The phytochemical investigation of Sigmatanthus trifoliatus Huber ex Emmerich (Rutaceae) allowed ... more The phytochemical investigation of Sigmatanthus trifoliatus Huber ex Emmerich (Rutaceae) allowed the isolation and identification of the coumarins seselin, osthol, coumurrayin and braylin, besides the furoquinoline alkaloids evolitrine, dictamnine, γ-fagarine and skimmianine. Their chemical structures were determined based on MS, NMR analyses, and supported by comparison with those reported in the literature. The essential oils composition of leaves, roots, and trunk were also analyzed, showing the compounds b-Caryophyllene (33.2%), germacrene-D (28.1%) and bornyl acetate (14.7%) as main components, respectively. The chemotaxonomic significance of the isolated compounds was discussed.
In an attempt to explore the biosynthetic potential of endosymbiotic fungi, the secondary metabol... more In an attempt to explore the biosynthetic potential of endosymbiotic fungi, the secondary metabolite profiles of the endophytic fungus, Anteaglonium sp. FL0768, cultured under a variety of conditions were investigated. In potato dextrose broth (PDB) medium, Anteaglonium sp. FL0768 produced the heptaketides, herbaridine A (1), herbarin (2), 1-hydroxydehydroherbarin (3), scorpinone (4), and the methylated hexaketide 9S,11R-(+)-ascosalitoxin (5). Incorporation of commonly used epigenetic modifiers, 5-azacytidine and suberoylanilide hydroxamic acid, into the PDB culture medium of this fungus had no effect on its secondary metabolite profile. However, the histone acetyl transferase inhibitor, anacardic acid, slightly affected the metabolite profile affording scorpinone (4) as the major metabolite together with 1-hydroxydehydroherbarin (3) and a different methylated hexaketide, ascochitine (6). Intriguingly, incorporaion of Cu 2+ into the PDB medium enhanced production of metabolites and drastically affected the biosynthetic pathway resulting in the production of pentaketide dimers, palmarumycin CE 4 (7), palmarumycin CP 4 (8), and palmarumycin CP 1 (9), in addition to ascochitine (6). The structure of the new metabolite 7 was established with the help of spectroscopic data and by MnO 2 oxidation to the known pentaketide dimer, palmarumycin CP 3 (10). Biosynthetic pathways to some metabolites in *
International journal of analytical chemistry, 2017
The concentration of diterpenes barbatusin (1) and 3β-hydroxy-3-deoxybarbatusin (2) in the extrac... more The concentration of diterpenes barbatusin (1) and 3β-hydroxy-3-deoxybarbatusin (2) in the extracts from leaves of Plectranthus grandis, P. barbatus, P. ornatus, and P. amboinicus was evaluated by HPLC-DAD analysis on a Luna C-18 column, using isocratic mixtures of water and acetonitrile as eluents. The regression equations were obtained with good linearity (r(2) > 0.99) and limit of quantifications was higher than 0.1 µg/mL. The precision (lower than 3.5%, within day) and accuracy (higher than 81.7% and lower than 107.6%) of the methods were adequate. Barbatusin (1) was detected in P. grandis (15.432 ± 2.28 mg/g) and P. barbatus (5.198 ± 3.45 mg/g) extracts, while compound 2 was detected in P. grandis (4.068 ± 3.34 mg/g), P. barbatus (0.654 ± 5.86 mg/g), P. amboinicus (0.160 ± 7.25 mg/g), and P. ornatus (0.763 ± 5.10 mg/g). The evaluated validation parameters were satisfactorily achieved, and the developed methodology represents a suitable tool for application in the quantificat...
Anteaglonialides A-F (1-6), bearing a spiro[6-(tetrahydro-7-furanyl)cyclohexane-1,2'-naphtho[... more Anteaglonialides A-F (1-6), bearing a spiro[6-(tetrahydro-7-furanyl)cyclohexane-1,2'-naphtho[1,8-de][1,3]-dioxin]-10-one skeleton, three new spirobisnaphthalenes, palmarumycins CE1-CE3 (7-9), nine known palmarumycin analogues, palmarumycins CP5 (10), CP4a (11), CP3 (12), CP17 (13), CP2 (14), and CP1 (15), CJ-12,371 (16), 4-O-methyl CJ-12,371 (17), and CP4 (18), together with a possible artifact, 4a(5)-anhydropalmarumycin CE2 (8a), and four known metabolites, O-methylherbarin (19), herbarin (20), herbaridine B (21), and hyalopyrone (22), were encountered in a cytotoxic extract of a potato dextrose agar culture of Anteaglonium sp. FL0768, an endophytic fungus of the sand spikemoss, Selaginella arenicola. The planar structures and relative configurations of the new metabolites 1-9 were elucidated by analysis of extensive spectroscopic data, and the absolute configuration of 1 was determined by the modified Mosher's ester method. Application of the modified Mosher's ester me...
