Chloroisosulochrin, Chloroisosulochrin Dehydrate, And Pestheic Acid, Plant Growth Regulators, Produced By Pestalotiopsis Theae

Shimada, Atsumi; Takahashi, I.; Kawano, Tsuyoshi; Kimurab, Y.

doi:10.1515/znb-2001-0813

Cited by 58 publications

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“…17 The molecular formula of compound 1 was established as C 17 The antimicrobial activity of guepinone (1), isosulochrin (2) and cloroisosulochrin (3) were evaluated in the presence of Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and Candida albicans. Guepinone (1) and isosulochrin (2) were completely inactive against the microorganisms tested and cloroisosulochrin (3) was toxic only to Staphylococcus aureus (13 mm inhibition zone).…”

Section: Resultsmentioning

confidence: 99%

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Novel anthraquinone derivatives produced by Pestalotiopsis guepinii, an endophytic of the medicinal plant Virola michelii (Myristicaceae)

Oliveira

Santos

et al. 2011

J. Braz. Chem. Soc.

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Um novo derivado de antraquinona, denominado guepinone (1), juntamente com as conhecidas substâncias isossulocrina (2) e cloroissosulocrina (3) foram isolados de uma cultura em arroz de Pestalotiopsis guepinii, um fungo endofitico de Virola michelii. Os compostos foram identificados pela análise de seus dados espectrométricos de RMN 1D e 2D e EM. A atividade antimicrobiana dos compostos isolados foi avaliada e a cloroisossulcrina (3) foi a mais ativa.A new anthraquinone derivative, named guepinone (1), along with the known substances isosulochrin (2) and chloroisosulochrin (3), were isolated from a rice culture of Pestalotiopsis guepinii, an endophytic fungus of Virola michelii. The compounds were identified by analysis of 1D and 2D NMR and MS spectral data. The antimicrobial activity of these compounds was evaluated and chloroisosulchrin (3) was the most active. Keywords: Virola michelii, Pestalotiopsis guepinii, anthraquinone derivatives, endophytic fungus IntroductionEndophytic fungi have been collected from nearly all plants studied. They colonize the plants without causing visible disease symptoms. The function of the host plant is not yet clear and is supposed to depend on the organ-fungus interaction of each plant indicating that there are no neutral interactions but a balanced antagonism between the plant and the endophytic fungi. Endophytic fungi are very useful in agriculture and industry. They can be used as a tool for introduction of genes of interest into the plants, 2,3 like plague and pathogen inhibitors. 4,5 They are also a source of primary and secondary metabolites of interest.In spite of the several reports concerning the production of substances by endophytic fungi that show biological activities, such as fungicide, herbicide and algicide, among others, 6 there are not many studies concerning the chemical composition of endophytic microorganisms, especially when we analize the wide fungic biodiversity and the specificity in the colonization of plants by fungi. This paper deals with the study of the metabolites produced by the fungus Pestalotiopsis guepinii isolated from Virola michelii.V. michelii belongs to the family Myristicaceae and it is used in folk medicine in the treatement of diseases caused by fungi and in the treatment of infections of the skin.7 Phytochemical study, anti-inflammatory and allelopathic activities of the leaves of the V. michelii were reported. [8][9][10][11] There have been described 205 species of Pestalotiopsis, 12 some of these produce secondary metabolites with important activities, like phytotoxic, antifungic, antioxidant and anticancer activities.13 Studies with P. guepinii lead Novel Anthraquinone Derivatives Produced by Pestalotiopsis guepinii J. Braz. Chem. Soc. 994 to the isolation of the diterpenoid taxol, an important anticancer drug.14 Pestalotiopsis also produce sesquiterpenes, other diterpenes, phenolic derivatives and anthraquinone derivatives. [14][15][16] This paper reports the isolation and structural elucidation of three anthraquinone derivat...

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Section: Resultsmentioning

confidence: 99%

“…[14][15][16] This paper reports the isolation and structural elucidation of three anthraquinone derivatives, a new lactone (1) named guepinone, isosulochrin (2) and chloroisosulochrin (3), 17 Figure 1. In addition, this is the first report of P. guepinii as an endophyte from V. michelii and its production of anthraquinones derivatives.…”

Section: Introductionmentioning

confidence: 99%

Novel anthraquinone derivatives produced by Pestalotiopsis guepinii, an endophytic of the medicinal plant Virola michelii (Myristicaceae)

Oliveira

Santos

et al. 2011

J. Braz. Chem. Soc.

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“…Pestheic acid, or dihydromaldoxin, is a chlorinated diphenyl ether isolated in 1996 by Adeboya et al, which acts as a plant growth regulator (Shimada et al, 2001). Its cytotoxic and genotoxic properties in eukaryote cells are still unknown.…”

Section: Introductionmentioning

confidence: 99%

Cellular responses induced in vitro by pestheic acid, a fungal metabolite, in a gastric adenocarcinoma cell line (PG100)

Sousa

Matos²,

Alcântara³

et al. 2013

Genet. Mol. Res.

