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Amino acid residues in ribonuclease MC1 from bitter gourd seeds which are essential for uridine specificity.

The ribonuclease MC1 (RNase MC1), isolated from seeds of bitter gourd (Momordica charantia), consists of 190 amino acids and is characterized by specific cleavage at the 5'-side of uridine. Site-directed mutagenesis was used to evaluate the contribution of four amino acids, Asn71, Val72, Leu73, and Arg74, at the alpha4-alpha5 loop between alpha4 and alpha5 helices for recognition of uracil base by RNase MC1. Four mutants, N71T, V72L, L73A, and R74S, in which Asn71, Val72, Leu73, and Arg74 in RNase MC1 were substituted for the corresponding amino acids, Thr, Leu, Ala, and Ser, respectively, in a guanylic acid preferential RNase NW from Nicotiana glutinosa, were prepared and characterized with respect to enzymatic activity. Kinetic analysis with a dinucleoside monophosphate, CpU, showed that the mutant N71T exhibited 7.0-fold increased K(m) and 2.3-fold decreased k(cat), while the mutant L73A had 14.4-fold increased K(m), although it did retain the k(cat) value comparable to that of the wild-type. In contrast, replacements of Val72 and Arg74 by the corresponding amino acids Leu and Ser, respectively, had little effect on the enzymatic activity. This observation is consistent with findings in the crystal structure analysis that Asn71 and Leu73 are responsible for a uridine specificity for RNase MC1. The role of Asn71 in enzymatic reaction of RNase MC1 was further investigated by substituting amino acids Ala, Ser, Gln, and Asp. Our observations suggest that Asn71 has at least two roles: one is base recognition by hydrogen bonding, and the other is to stabilize the conformation of the alpha4-alpha5 loop by hydrogen bonding to the peptide backbone, events which possibly result in an appropriate orientation of the alpha-helix (alpha5) containing active site residues. Mutants N71T and N71S showed a remarkable shift from uracil to guanine specificity, as evaluated by cleavage of CpG, although they did exhibit uridine specificity against yeast RNA and homopolynucleotides.

Amino Acid Sequence↗

Enzymatic synthesis of gamma-glutamylvaline to improve the bitter taste of valine.

The taste of several bitter amino acids is reduced, sourness produced, and preference increased by gamma-glutamylization. An enzymatic method for synthesizing gamma-Glu-Val involving bacterial gamma-glutamyltranspeptidase (GGT) was developed. The optimum reaction conditions for the synthesis of gamma-Glu-Val were 20 mM Gln, 300 mM Val, and 0.04 U/ml GGT, pH 10. After 3-hr incubation at 37 degrees C, 17.6 mM gamma-Glu-Val was obtained, with the yield being 88%. gamma-Glu-Val was purified on a Dowex 1 x 8 column and then identified by NMR.

Dipeptides↗

Photooxidative degradation of beer bittering principles: a key step on the route to lightstruck flavor formation in beer.

Isohumulones, dihydroisohumulones, tetrahydroisohumulones, and humulinones, important hop-derived bittering compounds in beer, were shown to give rise to reactive triacylmethyl radicals on interaction with triplet-excited riboflavin after spin trapping by 5,5-dimethyl-1-pyrroline N-oxide or 2-methyl-2-nitrosopropane, followed by electron paramagentic resonance spectroscopy combined with spectral simulation. Electron abstraction from the ionized beta-tricarbonyl chromophore, which is common to all five-membered ring hop derivatives, is the initial event on photoinduced degradation. Radicaloid decomposition of isohumulones leads to precursors for 3-methylbut-2-ene-1-thiol, the lightstruck constituent in beer. Interaction of reduced derivatives of isohumulones with triplet-excited riboflavin furnished radical precursors of volatile aldehydes, which may lead to the development of unpleasant stale or cardboard flavors.

Beer↗

Enrichment of refined olive oil with phenolic compounds: evaluation of their antioxidant activity and their effect on the bitter index.

