C-dideoxyhexosyl flavones from the stems and leaves of Passiflora edulis Sims

The stems and leaves of Passiflora edulis Sims, are used as a folk medicine for treating both anxiety and nervousness in American countries. Phytochemical investigation of the n-butanol (n-BuOH) fraction of this plant led to the isolation of four new 2,6-dideoxyhexose-C-glycosyl flavones, including luteolin-8-C-β-digitoxopyranosyl-4′-O-β-d-glucopyranoside (1), apigenin-8-C-β-digitoxopyranoside (2), apigenin-8-C-β-boivinopyranoside (3) and luteolin-8-C-β-boivinopyranoside (4), together with five known compounds (5–9). The structures of these compounds were elucidated by extensive spectroscopic methods. All compounds were evaluated for their neurite outgrowth enhancing activities and the results indicated that luteolin (7) enhanced NGF-induced neurite outgrowth in PC12 cells at 50.0 μM.     

Antioxidant properties of Agaricus blazei, Agrocybe cylindracea, and Boletus edulis

Three mushrooms are currently available in Taiwan, including Agaricus blazei, Agrocybe cylindracea, and Boletus edulis. Their ethanolic and hot water extracts were prepared and antioxidant properties studied. Ethanolic extracts from three mushrooms were more effective than hot water extracts in antioxidant activity using the conjugated diene method and scavenging ability on 1,1-diphenyl-2-picrylhydrazyl radicals whereas hot water extracts were more effective in reducing power, scavenging ability on hydroxyl radials and chelating ability on ferrous ions as evidenced by their lower EC₅₀ values. Overall, for both extracts, B. edulis was more effective among antioxidant properties assayed. Naturally occurring antioxidant components including total tocopherols (3.18-6.18 mg/g) and total phenols (5.67-5.81 mg/g) were found in the extracts and their contents were associated (r=0.636-0.907) with EC₅₀ value of antioxidant properties. Based on the results obtained, both extracts from these three mushrooms were effective in antioxidant properties.     

Physicochemical characterisation of gulupa (Passiflora edulis Sims. fo edulis) fruit from Colombia during the ripening

Gulupa (Passiflora edulis Sims. fo edulis) is a tropical fruit native to America. This study was undertaken to characterize the physicochemical properties of this fruit in three maturity stages. In all stages, the pH, °Brix, texture, and titratable acidity were determined. pH value and solid soluble content increased during ripening and titratable acidity decreased during this process; in contrast, texture values did not show significance variance. It was confirmed the presence of cyanidin-3-O-??-D-glucopyranoside as major anthocyanin. The changes on colour were followed by tristimulus colorimetry using image analysis, a very useful new approach for the measurement of non-homogeneous colours. By using PCA (Principal Component Analysis), clusters of data corresponding to each stage could be defined. Additionally, the volatile composition was followed by HS-SPME (Headspace-Solid Phase Microextraction) and GC/MS (Gas Chromatography/Mass Spectrometry) analyses. The results showed an increase in the amount of volatile during fruit ripening, with aliphatic esters as major constituents.     

Non-volatile taste components of Agaricus blazei, Agrocybe cylindracea and Boletus edulis

Three species of dried mushrooms are commercially available in Taiwan, namely Agaricus blazei (Brazilian mushroom), Agrocybe cylindracea (black popular mushroom) and Boletus edulis (king bolete), and their non-volatile taste components were studied. All mushrooms were high in contents of carbohydrate, crude fiber and protein but low in contents of crude ash and fat. Arabitol, myo-inositol, mannitol and trehalose were detected in these three mushrooms, whereas glucose was not found in B. edulis. Contents of total soluble sugars and polyols ranged from 150.33 to 225.08 mg/g. Total free amino acid contents were low in these three mushrooms and ranged from 8.97 to 14.91 mg/g. The contents of MSG-like components ranged from 1.24 to 4.40 mg/g were in the descending order of the A. blazei, A. cylindracea and B. edulis. Total 5′-nucleotides contents of A. blazei and A. cylindracea were higher than that of B. edulis whereas flavor 5′-nucleotides content of A. blazei was higher than those of A. cylindracea and B. edulis. Equivalent umami concentrations values in three mushrooms ranged from 10.46 to 135.90 g per 100 g. Overall, these three mushrooms possessed highly umami taste.     