Intermolecular forces are a useful concept that can explain the attraction between particulate ma... more Intermolecular forces are a useful concept that can explain the attraction between particulate matter as well as numerous phenomena in our lives such as viscosity, solubility, drug interactions, and dyeing of fibers. However, studies show that students have difficulty understanding this important concept, which has led us to develop a free educational software in English and Portuguese. The software can be used interactively by teachers and students, thus facilitating better understanding. Professors and students, both graduate and undergraduate, were questioned about the software quality and its intuitiveness of use, facility of navigation, and pedagogical application using a Likert scale. The results led to the conclusion that the developed computer application can be characterized as an auxiliary tool to assist teachers in their lectures and students in their learning process of intermolecular forces.
British Journal of Applied Science & Technology, 2013
ABSTRACT Aims: Use a natural compound derived from cashew nut shell liquid to the production of a... more ABSTRACT Aims: Use a natural compound derived from cashew nut shell liquid to the production of an additive inhibitor of the oxidation of lubricants oils. Study Design: This article describes the syntheses, characterization and evaluation of the antioxidant action of a phosphorylated compound derivate from hydrogenated cardol (diphenyl phosphorylated-cardol). Place and Duration of Study: Department of organic and inorganic chemistry (Universidade Federal do Ceará), between June 2009 and July 2010. Methodology: Cardol was isolated from hydrogenated cashew nut shell liquid through column chromatography eluted with a stepwise gradient of n-hexane/ethyl acetate. Diphenyl phosphorylated compound was synthesized through of reaction between cardol and diphenyl chloro-phosphate in basic medium. After purification and characterization the performance this compound was evaluated in minerals oils by thermal analyses, monitoring parameters as T(onset), T(endset), T(max) and IPDT, using samples doped in 1 %. Results: The cardol was isolated with 10 % of the yield and the diphenyl phosphorylated compound was synthesized with a yield of 61,4 %. The techniques of characterization (GC/MS, FT-IR and NMR) showed that the product was efficiently synthesized with a good degree of purity. The Thermo-gravimetric analysis showed that the addition of the new compound promoted a significant increase in thermal stability of mineral naphthenic oils, which confirms its action in inhibition of oxidative process. Conclusion: According to the experimental data a new phosphorylated antioxidant derived from hydrogenated cardol was efficiently synthesized and characterized. This compound presented excellent performance as inhibitor of oxidation of mineral oils, become these oils more resistant to thermal degradation process.
The cytotoxic activities of extracts (50 μg/ml) from 48 fungal strains, recovered from sediments ... more The cytotoxic activities of extracts (50 μg/ml) from 48 fungal strains, recovered from sediments of Pecém's offshore port terminal (Northeast coast of Brazil), against HCT-116 colon cancer cell lines were investigated. The most promising extract was obtained from strain BRF082, identified as Dichotomomyces cejpii by phylogenetic analyses of partial RPB2 gene sequence. Thus, it was selected for bioassay-guided isolation of the cytotoxic compounds. Large-scale fermentation of BRF082 in potato dextrose broth, followed by chromatographic purification of the bioactive fractions from the liquid medium, yielded gliotoxin (4) and its derivatives acetylgliotoxin G (3), bis(dethio)bis(methylsulfanyl)gliotoxin (1), acetylgliotoxin (5), 6-acetylbis(dethio)bis(methylsulfanyl)gliotoxin (2), besides the quinazolinone alkaloid fiscalin B. All isolated compounds were tested for their cytotoxicities against the tumor cell lines HCT-116, revealing 4 and 3 as the most cytotoxic ones (IC50 0.41 and ...
