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Purification and characterization of two new antimicrobial molecules produced by an endophytic strain of Paenibacillus polymyxa
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SERRANO, NADJA F.G.

; FERREIRA, DOUGLAS

; RODRIGUES-FILHO, EDSON

; TEIXEIRA, JOSÉ ANTÓNIO

; DUBREUIL, JEAN DANIEL

; SOUSA, CRISTINA P. DE

Anais da Academia Brasileira de Ciências

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2021, Volume 93 N. 3 elocation e20200486

Abstract: En | Text: En | PDF: En

Abstract An endophytic bacterium inhibiting pathogenic bacteria was isolated and the strain was genetically identified as Paenibacillus polymyxa. Biochemical characterization of fermentation broth indicated the presence of peptidic antimicrobial molecules. Liquid-liquid partition resulted in an organic fraction (OF) and an aqueous fraction (AF). OF presented a broad spectrum of activity against a panel of pathogenic bacteria and a fungus whereas the AF was active only against Gram-negative bacteria. AF was sequentially submitted to ion-exchange, desalting and reverse phase (RP) chromatography. A molecule with an RT of 2.45 min exhibited activity against all Gram-negative pathogenic strains tested beside P. mirabilis. The primary structure of the molecule, named AMP-Pp, was determined as Gly-Glu-Hyp-Gly-Ala by N-terminal sequencing. The molecular mass and amino acid sequence were confirmed by MS/MS. With a molecular mass of 463 Da, AMP-Pp is one of the smallest active natural peptides reported, yet. RP chromatography of OF resulted in four peaks. The first three peaks corresponded to known antimicrobials. MS analysis of peak 4 revealed the presence of an ion with m/z 3,376.4 Da, whose proposed molecular formula is C182H321N29O29. The compound, named polycerradin, showed a spectrum of activity against Gram-positive bacteria, Gram-negative bacteria (beside P. mirabilis) and a fungus.

https://doi.org/10.1590/0001-3765202120200486 119 downloads

Heterogeneous Microtubules of Self-assembled Silver and Gold Nanoparticles Using Alive Biotemplates
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Kubo, Andressa Mayumi

; Gorup, Luiz Fernando

; Amaral, Luciana Silva

; Rodrigues-Filho, Edson

; Camargo, Emerson Rodrigues de

Materials Research

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2018, Volume 21 N. 4 elocation e20170947

Abstract: En | Text: En | PDF: En

Microtubules were constructed by covering the fungus Aspergillus aculeatus sequentially with silver and gold nanoparticles, resulting in a stable hybrid mesostructured material that presented three distinct regions containing different combinations of silver and gold nanoparticles. These heterogeneities were determined by the hyphal growth since the impossibility to cover the dead fungus, which suggests the influence of the secondary metabolites produced by living fungus in the deposition mechanism.

https://doi.org/10.1590/1980-5373-mr-2017-0947 849 downloads

Larvicidal Activity of Beauveria bassiana Extracts against Aedes aegypti and Identification of Beauvericins
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Daniel, Juliana F. S.

; Silva, Andressa A.

; Nakagawa, Danielle H.

; Medeiros, Lívia S. de

; Carvalho, Mário G.

; Tavares, Lucineli J.

; Abreu, Lucas M.

; Rodrigues-Filho, Edson

Journal of the Brazilian Chemical Society

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jun 2017, Volume 28 N. 6 Pages 1003 - 1013

Abstract: En | Text: En | PDF: En

Beauveria bassiana is an entomopathogenic fungus that has been well known for its capacity to act as biopesticide on various disease vectors. The analysis of organic extracts of strains CG71 and UNI40 led to identification of cyclodepsipeptides beauvericin, beauvericin A or F, beauvericin E and bassianolide by ultra-high pressure liquid chromatography-high resolution mass spectrometry in tandem mode (UHPLC-HRMS/MS). The larvicidal activity on 3rd instar of Aedes aegypti revealed LC50 0.9887 and 0.4653 ppm in 24 and 48 hours (CG71 methanolic extract), LC50 0.7834 ppm in 48 hours (CG71 ethyl acetate), LC50 0.7834 and 1.8149 ppm (UNI 40 for ethyl acetate and methanolic extracts, respectively) in 48 hours. These findings highlight the potential of B. bassiana metabolites for controlling the vector of Dengue and Zika diseases.

https://doi.org/10.21577/0103-5053.20160253 1482 downloads

Rapid Detection of ACTG- and AK-Toxins in Alternaria alternata by LC-ESI-MS/MS Analysis and Antifungal Properties of Citrus Compounds
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Prieto, Kátia R.