The study of the antioxidant effects of biophenolic compounds is supported by the current interest in natural products and the ongoing replacement of synthetic antioxidants by natural antioxidants from plant sources. Olives and olive oil, especially extra virgin olive oil, contain a variety of bioactive compounds (phytochemicals) widely considered to be potentially beneficial for health. This research was focused on evaluating the antioxidant activity of the enriched refined olive oil to discover a possible functional food application. Different concentrations of individual and combined phenolic compounds were added to the refined olive oil as lipid matrix, and the antioxidant activity expressed as oxidative stability in hours was determined by using the Rancimat method. Additionally, the bitter index was evaluated to assess the effect of the enrichment in relation to the organoleptic quality. The results showed that the antioxidant activity depends on the concentration of the phenol used for the assay and the chemical structure. In general, the most positive effects were observed in 3,4-dihydroxy and 3,4,5-trihydroxy structures linked to an aromatic ring that conferred to the moiety a higher proton dislocation, thus facilitating the scavenging activity.

Antioxidants↗

Rapid high-performance liquid chromatography method to quantitate elaterinide in juice and reconstituted residues from a bitter mutant of hawkesbury watermelon.

A C(18) reversed-phase HPLC method has been developed to analyze the concentration of 2-O-beta-D-glycopyranosyl-cucurbitacin E (synonym, elaterinide) in juice or reconstituted residues of juice derived from a bitter mutant of Hawkesbury watermelon, Citrullus lanatus (Thunb.) Matsum. & Nakai. The method requires only two steps (homogenation and filtration) for sample preparation prior to column injection and, thus, is amenable to processing large numbers of test samples. Percent elaterinide in juice samples from whole fruit, processed in various ways, ranged from 0.0230 to 0.0808%. Error differences in percent elaterinide for repetitive analyses within the same lot of juice ranged from 1.2 to 5.6%.

Beverages↗

Stevisalioside A, a novel bitter-tasting ent-atisene glycoside from the roots of Stevia salicifolia.

A new acetylated ent-atisene glycoside, stevisalioside A [1], has been isolated as a bitter-tasting principle from Stevia salicifolia roots. The structure was established by the interpretation of spectral data, with the nmr assignments of this compound being based on 1H-1H COSY, 1H-13C HETCOR, and selective INEPT experiments. A rearrangement product 4 of the aglycone moiety obtained by alkaline hydrolysis supported the structure of 1. This is the first report of the occurrence of an atisane-type diterpene from the genus Stevia.

Carbohydrate Sequence↗

Ingestive responses of human newborns to salty, sour, and bitter stimuli.

Human newborns (1-4 days old) were offered two fluids differing in taste for 3 min each. The volumes ingested were measured. Infants offered water and bitter or sour solutions did not ingest them differentially, which corroborated earlier observations with weaker solutions. A sucrose solution was used to raise baseline ingestion above that of water. Infants offered the sucrose solution with and without urea, citric acid, or sodium chloride consumed less of it when citric acid was added. They were indiffferent to the addition of urea or sodium chloride. The failure to observe intakes lower than that of water suggests that newborns maximally inhibit their ingestion of water. The effects of sex, age, birth weight, and individual consistency on intake were assessed.

Age Factors↗

Exactly which synephrine alkaloids does Citrus aurantium (bitter orange) contain?

Following the withdrawal of ephedrine from the dietary supplement marketplace sales of products containing Citrus aurantium (CA) (bitter orange) for weight loss are believed to have increased dramatically. CA contains a number of constituents speculated to lead to weight loss, of which the most frequently cited constituent is synephrine. Concerns have been raised about the safety of products containing synephrine. To develop an adequate basis for clinical and public health recommendations, it is necessary to understand the nature of the synephrine alkaloids in CA. There are six possible isomers of synephrine (para, meta, ortho; and for each a d or l form). Some authors have stated that CA contains only p-synephrine, whereas other authors have stated that CA contains m-synephrine. This is an important distinction because the two molecules have different pharmacologic properties, which may differentially affect safety and efficacy. We are unable to identify published data that explicitly show whether CA contains p-synephrine, m-synephrine, or both. In this brief report, we show that at least one product purportedly containing synephrine alkaloids from CA contains both p-synephrine and m-synephrine. We believe this justifies further investigation into which synephrine alkaloids are present in CA and products purportedly containing synephrine alkaloids from CA and the relative quantities of each of the different isomers.

Alkaloids↗

Metabolic and physiological effects of ingesting extracts of bitter orange, green tea and guarana at rest and during treadmill walking in overweight males.

