Synthesis and anti-inflammatory activity of fluorinated isocoumarins and 3,4-dihydroisocoumarins

Qadeer, Ghulam; Rama, Nasim Hasan; Garduño-Ramı́rez, Marı́a Luisa

doi:10.1016/j.jfluchem.2007.02.021

Cited by 22 publications

(8 citation statements)

References 15 publications

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“…Damaging of the mucous membrane cells may provoke the production of reactive oxygen species (ROS), which promote inflammation (Yoshino et al, 2006). In this regard, the anti-inflammatory activities of the methanolic and alkaloid extracts from the four plant species were evaluated against TPA-induced mouse ear edema and their inhibitory activities compared with that of indomethacin, a commercially available anti-inflammatory drug that has 91.35% inflammation at a dose of 1.0 mg/ear (Qadeer et al, 2007). As evidenced in Table 1, the extracts from N. glauca that showed the highest anti-inflammatory activity were those from the stems (methanolic) (85.99%), flowers (methanolic) (81.93%), and roots (alkaloid), (80.5%).…”

Section: Resultsmentioning

confidence: 99%

“…The percentage of absorbance inhibition was calculated using the same equation as previously described. Anti-inflammatory activity of methanolic and alkaloid extracts on TPA-induced mouse ear edema This assay was conducted following the protocol previously described (Qadeer et al, 2007), where groups of three male CD-1 mice were used. Edema was induced by a topical application of 2.5 µg per ear of the edemogen TPA (12-O-tetradecanoylphorbol-13-acetate) dissolved in EtOH.…”

Section: Abts Assaymentioning

confidence: 99%

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Anti-Inflammatory and Antioxidant Activities of Methanol Extracts and Alkaloid Fractions of four Mexican Medicinal Plants of Solanaceae

et al. 2014

Afr. J. Trad. Compl. Alt. Med.

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Background: Methanol extracts and alkaloid fractions of different parts of four plant species belonging to Solanaceae family and used in Mexican traditional medicine were investigated for their total phenolic contents, anti-inflammatory and antioxidant properties. Materials and Methods: The total phenolic compounds of each extract was determined according to the Folin-Ciocalteu method, while the in vitro radical scavenging activities of the extracts were assessed using the DPPH and ABTS radicals. The in vivo anti-inflammatory activity was determined using the TPA-induced mouse ear edema model. Results:The methanol extracts contained the highest concentrations of phenolic compounds and also exhibited the best reducing power on the DPPH and ABTS radicals, in a concentration-dependent fashion. However, the anti-inflammatory activity did not follow the same trend, as some alkaloid fractions that showed low radical reducing power exhibited the strongest anti-inflammatory activity. Conclusion:The methanol extract obtained from the flowers of Nicotiana glauca presented the best overall performance with the largest amount of phenolic compounds (111 µg garlic acid equivalents/g of extract), the best antioxidant activity (94.80% inhibition of DPPH and 97.57% of ABTS) and the highest anti-inflammatory activity (81.93% inhibition of the inflammation).

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Section: Resultsmentioning

confidence: 99%

Section: Abts Assaymentioning

confidence: 99%

Anti-Inflammatory and Antioxidant Activities of Methanol Extracts and Alkaloid Fractions of four Mexican Medicinal Plants of Solanaceae

et al. 2014

Afr. J. Trad. Compl. Alt. Med.

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“…In a bioassay-guided study carried out to evaluate some previously obtained anti-inflammatory activity of L. racemosa extracts, the hexane (SMH), dichloromethane (SMD) and methanol (SMM) extracts were tested by the in vivo model of mouse ear inflammation induced with TPA as reported by Qadeer, G et al [9]. Our results showed that the extract with higher anti-inflammatory activity was SMD, with 58.3% of inhibition (Table 1).…”

