Novel Reduced Benzo[j]fluoranthen-3-ones from Cladosporium cf. cladosporioides with Cytokine Production and Tyrosine Kinase Inhibitory Properties.

Wrigley, Stephen K.; Ainsworth, A. Martyn; Kau, David A.; Martin, Steven M.; Bahl, Sangeeta; Tang, Jenny; Hardick, David J.; Rawlins, Philip; Sadheghi, Roya; Moore, Michael L.

doi:10.7164/antibiotics.54.479

Cited by 18 publications

(30 citation statements)

References 12 publications

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“…The pentacyclic active metabolite 1 has been demonstrated to be a tyrosine kinase inhibitor (Wrigley et al 2001). In several agar and liquid media tested, C. cladosporioides was able to form high biomass and sporulate, but the amount of this metabolite and related compounds occurred in a low amount in CSB (6 mg l −1…”

Section: Resultsmentioning

confidence: 99%

“…The purified compounds were checked for their identity by NMR, MS, and consistency with other spectroscopic data reported for reference compounds (Nasini et al 2004;Wrigley et al 2001).…”

Section: Methodsmentioning

confidence: 99%

“…cladosporioides (Wrigley et al 2001). These metabolites are novel reduced benzo [j]fluoranthen-ones, related in some aspects to bulgarein 2 and bulgarhodin, the first of which induces mammalian topoisomerase I-mediated DNA cleavage in vitro (Edwards and Lockett 1976;Fujii et al 1993).…”

Section: Introductionmentioning

confidence: 99%

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Enhancement of a pentacyclic tyrosine kinase inhibitor production in Cladosporium cf. cladosporioides by Cladosporol

Assante

Bava

Nasini

2006

Appl Microbiol Biotechnol

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The binaphthyl derivative cladosporol 3 was supplied from 60 to 200 mg l −1 to shaken cultures of Cladosporium cf. cladosporioides. Compared to blank, fungal biomass was not affected by adding cladosporol till 100 mg l . The production of the major pentacyclic metabolite 1, a cytokine production and tyrosine kinase inhibitor, was enhanced tenfold when cladosporol was supplied at the highest ratio (200 mg l −1 ) to shaken growing cultures of the fungus. The bioconversion of cladosporol to cladosporol D through reductive cleavage of the epoxide group was also observed. Interest in this kind of metabolites lies in their potential activity vs DNA topoisomerase I.

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Section: Resultsmentioning

confidence: 99%

“…The purified compounds were checked for their identity by NMR, MS, and consistency with other spectroscopic data reported for reference compounds (Nasini et al 2004;Wrigley et al 2001).…”

Section: Methodsmentioning

confidence: 99%

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Enhancement of a pentacyclic tyrosine kinase inhibitor production in Cladosporium cf. cladosporioides by Cladosporol

Assante

Bava

Nasini

2006

Appl Microbiol Biotechnol

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“…A series of pentacyclic composts, including the main metabolites with the production of cytokines and tyrosine kinase inhibitory properties, was recently isolated from Cladosporium cladosporioides (Wrigley et al, 2001). In a screening program dedicated to finding new and promising inhibitors such as topoisomerase I, the possibility of biotransformation of cladosporol derivatives of from the culture of Cladosporium cladosporioides was investigated (Sakagami et al, 1995).…”

Section: Production Of Metabolites Of the Fungus Cladosporiummentioning

confidence: 99%

Biological control and bioactive microbial metabolites: a coffee quality perspective

Chalfoun¹

2010

Ciênc. agrotec.