A fungal strain of Aspergillus sp. (BRF 030) was isolated from the sediments collected in the nor... more A fungal strain of Aspergillus sp. (BRF 030) was isolated from the sediments collected in the northeast coast of Brazil, and the cytotoxic activity of its secondary metabolites was investigated against HCT-116 tumour cell line. The cytotoxicity-guided fractionation of the extracts from this fungus cultured in potato-dextrose-sea water for 14 days at room temperature yielded the hetero-spirocyclic γ-lactams pseurotin A (1), pseurotin D (2) and pseurotin FD-838 (7), the alkaloids fumitremorgin C (5), 12,13-dihydroxy fumitremorgin C (6), methylsulochrin (4) and bis(dethio)bis(methylthio)gliotoxin (3). Among them, fumitremorgin C (5) and 12,13-dihydroxy fumitremorgin C (6) were the most active. The cytotoxic activities of the extracts from Aspergillus sp. grown from 7 to 28 days were investigated, and they were associated with the kinetic production of the compounds. The most active extracts (14 and 21 days) were those with the highest relative concentrations of the compounds fumitremor...
and 13 C NMR chemical shifts of praecansone B, pongaflavone and dehydrorotenone isolated from Tep... more and 13 C NMR chemical shifts of praecansone B, pongaflavone and dehydrorotenone isolated from Tephrosia egregia Sandw and obovatin from T. toxicaria Pers. were unambiguously assigned by 1D and 2D NMR experiments including 1 H, 1 H COSY, gHMQC and gHMBC, allowing the correction of literature assignments.
One-and two-dimensional NMR experiments were used for the unambiguous assignment of the 1 H and 1... more One-and two-dimensional NMR experiments were used for the unambiguous assignment of the 1 H and 13 C NMR chemical shifts of the furoquinoline alkaloid maculine (1) and the new furanocoumarin 3,8-dimethoxyfuro[3,2g]coumarin (2).
One-and two-dimensional NMR experiments were used for the unambiguous assignment of the 1 H and 1... more One-and two-dimensional NMR experiments were used for the unambiguous assignment of the 1 H and 13 C NMR chemical shifts of 3,3-diisopentenyl-N-methyl-2,4-quinoldione and five novel reaction derivatives.
The activity of crude plant extracts of nine species of Rutaceae against the trypomastigote form ... more The activity of crude plant extracts of nine species of Rutaceae against the trypomastigote form of Trypanosoma cruzi was evaluated at 4 mg/ml. Thirty-two crude extracts were tested and eight of them showed significant activity (\80%). The most active extract was obtained from the stems of Pilocarpus spicatus (97.3%). Fractionation of the active crude extracts provided 25 fractions which were tested against the trypomastigote form of T. cruzi at 2 mg/ml. Of these six showed significant activity (\80%). The most active fractions (100%) were obtained from the leaves of Almeidea coerulea (butanol fraction) and Conchocarpus inopinatus (dichloromethane fraction).
The phytochemical investigation of Sigmatanthus trifoliatus Huber ex Emmerich (Rutaceae) allowed ... more The phytochemical investigation of Sigmatanthus trifoliatus Huber ex Emmerich (Rutaceae) allowed the isolation and identification of the coumarins seselin, osthol, coumurrayin and braylin, besides the furoquinoline alkaloids evolitrine, dictamnine, γ-fagarine and skimmianine. Their chemical structures were determined based on MS, NMR analyses, and supported by comparison with those reported in the literature. The essential oils composition of leaves, roots, and trunk were also analyzed, showing the compounds b-Caryophyllene (33.2%), germacrene-D (28.1%) and bornyl acetate (14.7%) as main components, respectively. The chemotaxonomic significance of the isolated compounds was discussed.
In an attempt to explore the biosynthetic potential of endosymbiotic fungi, the secondary metabol... more In an attempt to explore the biosynthetic potential of endosymbiotic fungi, the secondary metabolite profiles of the endophytic fungus, Anteaglonium sp. FL0768, cultured under a variety of conditions were investigated. In potato dextrose broth (PDB) medium, Anteaglonium sp. FL0768 produced the heptaketides, herbaridine A (1), herbarin (2), 1-hydroxydehydroherbarin (3), scorpinone (4), and the methylated hexaketide 9S,11R-(+)-ascosalitoxin (5). Incorporation of commonly used epigenetic modifiers, 5-azacytidine and suberoylanilide hydroxamic acid, into the PDB culture medium of this fungus had no effect on its secondary metabolite profile. However, the histone acetyl transferase inhibitor, anacardic acid, slightly affected the metabolite profile affording scorpinone (4) as the major metabolite together with 1-hydroxydehydroherbarin (3) and a different methylated hexaketide, ascochitine (6). Intriguingly, incorporaion of Cu 2+ into the PDB medium enhanced production of metabolites and drastically affected the biosynthetic pathway resulting in the production of pentaketide dimers, palmarumycin CE 4 (7), palmarumycin CP 4 (8), and palmarumycin CP 1 (9), in addition to ascochitine (6). The structure of the new metabolite 7 was established with the help of spectroscopic data and by MnO 2 oxidation to the known pentaketide dimer, palmarumycin CP 3 (10). Biosynthetic pathways to some metabolites in *
International journal of analytical chemistry, 2017
The concentration of diterpenes barbatusin (1) and 3β-hydroxy-3-deoxybarbatusin (2) in the extrac... more The concentration of diterpenes barbatusin (1) and 3β-hydroxy-3-deoxybarbatusin (2) in the extracts from leaves of Plectranthus grandis, P. barbatus, P. ornatus, and P. amboinicus was evaluated by HPLC-DAD analysis on a Luna C-18 column, using isocratic mixtures of water and acetonitrile as eluents. The regression equations were obtained with good linearity (r(2) > 0.99) and limit of quantifications was higher than 0.1 µg/mL. The precision (lower than 3.5%, within day) and accuracy (higher than 81.7% and lower than 107.6%) of the methods were adequate. Barbatusin (1) was detected in P. grandis (15.432 ± 2.28 mg/g) and P. barbatus (5.198 ± 3.45 mg/g) extracts, while compound 2 was detected in P. grandis (4.068 ± 3.34 mg/g), P. barbatus (0.654 ± 5.86 mg/g), P. amboinicus (0.160 ± 7.25 mg/g), and P. ornatus (0.763 ± 5.10 mg/g). The evaluated validation parameters were satisfactorily achieved, and the developed methodology represents a suitable tool for application in the quantificat...
