Triglycerides constituted of short and medium chain fatty acids and dicarboxylic acids in Momordica charantia, as well as capric acid,inhibit PGE2 production in RAW264.7 macrophages

This study was aimed to identify compounds in bitter gourd (Momordica charantia) ethyl acetate extract (EAE), which inhibit lipopolysaccharide-induced prostaglandin E₂ (PGE₂) production in RAW264.7 cells. Bitter gourd EAE was partitioned between n-hexane and methanol/H₂O (90/10). The hexane fraction was further separated by repeated silica gel chromatographies, and a reverse phase (RP) C18 chromatography. Fraction RP-10 showed the highest inhibition effect on PGE₂ production (Max inhibition = 96%, IC₅₀ = 2.3 μg/ml) and was identified to be triglycerides constituted of short and medium chain fatty acids by ¹H NMR, IR and H–HCOSY, and dicarboxylic acids by GC/MS. Fatty acids with 3–20 carbons were tested for the inhibitory activity, and capric acid exhibited the highest effect (Max inhibition = 99%, IC₅₀ = 6.5 μM). In conclusion, triglycerides composed of short and medium chain fatty acids and dicarboxylic acids in bitter gourd inhibit PGE₂ production, and capric acid is the most potent inhibitor among the fatty acids.     

Fermentative behavior of Saccharomyces strains during microvinification of raspberry juice (Rubus idaeus L.)

Sixteen different strains of Saccharomyces cerevisiae and Saccharomyces bayanus were evaluated in the production of raspberry fruit wine. Raspberry juice sugar concentrations were adjusted to 16°Brix with a sucrose solution, and batch fermentations were performed at 22 °C. Various kinetic parameters, such as the conversion factors of the substrates into ethanol (Y_p/s), biomass (Y_x/s), glycerol (Y_g/s) and acetic acid (Y_ac/s), the volumetric productivity of ethanol (Q_p), the biomass productivity (P_x), and the fermentation efficiency (E_f) were calculated. Volatile compounds (alcohols, ethyl esters, acetates of higher alcohols and volatile fatty acids) were determined by gas chromatography (GC-FID). The highest values for the E_f, Y_p/s, Y_g/s, and Y_x/s parameters were obtained when strains commonly used in the fuel ethanol industry (S. cerevisiae PE-2, BG, SA, CAT-1, and VR-1) were used to ferment raspberry juice. S. cerevisiae strain UFLA FW 15, isolated from fruit, displayed similar results. Twenty-one volatile compounds were identified in raspberry wines. The highest concentrations of total volatile compounds were found in wines produced with S. cerevisiae strains UFLA FW 15 (87,435 μg/L), CAT-1 (80,317.01 μg/L), VR-1 (67,573.99 μg/L) and S. bayanus CBS 1505 (71,660.32 μg/L). The highest concentrations of ethyl esters were 454.33 μg/L, 440.33 μg/L and 438 μg/L for S. cerevisiae strains UFLA FW 15, VR-1 and BG, respectively. Similar to concentrations of ethyl esters, the highest concentrations of acetates (1927.67 μg/L) and higher alcohols (83,996.33 μg/L) were produced in raspberry wine from S. cerevisiae UFLA FW 15. The maximum concentration of volatile fatty acids was found in raspberry wine produced by S. cerevisiae strain VR-1. We conclude that S. cerevisiae strain UFLA FW 15 fermented raspberry juice and produced a fruit wine with low concentrations of acids and high concentrations of acetates, higher alcohols and ethyl esters.     

