Seeds and oil of the Styrian oil pumpkin: Components and biological activities

Cucurbita pepo subsp. pepo var. Styriaca is a phylogenetically young member of the Cucurbita spp. since the mutation leading to dark green seeds with stunted outer hulls arose only in the 19^th century. This mutation defined the so‐called Styrian oil pumpkin and facilitated the production of Styrian pumpkin seed oil. It is a regional specialty oil in the south‐eastern part of Europe. In this article, we describe the production and economic value of this edible oil as well as its composition on a molecular basis, including fatty acids, vitamins, phytosterols, minerals, polyphenols, and the compounds responsible for its pigments, taste and flavor. We also describe contaminants of Styrian pumpkin seed oil and the most relevant field pests of the Styrian oil pumpkin plant. Finally, we review the putative beneficial health effects of Styrian oil pumpkin seeds and of their products.     

Production technology and characteristics of Styrian pumpkin seed oil

Cucurbita pepo subsp. pepo var. Styriaca, the so‐called Styrian oil pumpkin, is a phylogenetically young member of the Cucurbita spp. A single mutation occurred only in the 19^th century and led to dark green seeds with stunted outer hulls. This mutation facilitated the production of Styrian pumpkin seed oil that became a regional specialty oil in the south‐eastern part of Europe during the last few decades. We describe in this article the production and economic value of this edible specialty oil as well as the most important parameters relevant for its quality. Furthermore, we report on its molecular composition including fatty acids, vitamins, phytosterols, minerals, polyphenols, and those compounds that are responsible for its color, taste and flavor. Finally, information is provided on potential contaminants of Styrian pumpkin seed oil as well as its putative beneficial health effects.     

Antimicrobial Activity of Isothiocyanates from Cruciferous Plants against Methicillin-Resistant Staphylococcus aureus (MRSA)

Purified isothiocyanates from cruciferous plants (Brassicacea, Syn. Cruciferae) plants were evaluated against 15 isolates of methicillin-resistant S. aureus isolated from diabetic foot-ulcer patients aiming the study of the potential usage of allyl-isothiocyanate, benzyl-isothiocyanate and 2-phenylethyl-isothiocyanate against this important bacteria. Disc diffusion and minimum inhibitory concentration methods were used to access the antimicrobial activity. The index (Ia) and rate (Ra) of the antibacterial activity for each compound were calculated. The results showed a highly dose-dependent compound and chemical structure antibacterial effectiveness. The results showed a strong relation between the chemical structure of isothiocyanates and its antibacterial effectiveness. The benzyl-isothiocyanate was the most effective with a minimum inhibitory concentration varying between 2.9 and 110 µg· mL⁻¹ with an antibacterial activity rate up to 87%. Moreover, their antibacterial activity was mainly bactericidal. This study provides scientific evidence that isothiocyanates have an interesting biological value and must be considered as an important tool to be used against MRSA.     

Effects of allelopathic compounds of corn pollen on respiration and cell division of watermelon

The effects of the allelopathic compounds of an 'ethanolic extract of corn pollen on growth, respiration, and cellular division of watermelon (Citrullus lanatus, var. peacock improved) were studied. Bioassays with the ethanolic extract showed an inhibition of radicle and hypocotyl growth. The effects on respiration were observed in isolated watermelon hypocotyl mitochondria. The ethanolic extract acts as an inhibitor of the electron pathway, decreasing oxygen consumption in state 3, with malate and succinate substrates. The specific inhibition site probably is located before the cytochromec. Ascorbate-TMPD as substrate reversed the inhibitory effect of the ethanolic extract. An evaluation of the mitotic index was made in slide preparations of previously treated meristematic cells. A decrease in mitotic activity of more than 50% was found, as well as irregular and pycnotic nuclei. The data obtained from this study reflect an important mechanism of action of the allelopathic compounds of corn pollen.This work was sponsored by Project number 001079, Consejo Nacional de Ciencia y Tecnología.     

