BIOFUMIGANT COMPOUNDS RELEASED BY FIELD PENNYCRESS (<Emphasis Type="Italic">Thlaspi arvense</Emphasis>) SEEDMEAL

Defatted field pennycress (Thlaspi arvense L.) seedmeal was found to completely inhibit seedling germination/emergence when added to a sandy loam soil containing wheat (Triticum aestivum L.) and arugula [Eruca vesicaria (L.) Cav. subsp. sativa (Mill.) Thell.] seeds at levels of 1.0% w/w or higher. Covering the pots with Petri dishes containing the soil-seedmeal mixture decreased germination of both species at the lowest application rate (0.5% w/w), suggesting that the some of the phytotoxins were volatile. CH₂Cl₂, MeOH, and water extracts of the wetted seedmeal were bioassayed against wheat and sicklepod (Senna obtusifolia (L.) H. S. Irwin & Barneby) radicle elongation. Only the CH₂Cl₂ extract was strongly inhibitory to both species. Fractionation of the CH₂Cl₂ extract yielded two major phytotoxins, identified by gas chromatography–mass spectrometry and NMR as 2-propen-1-yl (allyl) isothiocyanate (AITC) and allyl thiocyanate (ATC), which constituted 80.9 and 18.8%, respectively, of the active fraction. When seeds of wheat, arugula and sicklepod were exposed to volatilized AITC and ATC, germination of all three species was completely inhibited by both compounds at concentrations of 5 ppm or less. In field studies, where seedmeal was applied at 0.50, 1.25, and 2.50 kg/m² and tarped with black plastic mulch, all of the treatments significantly reduced dry weight of bioassay plants compared to the tarped control, with the highest seedmeal rate decreasing dry matter to less than 10% of the control 30 d after seedmeal application. Field pennycress seedmeal appears to offer excellent potential as a biofumigant for high-value horticultural crops for both conventional and organic growers.Names are necessary to report factually on available data; however, the USDA neither guarantees nor warrants the standard of the product, and the use of the name by USDA implies no approval of the product to the exclusion of others that may also be suitable.     

Isolation and identification of (3-methoxyphenyl)acetonitrile as a phytotoxin from meadowfoam (Limnanthes alba) seedmeal

Ethyl ether, ethanol, and water extracts of meadowfoam (Limnanthes alba Hartweg ex. Benth.) seedmeal were prepared and bioassayed against velvetleaf (Abutilon theophrasti Medicus) and wheat (Triticum aestivum L. Cardinal). Both the ethyl ether and ethanol fractions, but not the water extract, inhibited velvetleaf and wheat radicle elongation. Fractionation of the extracts indicated that (3-methoxyphenyl)acetonitrile (3-MPAN) was the active compound from both extracts, comprising >97% of the active ethanol fraction. 3-Methoxybenzyl isothiocyanate, which had been previously shown to be the major breakdown product of glucolimnanthin, the majorL. alba glucosinolate, was not detected in either extract. Radicle elongation of velvetleaf and wheat were inhibited by 3-MPAN with I₅₀ (the concentration required to inhibit growth by 50%) values of approximately 4 × 10^–4 M (velvetleaf) and 7×10^–4 M (wheat).Mention of firms or products does not imply endorsement by the U.S. Department of Agriculture over other firms or products not mentioned.     

Buckwheat trypsin inhibitor enters Hep G2 cells by clathrin-dependent endocytosis

Recombinant buckwheat trypsin inhibitor (rBTI) was studied to evaluate if it could enter cancer cells and to determine the mechanism. Fluorescein isothiocyanate-labelled buckwheat trypsin inhibitor (FITC-BTI) entered Hep G2 cells in a concentration-dependent manner. FITC-BTI colocalised with labelled transferrin (Tf) in the punctate structure, implying that rBTI enters Hep G2 cells by clathrin-dependent endocytosis. Incubation of Hep G2 cells with different chemical inhibitors abolished diffuse, but not punctate fluorescence, thus indicating that membrane potential plays a critical role in this process. Impairment of clathrin-mediated endocytosis by RNAi with clathrin heavy chain greatly reduced or completely abolished both diffuse and punctate fluorescence, further supporting a theory of a single route of endocytosis. Consistent with our working hypothesis, Hep G2 cells which were arrested in the M phase did not show any vesicular or diffuse FITC-BTI. We conclude from these results that both endocytosis and membrane potential are required for rBTI entry into Hep G2 cells.     

