Antioxidant and cyclooxygenase activities of fatty acids found in food

Several commercially available C-8 to C-24 saturated and unsaturated fatty acids (1-29) were assayed for cyclooxygenase-I (COX-I) and cyclooxygenase-II (COX-II) inhibitory and antioxidant activities. Among the saturated fatty acids tested at 60 microg mL(-1), there was an increase in antioxidant activity with increasing chain length from octanoic acid to myristic acid (C-8-C-14) and a decrease thereafter. All unsaturated fatty acids tested at 60 microg mL(-1) showed good antioxidant activity except for undecylenic acid (12), cis-5-dodecenoic acid (13), and nervonic acid (29). The highest inhibitory activities among the saturated fatty acids tested on cyclooxygenase enzymes COX-I and COX-II were observed for decanoic acid to lauric acid (3-5) at 100 microg mL(-1). Similarly, among the unsaturated fatty acids tested, the highest activities were observed for cis-8,11,14-eicosatrienoic acid (25) and cis-13,16-docosadienoic acid (27) at 100 microg mL(-1).     

Tumor cell proliferation and cyclooxygenase enzyme inhibitory compounds in Amaranthus tricolor

Amaranthus tricolor is consumed as a vegetable in Asia. Bioassay-directed isolation of leaves and stems of A. tricolor yielded three galactosyl diacylglycerols (1-3) with potent cyclooxygenase and human tumor cell growth inhibitory activities. The purified compounds were characterized by spectroscopic methods. In addition, the fatty acid moieties in diacyl galactosyl glyerols were characterized by GC-MS analyses. The galactosyl diacylglycerols 1-3 inhibited the cyclooxygenase-1 (COX-1) enzyme by 78, 63, and 93% and the cyclooxygenase-2 (COX-2) enzyme by 87, 74, and 95%, respectively. These compounds were tested for antiproliferative activity using human AGS (gastric), CNS (central nervous system; SF-268), HCT-116 (colon), NCI-H460 (lung), and MCF-7 (breast) cancer cell lines. Compound 1 inhibited the growth of AGS, SF-268, HCT-116, NCI-H460, and MCF-7 tumor cell lines with IC50 values of 49.1, 71.8, 42.8, 62.5, and 39.2 mug/mL, respectively. For AGS, HCT-116, and MCF-7 tumor cell lines, the IC50 values of compounds 2 and 3 were 74.3, 71.3, and 58.7 microg/mL and 83.4, 73.1, and 85.4, respectively. This is the first report of the COX enzyme inhibitory activity for galactosyl glycerols and antiproliferative activities against human colon, breast, lung, stomach, and CNS tumor cell lines.     

Mosquitocidal, nematicidal, and antifungal compounds from Apium graveolens L. seeds

The methanolic extract of Apium graveolens seeds was investigated for bioactive compounds and resulted in the isolation and characterization of mosquitocidal, nematicidal, and antifungal compounds sedanolide (1), senkyunolide-N (2), and senkyunolide-J (3). Their structures were determined by 1H and 13C NMR spectral methods. Compounds 1-3 gave 100% mortality at 25, 100, and 100 microg mL(-1), respectively, on the nematode, Panagrellus redivivus. Compound 1 showed 100% mortality at 50 microg mL(-1) on nematode, Caenorhabditis elegans, and fourth-instar mosquito larvae, Aedes aegyptii. Also, it inhibited the growth of Candida albicans and Candida parapsilasis at 100 microg mL(-1). Compounds 2 and 3 were isolated for the first time from A. graveolens. This is the first report of the mosquitocidal, nematicidal, and antifungal activities of compounds 1-3.     