Curupira tefeensis III: Occurrence of all-cis-1,4-Polyisoprene

An all-cis-1,4-polyisoprene (3.9%) was isolated from the light petroleum extract of the seeds of Curupira tefeensis (Olacaceae). The structure of the compound was elucidated by IR, ¹H- and ¹³C-NMR-spectroscopy.     

<Emphasis Type="SmallCaps">l</Emphasis>-DOPA Increases Lignification Associated with <Emphasis Type="BoldItalic">Glycine max</Emphasis> Root Growth-Inhibition

l-3,4-dihydroxyphenylalanine (l-DOPA), an allelochemical exuded from the roots of velvet bean [Mucuna pruriens (L.) DC. var. utilis], presents a highly inhibitory action to plant growth. The effects of l-DOPA on phenylalanine ammonia-lyase (PAL, EC 4.3.1.5) and peroxidase (POD, EC 1.11.1.7) activities, and phenolic compound and lignin content in soybean [Glycine max (L.) Merr.] roots were investigated to determine the possible phytotoxic mechanism. Three-day-old seedlings were cultivated in half-strength Hoagland nutrient solution (pH 6.0), without or with 0.1 to 1.0 mM l-DOPA in a growth chamber (25°C, 12-hr light to 12-hr darkness photoperiod, irradiance of 280 μmol m⁻² s⁻¹) for 24 hr. In general, the length, fresh weight, and dry weight of the roots decreased, whereas PAL and POD activities and phenolic compound and lignin content increased after l-DOPA treatments. Results showed the susceptibility of soybean to l-DOPA and reinforce the role of this nonprotein amino acid as a strong allelochemical. The present findings also suggest that l-DOPA-induced inhibition in soybean roots may be because of a cell wall stiffening process related to the formation of cross-linking between cell wall polymers linked to lignin production.     

Different Sensitivity of Control and MICU1- and MICU2-Ablated Trypanosoma cruzi Mitochondrial Calcium Uniporter Complex to Ruthenium-Based Inhibitors

The mitochondrial Ca²⁺ uptake in trypanosomatids shares biochemical characteristics with that of animals. However, the composition of the mitochondrial Ca²⁺ uniporter complex (MCUC) in these parasites is quite peculiar, suggesting lineage-specific adaptations. In this work, we compared the inhibitory activity of ruthenium red (RuRed) and Ru360, the most commonly used MCUC inhibitors, with that of the recently described inhibitor Ru265, on Trypanosoma cruzi, the agent of Chagas disease. Ru265 was more potent than Ru360 and RuRed in inhibiting mitochondrial Ca²⁺ transport in permeabilized cells. When dose-response effects were investigated, an increase in sensitivity for Ru360 and Ru265 was observed in TcMICU1-KO and TcMICU2-KO cells as compared with control cells. In the presence of RuRed, a significant increase in sensitivity was observed only in TcMICU2-KO cells. However, application of Ru265 to intact cells did not affect growth and respiration of epimastigotes, mitochondrial Ca²⁺ uptake in Rhod-2-labeled intact cells, or attachment to host cells and infection by trypomastigotes, suggesting a low permeability for this compound in trypanosomes.     

Chemical Composition and Antioxidant Activity of Seeds of Various Halophytic Grasses