; Medeiros, Lívia S. de

; Isidoro, Marsele M.

; Toffano, Leonardo

; Silva, Maria Fátima G. F. da

; Fernandes, João B.

; Vieira, Paulo C.

; Forim, Moacir R.

; Rodrigues-Filho, Edson

; Stuart, Rodrigo M.

; Machado, Marcos A.

Journal of the Brazilian Chemical Society

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aug 2016, Volume 27 N. 8 Pages 1493 - 1505

Abstract: En | Text: En | PDF: En

A methanol-soluble fraction of the dichloromethane extract from the culture broth of A. alternata AT4303 strain afforded the following five known mycotoxins: alternariol, alternariol monomethyl ether, altenusin, altenuene and altertoxin I. A hexane-soluble fraction of the dichloromethane extract yielded the steroids ergosterol and ergosterol peroxide, and alternariol monomethyl ether. The concentrated ethyl acetate extract afforded the nucleoside uridine, uracil and inosine. The micro-extracts obtained from this strain in solid media were analyzed using liquid chromatography-electrospray ionization-tandem mass spectrometry (LC-ESI-MS/MS), and the following five known toxins were identified: ACTG-C, D, E and F and AK-toxin II. The major toxins produced by the tangerine pathotype ACT-toxins appear to be absent in strain AT4303. However, the low concentration of ACT-toxins appears to be responsible for their lack of detection in this study. Some compounds isolated from citrus plants were tested for in vitro activity against this strain. The results indicated that 17.3 µM apigenin-7-O-rutinoside inhibited by 80% conidial germination and appressorium development.

https://doi.org/10.5935/0103-5053.20160195 1193 downloads

Copper and Manganese Cations Alter Secondary Metabolism in the Fungus Penicillium brasilianum
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Fill, Taícia Pacheco

; Pallini, Heloisa Fassina

; Amaral, Luciana da Silva

; Silva, José Vinicius da

; Bidóia, Danielle Lazarin

; Peron, Francieli

; Garcia, Francielle Pelegrin

; Nakamura, Celso Vataru

; Rodrigues-Filho, Edson

Journal of the Brazilian Chemical Society

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aug 2016, Volume 27 N. 8 Pages 1444 - 1451

Abstract: En | Text: En | PDF: En

The fungus Penicillium brasilianum LaBioMMi 136 was isolated as an endophyte from Melia azedarach and has shown to be a prominent producer of great diversity of secondary metabolites, although it does not express some biosynthetic routes to other natural compounds found in Penicillium genera. The present study aimed at the diversification of P. brasilianum secondary metabolism by varying the chemical composition used for its growth. Medium composition supplemented with CuSO4 and MnSO4 locked verruculogen biosynthesis and addressed proline to the production of a series of cyclodepsipeptides identified as JBIR 113, JBIR 114 and JBIR 115, never described for this species so far. The induced cyclodepsipeptide JBIR 113 was isolated by the use of combined chromatographic procedures and identified by spectroscopic methods. The unique structure with three neighboring cyclic amino acids proline and twice pipecolinic acid is rare as natural products and has been described for the first time in terrestrial organism. Verruculogen and JBIR 113 exhibited weak antiparasitary activity against Leishmania amazonensis.

https://doi.org/10.5935/0103-5053.20160163 1184 downloads

Botanical secondary metabolites as alternatives for pest management in Cuba
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Pino, Oriela

; Sánchez, Yaíma

; Rojas, Miriam M.

; Jorge, Fanny

; Buzzi, Ana

; González, Cecil

; Turtos, Daylen

; Acosta, Nerdys

; Rodríguez, Mayra

; Hernández, Dainé

; Regalado, Roberto E.