Benzyl Isothiocyanate Attenuates Inflammasome Activation in Pseudomonas aeruginosa LPS-Stimulated THP-1 Cells and Exerts Regulation through the MAPKs/NF-κB Pathway

Inflammasomes are a group of intracellular multiprotein platforms that play important roles in immune systems. Benzyl isothiocyanate (BITC) is a constituent of cruciferous plants and has been confirmed to exhibit various biological activities. The modulatory effects of BITC on inflammasome-mediated interleukin (IL)-1β expression and its regulatory mechanisms in Pseudomonas aeruginosa (P. aeruginosa) LPS/ATP-stimulated THP-1 cells was investigated. Monocytic THP-1 cells were treated with phorbol myristate acetate (PMA) to induce differentiation into macrophages. Enzyme-linked immunosorbent assays (ELISA) were performed to measure the levels of IL-1β produced in P. aeruginosa LPS/ATP-exposed THP-1 cells. Western blotting was performed to examine the BITC modulatory mechanisms in inflammasome-mediated signaling pathways. BITC inhibited IL-1β production in P. aeruginosa LPS/ATP-induced THP-1 cells. BITC also inhibited activation of leucine-rich repeat protein-3 (NLRP3) and caspase-1 in P. aeruginosa LPS/ATP-induced THP-1 cells. Furthermore, we show that mitogen-activated protein kinase (MAPK) and nuclear factor-κB (NF-κB) activation in P. aeruginosa LPS was attenuated by BITC. These BITC-mediated modulatory effects on IL-1β production may have therapeutic potential for inflammasome-mediated disorders such as a nasal polyp.     

Effect of hydrophilic and hydrophobic cyclodextrins on the release of encapsulated allyl isothiocyanate (AITC) and their potential application for plastic film extrusion

Allyl isothiocyanate (AITC), a natural pungent flavor from wasabi and horseradish, is well-known antimicrobial agents against foodborne pathogens. However, its highly volatile nature and low thermal stability restrict its application in the food packaging industry. Also, its strong organoleptic characteristics hinder its application at a higher dosage. We encapsulated AITC in β-cyclodextrin (β-CD) and triacetyl-β-CD (TA-β-CD) and evaluated the performance as slow releasing active compounds through low-density polyethylene (LDPE)–cyclodextrins (CDs) matrix. Also, the thermal, optical, mechanical, and barrier properties of two ternary blends, LDPE/β-CD/AITC(L-CDs) and LDPE/TA-β-CD/AITC(L-TACDs), were investigated to compare their compatibility under the plastic extrusion process. During the 15 days of the storage period, L-TACDs maintained more consistent AITC release and a higher concentration than L-CDs. Also, the blending of LDPE and TA-β-CD was more compatible with that of LDPE and β-CD. No significant optical, mechanical, and barrier property changes were observed in LDPE with less than 3% of TA-β-CD while L-CDs showed substantial agglomeration on the ternary blend films and the lower mechanical and barrier properties than pure LDPE. The results indicate that the LDPE films containing TA-β-CD/AITC can be applied as an effective antimicrobial packaging material for food and nonfood applications. © 2019 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2019 , 136, 48137.     

Synthesis and characterization of fluorescein isothiocyanate (FITC)-labeled PEO-PCL-PEO triblock copolymers for topical delivery

We present the synthesis of fluorescein isothiocyanate (FITC)-labeled poly(ethylene oxide)-block-poly(?-caprolactone)-block-poly(ethylene oxide) (PEO-PCL-PEO) triblock copolymers and their applications for tracking the penetration behavior of FITC-labeled copolymers in the hairless mouse skin. In the first step, PEO-PCL diblock copolymers with different ratios of PCL to PEO (i.e., [CL]/[EO]) were prepared by ring opening polymerization of ?-caprolactone (CL), where monomethoxy poly(ethylene glycol) (mPEG, M_n = 2000 g mol⁻¹) was used as a macro-initiator. FITC was successively reacted with octadecylamine, isophorone diisocyanate (IPDI), and then used as a linker to obtain PEO-PCL-PEO triblock copolymers from the PEO-PCL diblock copolymers. In aqueous solution, both FITC-labeled triblock copolymers show two UV absorption peaks at 489 and 455 nm, attributed to the monomeric FITC and H-aggregated FITC moieties, respectively. Due to the strong H-aggregation of FITC in the copolymer of high [CL]/[EO], fluorescent emission intensities considerably decreased at high concentrations of the copolymer. FITC-labeled copolymers exhibited more sharper polarized optical and fluorescence microscopic images compared to the mixtures of FITC and unlabeled copolymer in both solid crystalline and multiple emulsion state. Furthermore, the Frantz diffusion cell test was carried out to demonstrate the penetration behavior of the FITC-labeled copolymers in the hairless mouse skin.     