AFLP Analysis of the Phenetic Organization and Genetic Diversity in the Sugarcane Complex, Saccharum and Erianthus

Amplified fragment length polymorphism (AFLP) markers were evaluated for determining the phylogenetic relationships, and the diversity in the Saccharum complex using 30 clones belonging to S. officinarum, S. robustum, S. spontaneum, S. barberi, S. sinense and the related genus Erianthus. The phenetic tree of the species clones based on AFLP data was consistent with the known taxonomical relationships. AFLP gave higher resolution of closely related species into discrete groups than that by RAPD and RFLP markers, reported earlier. The levels of diversity within the various Saccharum species were also found to be higher than those obtained previously with the same set of clones using RAPD markers. The intraspecies similarity in S. barberi and S. sinense was much higher than interspecies similarity suggesting a clear separation of the two, which are considered ‘horticultural species’. The genetic similarity matrix derived from a single primer combination highly correlated (r = 0.980) with that obtained from all the 12 primer combination used in the study, thus highlighting the efficiency of a single primer combination in delineating species relationships. All the primer combinations could identify markers that are specific to each of the species and the genus Erianthus. Among the species, specific markers were highest in S. spontaneum followed by S. robustum, S. barberi, S. officinarum and S. sinense. Erianthus had a distinct profile with 30% of the total amplified fragments being specific to it. This offers great scope for identifying intergeneric hybrids, which has been very difficult using morphological traits and RAPD markers. High degree of correspondence between the results from the cluster analysis based on Jaccard's similarity index, Neighbour Joining tree based on Sokal and Michener distance matrix and AFTD (Analyses Factorielle on Table of Distances) analysis clearly demonstrated that AFLP markers would be an appropriate tool in providing better information about the relationships among the species, estimation of diversity, and in revealing species and genus specific markers that could be directly applied in sugarcane breeding programmes.     

Insulin secretion and cyclooxygenase enzyme inhibition by cabernet sauvignon grape skin compounds

Bioassay-guided isolation and purification of hexane and ethyl acetate extracts of Cabernet Sauvignon grape skin yielded nine compounds (1-9), which were identified as beta-sitosterol-6'-linolenoyl-3-O-beta-D-glucopyranoside (1), beta-sitosterol (2), beta-sitosterol-3-O-beta-D-glucoside (3), oleanolic acid (4), oleanolic aldehyde (5), resveratrol (6), (+)-epsilon-viniferin (7), (-)-catechin (8), and 1-triacontanol (9). The structures of these compounds were established by spectroscopic methods. The compounds were assayed for insulin production using an INS-1 cell assay. In a dose-response study, compound 4 stimulated insulin production of INS-1 cells by 20.23, 87.97, 1.13, and 6.38 ng of insulin/mg of protein at 6.25, 12.5, 25, and 50 microg/mL, respectively. This trend was similar to the dose-dependent insulin production of INS-1 cells by glucose. Compound 5 also showed a dose-dependent insulin production in this assay. The isolated compounds were also assayed for cyclooxygenase-1 and -2 (COX) enzyme inhibitory activities. At 100 microg/mL, compounds 2, 3, and 4 inhibited the COX-2 enzyme by 11, 12, and 10%, respectively, but did not show activities on the COX-1 enzyme. Compounds 6, 7, and 8 at 100 microg/mL inhibited the COX-1 enzyme by 98, 99, and 98%, respectively, and the COX-2 enzyme by 0, 47, and 72%, respectively. This is the first report of beta-sitosterol-6'-linolenoyl-3-O-beta-D-glucopyranoside (1) from grape skin and insulin secretion activities of compounds 4 and 5.     

Adsorption and exchange of Zinc in two representative Indian soils

Preliminary investigation on Zn adsorption, exchange and fixation in two representative Indian soils (Ap-horizons of Ferralsols) showed that nearly the entire amount of added Zn could revert to “fixed” forms rendering it inaccessible, at least temporarily, to growing plant roots.     

Ethyl p-methoxycinnamate isolated from a traditional anti-tuberculosis medicinal herb inhibits drug resistant strains of Mycobacterium tuberculosis in vitro

Many plants are used in Ayurveda for the treatment of tuberculosis. Our aim was to examine if these plants possess any specific molecule that inhibits Mycobacterium tuberculosis. One of them, Kaempferia galanga, yielded an anti-TB molecule, ethyl p-methoxycinnamate (EPMC). By resazurin microtitre assay (REMA), EPMC was shown to inhibit M. tuberculosis H37Ra, H37Rv, drug susceptible and multidrug resistant (MDR) clinical isolates (MIC 0.242-0.485 mM). No cross resistance was observed to any standard anti-TB drugs in the MDR strains. The compound did not inhibit any prototype bacteria tested. EPMC seems to be a potential anti-TB lead molecule.