Antimicrobial effects of cannabidiol on select agriculturally important Clostridia.

Amino acid-fermenting Clostridia have undesirable effects in agricultural systems, which can be mitigated by antibiotics, but resistance necessitates alternatives. Here, we demonstrate the efficacy of cannabidiol on growth and ammonia inhibition of five agriculturally relevant Clostridia: Clostridium sporogenes, Peptostreptococcus spp., Clostridioides difficile, Acetoanaerobium sticklandii, and Clostridium aminophilum.

Black and pinto beans (Phaseolus vulgaris L.) unique mexican varieties exhibit antioxidant and anti-inflammatory potential.

Oxidative stress and inflammation play a key role in diverse pathological conditions such as cancer and metabolic disorders. The objective of this study was to determine the antioxidant and anti-inflammatory potentials of crude extract (CE) and phenolic-enriched extract (PHE) obtained from the seed coats (SCs) of black bean (BB) and pinto bean (PB) varieties. Delphinidin-3-O-glucoside (46 mg/g SC), malvidin-3-O-glucoside (29.9 mg/g SC), and petunidin-3-O-glucoside (7.5 mg/g SC) were found in major concentrations in the PHE-BB. Pelargonidin (0.53 mg/g SC) was only identified in the PHE-PB. PHE from both varieties showed antioxidant and radical scavenging capacities, with strong correlations associated with total phenolic content (TPC). Polyphenolics, including catechin, myricetin, kaempferol, quercetin, and isorhamnetin glucosides, were identified in the extracts. In terms of the anti-inflammatory potentials, PHE-PB had an IC50 of 10.5 µg dry extract/mL (µg DE/mL) for cyclooxygenase-2 (COX-2) inhibition. The inhibition values for cyclooxygenase-1 (COX-1) ranged from 118.1 to 162.7 µg DE/mL. Regarding inducible nitric oxide synthase (iNOS) inhibition, PHE-BB had an IC50 of 62.6 µg DE/mL. As determined via in silico analysis, pelargonidin showed binding affinities of -7.8 and -8.5 kcal/mol for COX-1 and iNOS, respectively, and catechin had a value of -8.3 kcal/mol for COX-2. Phenolic-enriched extracts from seed coats of black and pinto beans showed good antioxidant and anti-inflammatory potential that warrants in vitro and in vivo studies.

Bioactivity of brassica seed meals and its compounds as ecofriendly larvicides against mosquitoes.

Strategic, sustainable, and ecofriendly alternatives to chemical pesticides are needed to effectively control mosquitoes and reduce the incidence of their vectored diseases. We evaluated several Brassicaceae (mustard family) seed meals as sources of plant derived isothiocyanates produced from the enzymatic hydrolysis of biologically inactive glucosinolates for the control of Aedes aegypti (L., 1762). Five defatted seed meals (Brassica juncea (L) Czern., 1859, Lepidium sativum L., 1753, Sinapis alba L., 1753, Thlaspi arvense L., 1753, and Thlaspi arvense-heat inactivated and three major chemical products of enzymatic degradation (allyl isothiocyanate, benzyl isothiocyanate and 4-hydroxybenzyl isothiocyanate) were assayed to determine toxicity (LC50) to Ae. aegypti larvae. All seed meals except the heat inactivated T. arvense were toxic to mosquito larvae. L. sativum seed meal was the most toxic treatment to larvae (LC50 = 0.04 g/120 mL dH2O) at the 24-h exposure. At the 72-h evaluation, the LC50 values for B. juncea, S. alba and T. arvense seed meals were 0.05, 0.08 and 0.1 g/120 mL dH2O, respectively. Synthetic benzyl isothiocyanate was more toxic to larvae 24-h post treatment (LC50 = 5.29 ppm) compared with allyl isothiocyanate (LC50 = 19.35 ppm) and 4-hydroxybenzyl isothiocyanate (LC50 = 55.41 ppm). These results were consistent with the higher performance of the benzyl isothiocyanate producing L. sativum seed meal. Isothiocyanates produced from seed meals were more effective than the pure chemical compounds, based on calculated LC50 rates. Using seed meal may provide an effective method of delivery for mosquito control. This is the first report evaluating the efficacy of five Brassicaceae seed meals and their major chemical constituent against mosquito larvae and demonstrates how natural compounds from Brassicaceae seed meals can serve as a promising ecofriendly larvicides to control mosquitoes.

