Bioactive alkaloids and phenolic Hippeastrum solandriflorum (Lindl.) - Amaryllidaceae

• Main Author: Kaline Rodrigues Carvalho
• Other Authors: Maria da ConceiÃÃo de Menezes Torres
• Format: Others
• Language: Portuguese
• Published: Universidade Federal do Cearà 2014
• Subjects: Amaryllidaceae; Hippeastrum solandriflorum; AlcalÃides isoquinolÃnicos; Atividade citotÃxica; Isoquinoline alkaloids; Cytotoxic activity; QUIMICA DOS PRODUTOS NATURAIS
• Online Access: http://www.teses.ufc.br/tde_busca/arquivo.php?codArquivo=13544

This work describes the phytochemical study of Hippeastrum solandriflorum(Amaryllidaceae)aiming the isolation and structural elucidation of new bioactive compounds, as well as its pharmacological investigation. The chemical investigation realized with the EtOH extract from bulbs, through chromatographic methods, including HPLC (reverse phase), resulting inthe isolation of ten compounds: a furan derivative: 5-(hydroxymethyl)furan-2-carbaldehyde(HS-1), two phenolic derivatives: piscidic acid (HS-2), eucomic acid (HS-3), and seven isoquinoline alkaloids: narciclasin ( HS-4), 2α-hydroxypseudolycorin (HS-5), 10α-hydroxy homolycorin (HS-6), galantamin (HS-7), sanguinin (HS-8),N-oxid galantamin (HS-9) andnarcissidin (HS10). The alkaloids (HS-5) and (HS-6) are being reported for the first time inthe literature, while the other ones have been isolated for the first time in the investigated species. The structures of all isolated compounds were determined based on spectrometricmethods (IR, HRMS, NMR 1H and13Câ1D and 2D), besides comparison with published data. The cytotoxic potential of all alkaloids were evaluated against several tumor cell lines:colon (HCT-116), leukemia (HL-60), ovary (OVCAR-8) and brain (SF-295) showing IC50ranging from 0.01 to 35.7 μM. === Este trabalho descreve o estudo fitoquÃmico de Hippeastrum solandriflorum (Amaryllidaceae) visando o isolamento e elucidaÃÃo estrutural de novos constituintes quÃmicos bioativos, bem como o estudo farmacolÃgico dos compostos obtidos. A investigaÃÃo quÃmica realizada com o extrato etanÃlico dos bulbos, atravÃs de mÃtodos cromatogrÃficos, incluindo CLAE (fase reversa), resultou no isolamento e identificaÃÃo de dez substÃncias, sendo um derivado do furano: 5-(hidroximetil)furan-2-carbaldeido (HS-1), dois derivados fenÃlicos: acido piscidico(HS-2), acido eucÃmico (HS-3) e sete alcaloides isoquinolÃnicos: Narciclasina (HS-4), 2α-hidroxipseudolicorina (HS-5), 10αhidroxi-homolicorina (HS-6), Galantamina (HS-7), Sanguinina (HS-8),N-oxido galantamina (HS-9), Narcissidina (HS-10). Os alcaloides (HS-5)e (HS-6) esta sendo relatado pela primeira vez na literatura e os demais como sendo inÃditos na espÃcie estudada. As substÃncias isoladas tiveram suas estruturas elucidadas por mÃtodos espectromÃtricos (IV, IES-EM e RMN de1H e13C 1D e 2D), alÃm de comparaÃÃo com dados da literatura. O potencial citotÃxicodos alcaloides isolados foi avaliado frente Ãs linhagens decÃlulas tumorais humanas: cÃlon (HCT-116), leucemia (HL-60), ovÃrio (OVCAR-8) e cÃrebro (SF-295) mostrando valores IC50 variando 0,01â35,7 μM.