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Redalyc.Lethality of Cytochalasin B and Other Compounds Isolated From Revista Argentina de Microbiología ISSN: 0325-7541 [email protected] Asociación Argentina de Microbiología Argentina Feitosa, André de O.; Dias, Amanda Cristina S.; Ramos, Gisele da C.; Bitencourt, Heriberto R.; Siqueira, José Edson S.; Santana B. Marinho, Patrícia; Barison, Andersson; Ocampos, Fernanda M.M.; do R. Marinho, Andrey Moacir Lethality of cytochalasin B and other compounds isolated from fungus Aspergillus sp. (Trichocomaceae) endophyte of Bauhinia guianensis (Fabaceae) Revista Argentina de Microbiología, vol. 48, núm. 3, julio-septiembre, 2016, pp. 259-263 Asociación Argentina de Microbiología Buenos Aires, Argentina Available in: http://www.redalyc.org/articulo.oa?id=213047799014 How to cite Complete issue Scientific Information System More information about this article Network of Scientific Journals from Latin America, the Caribbean, Spain and Portugal Journal's homepage in redalyc.org Non-profit academic project, developed under the open access initiative Rev Argent Microbiol. 2016;48(3):259---263 R E V I S T A A R G E N T I N A D E MICROBIOLOGÍA www.elsevier.es/ram BRIEF REPORTS Lethality of cytochalasin B and other compounds isolated from fungus Aspergillus sp. (Trichocomaceae) endophyte of Bauhinia guianensis (Fabaceae) a a a André de O. Feitosa , Amanda Cristina S. Dias , Gisele da C. Ramos , a a Heriberto R. Bitencourt , José Edson S. Siqueira , a b b Patrícia Santana B. Marinho , Andersson Barison , Fernanda M.M. Ocampos , a,∗ Andrey Moacir do R. Marinho a Universidade Federal do Pará, Instituto de Ciências Exatas e Naturais-Programa de Pós-graduac¸ão em Química, Belém, Pará, Brazil b Universidade Federal do Paraná, Departamento de Química-Programa de Pós-graduac¸ão em Química, Curitiba, Paraná, Brazil Received 6 October 2015; accepted 8 April 2016 Available online 24 August 2016 KEYWORDS Abstract Endophytic fungi are fungi that colonize internal tissues of plants; several biologically active compounds have been isolated from these fungi. There are few studies of compounds Endophytic fungi; isolated from endophytic fungi of Amazon plants. Thus, this study aimed the isolation and struc- Artemia salina; Secondary tural identification of ergosterol (1), ergosterol peroxide (2), mevalonolactone (3), cytochalasin metabolites B (4) and cytochalasin H (5) from Aspergillus sp. EJC 04, an endophytic fungus from Bauhinia guianensis. The cytochalasin B (4) and the diacetate derivative of cytochalasin B (4a) showed high lethality in the brine shrimp assay. This is the first occurrence of cytochalasins in Amazonian endophytic fungi from B. guianensis. © 2016 Asociacion´ Argentina de Microbiolog´ıa. Published by Elsevier Espana,˜ S.L.U. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by- nc-nd/4.0/). PALABRAS CLAVE Letalidad de citocalasina B y otros compuestos aislados del hongo Aspergillus spp. Hongos endófitos; (Trichocomaceae) endófito de Bauhinia guianensis (Fabaceae) Artemia salina; Metabolitos Resumen Los hongos endofíticos son hongos que colonizan los tejidos internos de las plantas; secundarios varios compuestos biológicamente activos se han aislado a partir de estos hongos. Existen pocos estudios de compuestos aislados de hongos endófitos de plantas amazónicas. Por lo tanto, este ∗ Corresponding author. E-mail address: [email protected] (A.M.d.R. Marinho). http://dx.doi.org/10.1016/j.ram.2016.04.002 0325-7541/© 2016 Asociacion´ Argentina de Microbiolog´ıa. Published by Elsevier Espana,˜ S.L.U. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/). 260 A.d.O. Feitosa et al. estudio tuvo como objetivo el aislamiento y la identificación estructural de ergosterol (1), peróxido de ergosterol (2), mevalonolactona (3), citocalasina B (4) y citocalasina H (5) a partir de Aspergillus spp. EJC 04, un hongo endofítico de Bauhinia guianensis. La citocalasina B (4) y el derivado diacetato de citocalasina B (4a) mostraron una alta letalidad en el ensayo de Artemia salina. Esta es la primera aparición de citocalasinas en hongos endófitos amazónica de B. guianensis. © 2016 Asociacion´ Argentina de Microbiolog´ıa. Publicado por Elsevier Espana,˜ S.L.U. Este es un art´ıculo Open Access bajo la licencia CC BY-NC-ND (http://creativecommons.org/licenses/by- nc-nd/4.0/). ◦ ® The Aspergillus genus has more than one hun- for 45 min at 121 C (autoclave Prismatec ). Small pieces dred species, and belongs to the Ascomycota division, of PDA containing mycelium of Aspergillus sp. were added Deuteromycotina subdivision, Hyphomycetes class, Monil- to 4 Erlenmeyer flasks under sterile conditions, then, the ◦ iales order, Moniliaceae family. The species are widely Erlenmeyer flasks were incubated at 25 C for 23 days, two found in nature, they can be isolated from plants, soil, air Erlenmeyer flasks were used as control. Biomass was mace- 13 ® and decaying matter . Several species have been described rated with ethyl acetate (Tedia ) (3× 