Fusarium head blight resistance exacerbates nutritional loss of wheat grain at elevated CO2.

The nutritional integrity of wheat is jeopardized by rapidly rising atmospheric carbon dioxide (CO2) and the associated emergence and enhanced virulence of plant pathogens. To evaluate how disease resistance traits may impact wheat climate resilience, 15 wheat cultivars with varying levels of resistance to Fusarium Head Blight (FHB) were grown at ambient and elevated CO2. Although all wheat cultivars had increased yield when grown at elevated CO2, the nutritional contents of FHB moderately resistant (MR) cultivars were impacted more than susceptible cultivars. At elevated CO2, the MR cultivars had more significant differences in plant growth, grain protein, starch, fructan, and macro and micro-nutrient content compared with susceptible wheat. Furthermore, changes in protein, starch, phosphorus, and magnesium content were correlated with the cultivar FHB resistance rating, with more FHB resistant cultivars having greater changes in nutrient content. This is the first report of a correlation between the degree of plant pathogen resistance and grain nutritional content loss in response to elevated CO2. Our results demonstrate the importance of identifying wheat cultivars that can maintain nutritional integrity and FHB resistance in future atmospheric CO2 conditions.

Phenolic sucrose esters: evolution, regulation, biosynthesis, and biological functions.

Phenolic sucrose esters (PSEs) are a diverse group of specialized metabolites that are present in several angiosperm lineages. Phylogenetic reconstruction and structural variation suggest that these metabolites may have evolved independently in monocots and dicots. Constitutive variation in PSE abundance across plant organs and developmental stages is correlated with transcriptional regulation of the upstream phenylpropanoid pathway, whereas pathogen induction is regulated by stress-related phytohormones such as ethylene. Shared structural features of PSEs indicate that their biosynthesis may involve one or more hydroxycinnamoyl transferases and BAHD acetyltransferases, which could be identified by correlative analyses of multi-omics datasets. Elucidation of the core biosynthetic pathway of PSEs will be essential for more detailed studies of the biological function of these compounds and their potential medicinal and agricultural applications.

Liposomes Loaded with Unsaponifiable Matter from Amaranthus hypochondriacus as a Source of Squalene and Carrying Soybean Lunasin Inhibited Melanoma Cells.

Amaranthus hypochondriacus is a source of molecules with reported health benefits such as antioxidant activity and cancer prevention. The objective of this research was to optimize the conditions for preparing a liposome formulation using amaranth unsaponifiable matter as a source of squalene in order to minimize the particle size and to maximize the encapsulation efficiency of liposomes for carrying and delivering soybean lunasin into melanoma cell lines. Amaranth oil was extracted using supercritical dioxide carbon extraction (55.2 MPa pressure, 80 °C temperature, solvent (CO2)-to-feed (oil) ratio of 20). The extracted oil from amaranth was used to obtain the unsaponifiable enriched content of squalene, which was incorporated into liposomes. A Box-Behnken response surface methodology design was used to optimize the liposome formulation containing the unsaponifiable matter, once liposomes were optimized. Soybean lunasin was loaded into the liposomes and tested on A-375 and B16-F10 melanoma cells. The squalene concentration in the extracted oil was 36.64 ± 0.64 g/ 100 g of oil. The particle size in liposomes was between 115.8 and 163.1 nm; the squalene encapsulation efficiency ranged from 33.14% to 76.08%. The optimized liposome formulation contained 15.27 mg of phospholipids and 1.1 mg of unsaponifiable matter. Cell viability was affected by the liposome formulation with a half-maximum inhibitory concentration (IC50) equivalent to 225 µM in B16-F10 and 215 µM in A-375. The liposomes formulated with lunasin achieved 82.14 ± 3.34% lunasin encapsulation efficiency and improved efficacy by decreasing lunasin IC50 by 31.81% in B16-F10 and by 41.89% in A-375 compared with unencapsulated lunasin.

Changes in Wheat Nutritional Content at Elevated [CO2] Alter Fusarium graminearum Growth and Mycotoxin Production on Grain.

