Estudo químico e biológico dos fungos endofíticos Microascus sp. e Nodulisporium sp. associados à alga vermelha Asparagopsis Taxiformis
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Data
2016-03-14
Autores
Santos, Camila Souza [UNESP]
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Universidade Estadual Paulista (Unesp)
Resumo
O presente trabalho apresenta os resultados obtidos sobre o estudo químico e biológico dos fungos endolíticos Nodulisporium sp. e Microascus sp. associados à alga vermelha Asparagopsis taxiformis. Para tanto, fez-se uso das técnicas cromatográficas de separação CLAE (cromatografia líquida de alta eficiência), CG-EM (cromatografia gasosa acoplada a espectrometria de massas) e cromatografia em coluna (CC), além da avaliação dos potenciais antifúngico, anticolinesterásico e citotóxico dos extratos brutos, frações e subfrações de Nodulisporium sp. e Microascus sp. O estudo químico levou ao isolamento de quatro substâncias pertencentes à classe das diidroisocumarinas (substâncias S1, S2, S10 e S11), duas dicetopiperazinas (substâncias S3 e S4), um composto fenólico (S12), uma isoflavona (S8), um derivado hidroxiimino (S9), uma mistura contendo uma amida (S5) e um diol vicinal (S6), além do isolamento de um composto aromático (substância S7), ainda em fase de identificação. As estruturas das substâncias isoladas foram identificadas com base nos dados espectroscópicos de ressonância magnética nuclear uni e bidimensional (RMN de 1H, RMN de 13C, TOCSY-1D, HSQC, HMBC, COSY e HSQC-TOCSY), UV-Vis e espectrometria de massas (EM). Comporta ressaltar que o diol vicinal (S6) está sendo descrito pela primeira vez na literatura e que as demais substâncias isoladas não haviam sido relatadas para os gêneros Nodulisporium ou Microascus. A avaliação das atividades antifúngica e anticolinesterásica evidenciaram o potencial de bioatividade de extratos e frações de Nodulisporium sp. e Microascus sp, sendo reveladas atividades forte e moderada frente às enzimas acetilcolinesterase humana e de enguia elétrica. Este é o primeiro estudo químico e biológico relatado na literatura para os endófitos Nodulisporium sp. e Microascus sp. associados à alga vermelha Asparagopsis taxiformis e seus resultados promissores destacam a elevada quimiodiversidade dos extratos e frações dos fungos endofíticos obtidos do ambiente marinho, bem como seu potencial de bioatividade. Evidenciam ainda a importância de se aprofundar os estudos destas linhagens fúngicas visando contribuições relevantes na busca de protótipos para novos agentes terapêuticos através da exploração sustentável da biodiversidade marinha brasileira.
This work presents results from the chemical and biological study of endophytic fungal strains of Nodulisporium sp and Microascus sp associated to the red alga Asparagopsis taxiformis. Chromatographic separation techniques as HPLC, GC-MS and CC have been used in addition to bioassays for evaluation of the antifungal, anticholinesterasic and cytotoxic potential of crude extracts, fractions and subfractions of Nodulisporium sp and Microascus sp fungal strains. The chemical study led to the isolation of four dihydroisocoumarins (compounds S1, S2, S10 and S11), two diketopiperazines (compounds S3 and S4), one phenolic compound (S12), one isoflavone (S8), one hydroxyl-imino derivative (S9), a mixture containing one amide (S5) and one novel vicinal diol (S6), in addition to one aromatic compound (compounds S7) still under structural investigation. Their structures were identified based on 1D and 2D NMR spectroscopic data (1H and 13C NMR, TOCSY-1D, HSQC, HMBC, COSY and HSQC-TOCSY), UV-Vis and mass spectrometry (MS). Compound S6 is an aliphatic vicinal diol and is herein described as a novel compound whereas the remaining compounds had not been described before neither for Nodulisporium nor Microascus genera. Antifungal and anticholinesterase activities evaluation of extracts and fractions of Nodulisporium sp e Microascus sp evidenced their strong and moderate potential against human and electric eel acetylcholinesterase enzymes. This is the first report on the chemical and biological studies of endophytic fungi Nodulisporium sp and Microascus sp, associated to the red algae Asparagopsis taxiformis. Their promising results highlight the outstanding chemodiversity of extracts and fractions from such fungal strains from marine environment as well as their bioactivity potential. They also evidence the importance of further investigating such fungal strains aiming at relevant contributions in the search for novel therapeutic agents through sustainable exploration of Brazilian marine biodiversity.
This work presents results from the chemical and biological study of endophytic fungal strains of Nodulisporium sp and Microascus sp associated to the red alga Asparagopsis taxiformis. Chromatographic separation techniques as HPLC, GC-MS and CC have been used in addition to bioassays for evaluation of the antifungal, anticholinesterasic and cytotoxic potential of crude extracts, fractions and subfractions of Nodulisporium sp and Microascus sp fungal strains. The chemical study led to the isolation of four dihydroisocoumarins (compounds S1, S2, S10 and S11), two diketopiperazines (compounds S3 and S4), one phenolic compound (S12), one isoflavone (S8), one hydroxyl-imino derivative (S9), a mixture containing one amide (S5) and one novel vicinal diol (S6), in addition to one aromatic compound (compounds S7) still under structural investigation. Their structures were identified based on 1D and 2D NMR spectroscopic data (1H and 13C NMR, TOCSY-1D, HSQC, HMBC, COSY and HSQC-TOCSY), UV-Vis and mass spectrometry (MS). Compound S6 is an aliphatic vicinal diol and is herein described as a novel compound whereas the remaining compounds had not been described before neither for Nodulisporium nor Microascus genera. Antifungal and anticholinesterase activities evaluation of extracts and fractions of Nodulisporium sp e Microascus sp evidenced their strong and moderate potential against human and electric eel acetylcholinesterase enzymes. This is the first report on the chemical and biological studies of endophytic fungi Nodulisporium sp and Microascus sp, associated to the red algae Asparagopsis taxiformis. Their promising results highlight the outstanding chemodiversity of extracts and fractions from such fungal strains from marine environment as well as their bioactivity potential. They also evidence the importance of further investigating such fungal strains aiming at relevant contributions in the search for novel therapeutic agents through sustainable exploration of Brazilian marine biodiversity.
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Palavras-chave
Fungo endofítico, Alga marinha, Nodulisporium, Microascus, Asparagopsis taxiformis, Anticolinesterase, Antifúngico, Marine algae, Antifungal