Biological activity of phenolic lipids

Stasiuk, Maria; Kozubek, Arkadiusz

doi:10.1007/s00018-009-0193-1

Cited by 223 publications

(177 citation statements)

References 178 publications

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“…The ability of these type of compounds to inhibit bacterial growth appears to depend on their interaction with proteins and/or their membrane disrupting properties. 64,68 It is important to highlight that phenolic lipids, for example, are highly active for Gram-positive bacteria, Mycobacterium smegmatis and Mycobacterium tuberculosis, as well as for phytopathogenic bacteria, 68,69 matching the results obtained in this work.…”

Section: Resultssupporting

confidence: 77%

Synthesis, Antibacterial and Antitubercular Evaluation of Cardanol and Glycerol‑Based β-Amino Alcohol Derivatives

Manda

Prasad

Thatikonda

et al. 2017

J. Braz. Chem. Soc.

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The synthesis of novel amino alcohol derivatives based on cardanol and glycerol were achieved in good yields and characterized by 1 H and 13 C NMR (nuclear magnetic resonance) and MS (mass spectrometry). In addition, we evaluated the in vitro antimicrobial activity against Gram-positive (Staphylococcus aureus, standard and clinical strains), Gram-negative (Escherichia coli) and M. tuberculosis bacterial strains. The bioassay results indicated that four compounds showed activity against S. aureus, including the clinical resistant strain, with MIC (minimum inhibitory concentration) ranging from 3.90 to 15.60 µg mL -1 and M. tuberculosis, with MIC 90 (minimum inhibitory concentration required to inhibit the growth of 90% of organisms) ranging from 3.18 to 7.36 µg mL -1 .Keywords: CNSL, cardanol, amino alcohols, epoxide ring opening, antimicrobial activity IntroductionThe synthesis of fine chemicals from natural renewable resources has received great interest in synthetic community and is becoming a significant and challenging theme for researchers of both the academic and industrial sectors. Among the renewable materials, cardanol has attracted considerable attention due to its unique nature.1 Cardanol is a low cost, naturally occurring renewable non-isoprenoic phenolic lipid-mixture of cashew nut shell liquid (CNSL). The structural benefits of cardanol are carrying reactive phenolic group and hydrophobic alkyl/alkenyl side chain at meta-position of phenolic group. With these unique structural features, cardanol and its derivatives are renowned amphiphilic building blocks and precursors of high-value fine chemicals and supramolecular structures. Its derivatives present many biological activities such as: fungicidal, bactericidal, molluscicidal, larvicidal, anti-inflammatory, antioxidant and, towards serious disorders like cancer and obesity. [2][3][4][5][6][7][8][9] It is also described in the literature in recent years, that cardanol frameworks are involved to build phenolic resins, 10-12 bio-based polymers, 13 epoxy curing resins, 14-16 reactive diluents, 17,18 and fluorescent compounds. 19,20 Similarly, glycerol is another important renewable material used in the synthesis of higher value-added fine chemicals through green chemistry procedures in the last years. It may be applied, for instance, to generate hydrogen gas, 21 Synthesis, Antibacterial and Antitubercular Evaluation of Cardanol and Glycerol-Based β-Amino Alcohol Derivatives J. Braz. Chem. Soc. 640 Cardanol and glycerol can be starting materials to prepare β-amino alcohols which is a vital interesting class of organic intermediates due to their abundant existence in nature and they are useful in the preparation of wide range of biologically active natural and synthetic frameworks, pharmaceuticals (e.g. β-blockers), unnatural β-amino acids, pesticides and chiral auxiliaries. [29][30][31][32] Additionally, β-amino alcohols have many applications as antibiotics, anti-bacterial drugs and, steroids.33 One of the most classical approaches toward the syn...

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Section: Resultssupporting

confidence: 77%

Synthesis, Antibacterial and Antitubercular Evaluation of Cardanol and Glycerol‑Based β-Amino Alcohol Derivatives

Manda

Prasad

Thatikonda

et al. 2017

J. Braz. Chem. Soc.

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“…Phenolic compounds such as cardol and methylcardol, from tCNSL under alkaline conditions form liposomal structure, providing a controlled release (Stasiuk and Kozubek, 2010). Spanghero et al (2008) suggest the effects of functional oils may be pH dependent, acting more effectively when rumen pH is close to 5.5 which were not observed in the present study.…”

Section: Resultscontrasting

confidence: 58%

“…These compounds are the main active constituents of tCNSL and have antibacterial, antiprotozoal, and antifungal properties (Stasiuk and Kozubek, 2010).…”

