The insecticidal activity of some fungal dihydroisocoumarins

Grove, John Frederick; Pople, Michael

doi:10.1007/bf00443751

Cited by 29 publications

(23 citation statements)

References 15 publications

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“…The structures of these compounds were established by 1D and 2D NMR spectroscopic analysis, mass spectrometric (ESI-MS) data, X-ray crystallography, as well as comparison with the previous literatures values. 14-16 All compounds were further evaluated for their antifungal activity against seven plant pathogens using an in vitro micro-dilution broth assay. In the micro-dilution broth assay, cladosporin, 1 , also named asperentin, caused 92.7% growth inhibition of Co. acutatum , 90.1% of Co. fragariae, and 95.4% of Co. gloeosporioides at 30 μM.…”

Section: Resultsmentioning

confidence: 99%

Antifungal Activity against Plant Pathogens of Metabolites from the Endophytic Fungus Cladosporium cladosporioides

Wang

Radwan²,

Taráwneh³

et al. 2013

J. Agric. Food Chem.

108

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Bioassay-guided fractionation of Cladosporium cladosporioides (Fresen.) de Vries extracts led to the isolation of four compounds, including cladosporin, 1, isocladosporin, 2, 5′-hydroxyasperentin, 3, and cladosporin-8-methyl ether, 4. An additional compound 5′,6-diacetyl cladosporin, 5, was synthesized by acetylation of compound 3. Compounds 1-5 were evaluated for antifungal activity against plant pathogens. Phomopsis viticola was the most sensitive fungus to the tested compounds. At 30 μM, compound 1 exhibited 92.7%, 90.1%, 95.4% and 79.9% growth inhibition against Colletotrichum acutatum, Co. fragariae, Co. gloeosporioides and Phomopsis viticola, respectively. Compound 2 showed 50.4%, 60.2% and 83.0% growth inhibition at 30 μM against Co. fragariae, Co. gloeosporioides and P. viticola, respectively. Compounds 3 and 4 were isolated for the first time from Cladosporium cladosporioides. Moreover, the identification of essential structural features of the cladosporin nuclei has also been evaluated. These structures provide new templates for the potential treatment and management of plant diseases.

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Section: Resultsmentioning

confidence: 99%

Antifungal Activity against Plant Pathogens of Metabolites from the Endophytic Fungus Cladosporium cladosporioides

Wang

Radwan²,

Taráwneh³

et al. 2013

J. Agric. Food Chem.

108

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“…(76). Cladosporin has been reported to show antiplasmodial, anti microbial, insecticidal and antitumor activities (72)(73)(74)(75)(76).…”

Section: Discussionmentioning

confidence: 99%

Screening of metabolites from endophytic fungi of some Nigerian medicinal plants for antimicrobial activities

Eze

Nnanna

Okezie

et al. 2019

The EuroBiotech Journal

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Endophytic fungi associated with Nigerian plants have recently generated significant interest in drug discovery programmes due to their immense potential to contribute to the discovery of new bioactive compounds. This study was carried out to investigate the secondary metabolites of endophytic fungi isolated from leaves of Newbouldia laevis, Ocimum gratissimum, and Carica papaya The plants were collected from Agulu, Anambra State, South-East Nigeria. Endophytic fungal isolation, fungal fermentation; and extraction of secondary metabolites were carried out using standard methods. The crude extracts were screened for antimicrobial activities using the agar well diffusion method, and were also subjected to high performance liquid chromatography (HPLC) analysis to identify their constituents. A total of five endophytic fungi was isolated, two from N. laevis (NL-L1 and NL-L2), one from O. gratissimum (SL-L1), and two from C. papaya (PPL-LAC and PPL-LE2). In the antimicrobial assay, the extracts of NL-L2, SL-L1, and PPL-LE2 displayed mild antibacterial activity against both Gram negative and Gram positive test bacteria. PPL-LAC extract showed mild activity only against S. aureus, while no antimicrobial activity was recorded for NL-L1 extract. All the endophytic fungal extracts showed no activity against the test fungi C. albicans and A. fumigatus HPLC analysis of the fungal extracts revealed the presence of ethyl 4-hydroxyphenyl acetate and ferulic acid in NL-L1; ruspolinone in NL-L2; protocatechuic acid, scytalone, and cladosporin in SL-L1; indole-3-acetic acid and indole-3-carbaldehyde in PPL-LE2; and indole-3-acetic acid in PPL-LAC. The findings of this study revealed the potentials possessed by these plants as source of endophytes that express biological active compounds. These endophytes hold key of possibilities to the discovery of novel molecules for pharmaceutical, agricultural and industrial applications.

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“…C. cladosporioides has also been involved in several human diseases causing pulmonary constrictions (asthma and pulmonary emphysema) and cutaneous infections (phaeohypoomycosis) ( Figure 1) [17,18]. Bioactive secondary metabolites that have been isolated from C. cladosporioides include cladosporin, isocladosporin, cladospolides A and B, cladosporol and the calphostins [19][20][21][22]. Cladospolides A and B are two geometrical isomers that were isolated by Hirota and co-workers in 1981 and 1985 respectively.…”

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confidence: 99%

Chemical and Biological Study of Cladosporin, an Antimicrobial Inhibitor: A Review

Wang

Wedge

Cutler

2016

Natural Product Communications

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Natural antifungal agents are generally broad-spectrum compounds with low mammalian and environmental toxicity. Cladosporin is a naturally occurring fungal metabolite mainly isolated from the endophytic fungus Cladosporium cladosporioides. This review article summarizes the chemistry and biological properties of cladosporin covering references published from 1971-2016, including the source, phytochemical characterization, biosynthesis, total synthesis, structure and activity (SAR), and biological activity of cladosporin. Cladosporin exhibited potent antibacterial, antifungal, insecticidal, and anti-inflammatory activities, as well as plant growth regulatory effects. More importantly, cladosporin was identified as having potent, nanomolar, antiparasitic activity against both Plasmodium falciparum blood and liver stages via specific inhibition of protein synthesis. This provides a new approach for the design of isocoumarinbased compounds for the treatment of malaria. Herbicidal activity and antifungal activity against Cryptococcus neoformans (IC 50 value of 17.7 μg/mL) of cladosporin are also described here in the review for the first time. Cladosporin selectively inhibited the growth of a monocot (agostis) and showed no activity against a dicot (lettuce), which indicates its great potential as a selective herbicide for monocots in agriculture use. The above data suggest that cladosporin has great potential utility as a lead compound in the development of agrochemicals against certain plant pathogens and pharmaceuticals against drug-resistant bacteria and parasites.

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The insecticidal activity of some fungal dihydroisocoumarins

Cited by 29 publications

References 15 publications

Antifungal Activity against Plant Pathogens of Metabolites from the Endophytic Fungus Cladosporium cladosporioides

Antifungal Activity against Plant Pathogens of Metabolites from the Endophytic Fungus Cladosporium cladosporioides

Screening of metabolites from endophytic fungi of some Nigerian medicinal plants for antimicrobial activities

Chemical and Biological Study of Cladosporin, an Antimicrobial Inhibitor: A Review

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