Antioxidant capacity and hydrophilic phytochemicals in commercially grown native Australian fruits

Hydrophilic phytochemicals and antioxidant capacities of eight commercially grown native Australian fruits were determined. Kakadu plum (Terminalia ferdinandiana) contained a 6-fold higher level of total phenolic compounds and quandong (Santalum acuminatum) a 1.9-fold higher level of total phenolic compounds (TP, Folin–Ciocalteu assay) than blueberry (Vaccinum sp., cv. Biloxi). Both fruits displayed superior oxygen radical-scavenging capacity (ORAC-H assay) that was, respectively 4.1-fold and 6.5-fold of that of blueberry. The total reducing capacity (TRC; ferric reducing antioxidant power (FRAP) assay) of Kakadu plum and quandong exceeded the TRC of blueberry, respectively, 13.1- and 2.3-times. The primary sources of antioxidant capacities in the evaluated fruits were phenolic acids (benzoic and cinnamic) and flavonoids (flavonols, flavanones and anthocyanins) tentatively detected by liquid chromatography–mass spectrometry (LC–PDA–MS/MS). A high level of vitamin C was recorded for Kakadu plum and Australian citrus fruits. The major organic acids detected were citric and malic acid.     

Chemical and biological variability of hot pepper fruits (Capsicum annuum var. acuminatum L.) in relation to maturity stage

The aim of the present work was to evaluate the chemical composition and the radical-scavenging and antioxidant activities of hot pepper fruits (Capsicum annuum L. var. acuminatum) at three maturity stages (small green, green and red). GC–MS analysis of n-hexane and chloroform fractions showed a different composition between the three stages of ripening. The first stage of maturation (small green) showed the highest radical-scavenging activity (IC₅₀ of 129 μg/ml). Using the bovine brain peroxidation assay, the methanolic extract of green pepper showed significant antioxidant activity (IC₅₀ of 522 μg/ml). Addition of methanolic extract of red and green pepper inhibited oxidation of linoleic acid. Methanolic extract of red pepper showed greater antioxidative potency than the others (IC₅₀ of 3 μg/ml). The different composition of lipophilic compounds and the various amount of phenolics, showed in the three stage of ripening of C. annuum var. acuminatum fruits, modifies the antioxidant activity.     

Variations in essential oil and fatty acid composition during Myrtus communis var. italica fruit maturation

The essential oil and fatty acid composition of Myrtus communis var. italica fruit during its ripening was determined. The effect of the harvesting time on some physical properties of Myrtus fruits, fruit weight and moisture content, were significant. The increase of fruit weight (from 2.54 to 8.79 g% fruits) during ripeness was correlated positively with that of moisture content (from 28% to 72%). Fruit essential oil yields varied from 0.003% to 0.01% and showed a remarkable increase at 60 days after flowering to reach a maximum of 0.11%. Forty-seven volatile compounds were identified in fruit essential oils; 1,8-cineole (7.31–40.99%), geranyl acetate (1.83–20.54%), linalool (0.74–18.92%) and α-pinene (1.24–12.64%) were the main monoterpene compounds. Total fatty acid contents varied from 0.81% to 3.10% during fruit maturation and the predominant fatty acids were linoleic (12.21–71.34%), palmitic (13.58–37.07%) and oleic (6.49–21.89%) acids. The linoleic acid proportions correlated inversely with palmitic and oleic acids during all the stages of ripening.     

Identification of antioxidant components and fatty acid profiles of the leaves and fruits from Averrhoa carambola

The antioxidant compounds of leaves and fruits from Averrhoa carambola were extracted with acetone:water (7:3, v/v) and distilled water. The acetone:water extracts (AWE) were separated into five different subfractions, three obtained by liquid–liquid extraction using n-hexane (HF), ethyl acetate (EAF) and water (WF), and the other two obtained by further fractionation of the WF on a Sephadex LH-20 column (WS1 and WS2). The antioxidant activities, total phenolics and total flavonoids of these extracts and fractions were investigated. Results showed that all the extracts and fractions possessed potent antioxidant activities, as measured by DPPH, ABTS and FRAP methods, with the strongest for WS2 fractions accompanied with the highest total phenolics and total flavonoids. Reversed-phase HPLC, normal-phase HPLC, MALDI-TOF-MS and ¹³C NMR analyses identified that the main antioxidant components present in WS2 fractions were essentially of procyanidin-type proanthocyanidins, consisting mainly of epicatechin units linked by B-type interflavan bonds. In addition, GC–MS analysis revealed that the most abundant fatty acids were α-linolenic acid (62.04 ± 1.65%) for leaves and oleic acid (55.44 ± 1.37%) for fruits. The amount of total unsaturated fatty acids in leaves and fruits comprised more than 77% of total fatty acid.     