Section: Introductionmentioning

confidence: 99%

Aumento das doses dietéticas de líquido de casca de castanha de caju na digestibilidade ruminal e intestinal de nutrientes em novilhos alimentados com uma dieta rica em grãos

et al. 2017

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sUMMAryThe objective was to evaluate the inclusion of technical cashew nut shell liquid (tCNSL) in the concentrate for cattle fed on a high-grain diet on feed intake, ruminal and total apparent digestibility coefficients of nutrients, fermentation characteristics and microbial efficiency. Four Holstein steers (445 ± 23.39 kg of body weight) fitted with ruminal and duodenal cannulae were used. The diets had (in DM basis) 144 g kg-1 of crude protein and 799 g kg-1 of total digestible nutrients, with a forage to concentrate ratio of 15:85. The experimental design was a 4 x 4 Latin square with 10-day experimental periods. The diets consisted of 0; 300; 600 and 1200 mg of tCNSL in DM of the concentrate. Intake and total apparent digestibility coefficient of nutrients, on DM basis, were not affected by experimental diets. However, ruminal digestibility of ether extract showed quadratic response in which animals fed 0 and 300 mg tCNSL kg-1 of concentrate had the lowest values for ruminal digestibility. Ruminal ammonia nitrogen, plasma urea nitrogen and microbial efficiency were not affected by treatments. However, ruminal pH tended to increase when animals were fed with tCNSL. Objetivou-se avaliar os efeitos da inclusão do líquido da casca da castanha de caju (tCNSL) na dieta de bovinos alimentados com dietas ricas em grão, sobre a ingestão e o coeficiente de digestibilidade ruminal e total dos nutrientes; as características de fermentação ruminal, eficiência de síntese microbiana no rúmen e parâmetro sanguíneo, através do nitrogênio ureico plasmático. Foram utilizados quatro novilhos da raça Holandesa (445 ± 23,39 kg de peso vivo) providos de cânula ruminal e duodenal, recebendo uma dieta com 144 g kg-1 de proteína bruta e 799 g kg-1 de nutrientes digestíveis totais, com uma relação volumoso:concentrado de 15:85. O delineamento experimental foi o quadrado latino 4 x 4 com 10 dias de períodos experimentais. As dietas foram compostas de 0, 300, 600 e 1200 mg de tCNSL na matéria seca (MS) do concentrado. A ingestão e os coeficientes de digestibilidade aparente total dos nutrientes, com base na MS, não foram influenciados pela inclusão de tCNSL na dieta. O coeficiente de digestibilidade ruminal (CDR) do extrato etéreo apresentou resposta quadrática, em que os animais que consumiram 0 e 300 mg tCNSL d-1 apresentaram menores valores de CDR. O uso do LCCt não influenciou o nitrogênio amoniacal no rúmen, o nitrogênio ureico plasmático e a eficiência de síntese microbiana. No entanto, houve tendência de maior pH ruminal quando os animais consumiram o LCCt. PAlAvrAs-chAve AdicionAisAditivo. Cardol. Cardanol. Digestibilidade. Fermentação ruminal.

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“…More in general, the ability to cleave DNA was repetitively reported for resorcinolic lipids. This is the case of 5-n-tridecyl and 5-n-pentadecenylresorcinols extracted from the plant Hakea sp., which exhibited the ability to induce Cu 2+ -dependant scission of the replicating strand in plasmid DNA φX174 (Stasiuk & Kozubek 2010). Some authors also reported that several bis-dihydroxyalkylbenzenes are capable of mediating Cu 2+ -dependent DNA cleavage and strongly inhibiting DNA polymerase β.…”

Section: Resultsmentioning

confidence: 99%

“…The molecule belongs to a large group of natural compounds known as resorcinolic lipids (also called alkylresorcinols, or 5-alkylresorcinols), widely detected in plants, fungi, algae, and in one animal species, the marine sponge Haliclona sp. (Kozubek & Tyman 1999;Stasiuk & Kozubek 2010). The common structural motif of resorcinolic lipids resides in the 1,3-dihydroxybenzene (resorcinol) unit bearing an alkyl or an alkenyl chain at 5-position of the aromatic ring.…”

Section: Introductionmentioning

confidence: 99%

Antimicrobial activity of the protozoan toxin climacostol and its derivatives

et al. 2012

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Climacostol is a defense toxin produced by the ciliated protozoan Climacostomum virens and belongs to resorcinolic lipids, a group of compounds that shows antimicrobial, antiparasitic, and cytotoxic activities. In this study we investigate the antimicrobial activity of climacostol and its alkyl and alkynyl derivatives against a panel of bacterial and fungal pathogens. Our results show a good and comparable antimicrobial activity of the three compounds, which have resulted effective against Gram-positive bacteria and Candida with MIC and MBC ranging from 8 to 32 mg L −1 , whereas no significant effect against Gram-negative species has been observed. Taken as a whole, the experimental data reported in the current study suggest that differences in the saturation rate of the lateral chain of climacostol are not related to the activity of the molecule. Therefore, it is likely that the general structure of the two moieties, i.e., the di-hydroxy-phenyl group and the alkenyl chains, contributes to the overall antibiotic behaviour.

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Biological activity of phenolic lipids

Cited by 223 publications

References 178 publications

Synthesis, Antibacterial and Antitubercular Evaluation of Cardanol and Glycerol‑Based β-Amino Alcohol Derivatives

Synthesis, Antibacterial and Antitubercular Evaluation of Cardanol and Glycerol‑Based β-Amino Alcohol Derivatives

Aumento das doses dietéticas de líquido de casca de castanha de caju na digestibilidade ruminal e intestinal de nutrientes em novilhos alimentados com uma dieta rica em grãos

Antimicrobial activity of the protozoan toxin climacostol and its derivatives

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