Increasing population has resulted in overexploitation of conventional seeds. The limited supply of water and salinization of agricultural lands are threats to crop production. This creates food insecurity and results in ever‐increasing prices of crops and edible oils. Halophytes that produce high‐quality seeds can serve as sources of oil and edible products. We analyzed the chemical composition and antioxidant activity of seeds from 5 halophytic grasses, i.e., Aeluropus lagopoides, Eragrostis ciliaris, Eragrostis pilosa, Panicum antidotale, and Sporobolus ioclados. These seeds contained crude protein (10–29%), carbohydrates (32–55%), crude fiber (4–21%), minerals (3.8–9.2%), and oil (4–11%), indicating their nutritional potential. Oils of these seeds had suitable fatty‐acid composition with 62–82% unsaturation and only 17–24% saturation. Out of this, 91–94% of the total oil constituted by linoleic, oleic, and palmitic acids. High contents of total phenols (2.8–4.2 mg gallic acid equivalent [GAE] g^?1), flavonoids (0.5–1.3 mg Quercetin equivalent [QE] g^?1), and tannins (0.3–1.3 mg catechin equivalent [CE] g^?1) supported their high antioxidant activity (1,1‐Diphenyl‐2‐picryl‐hydrazyl (DPPH) activity in terms of half maximal inhibitory concentration‐IC₅₀ 1.1–5.86 mg mL^?1; 2,2′‐azino‐bis3‐ethylbenzothiazoline‐6‐sulphonic acid (ABTS) 18.8–72.8 mmol Trolox g^?1; ferric‐reducing antioxidant power 2.0–4.4 mmol Fe⁺² g^?1). The reverse phase‐high‐pressure liquid chromatography analysis identified the presence of bioactive phenolic antioxidants (mainly gallic acid, chlorogenic acid, coumaric acid, ferulic acid, kaempferol, and quercetin). Due to these characteristic composition and salt tolerability, these plants can serve as potential sources of industrial raw materials for food, edible oil, phytochemicals, and oliochemicals.     

The Antifungal Compound Totarol of <Emphasis Type="Italic">Thujopsis dolabrata</Emphasis> var. <Emphasis Type="Italic">hondai</Emphasis> Seeds Selects for Fungi on Seedling Root Surfaces

Hinoki-asunaro (Thujopsis dolabrata Sieb. et Zucc. var. hondai Makino) is a tree endemic in Japan whose seeds produce several terpenoids. We hypothesized that antifungal compounds in seeds might select for fungi on the root surfaces of T. dolabrata var. hondai seedlings. We examined seed and soil fungi, their sensitivity to methanol extracts of the seeds, the fungi on root surfaces of seedlings grown in Kanuma pumice (a model mineral soil) and nursery soil, and the frequency at which each fungus was detected on the seedling root surface. We calculated correlation coefficients between fungal detection frequency on root surfaces and fungal sensitivity to seed extracts. We also isolated from the seeds the antifungal compound totarol that selected for fungi on root surfaces. Species of Alternaria, Cladosporium, Pestalotiopsis, and Phomopsis were the most frequently isolated fungi from seeds. Mortierella and Mucor were the dominant fungi isolated from Kanuma pumice, whereas Umbelopsis and Trichoderma were the main fungi isolated from nursery soil. Alternaria, Cladosporium, Mortierella, Pestalotiopsis, and Phomopsis were the dominant fungi isolated from root surfaces of seedlings grown in Kanuma pumice, and Alternaria, Cladosporium, Pestalotiopsis, Phomopsis, and Trichoderma were the main root-surface fungi isolated from seedlings grown in nursery soil. The fungal detection frequencies on root surfaces in both soils were significantly and negatively correlated with fungal sensitivity to the seed extract. A similar correlation was found between the fungal detection frequency on root surfaces and fungal sensitivity to totarol. We conclude that totarol is one factor that selects for fungi on root surfaces of T. dolabrata var. hondai in the early growth stage.     

Seed oil composition of <Emphasis Type="Italic">Paullinia cupana</Emphasis> var. <Emphasis Type="Italic">sorbilis</Emphasis> (Mart.) Ducke

The chemical composition of the oil extracted from the seeds of Paullinia cupana var. sorbilis (Mart.) Ducke (syn. P. sorbilis) was investigated. Cyanolipids constituted 3% of the total oil from guaraná seeds, whereas acylglycerols accounted for 28%. ¹H and ¹³C NMR analyses indicated that type 1 cyanolipids (1-cyano-2-hydroxymethylprop-2-ene-1-ol diesters) are present in the oil from P. cupana. GC and GC-MS analysis showed that cis-11-octadecenoic (cis-vaccenic acid) and cis-11-eicosenoic acids were the main FA (30.4 and 38.7%) esterified to the nitrile group. Paullinic acid (7.0%) was also an abundant component. Oleic acid (37.4%) was the dominant fatty acyl chain in the acylglycerols.     