Section: Resultsmentioning

confidence: 99%

Production of the Anti-Inflammatory Compound 6-O-Palmitoyl-3-O-β-D-glucopyranosylcampesterol by Callus Cultures of Lopezia racemosa Cav. (Onagraceae)

et al. 2014

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Lopezia racemosa Cav. is a plant used in Mexican traditional medicine to heal inflammatory diseases. From this plant we isolated the novel compound 6-O-palmitoyl-3-O-β-D-glucopyranosylcampesterol (1) and 6-O-palmitoyl-3-O-β-D-glucopyranosyl-β-sitosterol (2), previously reported to have cytotoxic activity on several cancer cell lines. We evaluated the anti-inflammatory activity of 1 in vivo by mouse ear edema induced with 12-O-tetradecanoylphorbol-13-acetate (TPA) and 57.14% inhibition was observed. The aim of our study was to obtain callus cultures derived from this plant species with the ability to produce the compounds of interest. Callus cultures were initiated on MS basal medium amended with variable amounts of naphthaleneacetic acid (NAA), or 2,4-dichlorophenoxyacetic acid (2,4-D), combined or not with 6-benzylaminopurine (BAP). Ten treatments with these growth regulators were carried out, using in vitro germinated seedlings as source of three different explants: hypocotyl, stem node, and leaf. Highest yield of 1 was observed on callus derived from leaf explants growing in medium OPEN ACCESSMolecules 2014, 19 8680 containing 1.0 mg/L 2,4-D and 0.5 mg/L BAP. Selected callus lines produced less 1 than wild plants but the in vitro cultured seedlings showed higher production. So we conclude that it could be attractive to further investigate their metabolic potential.

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“…Isochromen-1-ones are a class of compounds which exhibit a wide range of biological activities, including fungicidal (Findlay & Buthelezi, 1995), herbicidal and insecticidal , antibacterial (Zhang et al, 2008), anti-inflammatory (Qadeer, Rama & Garduñ o, 2007) and antitumour (Lam et al, 1989) activities. As part of a programme aimed at the production of new heterocyclic compounds containing an isochromene fragment, we have synthesized several 3,4-diamino derivatives using the methodology of Opatz & Ferenc (2005), and we report here the molecular and supramolecular structures of 3-amino-4-anilino-1H-isochromen-1-one, (I) (Fig.…”

Section: Commentmentioning

confidence: 99%

Hydrogen-bonded dimers in 3-amino-4-anilino-1H-isochromen-1-one and a hydrogen-bonded sheet in 3-amino-4-[methyl(phenyl)amino]-1H-isochromen-1-one

et al. 2013

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The molecules of 3-amino-4-anilino-1H-isochromen-1-one, C15H12N2O2, (I), and 3-amino-4-[methyl(phenyl)amino]-1H-isochromen-1-one, C16H14N2O2, (II), adopt very similar conformations, with the substituted amino group PhNR, where R = H in (I) and R = Me in (II), almost orthogonal to the adjacent heterocyclic ring. The molecules of (I) are linked into cyclic centrosymmetric dimers by pairs of N-H···O hydrogen bonds, while those of (II) are linked into complex sheets by a combination of one three-centre N-H···(O)2 hydrogen bond, one two-centre C-H···O hydrogen bond and two C-H···π(arene) hydrogen bonds.

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Synthesis and anti-inflammatory activity of fluorinated isocoumarins and 3,4-dihydroisocoumarins

Cited by 22 publications

References 15 publications

Anti-Inflammatory and Antioxidant Activities of Methanol Extracts and Alkaloid Fractions of four Mexican Medicinal Plants of Solanaceae

Anti-Inflammatory and Antioxidant Activities of Methanol Extracts and Alkaloid Fractions of four Mexican Medicinal Plants of Solanaceae

Production of the Anti-Inflammatory Compound 6-O-Palmitoyl-3-O-β-D-glucopyranosylcampesterol by Callus Cultures of Lopezia racemosa Cav. (Onagraceae)

Hydrogen-bonded dimers in 3-amino-4-anilino-1H-isochromen-1-one and a hydrogen-bonded sheet in 3-amino-4-[methyl(phenyl)amino]-1H-isochromen-1-one

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