; López, Lidia

; Corzo, Mylene

; Yglesia, Aleika

; Martínez, María A.

; Baños, Heyker L

; Suris, Moraima

; Ramírez, Susana

; Sánchez, Adayakni

; Rodríguez, Héctor

; Pérez, Yanebis

; Chico, Reinaldo

; Arias, Yailen

; González, Ivonne

; Hernández, Yusely

; Martínez, Benedicto

; Duarte, Yanisisa

; Infante, Danay

; Correa, Teresa M.

; Martínez, Dayamín

; Montes de Oca, Rodney

; Berroa, Georgina

; Cotilla, Lázaro

; Peteira, Belkis

; das Graças Fernandes da Silva, Maria Fátima

; Rodrigues Filho, Edson

; Akhtar, Yasmin

; Isman, Murray B.

Revista de Protección Vegetal

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dec 2015, Volume 30 Pages 36 - 36

Abstract: En | Text: En | PDF: En

ALLELOPATHIC POTENTIAL OF Serjania lethalis: EVIDENCE FROM Sesamum indicum
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De Cassia PEREIRA, Viviane

; ANESE, Simoni

; IMATOMI, Maristela

; Umeda GRISI, Patrícia

; MONTE CANEDO, Enzo

; JULIANO GUALTIERI, Sonia Cristina

; RODRIGUES-FILHO, Edson

Acta Biológica Colombiana

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jan 2015, Volume 20 N. 1 Pages 31 - 37

Abstract: Es En | Text: Es En | PDF: Es | PDF: En

El efecto de fracciones de extractos etanólicos de hojas jóvenes (y) y maduras (m) de Serjania lethalis A. St - Hil (Sapindaceae) fueron probados sobre el crecimiento de las plántulas y células de metaxilema de sésamo (Sesamum indicum L.). Los extractos etanólicos fueron preparados a partir del polvo de hojas jóvenes y maduras de S. lethalis y fraccionados por cromatografía en columna. Para el bioensayo de crecimiento de las plántulas germinadas se utilizaron semillas de sésamo y se mantuvo en contacto con las fracciones (F) en concentraciones de 0,8 , 0,4 y 0,2 mg mL-1. Después de siete días se midió la longitud del tallo principal y raíz. El bioensayo de crecimiento celular do metaxilema se realizó utilizando plántulas de sésamo cultivadas en soluciones que contienen fracciones en las mismas concentraciones. Los resultados indican que las fracciones ensayadas (Fy2 ; Fy3 ;Fy5 y Fm1) mostraron actividad en el crecimiento de las plántulas al interferir principalmente en crecimiento de la raíz. La fracción Fy5 mostró actividad similar a la causada por la actividad herbicida Oxyfluorofen. La misma fracción produjo la mayor inhibición del crecimiento celular de las raíces del metaxilema de sésamo a una concentración de 0,8 mg mL- 1. A partir del análisis de los resultados se concluyó que las fracciones de extracto etanolico de las hojas jóvenes son prometedoras fuentes de sustancias con propiedades fitotoxicas.

This study was designed to test the effect of different fractions of ethanolic extracts of young (y) and mature (m) leaves of Serjania lethalis A. St- Hil (Sapindaceae) on sesame (Sesamum indicum L.) seedling growth and metaxylem cells. Crude ethanolic extracts were prepared from the powder of young and mature S. lethalis leaves and fractionated by means of column chromatography. For the seedling growth bioassay, sesame seeds germinated at concentrations of 0.8, 0.4 and 0.2 mg mL-1 were used. After seven days, the lengths of the aerial part and of the primary root were measured. The sesame metaxylem cell growth bioassay was performed with seedlings grown in solutions containing the different fractions in the same concentrations as above. The tested fractions (Fy2; Fy3; Fy5 e Fm1) showed inhibitory activity on seedling growth, interfering mainly in root growth. The fraction Fy5 showed similar activity to the one caused by the herbicide Oxyfluorfen. This fraction was also responsible for causing the greatest inhibition of metaxylem cell growth in sesame roots at the concentration 0.8 mg mL-1. The results permitted to conclude that the different fractions found in the ethanolic extract of S. lethalis young leaves are promising sources of substances with phytotoxic properties.

https://doi.org/10.15446/abc.v20n1.41661 1665 downloads

Active polyketides isolated from Penicillium herquei
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MARINHO, ANDREY M.R.

