Lecanicillolide, an α-pyrone substituted spiciferone from the fungus Lecanicillium sp. PR-M-3

Wang, Zaiying; Shengshuang, Chen; Sang, Xia-Nan; Pan, Huaqi; Li, Zhan‐Lin; Hua, Hui‐Ming; Han, Aihong; Bai, Jiao

doi:10.1016/j.tetlet.2017.01.023

Cited by 9 publications

(7 citation statements)

References 20 publications

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“…Many structurally diverse secondary metabolites have been isolated from Lecanicillium genus, including indolosesquiterpenoids, phenopicolinic acid analogues, pregnanes, diterpenoids and spiciferone analogues [21][22][23]. In our study, the molecular networks led to the isolation and characterisation of five stephensiolides, as major compounds from our Lecanicillium sp.…”

Section: Discussionmentioning

confidence: 85%

Identification of Antimicrobial Compounds from Sandwithia guyanensis-Associated Endophyte Using Molecular Network Approach

Mai

Levasseur

Buisson

et al. 2019

Plants

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The emergence of multidrug resistant bacterial pathogens and the increase of antimicrobial resistance constitutes a major health challenge, leading to intense research efforts being focused on the discovery of novel antimicrobial compounds. In this study, endophytes were isolated from different parts of Sandwithia guyanensis plant (leaves, wood and latex) belonging to the Euphorbiaceae family and known to produce antimicrobial compounds, and chemically characterised using Molecular Network in order to discover novel antimicrobial molecules. One fungal endophyte extract obtained from S. guyanensis latex showed significant antimicrobial activity with Minimal Inhibitory Concentration on methicillin-resistant Staphylococcus aureus at 16 µg/mL. The chemical investigation of this fungus (Lecanicillium genus) extract led to the isolation of 5 stephensiolides compounds, four of which demonstrated antibacterial activity. Stephensiolide I and G showed the highest antibacterial activity on MRSA with a MIC at 4 and 16 µg/mL respectively.Plants 2020, 9, 47 2 of 11 chemical constituents of a wide variety of extracts in a single map [5,6]. Furthermore, MN offers the possibility to map additional information, such as biological, analytical and taxonomical details over networks [6][7][8]. In this study, we applied a related multi-informative prioritisation strategy based on the use of MN, with the aim of finding new antimicrobial structures from of a set of extracts from 42 Euphorbiaceae endophytes.The Euphorbiaceae family comprises approximately 283 genera and 7300 species, and has been found in various morphological types, including herbs, shrubs and trees [9]. Some species of the family are used as lubricants and purgatives, while others are used as a source of medicinal drugs for the treatment of diarrhoea, inflammation and swelling. Their milky latex secretions impart several toxic effects such as dermatitis, severe irritation to the eyes and stomach discomfort. Moreover, Euphorbia sp. latex has been shown to possess moderate antimicrobial properties and ability to protect against herbivores [10]. Together, the antimicrobial, insecticidal and toxicity properties of Euphorbia latex makes it a hostile environment for microbes and plant-feeding insect pests. However, it has been recently highlighted that Euphorbia sp. latex contains unexpectedly complex bacterial and fungal communities [11]. Meanwhile, endophytes, which are microorganisms residing in plant tissues without inducing any diseases in the host plants, have been shown to defend themselves as well the plants from pathogens and have a crucial role in plant survival. They also improve the ecological adaptability of the hosts by enhancing their tolerance to environmental stresses and resistance to phytopathogens and/or herbivores [12]. In addition, endophytes residing within plants may produce identical or similar secondary metabolites as their host plant, and therefore, have also been recognised as a potential source of novel bioactive molecules. These common compounds ...

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Section: Discussionmentioning

confidence: 85%

Identification of Antimicrobial Compounds from Sandwithia guyanensis-Associated Endophyte Using Molecular Network Approach

Mai

Levasseur

Buisson

et al. 2019

Plants

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“…The remaining four known structures were identified as lecanicillones A (7), 18 lecanicillolide (8), 16 spiciferone A (9), 13 and butoxyl-spiciferin (10), 25 by comparison of 1 H and 13 C NMR and mass spectrometric data with published data.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…To date, more than 500 fungal phytotoxins, including polyketides, phenols and phenolic acids, terpenoids, and cyclic peptides, have been discovered. , In contrast with synthetic herbicides, the structural complexity and novel mechanism render these natural phytotoxins available for development of new bioherbicides, as exemplified by aspterric acid . Among them, spiciferones with the fused γ-pyrone and cyclohexanone cycles have been deemed to be highly attractive owing to their intriguing structures and phytotoxicities since the first discovery of spiciferone A from the fungus Cochliobolus spicifer in 1989. − Recently, several new spiciferone derivatives, including lecanicillolide, globosumin, and lecanicillones A–C, have been obtained from diverse fungal species. However, spiciferone-derived dimers assembled by forming an undescribed ethylidene bridge, to the best of our knowledge, have never been reported from nature.…”