Rising atmospheric [CO2] has been shown to impact plant primary metabolism and the severity of Fusarium head blight (FHB) in wheat. In this study, we evaluated how changes in grain nutritional content due to growth at elevated [CO2] affected Fusarium graminearum growth and mycotoxin production. Susceptible (Norm) and moderately resistant (Alsen) hard spring wheat grains that had been grown at ambient (400 ppm) or elevated [CO2] (800 ppm) were independently inoculated with two F. graminearum fungal strains, which produce the trichothecene mycotoxin, deoxynivalenol. Under higher [CO2], FHB-susceptible and moderately resistant wheat had disproportionate losses in protein and mineral contents, with Alsen being more severely impacted. Furthermore, the F. graminearum strain 9F1 had increased mycotoxin biosynthesis in response to the loss of wheat nutritional content in Alsen. Our results demonstrate that future [CO2] conditions may provide a strain-specific pathogenic advantage on hosts, with greater losses in nutritional content.

Biopesticide synergy when combining plant flavonoids and entomopathogenic baculovirus.

Four crop plants known to be hosts for the lepidopteran Trichoplusia ni (soybean, green bean, cotton, and cabbage) were treated with the biopesticide AfMNPV baculovirus in a dosage response assay. Treated soybean had, on average, a 6-fold increase in virus activity compared with the other crops. Leaf trichomes on soybeans were not found to be responsible for the observed increase of insecticidal activity. Three flavonoid compounds (daidzein, genistein, and kaempferol) were uniquely found only in the soybean crop, and were not detected in cotton, cabbage, or green bean plant matter. The individual flavonoid compounds did not cause T ni. mortality in no-virus assays when incorporated into artificial insect diet. The combination of the three flavonoid compounds at leaf level concentrations significantly increased baculovirus activity in diet incorporation assays. When the daidzein, genistein, and kaempferol were added to artificial diet, at 3.5-6.5 × leaf level concentrations, virus activity increased 1.5, 2.3, and 4.2-fold for each respective flavonoid. The soybean flavonoid compounds were found to synergistically improve baculovirus activity against T. ni.

Quantitative NIR determination of isoflavone and saponin content of ground soybeans.

Over 3200 discrete soybean samples were obtained from production locations around the United States during the years 2012-2016. Ground samples were scanned on near infrared spectrometers (NIRS) and analyzed by HPLC for total isoflavone and total saponin composition, as well as total carbohydrate composition. Multiple Linear Regression (MLR) analysis of preprocessed spectral data was used to develop optimized models to predict isoflavone content. The selection of a suitable calibration model was based on a high regression coefficient (R2), and lower standard error of calibration (SEC) values. Robust validated predictions were obtained for isoflavones, however less than robust calibrations were obtained for the total saponins. The correlations were not as robust for predicting the carbohydrate composition. NIRS is a suitable, rapid, nondestructive method to determine isoflavone composition in ground soybeans. Useful isoflavone composition predictions for large numbers of soybean samples can be obtained from quickly obtained NIRS scans.

A comparison of the absorption and metabolism of the major quercetin in brassica, quercetin-3-O-sophoroside, to that of quercetin aglycone, in rats.

Although flavonoid sophorosides are common glycosides in brassica vegetables, red raspberries and other food plants, there is a lack of studies of absorption and metabolism of any sophoroside. The aim of this study was to characterize the absorption, phase II metabolism and microbial catabolism of quercetin-3-O-sophoroside, compared to that of quercetin aglycone. Quercetin-3-O-sophoroside was purified from Apocynum venetum and characterized by MS2, 1H and 13C NMR. Using an in situ rat gut model, we found intact, methylated, sulfated and both methylated and sulfated quercetin sophoroside in the plasma following jejunal introduction of the sophoroside; we found derivatives of benzoic acid, phenylacetic acid, and phenyl propionic acid in the cecal contents following cecal introduction. This novel finding, that quercetin sophoroside was absorbed intact, without deglycosylation, points to a possible role for the terminal sugar and/or the type of linkage among glycosidic moieties in the mechanism of absorption of flavonoid glycosides.

Unique Flavanol-Anthocyanin Condensed Forms in Apache Red Purple Corn.