; MARINHO, PATRÍCIA S.B.

; SANTOS, LOURIVALDO S.

; RODRIGUES FILHO, EDSON

; FERREIRA, IZABEL C.P.

Anais da Academia Brasileira de Ciências

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sep 2013, Volume 85 N. 3 Pages 909 - 912

Abstract: Pt En | Text: Pt En | PDF: Pt | PDF: En

Neste trabalho estamos relatando o isolamento por métodos clássicos de cromatografia de seis policetídeos de Penicillium herquei. Os compostos citreoseine ( 1) , emodina ( 2) , janthinona ( 3) , citrinina ( 4) , citrinina H1( 5) e dicitrinol ( 6) foram identificados por métodos espectrais de RMN 1D e 2D e EM. Os compostos 1, 2 e 3 foram testados contra formas promastigotas de Leishmania brasiliensis e 1 e 2 também foram ensaiados contra a Escherichia coli, Pseudomonas aeruginosa e Bacillus subtilis e mostraram boa atividade.

In this work we are reporting the isolation by classical methods of chromatography of six polyketides from Penicillium herquei. The compounds citreorosein ( 1) , emodin ( 2) , janthinone ( 3) , citrinin ( 4) , citrinin H1 ( 5) and dicitrinol ( 6) were identified by spectral methods of 1D and 2D NMR and MS. Compounds 1, 2 and 3 were tested against promastigotes forms of Leishmania brasiliensis and 1 and 2 were also assayed against Escherichia coli, Pseudomonas aeruginosa and Bacillus subtilis and showed good activity.

https://doi.org/10.1590/S0001-37652013005000048 3434 downloads

Larvicidal effects of endophytic and basidiomycete fungus extracts on Aedes and Anopheles larvae (Diptera, Culicidae)
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Bucker, Augusto

; Bucker, Nadia Cristina Falcao

; Souza, Antonia Queiroz Lima de

; Gama, Auricelia Matos da

; Rodrigues-Filho, Edson

; Costa, Fabio Medeiros da

; Nunez, Cecilia Veronica

; Silva, Ademir Castro e

; Tadei, Wanderli Pedro

Revista da Sociedade Brasileira de Medicina Tropical

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aug 2013, Volume 46 N. 4 Pages 411 - 419

Abstract: En | Text: En | PDF: En

Introduction In vitro bioassays were performed to access the larvicidal activity of crude extracts from the endophytic fungus Pestalotiopsis virgulata (Melanconiales, Amphisphaeriaceae) and the saprophytic fungus Pycnoporus sanguineus (Basidiomycetes, Polyporaceae) against the mosquitoes Aedes aegypti and Anopheles nuneztovari. Methods The extracts were tested at concentrations of 100, 200, 300, 400 and 500ppm. Ethyl acetate mycelia (EAM) extracts and liquid culture media (LCM) from Pe. virgulata and Py. sanguineus were tested against third instar larvae of Ae. aegypti and An. nuneztovari. Results The larvicidal activity of the EAM extracts from Pe. virgulata against Ae. aegypti had an LC50=101.8ppm, and the extract from the basidiomycete fungus Py. sanguineus had an LC50=156.8ppm against the Ae. aegypti larvae. The Pe. virgulata extract had an LC50=16.3ppm against the An. nuneztovari larvae, and the Py. sanguineus extract had an LC50=87.2ppm against these larvae. Conclusions These results highlight the larvicidal effect of EAM extracts from the endophyte Pe. virgulata against the two larval mosquitoes tested. Thus, Pe. virgulata and Py. sanguineus have the potential for the production of bioactive substances against larvae of these two tropical disease vectors, with An. nuneztovari being more susceptible to these extracts.

https://doi.org/10.1590/0037-8682-0063-2013 4809 downloads Cited 1 time in SciELO

10.