Evaluation of the anti-inflammatory efficacy of Passiflora edulis

The aim of this study was to investigate the anti-inflammatory effect of the aqueous extract of Passiflora edulis forma flavicarpa Degenerer leaves in the air pouch inflammation model induced by carrageenan, histamine or substance P, in mice. An aqueous extract was prepared by infusion and lyophilized. Part of the extract was fractionated with n-butanol, resulting in the butanolic and aqueous residual fractions. The anti-inflammatory activities of the lyophilized extract and these two derived fractions were evaluated. In the inflammation induced by carrageenan, aqueous extract (100 mg/kg, i.p.), butanolic fraction (50 mg/kg, i.p.), aqueous residual fraction (100 mg/kg, i.p.) and dexamethasone (0.5 mg/kg, i.p.) inhibited the leukocyte, neutrophil, myeloperoxidase, nitric oxide, and interleukin-1 beta (IL-1β) levels (p < 0.05). The aqueous extract and butanolic and aqueous residual fractions, but not dexamethasone, decreased macrophage inflammatory protein-2 (MIP-2) levels (p < 0.05). Only dexamethasone inhibited mononuclear cells (p < 0.01). In the inflammation induced by histamine, the aqueous extract, butanolic and aqueous residual fractions, and dexamethasone inhibited total and differential leukocytes (p < 0.01). In the inflammation induced by substance P, the aqueous extract, butanolic and aqueous residual fractions, and dexamethasone also inhibited total leukocytes and mononuclears (p < 0.01). Neutrophils were only inhibited by aqueous extract, butanolic fraction, and dexamethasone (p < 0.05). In conclusion, the active principle(s) present in the P. edulis aqueous extract and its two fractions showed pronounced anti-inflammatory properties, inhibiting cell migration, proinflammatory cytokines, enzymes and mediators.     

Caffeoylquinic acids from leaves of Etlingera species (Zingiberaceae)

3-O-caffeoylquinic acid, 5-O-caffeoylquinic acid (chlorogenic acid), and 5-O-caffeoylquinic acid methyl ester, as elucidated by ¹H and ¹³C NMR, were isolated from leaves of Etlingera elatior. This is the first report of caffeoylquinic acids (CQA) including chlorogenic acid (CGA) in Zingiberaceae. Leaves of Etlingera species were rich in total phenols and CQA, and non-cytotoxic to normal human liver and African green monkey kidney cells. Content of CQA of E. elatior, Etlingera fulgens, and Etlingera rubrostriata leaves was significantly higher than leaves of Ipomoea batatas, and comparable to flowers of Lonicera japonica. CGA found only in leaves of E. elatior and E. fulgens was significantly higher in content than flowers of L. japonica, the commercial source.     

Antioxidant properties of aqueous extracts from Terminalia catappa leaves

Aqueous extracts were prepared from green, yellow fallen and red fallen leaves of Terminalia catappa L. (Combretaceae) and their antioxidant activity, scavenging and chelating abilities were evaluated. Aqueous extracts from three different leaves showed high antioxidant activities and moderate scavenging abilities on hydroxyl radicals at 1 mg/ml. EC₅₀ values in antioxidant activity were 0.549-0.557 mg/ml whereas those in scavenging ability on hydroxyl radicals were 0.631-0.686 mg/ml for aqueous extracts prepared from three leaves with boiling water for 3 min. EC50 values in reducing power were 0.15-0.23 mg/ml. EC50 values in scavenging abilities on superoxide anion and 1,1-diphenyl-2-picrylhydryl radicals were 0.36-0.44 and 10.4-35.3 mg/ml, respectively. EC50 values in chelating abilities on ferrous and cupric ions were 0.41-2.50 and 8.96-9.89 mg/ml, respectively. Based on the results obtained, the aqueous extracts displayed higher antioxidant properties. Six phenolic compounds identified in the aqueous were p-hydroxybenzoic acid, 4-hydroxyphenylpropionic acid, m-coumaric acid, 3,4-dihydroxybenzoic acid, p-coumaric acid and gallic acid. Therefore, the aqueous extracts from three different leaves of T. catappa might be a potential antioxidant supplement for application in food products or as a drink.     