Anthocyanin pigments from purple corn are being explored as a potential alternative to artificial colorants and for their health-promoting properties. However, all pericarp-pigmented corn varieties examined to date primarily contain cyanidin-derived anthocyanins, which produce bluish-red or pink extracts. Here we describe the first pelargonidin-dominant pericarp-pigmented corn lines from the landrace Apache Red (AR). Anthocyanins were characterized from six AR families using high-performance liquid chromatography-mass spectrometry (HPLC-MS). From this, we identified two new flavanol-anthocyanin condensed forms in corn: catechin-(4,8)-pelargonidin 3,5-diglucoside and afzelechin-(4,8)-pelargonidin 3,5-diglucoside, which were subsequently confirmed with NMR. Additionally, several apigenin-derived C-glycosyl flavones were identified in abundance. With a diverse flavonoid profile containing an array of different anthocyanin species and flavones, Apache Red will be an important line in which to study control of the flavonoid biosynthesis pathway.

Dormancy-defense syndromes and tradeoffs between physical and chemical defenses in seeds of pioneer species.

Seeds of tropical pioneer trees have chemical and physical characteristics that determine their capacity to persist in the soil seed bank. These traits allow seeds to survive in the soil despite diverse predators and pathogens, and to germinate and recruit even decades after dispersal. Defenses in seedlings and adult plants often are described in terms of tradeoffs between chemical and physical defense, but the interplay of defensive strategies has been evaluated only rarely for seeds. Here we evaluated whether classes of seed defenses were negatively correlated across species (consistent with tradeoffs in defense strategies), or whether groups of traits formed associations across species (consistent with seed defense syndromes). Using 16 of the most common pioneer tree species in a neotropical lowland forest in Panama we investigated relationships among four physical traits (seed fracture resistance, seed coat thickness, seed permeability, and seed mass) and two chemical traits (number of phenolic compounds and phenolic peak area), and their association with seed persistence. In addition, seed toxicity was assessed with bioassays in which we evaluated the activity of seed extracts against representative fungal pathogens and a model invertebrate. We did not find univariate tradeoffs between chemical and physical defenses. Instead, we found that seed permeability - a trait that distinguishes physical dormancy from other dormancy types - was positively associated with chemical defense traits and negatively associated with physical defense traits. Using a linear discriminant analysis and a hierarchical cluster analysis we found evidence to distinguish three distinct seed defense syndromes that correspond directly with seed dormancy classes (i.e., quiescent, physical, and physiological). Our data suggest that short and long-term persistence of seeds can be achieved via two strategies: having permeable seeds that are well defended chemically, corresponding to the physiologically dormant defense syndrome; or having impermeable seeds that are well defended physically, corresponding to the physically dormant defense syndrome. In turn, transient seeds appear to have a lower degree of chemical and physical defenses, corresponding to the quiescent defense syndrome. Overall, we find that seed defense and seed dormancy are linked, suggesting that environmental pressures on seed persistence and for delayed germination can select for trait combinations defining distinct dormancy-defense syndromes.

Utilization of Quercetin as an Oviposition Stimulant by Lab-Cultured Coleomegillamaculata in the Presence of Conspecifics and a Tissue Substrate.

BACKGROUND: The discovery of natural products to improve the reproductive performance of mass-reared predators is an important aim for successful augmentative biological control. We tested the hypothesis that quercetin (a bioflavonoid) stimulates oviposition by the ladybird beetle Coleomegillamaculata in the presence of conspecifics and a tissue substrate. METHODS: We conducted bioassays in solitary cages (housing one female) and communal cages (housing 10 females) to estimate daily oviposition site preferences, egg production in response to quercetin in the presence or absence of a tissue paper substrate, and female “resting” positions. RESULTS: Females preferentially oviposited within 1⁻2 cm of quercetin powder, held in a tiny dish, at the base of cages. When given a choice, females oviposited in the dish with quercetin over a tissue paper substrate. In one of two experiments, they produced more egg clutches, regardless of oviposition site, when the quercetin and tissue were in close juxtaposition. Females “rested” on the tissue in the presence or absence of quercetin. CONCLUSION: This study provides evidence that quercetin can be utilized as an oviposition stimulant by C. maculata in a rearing system. Future research should determine if quercetin stimulates oviposition in other ladybird beetle species.

