ABSTRACT
The effects of anacardic acids and cardols isolated from the cashew nut and apple Anacardium occidentale (Anacardiaceae) on murine B16-F10 melanoma cells were tested. Although anacardic acids and cardols were found to inhibit tyrosinase, a key enzyme in melanin synthesis, melanogenesis in melanocytes was not suppressed in cultured cells but rather enhanced. Both anacardic acids and cardols exhibited moderate cytotoxicity.
Subject(s)
Anacardic Acids/pharmacology , Anacardium/chemistry , Cytotoxins/pharmacology , Melanocytes/drug effects , Resorcinols/pharmacology , Anacardic Acids/chemistry , Anacardic Acids/isolation & purification , Animals , Cytotoxins/chemistry , Cytotoxins/isolation & purification , Melanins/biosynthesis , Melanoma/pathology , Mice , Monophenol Monooxygenase/antagonists & inhibitors , Resorcinols/chemistry , Resorcinols/isolation & purification , Tumor Cells, CulturedABSTRACT
6-Alkylsalicylic acids inhibit the linoleic acid peroxidation catalyzed by soybean lipoxygenase-1 (EC 1.13.11.12, type 1) competitively and without pro-oxidant effects. This activity is largely dependent on the nature of their alkyl side chains. Inhibitory activities of anacardic acids, viz. 6-pentadec(en)ylsalicylic acids, isolated from the cashew Anacardium occidentale, were initially used for comparison because their aromatic head portions are the same. Consequently, the data should be interpreted to mean that changes in the hydrophobic side chain tail portions of the molecules evaluated correlate with the specific activity determined.
Subject(s)
Anacardic Acids/pharmacology , Lipoxygenase Inhibitors/pharmacology , Anacardic Acids/chemistry , Anacardic Acids/pharmacokinetics , Drug Evaluation, Preclinical , Free Radical Scavengers/chemistry , Free Radical Scavengers/pharmacokinetics , Free Radical Scavengers/pharmacology , Lipoxygenase Inhibitors/chemistry , Lipoxygenase Inhibitors/pharmacokinetics , Spectrometry, Mass, Electrospray IonizationABSTRACT
On the basis of antibacterial anacardic acids, 6-pentadecenylsalicylic acids, isolated from the cashew apple, Anacardium occidentale L. (Anacardiaceae), a series of 6-alk(en)ylsalicylic acids were synthesized and tested for their antibacterial activity against Streptococcus mutans ATCC 25175. Among them, 6-(4',8'-dimethylnonyl)salicylic acid was found to exhibit the most potent antibacterial activity against this cariogenic bacterium with the minimum inhibition concentration (MIC) of 0.78 microg/ml.
Subject(s)
Anacardic Acids/chemical synthesis , Anacardic Acids/pharmacology , Dental Caries/prevention & control , Drug Design , Anti-Bacterial Agents/chemical synthesis , Anti-Bacterial Agents/pharmacology , Drug Evaluation, PreclinicalABSTRACT
A series of anacardic acid analogues possessing different side chains viz. phenolic, branched, and alicyclic were synthesized and their antibacterial activity tested against methicillin-resistant Staphylococcus aureus (MRSA). The maximum activity against this bacterium occurred with the branched side-chain analogue, 6-(4',8'-dimethylnonyl)salicylic acid, and the alicyclic side-chain analogue, 6-cyclododecylmethyl salicylic acid, with the minimum inhibitory concentration (MIC) of 0.39 microg/mL, respectively. This activity was superior to that of the most potent antibacterial anacardic acid isolated from the cashew Anacardium occidentale (Anacardiaceae), apple and nut, that is, the 6-[8'(Z),11'(Z),14'-pentadecatrienyl]salicylic acid.
Subject(s)
Anacardic Acids/pharmacology , Anti-Bacterial Agents/pharmacology , Methicillin Resistance , Staphylococcus aureus/drug effects , Anacardic Acids/chemical synthesis , Anacardic Acids/chemistry , Anacardium/chemistry , Anti-Bacterial Agents/chemical synthesis , Anti-Bacterial Agents/chemistry , Drug Design , Malus/chemistry , Methicillin/pharmacology , Microbial Sensitivity Tests , Nuts/chemistry , Structure-Activity RelationshipABSTRACT
Bhilawanol diene (3) isolated from bhilawan nut shell liquid was found to be a potent inhibitor of both soybean and potato lipoxygenases with IC50 values of 0.85 microM and 1.1 microM, respectively. However, the monoene (2) and saturated (1) bhilawanols exhibited relatively lower inhibitory activity. In addition, inhibition studies with synthetic analogues of salicylic acid (4-8) suggested that the unsaturated lipophilic side chain may be an absolute requirement for inhibitory activity.