OBJECTIVE: This study examined the acute effects of ingesting a widely used commercial formula containing extracts of bitter orange, green tea and guarana (Gx) on the metabolic rate and substrate utilisation in overweight, adult males at rest (study 1) and during treadmill walking (study 2). SUBJECTS: Two different groups of 10 sedentary males with more than 20% body fat participated in studies 1 and 2. DESIGN: In each study, subjects participated in two experimental trials during which they were given two 500 mg capsules containing either Gx or a placebo (P) in a counterbalanced double-blind manner. Doses of the main active ingredients were 6 mg of synephrine, 150 mg caffeine and 150 mg catechin polyphenols. MEASUREMENTS: In study 1, subjects completed 7 h supine rest with baseline measures taken during the first hour, with expired gases, blood pressure, heart rate and venous blood being collected every 30 min for the remaining 6 h following ingestion of Gx or P. In study 2, subjects exercised for 60 min at 60% heart rate reserve following ingestion of Gx or P 1 h previously. Venous blood samples were collected twice at rest and at 5, 10, 15, 20, 30, 40, 50 and 60 min, with expired gas measurements taken at 4, 9, 14, 19, 29, 39, 49 and 59 min. In both studies, venous blood was analysed for NEFA, glycerol, glucose and lactate concentrations, while expired gases were used to calculate ATP production from carbohydrate and NEFA, as well as the total substrate utilised. RESULTS AND CONCLUSION: The results did not show any significant effect of Gx ingestion on total ATP utilisation during 6 h rest or during 60 min treadmill walking. Changes were observed in the relative contributions of CHO and NEFA oxidation to ATP production in both studies, such that there was an increase in ATP production from CHO and a decrease from NEFA. The increase in CHO oxidation was shown to be as high as 30% at rest.

Adenosine Triphosphate↗

Photooxidative degradation of beer bittering principles: product analysis with respect to lightstruck flavour formation.

Isohumulones, the main bittering agents in beer, are decomposed by light-induced reactions, thereby leading to radical precursors on the pathway to lightstruck flavour formation. Excited flavins, formed on visible-light irradiation, readily interact with isohumulones, as well as with reduced and oxidized derivatives thereof. From identification of both volatile and non-volatile reaction products thus formed, feasible degradation mechanisms are proposed.

Journal Article↗

Erythropoietic and anti-obesity effects of Garcinia cambogia (bitter kola) in Wistar rats.

The anti-obesity and erythropoietic effects of crude ethanolic extracts of Garcinia cambogia (bitter kola) seeds on Wistar rats (Rattus norvegicus) were investigated. The rats were divided into three dosage groups: A (0 mg/kg of body weight), B (200 mg/kg) and C (400 mg/kg). Weight changes, plasma lipoprotein levels and the lipid profile of the liver, gastrointestinal system and adipose tissue were monitored as indices for anti-obesity, while the RBC (red blood cell) count (assessed by using a haemocytometer) was monitored as a measure of erythropoiesis. The extract was administered by gavage for 5 weeks. The results for each test group was compared statistically with those for the control (P<0.05). Analysis of the results showed a significant increase in RBC counts in both test groups and a decrease in weights of experimental animals. There was a dose-dependent decrease in the plasma level of very-low-density lipoprotein and a dose-dependent increase in the level of chylomicrons. There was a slight, but significant, decrease in the level of high-density lipoprotein and a significant increase in the level of LDL (low-density lipoprotein). There was significant dose-dependent decrease in the TAG (triacylglycerol) pool of adipose tissue and the liver of the test groups, but a significant increase in the TAG pool of the gastrointestinal system. The increase in the TAG pool of the gastrointestinal system is possibly compensatory. The results therefore confirm that ethanolic extracts of G. cambogia seeds have both haematologically enhancing and anti-obesity effects. The decrease in the high-density-lipoprotein level and an increase in the LDL level may play an important role in cardiovascular disease.

Animals↗

Fluorimetric studies of the binding of Momordica charantia (bitter gourd) lectin with ligands.

The association constants for the binding of a series of ligands with a galactose-specific lectin from Momordica charantia (bitter gourd) has been determined through the ligand-induced quenching of protein fluorescence. Analysis of the iodide quenching suggested that there is a slight increase in the accessibility of tryptophan residues of the lectin on binding lactose.