Flavonoids of Zizyphus jujuba L. and Zizyphus spina-christi (L.) Willd (Rhamnaceae) fruits

The ripe edible fruits of jujube, Zizyphus jujuba Miller (syn. Z. sativa Gaertner, Z. vulgaris Lam.) and Christ’s thorn jujube Zizyphus spina-christi (L.) Willd (Rhamnaceae family) were phytochemically investigated, comparing their quali-quantitative flavonoids profile. Twelve compounds from both methanol extracts have been recognized as quercetin, kaempferol, and phloretin derivatives by means of HPLC/ESI-MS analyses. Six major compounds have been purified by Sephadex LH-20 column chromatography followed by HPLC and were characterized using NMR spectroscopy. One C-glycoside, 3′,5′-di-C-β-d-glucosylphloretin, was detected in Z. spina-christi. The quantitative analysis of all compounds was also reported showing a higher content of flavonoids in Z. jujuba.     

Matrix solid phase dispersion extraction of ginsenosides in the leaves of Panax ginseng C.M. Mey

The matrix solid phase dispersion (MSPD) was applied to the extraction of eight kinds of ginsenosides from the leaves of Panax ginseng C.M. Mey. The experimental conditions were examined and optimised. The extracts were analysed by high performance liquid chromatography (HPLC). When the diatomaceous earth was used as dispersant and 75% methanol was used as elution solvent, the highest extraction yields of the eight kinds of ginsenosides were obtained. For comparison, the reflux extraction was applied. The extraction yields obtained by the proposed method were comparable with those obtained by the reflux extraction. The proposed method is convenient, time-saving, and organic solvent minimising.     

Enhancement of antioxidant activity,total phenolic and flavonoid content of black soybeans by solid state fermentation with Bacillus subtilis BCRC 14715

In the present study, a solid state fermentation of black soybeans with Bacillus subtilis BCRC 14715 was performed. The effect of fermentation on the changes of total phenolic and flavonoid content and antioxidant activities including 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical-scavenging effect, and Fe²⁺-chelating ability exerted by various solvent (water, 80% methanol, 80% ethanol, 80% acetone) extracts of black soybeans was examined. It was found that fermentation enhanced the total phenolic and flavonoid content as well as antioxidant activity of the black soybean extract. Among the various extracts examined, the acetone extract of fermented black soybeans showed the highest total phenolic and flavonoid content. The acetone extract and the methanol extract of fermented black soybeans showed the highest DPPH free radical-scavenging effect and Fe²⁺-chelating ability, respectively. Analysis of extraction yields showed that the active principle associated with the DPPH radical-scavenging effect was most efficiently extracted from black soybeans using water, regardless of fermentation. Water and methanol effectively extract the Fe²⁺-chelating principles from non-fermented and fermented black soybeans, respectively.     

Isolation and evaluation of the antioxidant activity of phenolic constituents of the Garcinia brasiliensis epicarp

A new glycosylated biflavonone, morelloflavone-4′″-O-β-d-glycosyl, and the known compounds 1,3,6,7-tetrahydroxyxanthone, morelloflavone (fukugetin) and morelloflavone-7″-O-β-d-glycosyl (fukugeside) were isolated from the epicarp of Garcinia brasiliensis collected in Brazil. The structures of these compounds were established using ¹H and ¹³C NMR, COSY, gHMQC and gHMBC spectroscopy. The compounds exhibited antioxidant activity. The greatest potency was displayed by morelloflavone (2), with IC₅₀ = 49.5 mM against DPPH and absorbance of 0.583 at 400 μg/mL for the reduction of Fe³⁺. The weakest potency was displayed by 1,3,6,7-tetrahydroxyxanthone (1), with IC₅₀ = 148 mM against DPPH and absorbance of 0.194 at 400 μg/mL for the reduction of Fe³⁺.     