500 ml). The biomass 3 as producers of toxic metabolites . The Aspergillus fungi was separated of the ethyl acetate solution by filtration. have been an important source of natural products useful Then, the ethyl acetate extracts (10 g) were obtained after for exploration in medicine, agriculture and industry. Sev- evaporation of the resulting solution in rotary evaporator at ◦ ® eral compounds with cytotoxic activity have been isolated 45 C (Quimis ). Part of the ethyl acetate extract (5.0 g) was 1,16,19 from endophytic fungi . Compounds of the xanthones fractionated on silica gel column using hexane/ethyl acetate class isolated from Aspergillus sydowii showed immunosup- (9:1, 4:1, 7:3, 1:1, 3:7), ethyl acetate/methanol (3:7, 1:1) 17 pressive activities , and the tensyuic A acid isolated from and methanol, resulting in 9 fractions. The hexane/ethyl 6 Aspergillus niger showed antimicrobial activity . There are acetate 9:1 fraction (500 mg) was submitted on silica gel reports of the isolation of cytochalasin E from an endophytic column chromatography eluted with hexane/ethyl acetate 18 12 fungus that showed cytotoxicity . Petersen et al. isolated (9:1, 4:1, 7:3, 1:1, 3:7) and ethyl acetate, resulting in 92 from the fungus Aspergillus sclerotioniger cytochalasins fractions. The fractions were pooled (A1 to A8); the fraction sclerotionigrin A and B that showed cytotoxic activity A2 provided a white amorphous solid identified as ergosterol in vitro against lymphocytic leukemia cells. The aims of 1 (30 mg), and the A4 fraction provided a white amorphous this study were the isolation and structural identification solid identified as ergosterol peroxide 2 (35 mg). The hex- of ergosterol (1), ergosterol peroxide (2), mevalonolactone ane/ethyl acetate 8:2 fraction (600 mg) was submitted on (3), cytochalasin B (4), cytochalasin H (5), and the deriva- silica gel column chromatography eluted with hexane/ethyl tive 7,20-diacetyl-cytochalasin B (4a) from the endophytic acetate (9:1, 4:1, 7:3, 1:1, 3:7) and ethyl acetate, resulting fungus Aspergillus sp. EJC 04 cultures, and testing the in 100 fractions pooled as B1 to B9, the fraction B2 afforded a lethality of isolated compounds against Artemia salina. yellow oil identified as mevalonolactone 3 (6 mg). The ethyl 1 13 The H and C NMR experiments were recorded on a acetate fraction (2 g) was submitted on silica gel column NMR spectrometer (Mercury 300, Varian, Oxford, Oxford- chromatography, eluted with hexane/ethyl acetate (9:1, ® shire, UK) with CDCl3 (Cambridge ) as solvent and standard. 4:1, 7:3, 1:1, 3:7), ethyl acetate, ethyl acetate/methanol The MS spectra were carried out in the mass spectrome- (3:7, 1:1) and methanol, resulting in 120 fractions pooled ter using ESI (+) ion mode (Acquity TQD, Waters, Milford, as C1 to C12; fraction C5 afforded a white solid identified MA, USA). The specific rotation was performed on a specific as cytochalasin B 4 (100 mg) and the fraction C7 gave a rotation equipment (Nova Instruments No. 1412, Piracicaba, white solid identified as cytochalasin H 5 (5 mg). All com- Brazil). pounds 1--- 5 were identified by NMR and MS spectrometric The fungus Aspergillus sp. was obtained from a col- data. lection of ‘‘Laboratório de Bioensaios e Química de The cytochalasin B (4) was acetylated; for this, 10 mg of Micro-organismos --- LaBQuiM/UFPA’’. This collection con- compound 4 were removed and solubilized in 100 ␮l of pyri- ® tains isolates from Bauhinia guianensis. The fungus was dine (Tedia ), then it was added 250 ␮l of acetic anhydride ® inoculated into a Petri dish containing PDA (Potato Dex- (Tedia ) and kept at rest for 24 h at room temperature. After ® trose Agar) culture medium (Himedia ) and incubated at this period, the material was transferred to a separatory ◦ ® 25 C (BOD, Quimis ) for 8 days to reactivation. One strain is funnel, and it was added 25 ml of 5% HCl solution to remove deposited with a code EJC 04. The fungus Aspergillus EJC 04 excess pyridine, and extraction was performed with ethyl was identified by observing the morphology and microscopic acetate (3× 15 ml). The ethyl acetate phase was further aspects of the colony in an optical microscope and by DNA washed with distilled water (3× 25 ml) and after separation sequence through analyses of the ITS5 region. was added anhydrous sodium sulfate in the ethyl acetate Six Erlenmeyer flasks (1000 ml) containing 200 g of rice phase, which after filtered was evaporated to obtain the ® (Uncle Ben’s ) and 75 ml of water per flasks were autoclaved acetylated product 4a. Lethality of cytochalasin B and other compounds 261 21 28 20 22 18 24 O 23 27 11 17 19 13 25 H 1 14 O 26 H 9 H O HO 3 H HO 5 O 6 1 2 3 HO O 12 11 O OH 6 5 7 H H 30 10 8 14 16 25 3 9 29 4 17 13 15 OH HN HN O 26 18 1 O 23 28 22 20 O O 12 27 21 19 O O O O 11 OH 4 6 7 4a 5 H H 8 14 15 10 4 9 3 13 31 26 H 22 1 16 30 HN 21 20 17 18 27 19 O O 28 24 OH 29 23 O 5 25 Figure 1 Compounds isolated from Aspergillus sp.
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