Carbohydrates↗

HIV inhibitor from Thai bitter gourd.

Thai bitter gourd protein (MRK29) was isolated from Momordica charantia ripe fruit and seed. The purification was performed by ammonium sulfate fractionation and gel filtration chromatography. MRK29 possessed one isoelectric point of (pI) > or = 9, and the time of flight mass spectrum (TOFMS) indicated its molecular weight at 28.6 kD. The twenty amino acid sequence from the N-terminus was in the following order: 1Asp Val Asn Phe Arg Leu Ser Gly Ala 10Asp Pro Arg X Tyr Gly Met Phe Ile Glu 20Asp. MRK29 inhibited the HIV-1 reverse transcriptase with 50% IR at the concentration of 18 micrograms/ml. MRK29 was concentrated in the 30-60% salt precipitated fraction, at which the concentration of 0.175 microgram/ml exerted 82% reduction of viral core protein p24 expression in HIV-infected cells. MRK29 might have modulatory role on immune cells, because it increased 3-fold TNF activity.

Amino Acid Sequence↗

Isohumulones, bitter acids derived from hops, activate both peroxisome proliferator-activated receptor alpha and gamma and reduce insulin resistance.

The peroxisome proliferator-activated receptors (PPARs) are dietary lipid sensors that regulate fatty acid and carbohydrate metabolism. The hypolipidemic effects of fibrate drugs and the therapeutic benefits of the thiazolidinedione drugs are due to their activation of PPARalpha and -gamma, respectively. In this study, isohumulones, the bitter compounds derived from hops that are present in beer, were found to activate PPARalpha and -gamma in transient co-transfection studies. Among the three major isohumulone homologs, isohumulone and isocohumulone were found to activate PPARalpha and -gamma. Diabetic KK-Ay mice that were treated with isohumulones (isohumulone and isocohumulone) showed reduced plasma glucose, triglyceride, and free fatty acid levels (65.3, 62.6, and 73.1%, respectively, for isohumulone); similar reductions were found following treatment with the thiazolidinedione drug, pioglitazone. Isohumulone treatment did not result in significant body weight gain, although pioglitazone treatment did increase body weight (10.6% increase versus control group). C57BL/6N mice fed a high fat diet that were treated with isohumulones showed improved glucose tolerance and reduced insulin resistance. Furthermore, these animals showed increased liver fatty acid oxidation and a decrease in size and an increase in apoptosis of their hypertrophic adipocytes. A double-blind, placebo-controlled pilot study for studying the effect of isohumulones on diabetes suggested that isohumulones significantly decreased blood glucose and hemoglobin A1c levels after 8 weeks (by 10.1 and 6.4%, respectively, versus week 0). These results suggest that isohumulones can improve insulin sensitivity in high fat diet-fed mice with insulin resistance and in patients with type 2 diabetes.

Aged↗

Dietary isohumulones, the bitter components of beer, raise plasma HDL-cholesterol levels and reduce liver cholesterol and triacylglycerol contents similar to PPARalpha activations in C57BL/6 mice.

The effects of dietary isohumulones, the main components accounting for the bitter taste of beer, on lipid metabolism were examined. Young female C57BL/6N mice were fed diets containing isomerized hop extract (IHE), which consists mainly of isohumulones. Administration of IHE with an atherogenic (high-fat and high-cholesterol) diet for 2 weeks resulted in a significant increase in plasma HDL-cholesterol (P<0.01), along with a concomitant reduction in the atherosclerosis index, an increase in liver weight and a decrease in body weight gain in a dose-dependent manner. When animals received IHE with either a cholesterol or a basal diet for 1 week, significant decreases in the liver content of cholesterol (P<0.01) and triacylglycerol (cholesterol diet, P<0.01) were observed. Quantitative analyses of hepatic mRNA levels revealed that IHE administration resulted in up-regulation of mRNA for acyl-CoA oxidase, acyl-CoA synthetase, hydroxymethylglutaryl-CoA synthetase, lipoprotein lipase and fatty acid transport protein, and down-regulation of mRNA for Apo CIII and Apo AI. Administration of purified isohumulones effectively resulted in the same changes as IHE. Administration of fenofibrate, an agonist for PPARalpha, with a cholesterol diet caused marked hepatomegaly, an increase in plasma HDL-cholesterol, a decrease in hepatic cholesterol content, and alterations in hepatic mRNA levels similar to those observed in mice given IHE. Taken together, these results suggest that the modulation of lipid metabolism observed in mice fed diets containing isohumulones is, at least in part, mediated by activation of PPARalpha.