Antioxidative effects of leaves from Azadirachta species of different provenience

Twenty extracts of leaves from Azadirachta plants (Siamese neem tree of different provenience, neem tree and marrango tree), a traditional medicine, and frequently eaten in large amounts as parts of meals in Thailand, showed proportionality between total phenolics and radical-scavenging as measured, as reduction of Fremy’s salt by ESR-spectroscopy. Scavenging effect of extracts from the neem tree was significantly lower than those of the Siamese neem tree and the marrango tree. The ability of the extracts to trap carbon-centred 1-hydroxyethyl radicals indicates prooxidative activity for a very high concentration of extract. The extracts were found to be efficient scavengers of compounds known to initiate lipid oxidation, as demonstrated by rate constants (25 °C) for reaction with ferrylmyoglobin: k = (1.7 ± 0.3) × 10³ M⁻¹ s⁻¹ at pH 5.5 and k = (7.7 ± 1.4) × 10² M⁻¹ s⁻¹ at pH 7.4, respectively, and with riboflavin triplet-state: k = (1.30 ± 0.02) × 10⁹ M⁻¹ s⁻¹ at pH 7.4. The rate constants for deactivation of ferrylmyoglobin by the extracts were larger than the rate constant for deactivation by the pure phenolic compounds present in the extract, demonstrating synergistic effects. All extracts showed high efficiencies as chain-breaking antioxidants. This was indicated by lowering of oxygen consumption rates in a peroxidising lipid emulsion, suggesting a role as dietary antioxidants. Siamese neem tree leaf extracts were found to interact with α-tocopherol in peroxidising liposomes, resulting in synergistic effects.     

Isolation and characterisation of an anticoagulant oligopeptide from blue mussel, Mytilus edulis

A potent anticoagulant oligopeptide was isolated from the edible parts of blue mussel (Mytilus edulis). M. edulis anticoagulant peptide (MEAP) with an approximately 2.5 kDa molecular mass was similar to the amino acid sequence of the EF-hand domain of calmodulin from scallop adductor muscle. MEAP could potently prolong both the thrombin time and the activated partial thromboplastin time, and specifically interact with blood coagulation factors: FIX, FX, and FII. MEAP could inhibit proteolytic activation of FX by the intrinsic FXase and formation of FIIa by a prothrombinase complex in dose-dependant reactions. This study elucidated that MEAP prolonged blood clotting by inhibiting activation of FX in the intrinsic tenase complex (FIXa/VIIIa/PLs) and conversion of FII to FIIa in the prothrombinase complex (FXa/FVa/PLs).     

Hyperspectral transmittance imaging of the shell-free cooked clam Mulinia edulis for parasite detection

The clam Mulinia edulis is occasionally infected by the parasite Edotea magellanica. In this paper the normalized optical transmittance of the clam and its parasite have been disclosed for the first time using a hyperspectral imaging system. It has been identified that, in the spectral band of 600–950 nm, the normalized optical transmittance of clam’s mantle cavity changes in the presence or absence of the parasite. This relative change in the normalized optical transmittance has been used as an effective spectral feature for designing parasite detectors. As a proof of concept two detectors have been designed. The first detector, which relies on all the hyperspectral information, achieved a perfect detection accuracy in identifying parasite-infected clams. The second detector, which is based on a reduced number of hyperspectral bands, achieved an 85% detection accuracy. These results provide insights on the fundamental trade-off between detection accuracy and the amount of hyperspectral information for parasite detection in clams.     

Chemical characterization, bioactive compounds, and antioxidant capacity of jussara (Euterpe edulis) fruit from the Atlantic Forest in southern Brazil

Samples of fruit from the jussara palm plant (Euterpe edulis), collected in different regions of the state of Santa Catarina, Brazil, were analyzed for chemical composition, phenolic acids, anthocyanins, flavonoids and fatty acids profile. Results indicated that the jussara fruit has a high lipid content (18.45-44.08%), oleic acid (44.17-55.61%) and linoleic acid (18.19-25.36%) are the fatty acids found in the highest proportion, and other components were proteins (5.13-8.21%), ash (1.55-3.32%) and moisture (34.95-42.47%). Significant differences were found in the total phenolic, total monomeric anthocyanins and other flavonoids for the samples from the five cultivation regions. The fruit from region E harvested in summer, with high temperatures and medium altitudes, had the highest contents of total phenolics (2610.86 ± 3.89 mg 100 g⁻¹ GAE) and monomeric anthocyanins (1080.54 ± 2.33 mg 100 g^− 1 cy-3-glu). The phenolic compound included ferulic, gallic, hydroxybenzoic and p-coumaric acids, as well as catechin, epicatechin and quercetin. The results show promising perspectives for the exploitation of this tropical fruit with a chemical composition comprising considerable phenolic acids and flavonoids compounds and showing activity antioxidant.     