Gurum Seeds: A Potential Source of Edible Oil

Cucurbitaceae family seeds are mostly discarded as agro-industrial wastes. Gurum (Citrullus lanatus var. colocynthoide) is an underutilized wild cucurbit plant, closely related to desert watermelon, which is grown abundantly in some African countries. Gurum seeds can play a significant role in health and nutrition due to their high oil content. This review describes the nutritional composition of gurum seeds and their oil profile. Gurum seeds are a good source of oil (27–35.5%), fiber (26–31%), crude protein (15–18%), and carbohydrates (14–17%). Gurum seeds oil is extracted by supercritical CO₂ (SFE), screw press, and solvent extraction techniques. The gurum seeds oil is composed of unsaturated fatty acids with a high proportion of linoleic acid (C18:2) and oleic acid (C18:1). Gurum seeds oil contains various bioactive compounds, such as tocopherols, phytosterols, and polyphenols. It is reported that solvent extraction gives a higher yield than the screw press and SFE, but the SFE is preferred due to safety issues. More studies are required for producing better quality gurum seeds oil by using novel extraction techniques that can increase oil yield.     

Identification of the antibiotic phomalactone from the entomopathogenic fungusHirsutella thompsonii var.synnematosa

Dichloromethane extracts of culture broth from three strains of the entomopathogenic fungusHirsutella thompsonii var.synnematosa were toxic to two species of tephritid fruit fly and inhibited conidial germination in vitro in several other entomopathogenic fungi includingBeauveria bassiana, Tolypocladium spp., andMetarhizium anisopliae. A major metabolite, toxic to apple maggot,Rhagoletis pomonella, and inhibitory to conidial germination inB. bassiana, was isolated and identified as the antibiotic (+)-phomalactone, 6-(1-propenyl)-5,-6-dihydro-5-hydroxypyran-2-one. This is the first biologically active compound of low molecular weight isolated from the genusHirsutella.Mention of a commercial or proprietary product does not constitute an endorsement by the USDA.     

A Comparative Study of the Properties of Six Sudanese Cucurbit Seeds and Seed Oils

The proximate analysis of seeds and physicochemical properties of oils extracted from six Sudanese cucurbit seeds Cucumis mello var. agrestis, Cucumis melo var. flexuosus, Cucumis sativus, Citrullus lanatus var. colocynthoides, Cucumis prophetarum, and Luffa echinata were examined by established methods. For each variety, the proximate analysis showed ranges for moisture, protein, and carbohydrates as 3.70–6.87, 14.50–17.50, and 15.62–28.89% on a dry matter basis, respectively. The oils were extracted by Soxhlet using petroleum ether, with yields that ranged from 10.9 to 27.10% (wt/wt). The obtained extracted oils were subjected to phyiscochemical, fatty acid, and tocopherol analysis. The physicochemical characterization of the oil revealed that the refractive indices and relative densities of the oils fell within the narrow ranges of 1.334–1.442 and 0.874–0.920 g/cm³, respectively. Unsaponifiable matters ranged between 0.8 and 1.2 mg KOH/g, whilst peroxide values (PV) ranged from 2.3 to 4.1 meq/kg. The ranges of the values for free fatty acid (FFA %) were 1.2–4.0%. The predominant fatty acids were 16:0, 18:0, 18:1, and 18:2 with ranges of 8.9–14.2, 6.0–9.4, 14.6–32.1, and 43.6–65.5%, respectively. γ-Tocopherol was the predominant tocopherol in all samples ranging from 0.8 to 43.2% of the total tocopherols, followed by δ-tocopherol and α-tocopherol.     