Acyl-CoA Oxidase↗

Reduced adiposity in bitter melon (Momordica charantia) fed rats is associated with lower tissue triglyceride and higher plasma catecholamines.

Slower weight gain and less visceral fat had been observed when rats fed a high-fat diet were supplemented with freeze-dried bitter melon (BM) juice; the metabolic consequences and possible mechanism(s) were further explored in the present study. In a 4-week experiment, rats were fed a low-fat (70 g/kg) or a high-fat (300 g/kg) diet with or without BM (7.5 g/kg or 0.75%). BM-supplemented rats had lower energy efficiency, visceral fat mass, plasma glucose and hepatic triacylglycerol, but higher serum free fatty acids and plasma catecholamines. In the second experiment, 7-week BM supplementation in high-fat diet rats led to a lowering of hepatic triacylglycerol (P<0.05) and steatosis score (P<0.05) similar to those in rats fed a low-fat diet. BM supplementation did not affect serum and hepatic cholesterol. However, plasma epinephrine and serum free fatty acid concentrations were increased (P<0.05). In the third experiment, BM(7.5 and 15 g/kg) and 1.5 % BM lowered triacylglycerol concentration in red gastrocnemius and tibialis anterior (P<0.05) muscle, but a dose-response effect was not observed. These data suggest that chronic BM feeding leads to a general decrease in tissue fat accumulation and that such an effect is mediated in part by enhanced sympathetic activity and lipolysis. BM or its bioactive ingredient(s) could be used as a dietary adjunct in the control of body weight and blood glucose.

Animal Feed↗

Purification and characterization of a cytostatic factor from the bitter melon Momordica charantia.

In this report we describe the purification and characterization of a cytostatic factor from the bitter melon (Momordica charantia). As determined by gel filtration and sodium dodecyl sulfate-polyacrylamide gel electrophoresis (SDS-PAGE), this purified factor is a single component with an apparent molecular weight of 11,000. The factor is not sensitive to boiling or to pretreatments with trypsin, ribonuclease (RNAse), or deoxyribonuclease (DNAse). As determined by radioactive precursor uptake studies, the purified factor preferentially inhibits RNA synthesis in intact tissue culture cells. Some inhibition of protein synthesis and DNA synthesis also occurs. The factor is preferentially cytostatic for IM9 human leukemic lymphocytes when compared to normal human peripheral blood lymphocytes.

Animals↗

Purification and characterization of a cytostatic factor with anti-viral activity from the bitter melon.

We have previously reported that a crude aqueous extract of the bitter melon (Momordica charantia) has both cytostatic and cytotoxic activities, and is a competitive inhibitor of guanylate cyclase activity. This crude preparation kills human leukemic lymphocytes in a dose-dependent manner while not affecting the viability of normal human lymphocytes at these same doses. In this report we describe the purification and characterization of one of these cytostatic factors which also exhibits anti-viral activity. The partially purified factor was both cytostatic to BHK-21 cells and inhibitory to VSV plaque formation in a dose-dependent manner. This preparation was inhibitory to both viral and host cell RNA and protein synthesis as early as 30 min after addition to these samples. As determined by gel filtration and sodium dodecyl sulfate-polyacrylamide gel electrophoresis (SDS-PAGE), this purified factor is a single component with a molecular weight corresponding to 40,000 daltons. The factor is sensitive to boiling and to pre-treatments with trypsin, but not ribonuclease (RNAse), or deoxyribonuclease (DNAse). As determined by radioactive precursor uptake and incorporation studies, the purified factor inhibits both RNA and protein synthesis in intact tissue culture cells and inhibits protein synthesis in a cell-free wheat germ system. DNA synthesis was slightly stimulated. The purified factor is cytostatic for both BHK-21 and for the IM9 leukemic cell lines for at least 120 h. The cytostatic component had no effect on cellular cyclic GMP metabolism.

Animals↗