Production of 5-hydroxy-7-methoxy-4-methylphthalide in a culture of Penicillium crustosum
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Valente, Angela M.M.P.

; Ferreira, Antonio G.

; Daolio, Cristina

; Rodrigues Filho, Edson

; Boffo, Elisangela F.

; Souza, Antonia Q.L.

; Sebastianes, Fernanda L.S.

; Melo, Itamar S.

Anais da Academia Brasileira de Ciências

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jun 2013, Volume 85 N. 2 Pages 487 - 496

Abstract: Pt En | Text: Pt En | PDF: Pt | PDF: En

As reações químicas realizadas por microorganismos têm sido utilizadas como uma ferramenta na química moderna. Este artigo relata a produção de ácido micofenólico e uma nova ftalida pelo fungo endofítico Penicillium crustosum obtido a partir de grãos de café. O fungo foi cultivado em meio líquido durante um período de sete dias, e depois disso, o meio de cultura foi dividido em quatro lotes: A, B, C e D, nos quais diferentes substâncias orgânicas foram adicionadas. O lote A foi mantido como controle para avaliar a ocorrência de biotransformação. Os ácidos orgânicos foram adicionados ao meio de cultura dos lotes B (ácidos ferúlico e quínico) e C [ácido cinâmico e 3,4-(metilenodioxi) cinâmico], e cafeína foi adicionada ao lote D. Todos estes compostos orgânicos foram dissolvidos em DMSO, e a fermentação foi mantida por mais 13 dias, totalizando 20 dias. O ácido micofenólico foi isolado a partir da cultura sem adição de ácidos (lote A). O ácido micofenólico e uma nova ftalida, 5-hidroxi-7-metoxi-4-metilftalida, foram isolados a partir dos lotes B e C, e ácido micofenólico e cafeína (adicionada ao meio de cultura) foram isolados a partir do lote D. As estruturas foram determinadas pela técnica de RMN e confirmadas pelas técnicas de MS e MS/MS.

The chemical reactions carried out by microorganisms have been used as a tool in modern chemistry. This paper reports the production of mycophenolic acid and a new phthalide by the endophytic fungus Penicillium crustosum obtained from coffee seeds. The fungus was cultivated in a liquid medium for a period of seven days and after that the culture medium was divided into four treatments: A, B, C and D, to which different organic substances were added. Treatment A was maintained as the control to evaluate the occurrence of biotransformation. Organic acids were added to the culture media of treatments B (ferulic and quinic acids) and C [cinnamic and 3,4-(methylenedioxy) cinnamic acids], and caffeine was added in the treatment D. All these organic compounds were dissolved in DMSO, and the fermentation was maintained for more 13 days, totalizing 20 days. Mycophenolic acid was isolated from the culture with no added acids (treatment A). Mycophenolic acid and a new phthalide, 5-hydroxy-7-methoxy-4-methylphthalide were isolated from treatments B and C, and mycophenolic acid and caffeine (added to the culture medium) were isolated from treatment D. The structures were determined by NMR techniques and confirmed by MS and MS/MS techniques.

https://doi.org/10.1590/S0001-37652013005000024 3557 downloads

11.

Evaluation of herbicidal potential of depsides from Cladosporium uredinicola, an endophytic fungus found in Guava fruit
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Medeiros, Lívia S. de

; Sampaio, Olívia M.

; Silva, Maria Fátima das G. F. da

; Rodrigues Filho, Edson

; Veiga, Thiago André M.