Isolation of hesperidin from peels of thinned Citrus unshiu fruits by microwave-assisted extraction

Simultaneous extraction by microwave-irradiation and crystallisation were performed in the same pot of solvent of 70% (v/v) aqueous ethanol for isolation of hesperidin from thinned immature fruit peels of Citrus unshiu as refining of Citrus waste biomass. The hesperidin content in immature fruits peels was about 3.2-fold higher than that of mature fruit. After microwave-assisted extraction (MAE), the yield of hesperidin reached 58.6 mg/g, which was comparable to the amount obtained after extraction using DMSO:methanol (1:1, v/v) as a solvent for 30 min at room temperature. Heating temperature and time for isolation of hesperidin crystallites were optimised as 140 °C and 8 min by using response surface methodology. Under this optimal condition, 86.8% (47.7 mg/g) of total hesperidin was isolable by MAE and low-temperature storage (5 °C, 24 h).     

Changes on essential oil composition of coriander (Coriandrum sativum L.) fruits during three stages of maturity

The essential oils composition of coriander (Coriandrum sativum L.) fruits obtained by hydrodistillation was studied at three stages of maturity by GC–FID and GC–MS. Essential oil yields showed marked increase during maturation process and forty one compounds were identified. Geranyl acetate (46.27%), linalool (10.96%), nerol (1.53%) and neral (1.42%) were the main compounds at the first stage of maturity (immature fruits). At the middle stage, linalool (76.33%), cis-dihydrocarvone (3.21%) and geranyl acetate (2.85%) were reported as the main constituents. Essential oils at the final stage of maturity (mature fruits) consist mainly on linalool (87.54%) and cis-dihydrocarvone (2.36%). Additionally, accumulation of monoterpene alcohols and ketones was observed during maturation process of coriander fruit.     

Quali-quantitative analysis of flavonoids of Cornus mas L. (Cornaceae) fruits

The methanol extract obtained from the ripe fruits of Cornus mas L. (Cornaceae) have been phytochemically studied. On the basis of HPLC–PDA–MS/MSⁿ analysis eight compounds have been identified as quercetin, kaempferol, and aromadendrin glycosilated derivatives. Three major compounds have been also isolated by Sephadex LH-20 column chromatography followed by HPLC and characterised by NMR spectroscopy. Moreover, LC–PDA–MS analysis of the red pigment revealed the presence of three anthocyanins. The quantitative analysis of all compounds was reported.     

Volatile compounds of leaves and fruits of Mangifera indica var. coquinho (Anacardiaceae) obtained using solid phase microextraction and hydrodistillation

Volatile compounds present on fruits and leaves of Mangifera indica var. coquinho were investigated by headspace solid phase microextraction (HS-SPME) and hydrodistillation (HD). Conventional techniques, such as hydrodistillation, may impart chemical changes to the original oil composition being also time-consuming. On the other hand, HS-SPME provides solvent-less extractions, shorter extraction times and may supply complementary information about the composition of the compounds. The HS-SPME technique was previously evaluated by the comparative study among the fibres: commercial PDMS, NiTi-ZrO₂ and NiTi-ZrO₂-PDMS. The fibre NiTi-ZrO₂-PDMS showed better sensitivity and precision and was used on the extraction of components. The influence of several parameters like the time and temperature of extraction and desorption time were examined to obtain better efficiency. Fruits and leaves were analysed in mature and immature stages. The profiles corresponding to the volatile compounds detected by both techniques are discussed.     