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ABSTRACT. There is a constant search for new cancer treatments that are less aggressive and economically affordable. In this context, natural products extracted from plants, fungi, and microorganisms are of great interest. Pestheic acid, or dihidromaldoxin, is a chlorinated diphenylic ether extracted from the phytopathogenic fungus Pestalotiopsis guepinii (Amphisphaeriaceae). We assessed the cytotoxic, cytostatic, and genotoxic effects of pestheic acid in a gastric adenocarcinoma cell line (PG100). A decrease in clonogenic survival was observed. Pestheic acid also induced significant increases in both micronucleus and nucleoplasmic bridge frequency. However, we did not observe changes in cell cycle kinetics or apoptosis induction. Reactive oxygen species induced by diphenylic ethers may explain the genotoxicity and mutagenicity of pestheic acid. The absence of repair checkpoints that we observed is probably due to the fact that the PG100 cell line lacks the TP53 gene, which is common in gastric cancers. Even though pestheic acid has had a clear cytotoxic effect, the minimal inhibitory concentration was high, which shows that pestheic acid is not an active anticancer compound under these conditions.

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“…[2][3][4][5][6][7][8][9][10][11][12][13][14] During the course of our continuing search for new bioactive natural products from this fungal genus, a subculture of P. fici (AS 3.9138 = W106-1), isolated from the branches of the tea plant Camellia sinensis (Theaceae) in the suburb of Hangzhou, Peoples Republic of China, was grown in different solid-substrate fermentation cultures. Chemical studies of the resulting crude extracts had afforded structurally unique natural products showing inhibitory effects on replication of HIV-1 virus in C8166 cells [15,16] including chloropupukeananin (1), [15] the first chlorinated pupukeanane analogue with a highly functionalized tricyclo-[4.3.1.0 3,7 ]-decane skeleton and its putative biosynthetic precursors 2 and 3 ( Figure 1), [15] and the pestaloficiols, [16] new 6,7-dihydroxy-5,6,7,8-tetrahydro-2H-chromen-4(3H)-ones possessing a cyclopropane moiety.…”

Section: Introductionmentioning

confidence: 99%

Chloropupukeanolides C–E: Cytotoxic Pupukeanane Chlorides with a Spiroketal Skeleton from Pestalotiopsis fici

Liu

Bruhn

Guo

et al. 2011

Chemistry A European J

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Chloropupukeanolides C-E (8-10), three highly functionalized secondary metabolites featuring a novel spiroketal skeleton derived from the chlorinated tricyclo-[4.3.1.0(3, 7)]-decane (pupukeanane) and the 2,6-dihydroxy-4-methylbenzoic acid moieties, were isolated from the scale-up fermentation extract of the plant endophytic fungus Pestalotiopsis fici. The constitutions of compounds 8-10 were elucidated primarily by NMR experiments. Their relative configurations were deduced by analogy to metabolites 4-6, which were previously isolated from the same fungus. The absolute configuration of 8 was assigned by X-ray crystallography and those of 9 and 10 by quantum-chemical CD calculations. Biogenetically, chloropupukeanolides C-E (8-10) are presumably derived from the same oxidation-induced Diels-Alder reaction pathway as compounds 1 and 4-7, via the putative biosynthetic precursors 2 and 3. The opposite configurations of the complete "Southern parts" of 8 and 9 suggests that this Diels-Alder reaction is stereochemically not very selective. Compounds 8-10 showed significant cytotoxicity against a small panel of human tumor cell lines and weak activities against the pathogens of tropical diseases.

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Chloroisosulochrin, Chloroisosulochrin Dehydrate, And Pestheic Acid, Plant Growth Regulators, Produced By Pestalotiopsis Theae

Cited by 58 publications

References 0 publications

Novel anthraquinone derivatives produced by Pestalotiopsis guepinii, an endophytic of the medicinal plant Virola michelii (Myristicaceae)

Novel anthraquinone derivatives produced by Pestalotiopsis guepinii, an endophytic of the medicinal plant Virola michelii (Myristicaceae)

Cellular responses induced in vitro by pestheic acid, a fungal metabolite, in a gastric adenocarcinoma cell line (PG100)

Chloropupukeanolides C–E: Cytotoxic Pupukeanane Chlorides with a Spiroketal Skeleton from Pestalotiopsis fici

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