Purification and characterization of soluble invertases from suspension-cultured bamboo (Bambusa edulis) cells

An alkaline invertase (IT I) and an acid invertase (IT II) were purified from the soluble fraction of suspension cultured bamboo cells. Both purified invertases were homogeneous as examined by SDS–polyacrylamide gel electrophoresis (SDS–PAGE) and were identified as β-fructofuranosidases able to attack the β-fructofuranoside from the fructose end. With respect to sucrose hydrolysis, the optimal pHs were 7.0 and 4.5 for IT I and IT II, respectively. The Km’s were 10.9 and 3.7 mM. The IT I and IT II molecular masses were 240 and 68 kDa, respectively, as estimated by gel filtration. The isoelectric points were 4.8 and 7.4. IT I was a homotetrameric enzyme activated by bovine serum albumin (BSA). IT II was a monomeric enzyme activated by BSA, concanavalin A (ConA) and urease. Both isoforms were significantly inhibited by heavy metal ions Ag⁺ (5 mM) and Hg²⁺ (1 mM), and mercaptide forming agent ρ-chloromercuribenzoic acid (PCMB; 0.5 mM).     

The inhibitory effect of Plectranthus barbatus and Plectranthus ecklonii leaves on the viability,glucosyltransferase activity and biofilm formation of Streptococcus sobrinus and Streptococcus mutans

Aqueous extracts of Plectranthus barbatus and Plectranthus ecklonii are traditionally used as anti-inflammatory and anti-fungal agents. The effect of these extracts and of its main component, rosmarinic acid, on the viability of the cariogenic bacteria, Streptococcus sobrinus and Streptococcus mutans, was determined by MIC and MBC. The influence of these extracts on the biofilm formation as well as on the inhibition of glucosyltransferase enzyme, produced by these species, was also analysed. Aqueous extracts of P. barbatus and P. ecklonii were stronger inhibitors than rosmarinic acid. MIC values of 3.8 and 4.7 mg/ml for S. sobrinus and 2.9 and 5.0 for S. mutans were obtained, while rosmarinic acid presented MIC values of 8.4 and 7.3 mg/ml. P. barbartus, P. ecklonii and rosmarinic acid presented MBC values of 9.5, 9.0 and 12.0 mg/ml for S. sobrinus, and 9.5, 10.0 and 12.5 mg/ml for S. mutans. The inhibition of biofilm formation by P. barbatus, P. ecklonii and rosmarinic acid presented IC₅₀ values of, respectively, 0.6, 1.0 and 3.1 mg/ml for S. sobrinus and 1.4 and 2.7 and 1.3 mg/ml for S. mutans. The glucosyltransferase inhibition activity by theses extracts and rosmarinic acid was calculated and IC₅₀ values presented were, respectively, 1.1, ca 1.2 and 2.1 mg/ml for S. sobrinus and 3.1, 1.6 and 3.9 mg/ml for S. mutans were obtained. These extracts may be useful in the prevention of dental carie.     

Evaluation of the antioxidant activity of passion fruit (Passiflora edulis and Passiflora alata) extracts on stimulated neutrophils and myeloperoxidase activity assays

The antioxidant activity of methanol extracts from Passiflora edulis and Passiflora alata pulp, and P. edulis rinds, healthy or infected with the passion fruit woodiness virus (PWV), was investigated using the oxidant activities of the neutrophil and the neutrophil granule enzyme myeloperoxidase (MPO), both playing key roles in inflammation. The reactive oxygen species produced by stimulated neutrophils were evaluated by lucigenin-enhanced chemiluminescence (CL) and the activity of purified MPO was measured by SIEFED (Specific Immunological Extraction Followed by Enzymatic Detection), a technique for studying the direct interaction of a compound with the enzyme. The rind extracts of P. edulis possessed higher and dose-dependent inhibitory effects on CL response and on the peroxidase activity of MPO than total pulp extracts from both passion fruit species. The quantification of isoorientin in the extracts showed a correlation with their antioxidant activity, suggesting the potential of P. edulis rinds as functional food or as a possible source of natural flavonoids.     

Heptadecanols from the leaves of Persea americana var. americana

From the leaves of Persea americana var. americana, eleven heptadecanol derivatives were identified. Their structures were elucidated on the basis of spectroscopic analyses. The absolute configurations were determined by chemical reaction, NOESY experiment and further comparison of the optical rotation value with the literature value. Additionally, the ratios of the contents of six heptadecanol derivatives in leaves, immature fruits, mature fruits and seeds of P. americana were estimated by LC-MS in multiple reaction monitoring (MRM) mode.     