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The improvement of techniques of biological control and the use of metabolites produced by microorganisms to obtain products that can be applied in various fields, is getting stronger in face of the undeniable advantages in relation to the models currently in adopted. This review, besides general considerations about the principles and the application of measures of biological control and usage of metabolites produced by microorganisms as sustainable alternatives for the agrochemical segment, among others, reports the experience lived by the author and the institutions to which she is associated, concerning identification, characterization and development of a biological fungicide resulting from the encapsulation of the fungus Cladosporium cladosporioides (Fres.) de Vries, after proving its bioprotecting action on the quality of the coffee. The possibility of using microorganisms as a source of metabolites obtained from biological extracts, with applications in various fields, is also presented and discussed.Index terms: Biological fungicides, fungus metabolites, coffee, Cladosporium cladosporioides (Fres.) de Vries. RESUMOO aprimoramento das técnicas de controle biológico e o aproveitamento de metabólitos produzidos por microrganismos para obtenção de produtos aplicáveis em várias áreas do conhecimento humano, vem se fortalecendo diante de inegáveis vantagens em relação aos modelos hoje adotados. A presente revisão, além de considerações gerais sobre princípios e aplicações de medidas de controle biológico e de aproveitamento de metabólitos produzidos por microrganismos como alternativas de sustentabilidade para o segmento de agroquímicos entre outros, relata a experiência vivenciada pela autora e instituições às quais encontra-se associada com relação à identificação, caracterização e desenvolvimento de um fungicida biológico resultante do encapsulamento do fungo Cladosporium cladosporioides (Fres.) de Vries, após a comprovação de sua ação bioprotetora sobre a qualidade do café. A possibilidade da utilização de microrganismos como fonte de metabólitos obtidos de extratos biológicos, com aplicações em vários setores do conhecimento, também é apresentada e discutida. Fungus associated to coffee grains and fruitsVarious fungi are found associated to coffee grains and fruits throughout the productive cycle and may, under specific conditions, cause loss of quality, producing foul odors and unpleasant flavor. They can sometimes produce toxic metabolites (micotoxins), compromising the safety of the final product.The first reports of the influence of fungi on the quality of coffee date from 1936, when Krug (1940a) noticed, using a pocket magnifier, the presence of a reddish mycelial fungus initially identified as belonging to the Fusarium genus. Thenceforth he began a series of works about the origin of hard coffees. He initially studied the influence of coffee picked from the ground on the quality of the beverage. He found a relation between bad quality beverage and the presence of grains picked from the gro...

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“…In order to ocontinuously explore the effects of high salt stress on halotolerant microbial natural products, a halotolerant fungal strain OUCMDZ‐187, identified as Cladosporium cladosporioides , was isolated from the roots of the mangrove plant, Rhizophora stylosa (Rhizophoraceae) collected in Shankou, Guangxi Province of China. The fungus C. cladosporioides has been reported to produce lactones, benzene derivatives, cladosporin, cladospolide, benzo[ j ]fluoranthen‐3‐ones, and UCN‐1028 . In this study, C. cladosporioides OUCMDZ‐187 was cultured at 10% salinity and the fermentation broth was extracted by ethyl acetate (EtOAc).…”

Section: Introductionmentioning

confidence: 99%

Fatty acid derivatives from the halotolerant fungus Cladosporium cladosporioides

Peng

Wang

Zhu

et al. 2017

Magnetic Reson in Chemistry

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Halotolerant fungus Cladosporium cladosporioides OUCMDZ‐187 was isolated from the mangrove plant Rhizophora stylosa collected in Shankou, Guangxi Province of China. Three new fatty acid esters cladosporesters A–C (1–3) and 5 new fatty acids cladosporacids A–E (4–8) were isolated from the ethyl acetate extract of the fermentation broth of OUCMDZ‐187 in a hypersaline (10% salt) medium. Their structures were elucidated by UV, IR, MS, specific rotation, and 1D and 2D NMR data.

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Novel Reduced Benzo[j]fluoranthen-3-ones from Cladosporium cf. cladosporioides with Cytokine Production and Tyrosine Kinase Inhibitory Properties.

Cited by 18 publications

References 12 publications

Enhancement of a pentacyclic tyrosine kinase inhibitor production in Cladosporium cf. cladosporioides by Cladosporol

Enhancement of a pentacyclic tyrosine kinase inhibitor production in Cladosporium cf. cladosporioides by Cladosporol

Biological control and bioactive microbial metabolites: a coffee quality perspective

Fatty acid derivatives from the halotolerant fungus Cladosporium cladosporioides

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