Soluble and insoluble dietary fiber in cereals and legumes cultivated in Chile

Insoluble, soluble and total dietary fiber (DF) were determined in 35 varieties of certified whole seeds (without processing) of cereals (rice, oat, rye, and wheat) and legumes (pea, cowpea, beans, chikpea, lentil and lupine). The enzymatic method of Asp, Johansson and Siljestrom was used, with modifications in relation to time of incubation with alpha amylase, filtration system and volumes of the filtrates. Results were expressed as g/100 g dry weight. Total DF for cereals showed a range from 10.1 (wheat var. Chasqui) to 22.2 (rice var Quella). Rye, var. Tetra Baer and oats var. Pony Baer presented the highest soluble fiber content (3.3 and 3.9, respectively). In legumes, total DF fluctuated between 12.7 (pea, var. yellow) and 36.6 (lupine, var. Multolupa). Bean, var. Pinto INIA and lupine var. Multolupa presented the highest soluble fiber values (5.8 for both). Based on the results of this research work, it might be concluded that great variation exists in regard to the amount of total soluble and insoluble DF in cereals and legumes, a fact which impedes generalization as to its content in each food item.     

氢化诺卜基双子季铵盐的合成及抑菌活性

将氢化诺卜基二甲基胺分别与3种α,w-二氯代烷反应制备了 3种新型含氢化诺 卜基的双子季铵盐:四亚甲基-1,4-双(氢化诺卜基二甲基氯化铵)(2a)、五亚甲基-1,5-双(氢化诺卜基二甲基氯化铵)(2b)和六亚甲基-1,6-双(氢化诺卜基二甲基氯化铵)(2c).对其结构进行NMR和MS表征,并采用菌丝生长速率法测定了这...     

6‐Aryl and Heterocycle Quinazoline Derivatives as Potent EGFR Inhibitors with Improved Activity toward Gefitinib‐Sensitive and ‐Resistant Tumor Cell Lines

A group of novel anilinoquinazoline derivatives with variable aryl and heterocyclic substituents at position 6 were synthesized and tested for their EGFR‐inhibitory activity. Aryl and heterocyclic rings were attached to the quinazoline scaffold through different linkages such as imine, amide, and thiourea. Most of the aryl and heterocyclic derivatives showed potent inhibition of wild‐type EGFR with IC₅₀ values in the low nanomolar range. Among these, thiourea derivatives 6 a , 6 b and compound 10 b also retained significant activity toward the gefitinib‐insensitive EGFR^T790M/L858R mutant, displaying up to 24‐fold greater potency than gefitinib. In addition, cell growth inhibitory activity was tested against cancer cell lines with wild‐type (KB cells) and mutant EGFR (H1975 cells). Several compounds including 6 a were found to be more potent than the reference compound gefitinib toward both cell lines, as was the case for compound 10 b against H1975 cells. Therefore, compounds 6 a and 10 b in particular may serve as new leads for the development of inhibitors effective against wild‐type EGFR as well as gefitinib‐resistant mutants.     

Characterization of Condensed Tannins Purified From Legume Forages: Chromophore Production,Protein Precipitation,and Inhibitory Effects on Cellulose Digestion

To identify simple screening tools for selecting condensed tannin (CT)-containing forages as candidate sources for further study, CT were isolated from nine legumes, and their molecular weights (MW), chromophore production, capacity to precipitate bovine serum albumin (BSA) and Fraction 1 protein (Rubisco) isolated from alfalfa, and inhibition of filter paper digestion were compared. Sources were as follows: leaves of sericea lespedeza (Lespedeza cuneata Dum.-Cours.), crown vetch (Coronilla varia L.), and sainfoin (Onobrychis viciifolia Scop.); stems of hedysarum (Hedysarum alpinum L.); seeds of alfalfa (Medicago sativa L.); and whole plants of birdsfoot trefoil (Lotus corniculatus var. corniculatus L.) and three varieties of big trefoil (Lotus pedunculatus Cav.), viz., Lotus uliginosus Schkuhr, L. uliginosus var. glabriusculus, and L. uliginosus var. villosus. Molecular weights and sizes (degrees of polymerization) of the CT varied considerably within and among plant species. Average MW ranged from 3036 Da (crown vetch) to 7143 Da (lespedeza). All CT exhibited greater capacity (w/w basis) to bind alfalfa Rubisco than BSA. Relative astringencies (μg CT required to precipitate 1 mg protein) against BSA ranged from 262.5 for CT from lespedeza to 435.5 for CT from L. corniculatus, and against Rubisco, from 49.6 (sainfoin) to 108.2 (alfalfa seed). Including CT at 300 μg/ml in cultures of Fibrobacter succinogenes reduced digestion of cellulose filter paper by 19.8% (sainfoin) to 92.4% (crown vetch) and increased the specific activity of cell-associated endoglucanase. There were no correlations between inhibitory effects of CT on filter paper digestion and (1) chromophore formation during CT assay by butanol–HCl, vanillin–HCl, or H₂SO₄; (2) precipitation of BSA or alfalfa Rubisco; and (3) MW of CT. The most inhibitory CT for cellulose digestion included those with broad and with narrow MW distributions. Sainfoin was the most desirable source of CT, as it had the highest capacity to bind alfalfa protein and was least inhibitory to cellulose digestion by F. succinogenes. This study suggests that these properties are not easily defined via chemical means, and that biological assays using rumen bacteria may help identify those CT with properties of nutritional interest.     

