Three Highly Oxygenated Caryophyllene Sesquiterpenes from Pestalotiopsis sp., a Fungus Isolated from Bark of Pinus taeda

Rf, Magnani; Rodrigues-Fo, Edson; Daolio, Cristina; Ferreira, Antônio G.; Aq, de Souza

doi:10.1515/znc-2003-5-605

Cited by 31 publications

(27 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[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.

View full text Add to dashboard Cite

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...

show abstract

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.

View full text Add to dashboard Cite

show abstract

“…20 Therefore, 3 was assigned 1R, 2R, 5S, 6S, 8R, 9S, 10R, 11R, and 12S absolute configuration. Cytosporinols A-C (1-3) are closely related to the known taedolidol, 3 6-epitaedolidol, 3 and punctaporonin C (4), 7-9 all possessing the rare oxatetracyclo[6.3.2.0 1,4 .0 5,13 ]tridecane skeleton, but differ by having different substituents at C-6 (1), C-10 (1-3), and C-11 (3), as well as a tetrasubstituted olefin (1) and a terminal olefin (2). In addition, 1-3 are structurally similar to a synthetic byproduct 5 created in the acid-mediated cyclization of the nonatural enantiomer pestalotiopins, 23,24 but differ in having different configurations for all stereogenic centers and substituents at C-6 and C-11, respectively.…”

Section: Resultsmentioning

confidence: 99%

“…In addition, 1-3 are structurally similar to a synthetic byproduct 5 created in the acid-mediated cyclization of the nonatural enantiomer pestalotiopins, 23,24 but differ in having different configurations for all stereogenic centers and substituents at C-6 and C-11, respectively. Biogenetically, 1-3 could be derived from co-isolated fuscoatrol A 5 as proposed for the cytosporolides, 16 first via addition and cyclization to form 6, an intermediate of the C-6 deacetylate of (+)-pestalotiopsin A, 1 and then the acidcatalyzed cyclizations of 6 via two intermediates 7 and 8 could afford the key putative intermediate 9, 23 from which 1-3, taedolidol, 3 6-epitaedolidol, 3 and punctaporonin C (4) 7-9 could be generated via different routes (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

Cytosporinols A-C, new caryophyllene sesquiterpenoids from Cytospora sp.

Li¹,

Li²,

Cui³

et al. 2012

Nat. Prod. Bioprospect.

View full text Add to dashboard Cite

Abstract:Three new caryophyllene sesquiterpenoids, cytosporinols A-C (1-3), have been isolated from solid cultures of Cytospora sp. The structures of 1-3 were elucidated primarily by NMR spectroscopy, and 3 was further confirmed by X-ray crystallography. The absolute configurations of the C-11 secondary alcohol in 1 and the 6,8-diol moiety in 3 were deduced using the modified Mosher and Snatzke's method, respectively. Compounds 2 and 3 showed moderate cytotoxicity against HeLa cells.

show abstract

“…The structure was solved Table 3. 13 by direct methods using SHELXL-97 25 and refined using full-matrix least-squares difference Fourier techniques. All non-hydrogen atoms were refined with anisotropic displacement parameters, and all hydrogen atoms were placed in idealized positions and refined as riding atoms with the relative isotropic parameters.…”

Section: Methodsmentioning

confidence: 99%

Pestalotheols A−D, Bioactive Metabolites from the Plant Endophytic Fungus Pestalotiopsis theae

Tian

Liu

et al. 2008

J. Nat. Prod.

View full text Add to dashboard Cite

Pestalotheols A-D (1-4), four new metabolites, have been isolated from cultures of an isolate of the plant endophytic fungus Pestalotiopsis theae. The structures of these compounds were determined by NMR spectroscopy, and 1 is further confirmed by X-ray crystallography. The absolute configurations of compounds 1 and 3 were assigned by application of the modified Mosher method. Pestalotheol C (3) displayed an inhibitory effect on HIV-1 LAI replication in C8166 cells with an EC 50 value of 16.1 µM.

show abstract

Three Highly Oxygenated Caryophyllene Sesquiterpenes from Pestalotiopsis sp., a Fungus Isolated from Bark of Pinus taeda

Cited by 31 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)

Cytosporinols A-C, new caryophyllene sesquiterpenoids from Cytospora sp.

Pestalotheols A−D, Bioactive Metabolites from the Plant Endophytic Fungus Pestalotiopsis theae

Contact Info

Product

Resources

About