INTRODUCTION: Limonoids are tetranortriterpenoids of considerable interest due to their structural varieties and biological activities, such as insecticidal, antibacterial, antifungal, antimalarial, anticancer and antiviral. They contain oxygen atoms that confer a moderate polarity and are responsible for the difficulties in their separation by traditional chromatographic methods. High-speed countercurrent chromatography (HSCCC) is a versatile liquid-liquid separation technique, in which the sample is distributed between two non-miscible phases to achieve separation. OBJECTIVE: To isolate limonoids from a complex Carapa guianensis seed extract by gradient elution HSCCC and to identify them by spectrometric and spectroscopic methods. METHODOLOGY: The hexane extract of Carapa guianensis squeezed seeds was prepared by Soxhlet extraction. From this extract, 800 mg were submitted to gradient mode HSCCC, using the solvent systems hexane:ethyl acetate:methanol:water 1:2:X:1, X = 1.5 (system A) and X = 1.75 (system B). The upper organic phase of the system A was used as stationary phase, and the lower aqueous phases of both systems as mobile phases. In this procedure, 165 fractions of 4 mL (660 mL) were collected. RESULTS: Six compounds were isolated. Spectrometric and spectroscopic analysis allowed the identification of the substances, as follows: methyl angolensate (28.7 mg), 7-deacetoxy-7-oxogedunin (17.9 mg), deacetylgedunin (3.7 mg), 6alpha-acetoxygedunin (40.1 mg), gedunin (21.0 mg), and andirobin (5.8 mg). CONCLUSION: The use of gradient mode in HSCCC was a good alternative, exploiting small variations of partition coefficient between the substances. Thus it was possible to isolate them in a good relative abundance, compared with classical chromatographic methods.
INTRODUCTION:Limonoids are tetranortriterpenoids of considerable interest due to their structural varieties and biological activities, such as insecticidal, antibacterial, antifungal, antimalarial, anticancer and antiviral. They contain oxygen atoms that confer a moderate polarity and are responsible for the difficulties in their separation by traditional chromatographic methods. High-speed countercurrent chromatography (HSCCC) is a versatile liquid-liquid separation technique, in which the sample is distributed between two non-miscible phases to achieve separation. OBJECTIVE: To isolate limonoids from a complex Carapa guianensis seed extract by gradient elution HSCCC and to identify them by spectrometric and spectroscopic methods. METHODOLOGY: The hexane extract of Carapa guianensis squeezed seeds was prepared by Soxhlet extraction. From this extract, 800 mg were submitted to gradient mode HSCCC, using the solvent systems hexane:ethyl acetate:methanol:water 1:2:X:1, X = 1.5 (system A) and X = 1.75 (system B). The upper organic phase of the system A was used as stationary phase, and the lower aqueous phases of both systems as mobile phases. In this procedure, 165 fractions of 4 mL (660 mL) were collected. RESULTS: Six compounds were isolated. Spectrometric and spectroscopic analysis allowed the identification of the substances, as follows: methyl angolensate (28.7 mg), 7-deacetoxy-7-oxogedunin (17.9 mg), deacetylgedunin (3.7 mg), 6alpha-acetoxygedunin (40.1 mg), gedunin (21.0 mg), and andirobin (5.8 mg). CONCLUSION: The use of gradient mode in HSCCC was a good alternative, exploiting small variations of partition coefficient between the substances. Thus it was possible to isolate them in a good relative abundance, compared with classical chromatographic methods.
Authors: Luis Eduardo Mosquera Narvaez; Lindalva Maria de Meneses Costa Ferreira; Suellen Sanches; Desireé Alesa Gyles; José Otávio Carréra Silva-Júnior; Roseane Maria Ribeiro Costa Journal: Molecules Date: 2022-04-24 Impact factor: 4.927
Authors: Flávia L M Jesus; Fernanda B de Almeida; Jonatas L Duarte; Anna E M F M Oliveira; Rodrigo A S Cruz; Raimundo N P Souto; Ricardo M A Ferreira; Regina Gendzelevski Kelmann; José C T Carvalho; Ana C Lira-Guedes; Marcelino Guedes; Conxita Solans; Caio P Fernandes Journal: Evid Based Complement Alternat Med Date: 2017-07-17 Impact factor: 2.629
Authors: Carlos F Araujo-Lima; Andreia S Fernandes; Erika M Gomes; Larisse L Oliveira; Andrea F Macedo; Rosemar Antoniassi; Allan E Wilhelm; Claudia A F Aiub; Israel Felzenszwalb Journal: Oxid Med Cell Longev Date: 2018-05-02 Impact factor: 6.543