Journal of the Brazilian Chemical Society

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aug 2012, Volume 23 N. 8 Pages 1551 - 1557

Abstract: Pt En | Text: Pt En | PDF: Pt | PDF: En

Dois produtos naturais produzidos por Cladosporium uredinicola, um fungo endofítico isolado da goiaba, tiveram seus efeitos sobre a fotossíntese avaliados. Os compostos inibiram o fluxo de elétrons (basal, fosforilante e desacoplado) de água a metilviologênio (MV). Esses compostos atuam como inibidores da reação de Hill em tilacóides de espinafre frescos. Esses policetídeos pertencem à classe dos depsídeos e inibiram o fluxo de elétrons das reações parciais do fotossistema II (PS II) de água a 2,5-dicloro-1,4-benzoquinona (DCBQ), de água a silicomolibdato de sódio (SiMo Na+), e ainda inibiram parcialmente de 1,5-difenilcarbazida (DPC) a 2,6-dicloroindofenol (DCPIP). Esses resultados estabeleceram que os sítios de inibição dos depsídeos estão localizados tanto no lado doador quanto no aceptor do PS II, entre P680 e Q A. Medidas de fluorescência da clorofila a corroboraram para elucidar esse mecanismo de ação. Nenhum dos compostos inibiu o fluxo de elétrons no fotossistema I (PS I).

Two natural products produced by Cladosporium uredinicola, an endophytic fungus isolated from guava fruit, were evaluated for their effects on photosynthesis. Both of them inhibited electron flow (basal, phosphorylating, and uncoupled) from water to methylviologen (MV), acting as Hill reaction inhibitors in freshly lysed spinach thylakoids. These polyketides, belonging to depsides class, inhibited partial reactions of photosystem II (PS II) electron flow from water to 2,5-dichloro-1,4-benzoquinone (DCBQ), from water to sodium silicomolybdate (SiMo Na+), and partially inhibited electron flow from 1,5-diphenylcarbazide (DPC) to 2,6-dichloroindophenol (DCPIP). These results established that the depsides sites of inhibition are located on the donor and acceptor sides of PS II, between P680 and Q A. Chlorophyll a fluorescence measurements corroborated this mechanism of action. None of the tested compounds inhibited photosystem I (PS I) electron transport.

2345 downloads

12.

Triterpenes and flavonoids from the roots of Mauritia flexuosa
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Koolen, Hector H. F.

; Soares, Elzalina R.

; Silva, Felipe M. A. da

; Souza, Antonia Q. L. de

; Rodrigues Filho, Edson

; Souza, Afonso D. L. de

Revista Brasileira de Farmacognosia

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feb 2012, Volume 22 N. 1 Pages 189 - 192

Abstract: En | Text: En | PDF: En

Mauritia flexuosa L. f., Arecaceae, is an endemic species of South America. This species was studied with the intent to isolate the constituents of its roots. After the fractionation of the n-hexane and methanolic extracts from the roots of M. flexuosa, six triterpenes were obtained: friedelin, taraxerone, lupenyl acetate, lupenone, betulin and betulinic acid, along with three flavonoids: rutin, quercitrin and quercetin. All the compounds were identified by analysis of NMR and MS data and comparison with the literature. All those compounds are been reported for the first time in Mauritia, and the chemosystematic significance of the flavonoids isolated in this genus is discussed.

19684 downloads

13.

Metabólitos secundários dos nudibrânquios Tambja stegosauriformis, Hypselodoris lajensis e Okenia zoobotryon e dos briozoários Zoobotryon verticillatum e Bugula dentata da costa do Brasil
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Pereira, Fábio R.

; Berlinck, Roberto G. S.

; Rodrigues Filho, Edson

; Veloso, Katyuscya

; Ferreira, Antonio G.

; Padula, Vinicius

Química Nova

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2012, Volume 35 N. 11 Pages 2194 - 2201

Abstract: Pt En | Text: Pt En | PDF: Pt | PDF: En

The chemical investigation of the MeOH extract from the bryozoan B. dentata MeOH yielded tambjamines A (1), C (3), D (4), K (6), aldehyde 8 and the new tambjamine J1(9), while the extract of its predator, the nudibranch Tambja stegosauriformis, yielded tambjamines C and K, along with aldehyde 8. Furodisinin lactone (11) was isolated from the nudibranch Hypselodoris lajensis, a compound previously isolated from Dysidea sponges. The alkaloid 2,5,6-tribromo-N-methylgramine (12) was isolated from the nudibranch Okenia zoobotryon and from its prey, the bryozoan Zoobotryon verticillatum, the only source of 12 previously known.

3043 downloads

14.