HPLC–MS identification and quantification of flavonol glycosides in 28 wild and cultivated berry species

Berries and red fruits are rich dietary sources of polyphenols with reported health benefits. More than 50 different flavonols (glycosides of quercetin, myricetin, kaempferol, isorhamnetin, syringetin and laricitrin) have been detected and quantified with HPLC–MSⁿ in fruits of blueberry, bilberry, cranberry, lingonberry, eastern shadbush, Japanese wineberry, black mulberry, chokeberry, red, black and white currants, jostaberry, red and white gooseberry, hardy kiwifruit, goji berry, rowan, dog rose, Chinese and midland hawthorn, wild and cultivated species of blackberry, raspberry, strawberry and elderberry. The phenolic constituents and contents varied considerably among the analyzed berry species. Elderberry contained the highest amount of total flavonols (450–568 mg kg⁻¹ FW), followed by berry species, containing more than 200 mg kg⁻¹ FW of total: chokeberry (267 mg kg⁻¹), eastern shadbush (261 mg kg⁻¹), wild grown blackberry (260 mg kg⁻¹), rowanberry (232 mg kg⁻¹), american cranberry (213 mg kg⁻¹) and blackcurrants (204 mg kg⁻¹). Strawberry (10.5 mg kg⁻¹) and white currants (4.5 mg kg⁻¹) contained the lowest amount of total flavonols. Quercetins represent the highest percentage (46–100%) among flavonols in most analyzed berries. In wild strawberry and gooseberry the prevailing flavonols belong to the group of isorhamnetins (50–62%) and kaempferols, which represent the major part of flavonols in currants (49–66%). Myricetin glycosides could only be detected in chokeberry, rowanberry and species from the Grossulariaceae, and Adoxaceae family and Vaccinium genus. Wild strawberry and blackberry contained from 3- to 5-fold higher total flavonols than the cultivated one.     

Infusion and decoction of wild German chamomile: Bioactivity and characterization of organic acids and phenolic compounds

Natural products represent a rich source of biologically active compounds and are an example of molecular diversity, with recognised potential in drug discovery. Herein, the methanol extract of Matricaria recutita L. (German chamomile) and its decoction and infusion (the most consumed preparations of this herb) were submitted to an analysis of phytochemicals and bioactivity evaluation. The antioxidant activity was determined by free radicals scavenging activity, reducing power and inhibition of lipid peroxidation; the antitumour potential was tested in human tumour cell lines (breast, lung, colon, cervical and hepatocellular carcinomas), and the hepatotoxicity was evaluated using a porcine liver primary cell culture (non-tumour cells). All the samples revealed antioxidant properties. The decoction exhibited no antitumour activity (GI₅₀ > 400 μg/mL) which could indicate that this bioactivity might be related to compounds (including phenolic compounds) that were not extracted or that were affected by the decoction procedure. Both plant methanol extract and infusion showed inhibitory activity to the growth of HCT-15 (GI₅₀ 250.24 and 298.23 μg/mL, respectively) and HeLa (GI₅₀ 259.36 and 277.67 μg/mL, respectively) cell lines, without hepatotoxicity (GI₅₀ > 400 μg/mL). Infusion and decoction gave higher contents of organic acids (24.42 and 23.35 g/100 g dw). Otherwise, the plant methanol extract contained the highest amounts of both phenolic acids (3.99 g/100 g dw) and flavonoids (2.59 g/100 g dw). The major compound found in all the preparations was luteolin O-acylhexoside. Overall, German chamomile contains important phytochemicals with bioactive properties (mainly antitumour potential selective to colon and cervical carcinoma cell lines) to be explored in the pharmaceutical, food and cosmetics industries.     