Phytochemicals and antioxidant activity of different parts of bambangan (Mangifera pajang) and tarap (Artocarpus odoratissimus)

Mangifera pajang (family: Anacardiaceae; local name: bambangan) and Artocarpus odoratissimus (familiy: Moraceae; local name: tarap) are popular edible fruits in Sabah, Malaysia. The flesh, kernel and peel from M. pajang; seed and flesh from A. odoratissimus were analysed for total antioxidant activity, total polyphenol, total flavonoid and total anthocyanins contents. M. pajang kernel extract displayed the highest free radical scavenging and ferric reducing activities. Total phenolic content of the samples were in the range of 5.96–103.3 mg gallic acid equivalent/g. M. pajang kernel and M. pajang flesh contained the highest and lowest total flavonoid content with the values of 10.98 and 0.07 mg rutin equivalent/g, respectively. The antioxidant activities of extracts were significantly correlated with the total phenolic and flavonoid content (but not the anthocyanins content). The phytochemicals and antioxidant properties of M. pajang and A. odoratissimus, especially their by-products (kernel/seed), indicate that they may impart health benefits when consumed and should be regarded as a valuable source of antioxidant-rich nutraceuticals.     

Terpenoids and hexenes from the leaves of Crataegus pinnatifida

Crataegus pinnatifida have long been used in traditional Chinese medicine and European herbal medicine, and are widely consumed as food, in the form of juice, drink, jam and canned fruit. Four new compounds, a sesquiterpene and its glycoside (1–2), two monoterpene glycosides (3–4), together with eight known compounds (5–12), were isolated from the leaves of C. pinnatifida. Their structures were elucidated as (5Z)-6-[5-(2-hydroxypropan-2-yl)-2-methyltetrahydrofuran-2-yl]-3-methylhexa-1,5-dien-3-ol (1), (5Z)-6-[5-(2-O-β-d-glucopyranosyl-propan-2-yl)-2-methyl tetrahydrofuran-2-yl]-3-methylhexa-1,5-dien-3-ol (2), 5-ethenyl-2-[2-O-β-d-glucopyranosyl-(1″ → 6′)-β-d-glucopyranosyl-propan-2-yl]-5-methyltetrahydrofuran-2-ol (3), 4-[4β-O-β-d-xylopyranosyl-(1″ → 6′)-β-d-glucopyranosyl-2,6,6-trimethyl-1-cyclohexen-1-yl]-butan-2-one (4), (Z)-3-hexenyl O-β-d-glucopyranosyl-(1″ → 6′)-β-d-glucopyranoside (5), (Z)-3-hexenyl O-β-d-xylopyranosyl-(1″ → 6′)-β-d-glucopyranoside (6), (Z)-3-hexenyl O-β-d-rhamnopyranosyl-(1″ → 6′)-β-d-glucopyranoside (7), (3R,5S,6S,7E,9S)-megastiman-7-ene-3,5,6,9-tetrol (8), (3R,5S,6S,7E,9S)-megastigman-7-ene-3,5,6,9-tetrol9-O-β-d-glucopyranoside (9), (6S,7E,9R)-6,9-dihydroxy-4,7-megastigmadien-3-one 9-O-[β-d-xylopyranosyl-(1″ → 6′)-β-d-glucopyranoside] (10), Linarionoside C (11), and (3S,9R)-3,9-dihydroxy-megastigman-5-ene 3-O-primeveroside (12), using a combination of mass spectroscopy, 1D and 2D NMR spectroscopy and chemical analysis. Cytotoxicity of the new compounds was assayed against selected human glioma (U87) cell lines.     

Effects of simulated digestion in vitro on cell wall polysaccharides from kiwifruit (Actinidia spp.)

Cell wall polysaccharides are resistant to digestion and absorption in the human small intestine and are considered to be delivered to the colon in a chemically unaltered state. In this paper, pulp from green and gold kiwifruit was subjected to in vitro upper-intestinal tract digestion and the chemical and physical changes to cell wall polysaccharides (dietary fibre) were investigated. Yields of insoluble fibre decreased slightly with simulated digestion while soluble fibre yields increased. Constituent sugar and glycosyl linkage analysis of the soluble and insoluble fibre fractions revealed that the chemical composition and structure of the non-starch polysaccharides remained largely unchanged. However, the degree of methylesterification of galacturonic acid residues present in the pectin-rich soluble fibre fractions of both fruit decreased with treatment; size-exclusion chromatography detected changes in the molecular weight profiles of these fractions. These changes may affect the physicochemical properties and fermentability of kiwifruit dietary fibre in the large intestine.