Additional Coumarins from Kielmeyera reticulata

Cruz, Frederico G.; Moreira, Luciana de M.; Santos, Nelson A. S.; Guédès, Michel

doi:10.1590/s0103-50532002000500029

Cited by 9 publications

(5 citation statements)

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“…Despite 4-alkyl and 4-phenyl coumarins having been identified as the major constituents of some species that occur mainly in the cerrado (Gottlieb et al, 1969;Gottlieb & Stefani, 1970) and restinga (Cruz et al, 2002;Nogueira et al, 2008) and xanthones from species collected in the atlantic forest (Garcia-Cortez et al,1998;Pinheiro et al, 2003a), K. variabilis did not demonstrate the same pattern as observed by previous studies. The presence of flavonoids in this species is in agreement with previous reports from other genera in the Calophylleae tribe as Caraipa (Silveira et al, 2010), Mesua (Banerji & Chowdhury, 1993) and Calophyllum (Cechinel et al, 2009).…”

Section: Resultsmentioning

confidence: 57%

Chemical constituents and leishmanicidal activity from leaves of Kielmeyera variabilis

Cota¹,

Siqueira²,

Oliveira³

et al. 2012

Rev. bras. farmacogn.

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Abstract:Many phenolic compounds such as xanthones, quinones and coumarins have been isolated from Kielmeyera species; however the presence of flavonoids have been showed in other genera in the Calophylleae tribe as Caraipa, Mesua and Calophyllum. Six known glycosidic flavonoids: quercetin 3-β-O-galactopyranoside (1), quercetin 3-β-O-glucopyranoside (2), quercetin 3-O-α-rhamnoside (3), luteolin 6-C-β-glucopyranoside (4), isovitexin (5), kaempferol 3-O-α-rhamnoside (6) and one triterpene, lupenone (7) were isolated, for the first time, from organic crude extract of Kielmeyera variabilis Mart. & Zucc., Calophyllaceae, leaves. The crude organic extract from K. variabilis leaves exhibited 95% of leishmanidal activity at 20 µg/mL on amastigote-like form of Leishmania (Leishmania) amazonensis in vitro model and only compound 3 showed 40-45% of growth inhibition at concentration ranging from 0.78 to 20 µg/mL. In addition, quercetin 3-O-α-rhamnoside (quercitrin) was found to be the major metabolite. Our results and previous reports suggest that synergistic effects of flavonoid glycosides are the cause of significant leishmanidal activity of the crude organic extract from K. variabilis leaves.

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Section: Resultsmentioning

confidence: 57%

Chemical constituents and leishmanicidal activity from leaves of Kielmeyera variabilis

Cota¹,

Siqueira²,

Oliveira³

et al. 2012

Rev. bras. farmacogn.

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“…Kielmeyera reticulata Saddi is an endemic shrub of Bahia State, Brazil, and prior studies with extracts from its stems revealed the presence of mainly prenylated 4-phenyl and 4-alkylcoumarins. , The present study describes the purification of four new chromenones, named kielmeyerones A–D ( 1–4 ) (Figure ), for which the structures are related to 4-alkylcoumarins found in this and other species of the Kielmeyera genus. Moreover, its anti-inflammatory and antinociceptive properties have been described for the first time.…”

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confidence: 72%

Anti-Inflammatory and Antinociceptive Properties of Kielmeyerone A, a Chromenone Isolated from the Roots of Kielmeyera reticulata

et al. 2021

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Four new chromenones, kielmeyerones A−D (1− 4), were obtained from the roots of Kielmeyera reticulata. Their structures were elucidated based on spectroscopic data (NMR and HRESIMS) interpretation. The pharmacological activity of kielmeyerone A (1), the major compound, was evaluated using in vitro and in vivo inflammation and pain models. During in vitro screening, 1, at noncytotoxic concentrations (0.097−1.56 μM), inhibited NO production by J774 macrophages stimulated with LPS and IFN-γ. In the complete Freund's adjuvant-induced inflammation model in mice, 1 (12.5−50 mg/kg) inhibited paw edema, demonstrating an anti-inflammatory effect. Additionally, 1 (12.5−50 mg/kg) induced a dose-dependent antinociceptive effect in the late phase of the formalin test, a profile similar to those of nonsteroidal anti-inflammatory drugs. Mice treated with 1 (100 mg/kg) did not show motor performance alterations using a rotarod test. Thus, the present study has characterized new chromenones from Kielmeyera reticulata and has provided evidence of the anti-inflammatory and antinociceptive properties of one of these, kielmeyerone A (1).

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“…Because the chemical profile of this genus is characterized by the occurrence of phenolic compounds such as xanthones, 4‐phenyl, and 4‐alkylcoumarins (Garcia Cortez et al ., ; Cruz et al ., ; Cruz et al ., ; Scio et al ., ; Nogueira et al ., ) and on the basis of the results by HPLC‐DAD analysis, we suggest that these compounds could be present in the methanolic extract from stems of K . rugosa (MEKR).…”

Section: Discussionmentioning

confidence: 99%

Involvement of Cerebral Nervous System Areas and Cytokines on Antihyperalgesic and Anti‐Inflammatory Activities of Kielmeyera rugosa Choisy (Calophyllaceae) in Rodents

Melo

Brito

Santos

et al. 2014

Phytotherapy Research

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Kielmeyera rugosa is a medicinal plant known in Northeastern Brazil as 'pau-santo', and it is used in the treatment of several tropical diseases such as malaria, schistosomiasis, and leishmaniasis. We evaluated antihyperalgesic and anti-inflammatory activities of methanol stem extract of K. rugosa (MEKR) in mice. The mechanical hyperalgesia induced by carrageenan and tumor necrosis factor-alpha (TNF-α), prostaglandin E2 , and dopamine were assessed. We also investigated the anti-inflammatory effect of MEKR on carrageenan-induced pleurisy and paw edema. Ninety minutes after the treatment, the animals were submitted to an imunofluorescence for Fos protein. MEKR (100, 200, and 400 mg/kg; p.o.) inhibited the development of mechanical hypernociception and edema. MEKR significantly decreased TNF-α and interleukin 1β levels in pleural lavage and suppressed the recruitment of leukocytes. MEKR (1, 10, and 100 mg/mL) did not produce cytotoxicity, determined using the methyl-thiazolyl-tetrazolium assay in vitro. The locomotor activity was not affected. MEKR activated significantly the bulb olfactory, piriform cortex, and periaqueductal gray of the central nervous system. Our results provide first time evidence to propose that MEKR attenuates mechanical hyperalgesia and inflammation, in part, through an activation of central nervous system areas, mainly the periaqueductal gray and piriform cortex areas.

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Additional Coumarins from Kielmeyera reticulata

Abstract: Do extrato hexânico e da fase extraída com diclorometano do extrato metanólico de Kielmeyera

Cited by 9 publications

References 10 publications

Chemical constituents and leishmanicidal activity from leaves of Kielmeyera variabilis

Chemical constituents and leishmanicidal activity from leaves of Kielmeyera variabilis

Anti-Inflammatory and Antinociceptive Properties of Kielmeyerone A, a Chromenone Isolated from the Roots of Kielmeyera reticulata

Involvement of Cerebral Nervous System Areas and Cytokines on Antihyperalgesic and Anti‐Inflammatory Activities of Kielmeyera rugosa Choisy (Calophyllaceae) in Rodents

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