Anteaglonialides A-F (1-6), bearing a spiro[6-(tetrahydro-7-furanyl)cyclohexane-1,2'-naphtho[... more Anteaglonialides A-F (1-6), bearing a spiro[6-(tetrahydro-7-furanyl)cyclohexane-1,2'-naphtho[1,8-de][1,3]-dioxin]-10-one skeleton, three new spirobisnaphthalenes, palmarumycins CE1-CE3 (7-9), nine known palmarumycin analogues, palmarumycins CP5 (10), CP4a (11), CP3 (12), CP17 (13), CP2 (14), and CP1 (15), CJ-12,371 (16), 4-O-methyl CJ-12,371 (17), and CP4 (18), together with a possible artifact, 4a(5)-anhydropalmarumycin CE2 (8a), and four known metabolites, O-methylherbarin (19), herbarin (20), herbaridine B (21), and hyalopyrone (22), were encountered in a cytotoxic extract of a potato dextrose agar culture of Anteaglonium sp. FL0768, an endophytic fungus of the sand spikemoss, Selaginella arenicola. The planar structures and relative configurations of the new metabolites 1-9 were elucidated by analysis of extensive spectroscopic data, and the absolute configuration of 1 was determined by the modified Mosher's ester method. Application of the modified Mosher's ester me...
Intermolecular forces are a useful concept that can explain the attraction between particulate ma... more Intermolecular forces are a useful concept that can explain the attraction between particulate matter as well as numerous phenomena in our lives such as viscosity, solubility, drug interactions, and dyeing of fibers. However, studies show that students have difficulty understanding this important concept, which has led us to develop a free educational software in English and Portuguese. The software can be used interactively by teachers and students, thus facilitating better understanding. Professors and students, both graduate and undergraduate, were questioned about the software quality and its intuitiveness of use, facility of navigation, and pedagogical application using a Likert scale. The results led to the conclusion that the developed computer application can be characterized as an auxiliary tool to assist teachers in their lectures and students in their learning process of intermolecular forces.
British Journal of Applied Science & Technology, 2013
ABSTRACT Aims: Use a natural compound derived from cashew nut shell liquid to the production of a... more ABSTRACT Aims: Use a natural compound derived from cashew nut shell liquid to the production of an additive inhibitor of the oxidation of lubricants oils. Study Design: This article describes the syntheses, characterization and evaluation of the antioxidant action of a phosphorylated compound derivate from hydrogenated cardol (diphenyl phosphorylated-cardol). Place and Duration of Study: Department of organic and inorganic chemistry (Universidade Federal do Ceará), between June 2009 and July 2010. Methodology: Cardol was isolated from hydrogenated cashew nut shell liquid through column chromatography eluted with a stepwise gradient of n-hexane/ethyl acetate. Diphenyl phosphorylated compound was synthesized through of reaction between cardol and diphenyl chloro-phosphate in basic medium. After purification and characterization the performance this compound was evaluated in minerals oils by thermal analyses, monitoring parameters as T(onset), T(endset), T(max) and IPDT, using samples doped in 1 %. Results: The cardol was isolated with 10 % of the yield and the diphenyl phosphorylated compound was synthesized with a yield of 61,4 %. The techniques of characterization (GC/MS, FT-IR and NMR) showed that the product was efficiently synthesized with a good degree of purity. The Thermo-gravimetric analysis showed that the addition of the new compound promoted a significant increase in thermal stability of mineral naphthenic oils, which confirms its action in inhibition of oxidative process. Conclusion: According to the experimental data a new phosphorylated antioxidant derived from hydrogenated cardol was efficiently synthesized and characterized. This compound presented excellent performance as inhibitor of oxidation of mineral oils, become these oils more resistant to thermal degradation process.