Combined effect of high pressure treatment and anti-microbial bio-sourced materials on microorganisms' growth in model food during storage

Antimicrobial bio-sourced films based on poly(lactic acid) containing either carvacrol or allyl isothiocyanate (AITC) were prepared and their antimicrobial properties were assessed on Botrytis cinerea during storage and after a high pressure (HP) “pasteurisation-like” treatment (up to 800 MPa at ambient temperature). A dry process (extrusion + thermomoulding) was used to shape the material. The high temperature encountered during film processing dramatically decreased the carvacrol and AITC content in the film, leading to a less efficient antimicrobial activity. The use of β-cyclodextrin (β-CD) to encapsulate the active compounds before film processing proved to be efficient to protect the AITC against thermal degradation and to control its release from the films during its use. PLA-based films containing either AITC or β-CD encapsulated AITC showed a significant activity against B. cinerea. An effective combination between the antimicrobial activity of AITC-based films and the high pressure treatment was observed on a model food system (PDA) inoculated with N × 10⁴ (N ~ 1–9) conidia of B. cinerea. An HP treatment of only 300 MPa associated with an antimicrobial PLA/β-CD system providing an initial quantity of active agents equivalent to 4 mg of AITC/L of air (i.e. almost 2 folds lower than the minimal inhibition concentration of the active packaging used alone, which was determined to be equal to 10 mg/L of air in the same conditions) was found more efficient (total inhibition of B. cinerea growth during 10 days) than an 800 MPa HP treatment used alone (increase of the lag phase growth of 3.3 days).

Industrial relevance

The consumer demand for “fresh like” product containing reduced amount of preservatives without compromising human and environmental safety needs the development of new preservation strategies. As a consequence, the concept of “hurdle technologies” has risen up. The combined effect of HP treatment and volatile antimicrobial packaging allowed the use of lower individual treatment intensities to inhibit B. cinerea growth. Combining such “hurdles” is of relevance in the context of development of low-cost and eco-friendly food technologies.     

Stability and Antimicrobial Activity of Allyl Isothiocyanate during Long-Term Storage in an Oil-in-Water Emulsion

Abstract: This study investigated the stability and antimicrobial activity of allyl isothiocyanate (AITC) in medium chain triglyceride (MCT) or soybean oil (SBO) dispersed in an oil-in-water (o/w) system during long-term storage. Oil type, content, and oxidative stability affect the stability and antimicrobial activity of AITC during storage. High oil content is favorable for AITC stability in the emulsion. Notably, AITC with MCT is more stable than AITC with SBO with the same oil content. Consequently, AITC with MCT is more effective than AITC with SBO in inhibiting G(−) bacteria (E. coli O157:H7, Salmonella enterica, and Vibrio parahaemolyticus) and G(+) bacteria (Staphylococcus aureus and Listeria monocytogenes).     

异硫氰酸镱苄胺配合物的合成及其热分解非等温动力学研究

本文叙述了异硫氰酸镱苄胺配合物Yb(NCS)_3·4C_6H_5CH_2NH_2的合成方法。通过对该配合物进行热分解非等温动力学研究,推断了该配合物的热分解反应机理及动力学补偿效应表达式。     

苯基异硫腈钴（I）配合物的合成与结构及性质

本文报导了三－三苯基膦氧化钴（Ｉ）与过量的异硫氰酸苯酯反应，依据快原子轰击质谱（ＦＡＢ－ＭＳ），证实生成物的结构为四员钴杂环配合物。该配合物不稳定，容易脱硫，生成苯基异腈钴（Ⅱ）配合物。