Caldensin, A New Natural N-Methylaristolactam from Piper caldense

Cardozo, Euclides Lara; Chaves, María Célia de Oliveira

doi:10.1076/phbi.41.3.216.15091

Cited by 12 publications

(9 citation statements)

References 10 publications

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“…Among the species of the Brazilian flora, the genus Piper L. is one of the largest in the Piperaceae family, with 290 species and 45 varieties occurring in Brazil [9]. Some species of the genus are used as a flavoring of food and treatment of diseases [10]. A scientific study evidenced the antimicrobial potential of four species of the genus against Staphylococcus aureus and three strains of Candida, including C. albicans [11].…”

Section: Introductionmentioning

confidence: 99%

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Antibiotic Potential and Chemical Composition of the Essential Oil of Piper caldense C. DC. (Piperaceae)

et al. 2020

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Infections by multiresistant microorganisms have led to a continuous investigation of substances acting as modifiers of this resistance. By following this approach, the chemical composition of the essential oil from Piper caldense leaf and its antimicrobial potential were investigated. The antimicrobial activity was determined by broth microdilution method providing values for minimum inhibitory concentration (MIC), IC50, and minimum fungicidal concentration (MFC). The essential oil was tested as a modulator for several antibiotics, and its effect on the morphology of Candida albicans (CA) strains was also investigated. The chemical characterization revealed an oil composed mainly of sesquiterpenes. Among them are caryophyllene oxide (13.9%), spathulenol (9.1%), δ-cadinene (7.6%) and bicyclogermacrene (6.7%) with the highest concentrations. The essential oil showed very low activity against the strains of CA with the lowest values for IC50 and MFC of 1790 μg/mL and 8192 μg/mL, respectively. The essential oil modulated the activity of fluconazole against CA URM 4387 strain, which was demonstrated by the lower IC50 obtained, 2.7 μg/mL, whereas fluconazole itself presented an IC50 of 7.76 μg/mL. No modulating effect was observed in the MFC bioassays. The effect on fungal morphology was observed for both CA INCQS 40006 and URM 4387 strains. The hyphae projection was completely inhibited at 4096 μg/mL and 2048 μg/mL, respectively. Thus, the oil has potential as an adjuvant in antimicrobial formulations.

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Section: Introductionmentioning

confidence: 99%

“…Among the species of the genus, Piper caldense C. DC., is popularly known in Brazil as "pimenta d'água" or "pimenta d'arda", being commonly used for the treatment of snake bites, sedative and stomach problems [10]. Research using P. caldense essential oil has revealed promising antimicrobial potential [12,13].…”

Section: Introductionmentioning

confidence: 99%

Antibiotic Potential and Chemical Composition of the Essential Oil of Piper caldense C. DC. (Piperaceae)

et al. 2020

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“…Compounds 3-10 were identified as the previously reported natural products, aristolactam AII (3) (Priestap, 1985), enterocarpam II (4) (Kamaliah et al, 1986), caldensine (5) (Cardozo Júnior and Oliveira Chaves, 2003), sauristolactam (6) (Rao and Reddy, 1990), (-)-anonaine (7) (Guinaudeau et al, 1983;Simas et al, 2001) asimilobine (8) (Guo et al, 2011), altholactone (9) (Loder and Nearn, 1977) and (+)goniofufurone (10) (Fang et al, 1990) following 1D / 2D NMR ( 1 H, gCOSY, gHSQC, gHMBC, ROESY) and MS data analysis and comparison with literature values. Optical rotations were recorded for compounds 7, 8, 9 and 10 and were shown to match literature data: (Guinaudeau et al, 1983), (Guo et al, 2011), (Enders and Barbion, 2008) and (Prasad and Gholap, 2008) respectively.…”

Section: Identification Of Known Compoundsmentioning

confidence: 99%

Pyridocoumarin, aristolactam and aporphine alkaloids from the Australian rainforest plant Goniothalamus australis

et al. 2013

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Chemical investigation of the CH(2)Cl(2)/CH(3)OH extracts from aerial parts of the Australian plant Goniothalamus australis has resulted in the isolation of two pyridocoumarin alkaloids, goniothalines A (1) and B (2) as well as eight known natural products, aristolactam AII (3), enterocarpam II (4), caldensine (5), sauristolactam (6), (-)-anonaine (7), asimilobine (8), altholactone (9) and (+)-goniofufurone (10). The chemical structures of all compounds were determined by extensive spectroscopic and spectrometric analysis. Methylation of 2 using TMS-diazomethane afforded 1, which unequivocally established that both 1 and 2 possessed a 10-methyl-2H-pyrano[2,3-f]quinolin-2-one skeleton. These pyridocoumarin alkaloids are putatively proposed to arise biosynthetically from an aporphinoid precursor. Compounds 1-10 were evaluated for in vitro antimalarial activity against a chloroquine-sensitive Plasmodium falciparum line (3D7). Sauristolactam (6) and (-)-anonaine (7) exhibited the most potent antiparasitic activity with IC(50) values of 9 and 7 μM, respectively.

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“…A continuing search on the chemistry and bioactive agents from Brazilian north-northeast Piperaceae species have resulted in the isolation of amides, [2][3][4][5] aristolactams 6,7 and propenylphenols. [8][9][10][11][12] In this paper, we report the isolation and structure elucidation of (S)-8-formyl-3',5-dihydroxy-7-methoxy-6-methylflavanone (1), 3'-formyl-3,4',6'-trihydroxy-2'-methoxy-5'-methylchalcone (2), and ethyl 3,4-methylenedioxy-5-methoxy-7,8-dihydrocinnamate (3) from the branches of P. montealegreanum ( Figure 1).…”

Section: Introductionmentioning

confidence: 99%