Insect-derived compounds affect the behaviour of Liposcelis bostrychophila: Effects of combination and structure

A methanol fraction (MFr), prepared from 80% methanol extracts of whole Liposcelis bostrychophila, repels conspecifics when presented to groups of insects at 8000 ppm. To examine the reason for this repellent effect, bioassays tested a mixture of fatty acids and fatty acid methyl esters that are present in the MFr at concentrations ranging from 0.02 to 1.2 mM. This mixture of compounds contributes significantly to the repellence of the MFr. Therefore, an interaction among compounds can affect the settling behaviour of L. bostrychophila, even though the individual compounds do not have any effect. Other experiments further investigated the repellence of C₁₆ and C₁₈ fatty acids. In the majority of instances groups of insects consistently settled on the disc impregnated with either stearic acid or the compound with the most saturated bonds. The one exception was C_18:2 versus C_18:3 where more insects settled on C_18:3. This repellent effect of unsaturated fatty acids was also evident in five-way choice tests using a series of C₁₈ fatty acids, where stearic acid (10 mM) was consistently selected by groups of L. bostrychophila instead of oleic, linoleic and linolenic acid. The discrimination between and among fatty acids could be due to the differences in their physical properties which affect how the compounds are perceived by the insects. The fact that the most unsaturated fatty acids repel the insects presents the possibility that volatile insect-derived compounds could be utilised as repellents for this increasingly important pest.     

Characterization of a new anthocyanin in black raspberries (Rubus occidentalis) by liquid chromatography electrospray ionization tandem mass spectrometry

Anthocyanin composition of black raspberry (Rubus occidentalis) was studied using high-performance liquid chromatography coupled to photodiode array (PDA) detection and electrospray ionization mass spectrometry (LC-ESI/MS) and tandem mass spectrometry (MS/MS). Pelargonidin 3-rutinoside was isolated and identified in black raspberries using HPLC, UV–Vis spectroscopy, MS, and NMR spectroscopy. No pelargonidin derivative had been previously found in Rubus occidentalis. In addition, the presence and identities of four previously reported anthocyanins (cyanidin 3-glucoside, cyanidin 3-sambubioside, cyanidin 3-rutinoside and cyanidin 3-xylosylrutinoside) were confirmed by HPLC/MS and MS/MS analyses.     

Study of natural mango juice spoilage and microbial contamination with Penicillium expansum by high resolution H NMR spectroscopy

High resolution ¹H NMR has been applied to monitor the changes in the composition of natural mango juice subjected to spoilage and to microbial contamination with Penicillium expansum. A vast number of compounds undergoing changes upon these processes have been identified and their variations followed throughout time (132 h). Besides the formation of typical fermentation products (e.g. acetate, lactic acid, acetoin and isopropanol/2,3-butanediol) and the utilization of the major sugars (sucrose, glucose and fructose), there were changes in organic acids (e.g. decreases of quinic and shikimic acids with formation of 3,4,5-trihydroxycyclohexane acid in spoiled juice, and decreases of citric and malic acids in contaminated juice), amino acids (decreases of alanine, leucine, isoleucine and valine), and less abundant components such as oligosaccharides and aromatic compounds. The possibility of using these changes as early indicators of natural spoilage or P. expansum contamination is discussed.     

Optimization of extraction process for phenolic acids from black cohosh (Cimicifuga racemosa) by pressurized liquid extraction

An investigation to optimize the extraction of phenolic acids from black cohosh using a pressurized liquid extractor system was studied with the aim of developing a generalized approach for sample preparation of phenolic compounds from plant matrices. Operating parameters such as solvent composition, solid‐to‐solvent ratio, temperature, particle size distribution, and number of extraction cycles were identified as main variables that influence extraction efficiency. A mixture of methanol and water (60:40 v/v) was found to be the best solvent for total phenolics (TP) and individual phenolic acids. The four phenolic acids extracted from black cohosh were identified by HPLC and LC‐MS as caffeic acid, ferulic acid, sinapic acid and isoferulic acid. Over 96% of the measured phenolics were extracted in first two cycles. The extraction efficiency for black cohosh with MeOH:H₂O (60:40 v/v) was found to be maximum at a solid‐to‐solvent ratio of 80 mg ml^?1. TP content of the extract was found to increase with temperature up to 90 °C. Particle size was found to have a large impact on extraction efficiency of TP. Samples with particle size between 0.25 mm and 0.425 mm provided optimum extraction of phenolics from black cohosh. Published in 2005 for SCI by John Wiley & Sons, Ltd.