Design,Synthesis, and Structure-Activity Relationship Study of Pyrazolones as Potent Inhibitors of Pancreatic Lipase

Pancreatic lipase (PL), a key target for the prevention and treatment of obesity, plays crucial roles in the hydrolysis and absorption of in dietary fat. In this study, a series of pyrazolones was synthesized, and their inhibitory effects against PL were assayed by using 4-methylumbelliferyl oleate (4-MUO) as optical substrate for PL. Comprehensive structure–activity relationship analysis of these pyrazolones led us to design and synthesize a novel compound P32 (5-(naphthalen-2-yl)-2-phenyl-4-(thiophen-2-ylmethyl)-2,4-dihydro-3H-pyrazol-3-one) as a potent mixed-competitive inhibitor of PL (IC₅₀=0.30 μM). In addition, P32 displayed some selectivity over other known serine hydrolases. A molecular docking study for P32 demonstrated that the inhibitory activity of P32 towards PL could be attributed to the π-π interactions of 2-naphthyl unit (R¹) and hydrophobic interactions of phenyl moiety (R³) with the active site of PL. Thus, P32 could serve as promising lead compound for the development of more efficacious and selective pyrazolones-type PL inhibitors for biomedical applications.     

Applications of phytic acid

Phytic acid (myo-inositol hexaphosphate) constitutes 1-3% of most plant seeds. Its tremendous chelating potential and its effects on the absorption of polycationic nutrilites such as Ca²⁺, Zn²⁺ and Fe³⁺ have been the subject of intense investigation for several decades. Yet in the American literature there is virtually no information available on other chemical properties of phytic acid or on its beneficial utilization. This review summarizes the present medical, dental, nutritional and industrial applications of phytic acid and suggests additional novel uses for this inexpensive and easily obtained chemical.     

Relationships between chemical structure and inhibitory activity of C6 through C9 volatiles emitted by plant residues

Leaf, stem, flower, fruit, and root residues of a wide variety of plants have been reported to emit bioactiven-alkanes, 2-alkanols,n-alkanals, 2-alkenals, 2-alkanones, andn-alkanoic acids containing from six to nine carbon atoms. During a 72-hr exposure to the vapor phase of these compounds (6.9, 20.8 or 34.4 M/liter), germination of onion, carrot, and tomato seeds was inhibited to varying degrees. The extent of inhibition caused by these plant residue volatiles depended upon the compound type and concentration, carbon-chain length, and the seed species tested. Tomato seeds recovered more fully from exposure to these volatile inhibitors than did those of carrot and onion. Degree of recovery in all three species depended on the type and concentration of volatile present. The C₇ and C₈ compounds were the most inhibitory among these 24 volatiles. Of the six classes of chemicals examined, the 2-alkenals were the most inhibitory, followed by the 2-alkanols,n-alkanals, and 2-alkanones, which were equally effective as seed germination inhibitors. The straight-chain alkanes and alkanoic acids were relatively noninhibitory. Tests of a C₇ and C₉ alkadienal indicated that the C₇ compound was the more inhibitory.Mention of a commercial or proprietary product does not constitute an endorsement by the U.S. Department of Agriculture.