An antimicrobial alkaloid and other metabolites produced by Penicillium sp. An endophytic fungus isolated from Mauritia flexuosa L. f.
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Koolen, Hector Henrique Ferreira

; Soares, Elzalina Ribeiro

; Silva, Felipe Moura Araújo da

; Almeida, Richardson Alves de

; Souza, Afonso Duarte Leão de

; Medeiros, Lívia Soman de

; Rodrigues Filho, Edson

; Souza, Antonia Queiroz Lima de

Química Nova

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2012, Volume 35 N. 4 Pages 771 - 774

Abstract: En | Text: En | PDF: En

The alkaloid glandicoline B (1) and six other compounds: ergosterol (2), brassicasterol (3), ergosterol peroxide (4), cerevisterol (5), mannitol (6) and 1-O-α-D-glucopyranoside (7) were isolated from Penicillium sp. strain PBR.2.2.2, a fungus from Mauritia flexuosa roots. The structures of the isolated metabolites were established by spectral analysis. MeOH extract of the fungal mycelium at 500 µg mL-1 exhibited antimicrobial activity against Staphylococcus aureus and the compound 1 at 100 µg mL-1 was active against S. aureus, Micrococcus luteus and Escherichia coli. The relationship between the bioactive properties of the fungus PBR.2.2.2 and those achieved for glandicoline B, as well the potential of this substance as bactericide is discussed.

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15.

Phenylpropanoid substituted flavan-3-ols from Trichilia catigua and their in vitro antioxidative activity
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Resende, Flávia O.

; Rodrigues-Filho, Edson

; Luftmann, Heinrich

; Petereit, Frank

; Mello, João C. Palazzo de

Journal of the Brazilian Chemical Society

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nov 2011, Volume 22 N. 11 Pages 2087 - 2093

Abstract: Pt En | Text: Pt En | PDF: Pt | PDF: En

O novo flavan-3-ol contendo um substituinte fenilpropanoide apocinina E, juntamente com oito substâncias conhecidas, epicatequina, procianidina B2, procianidina B4, procianidina C1, cinchonaína Ia, cinchonaína Ib, cinchonaína IIb e cinchonaína IIa foram isoladas a partir do extrato acetona-H2O das cascas secas de Trichilia catigua. As substâncias cinchonaína Ib e cinchonaína IIb foram reavaliadas em relação à sua estereoquímica. Todas as substâncias foram caracterizadas por análises espectroscópicas incluindo ressonância magnética nuclear (NMR) 1D e 2D e espectrometria de massa (MS) de seus derivados acetilados. A configuração absoluta do substituinte fenilpropanoide foi determinada por espectropolarimetria de dicroísmo circular (CD) e pela análise do efeito anisotrópico empregando modelo de Dreiding, e por experimento de espectroscopia de efeito nuclear Overhauser (NOESY NMR). As nove substâncias mostraram maior atividade sobre o sequestro de radical livre e poder de redução do que o ácido ascórbico e Trolox frente ao radical livre 2,2-difenil-1-picrilhidrazila e no sistema do teste de redução do ferro (Fe3+-Fe2+).

The new phenylpropanoid substituted flavan-3-ol apocynin E, together with eight known compounds, epicatechin, procyanidin B2, procyanidin B4, procyanidin C1, cinchonain Ia, cinchonain Ib, cinchonain IIb, and cinchonain IIa were isolated from an acetone-H2O extract of the air-dried stem bark of Trichilia catigua. The cinchonain Ia e Ib were reevaluated to its estereochemistry. All the compounds were characterized by spectroscopic analysis including 1D and 2D nuclear magnetic resonance (NMR) and mass spectrometry (MS) of their peracetate derivatives. The absolute configuration of the phenylpropanoid moiety was determined by circular dichroism (CD) spectra and by analyzing the anisotropic effects in the Dreiding model and nuclear Overhauser effect (NOESY NMR) experiments. The nine isolated compounds showed higher radical scavenging activity and reducing power than ascorbic acid and Trolox in the free-radical 2,2-diphenyl-1-picrylhydrazyl and Fe3+-Fe2+ reduction assay systems.

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