Section: Introductionmentioning

confidence: 99%

“…9 Among them, spiciferones with the fused γ-pyrone and cyclohexanone cycles have been deemed to be highly attractive owing to their intriguing structures and phytotoxicities since the first discovery of spiciferone A from the fungus Cochliobolus spicifer in 1989. 13−15 Recently, several new spiciferone derivatives, including lecanicillolide, 16 globosumin, 17 and lecanicillones A−C, 18 have been obtained from diverse fungal species. However, spiciferone-derived dimers assembled by forming an undescribed ethylidene bridge, to the best of our knowledge, have never been reported from nature.…”

Section: ■ Introductionmentioning

confidence: 99%

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Ethylidene-Tethered Chromene–Pyrone Hybrids as Potential Plant-Growth Regulators from an Endolichenic Phaeosphaeria Species

Zhai

Zhang

Gao

et al. 2023

J. Agric. Food Chem.

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Phaeosphaeria sp., a lichen-associated fungus, produced six skeletally new dimeric spiciferones (1–6) and four known metabolites (7–10). The new structures were elucidated by spectroscopic analysis, and their absolute configurations were determined by electronic circular dichroism calculations. Compounds 1 and 3–6 represent the first examples of ethylidene-bridged dimers from the building blocks 4H-chromene-4,7(8H)-dione and α-pyrone, and 2 is a unique homodimer of spiciferone. Compounds 1, 2, and 5–9 significantly inhibited the growth of weed-like dicot Arabidopsis thaliana at 100.0 μM. Notably, 8 showed the strongest inhibitory activity against the fresh weight and root elongation of A. thaliana with the IC50 values of 32.04 and 26.78 μM, respectively, whereas 1, 8, and 9 stimulated the growth of A. thaliana at lower concentrations. Meanwhile, compounds 2 and 6 exhibited weak inhibitory effects on the root elongation of monocot rice, while 1 and 8 exhibited growth-promoting effects on the shoot and root elongation of rice in a roughly dose-dependent manner.

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“…An unidentified Lecanicillium sp. was reported to produce lecanicillolide [86], and lecanicillones A-C, three unusual dimeric spiciferones with an acyclobutane ring displaying moderate cytotoxic effects [87]. More interesting inhibitory effects on tube formation by endothelial cells, implying antiangiogenic properties, were reported for the decalin polyketide 11-norbetaenone, from a strain of L. antillanum [88].…”

Section: Biochemical Factors Involved In the Tritrophic Interaction W...mentioning

confidence: 98%

Endophytism of Lecanicillium and Akanthomyces

Nicoletti

Becchimanzi

2020

Agriculture

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The rise of the holobiont concept confers a prominent importance to the endophytic associates of plants, particularly to species known to be able to exert a mutualistic role as defensive or growth-promoting agents. The finding that many entomopathogenic fungi are harbored within plant tissues and possess bioactive properties going beyond a merely anti-insectan effect has recently prompted a widespread investigational activity concerning their occurrence and functions in crops, in the aim of an applicative exploitation conforming to the paradigm of sustainable agriculture. The related aspects particularly referring to species of Lecanicillium and Akanthomyces (Sordariomycetes, Cordycipitaceae) are revised in this paper, also in light of recent and ongoing taxonomic reassessments.

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Lecanicillolide, an α-pyrone substituted spiciferone from the fungus Lecanicillium sp. PR-M-3

Cited by 9 publications

References 20 publications

Identification of Antimicrobial Compounds from Sandwithia guyanensis-Associated Endophyte Using Molecular Network Approach

Identification of Antimicrobial Compounds from Sandwithia guyanensis-Associated Endophyte Using Molecular Network Approach

Ethylidene-Tethered Chromene–Pyrone Hybrids as Potential Plant-Growth Regulators from an Endolichenic Phaeosphaeria Species

Endophytism of Lecanicillium and Akanthomyces

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