The cytotoxic activities of extracts (50 μg/ml) from 48 fungal strains, recovered from sediments ... more The cytotoxic activities of extracts (50 μg/ml) from 48 fungal strains, recovered from sediments of Pecém's offshore port terminal (Northeast coast of Brazil), against HCT-116 colon cancer cell lines were investigated. The most promising extract was obtained from strain BRF082, identified as Dichotomomyces cejpii by phylogenetic analyses of partial RPB2 gene sequence. Thus, it was selected for bioassay-guided isolation of the cytotoxic compounds. Large-scale fermentation of BRF082 in potato dextrose broth, followed by chromatographic purification of the bioactive fractions from the liquid medium, yielded gliotoxin (4) and its derivatives acetylgliotoxin G (3), bis(dethio)bis(methylsulfanyl)gliotoxin (1), acetylgliotoxin (5), 6-acetylbis(dethio)bis(methylsulfanyl)gliotoxin (2), besides the quinazolinone alkaloid fiscalin B. All isolated compounds were tested for their cytotoxicities against the tumor cell lines HCT-116, revealing 4 and 3 as the most cytotoxic ones (IC50 0.41 and ...
A fungal strain of Aspergillus sp. (BRF 030) was isolated from the sediments collected in the nor... more A fungal strain of Aspergillus sp. (BRF 030) was isolated from the sediments collected in the northeast coast of Brazil, and the cytotoxic activity of its secondary metabolites was investigated against HCT-116 tumour cell line. The cytotoxicity-guided fractionation of the extracts from this fungus cultured in potato-dextrose-sea water for 14 days at room temperature yielded the hetero-spirocyclic γ-lactams pseurotin A (1), pseurotin D (2) and pseurotin FD-838 (7), the alkaloids fumitremorgin C (5), 12,13-dihydroxy fumitremorgin C (6), methylsulochrin (4) and bis(dethio)bis(methylthio)gliotoxin (3). Among them, fumitremorgin C (5) and 12,13-dihydroxy fumitremorgin C (6) were the most active. The cytotoxic activities of the extracts from Aspergillus sp. grown from 7 to 28 days were investigated, and they were associated with the kinetic production of the compounds. The most active extracts (14 and 21 days) were those with the highest relative concentrations of the compounds fumitremor...
and 13 C NMR chemical shifts of praecansone B, pongaflavone and dehydrorotenone isolated from Tep... more and 13 C NMR chemical shifts of praecansone B, pongaflavone and dehydrorotenone isolated from Tephrosia egregia Sandw and obovatin from T. toxicaria Pers. were unambiguously assigned by 1D and 2D NMR experiments including 1 H, 1 H COSY, gHMQC and gHMBC, allowing the correction of literature assignments.
One-and two-dimensional NMR experiments were used for the unambiguous assignment of the 1 H and 1... more One-and two-dimensional NMR experiments were used for the unambiguous assignment of the 1 H and 13 C NMR chemical shifts of the furoquinoline alkaloid maculine (1) and the new furanocoumarin 3,8-dimethoxyfuro[3,2g]coumarin (2).
One-and two-dimensional NMR experiments were used for the unambiguous assignment of the 1 H and 1... more One-and two-dimensional NMR experiments were used for the unambiguous assignment of the 1 H and 13 C NMR chemical shifts of 3,3-diisopentenyl-N-methyl-2,4-quinoldione and five novel reaction derivatives.
The activity of crude plant extracts of nine species of Rutaceae against the trypomastigote form ... more The activity of crude plant extracts of nine species of Rutaceae against the trypomastigote form of Trypanosoma cruzi was evaluated at 4 mg/ml. Thirty-two crude extracts were tested and eight of them showed significant activity (\80%). The most active extract was obtained from the stems of Pilocarpus spicatus (97.3%). Fractionation of the active crude extracts provided 25 fractions which were tested against the trypomastigote form of T. cruzi at 2 mg/ml. Of these six showed significant activity (\80%). The most active fractions (100%) were obtained from the leaves of Almeidea coerulea (butanol fraction) and Conchocarpus inopinatus (dichloromethane fraction).
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