the essential oils (EOs) of aerial parts of Salvia multicaulis Vahl, collected during the same week from two different Lebanese regions, were investigated. The EOs were obtained by hydrodistillation using a Clevenger-type apparatus and characterized by GC and GC/MS analyses. The minimum inhibitory concentrations of these EOs were determined against one Gram-negative and two Gram-positive bacteria, one yeast, and five dermatophytes using the broth microdilution technique. One EO was notably active against Staphylococcus aureus, methicillin-resistant S. aureus, and all of the Trichophyton species tested. Nerolidol was found to be the major compound in the active oil; nerolidol was also absent from the inactive oil. This study demonstrated that nerolidol shows antimicrobial activity and therefore significantly contributes to the antimicrobial potential of the oil. The chemical diversity of worldwide S. multicaulis EOs was analyzed, revealing that the EOs of this study belong to two different chemotypes found in the literature. The nerolidol chemotype appears to be restricted to Lebanon, and it can be used as antimicrobial agent against external bacterial and fungal infections.

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Antibacterial Ilicicolinic Acids C and D and Ilicicolinal from Neonectria discophora SNB-CN63 Isolated from a Termite Nest

Cited by 36 publications

References 16 publications

New Metabolites Produced by Cylindrocarpon sp. SY‐39 from a Driftwood

New Metabolites Produced by Cylindrocarpon sp. SY‐39 from a Driftwood

Symbiosis-inspired approaches to antibiotic discovery

Chemical Diversity and Antimicrobial Activity of Salvia multicaulis Vahl Essential Oils

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