Do Bioflavonoids in Juniperus virginiana Heartwood Stimulate Oviposition in the Ladybird Coleomegilla maculata?

Maximizing the reproductive potential of ladybird beetles fed factitious foods or artificial diets, in lieu of natural prey, is a major challenge to cost-effective mass rearing for augmentative biological control. In this study, we tested the hypothesis that compounds in redcedar, Juniperus virginiana, stimulate oviposition in the ladybird Coleomegilla maculata. We also tested the prediction that several bioflavonoids, identified in heartwood fractions, elicited this behavioral response. Phenolic compounds were extracted from J. virginiana heartwood sawdust, separated into several fractions, then presented to adult beetles, in a powdered, pure form, in the laboratory. Females preferentially oviposited within 1 to 2 cm of fractions B, C, D, and E, but not A or the unfractionated extract, at the base of test cages. Chemical analysis identified bioflavonoids in heartwood fractions and subsequent bioassays using several identified in fractions C, D, and E confirmed that quercetin, taxifolin, and naringenin (to a lesser extent) stimulated oviposition. All tested fractions and bioflavonoids readily adhered to the chorion of freshly laid eggs but did not reduce egg hatch. This study demonstrates that several bioflavonoids stimulate oviposition by C. maculata and could be useful for mass rearing programs.

Quinovosamycins: new tunicamycin-type antibiotics in which the α, ß-1″,11'-linked N-acetylglucosamine residue is replaced by N-acetylquinovosamine.

Tunicamycins (TUN) are potent inhibitors of polyprenyl phosphate N-acetylhexosamine 1-phosphate transferases (PPHP), including essential eukaryotic GPT enzymes and bacterial HexNAc 1-P translocases. Hence, TUN blocks the formation of eukaryotic N-glycoproteins and the assembly of bacterial call wall polysaccharides. The genetic requirement for TUN production is well-established. Using two genes unique to the TUN pathway (tunB and tunD) as probes we identified four new prospective TUN-producing strains. Chemical analysis showed that one strain, Streptomyces niger NRRL B-3857, produces TUN plus new compounds, named quinovosamycins (QVMs). QVMs are structurally akin to TUN, but uniquely in the 1″,11'-HexNAc sugar head group, which is invariably d-GlcNAc for the known TUN, but is d-QuiNAc for the QVM. Surprisingly, this modification has only a minor effect on either the inhibitory or antimicrobial properties of QVM and TUN. These findings have unexpected consequences for TUN/QVM biosynthesis, and for the specificity of the PPHP enzyme family.

Interspecific variation in persistence of buried weed seeds follows trade-offs among physiological, chemical, and physical seed defenses.

Soil seedbanks drive infestations of annual weeds, yet weed management focuses largely on seedling mortality. As weed seedbanks increasingly become reservoirs of herbicide resistance, species-specific seedbank management approaches will be essential to weed control. However, the development of seedbank management strategies can only develop from an understanding of how seed traits affect persistence.We quantified interspecific trade-offs among physiological, chemical, and physical traits of weed seeds and their persistence in the soil seedbank in a common garden study. Seeds of 11 annual weed species were buried in Savoy, IL, from 2007 through 2012. Seedling recruitment was measured weekly and seed viability measured annually. Seed physiological (dormancy), chemical (phenolic compound diversity and concentration; invertebrate toxicity), and physical traits (seed coat mass, thickness, and rupture resistance) were measured.Seed half-life in the soil (t0.5) showed strong interspecific variation (F10,30 = 15, p < .0001), ranging from 0.25 years (Bassia scoparia) to 2.22 years (Abutilon theophrasti). Modeling covariances among seed traits and seedbank persistence quantified support for two putative defense syndromes (physiological-chemical and physical-chemical) and highlighted the central role of seed dormancy in controlling seed persistence.A quantitative comparison between our results and other published work indicated that weed seed dormancy and seedbank persistence are linked across diverse environments and agroecosystems. Moreover, among seedbank-forming early successional plant species, relative investment in chemical and physical seed defense varies with seedbank persistence. Synthesis and applications. Strong covariance among weed seed traits and persistence in the soil seedbank indicates potential for seedbank management practices tailored to specific weed species. In particular, species with high t0.5 values tend to invest less in chemical defenses. This makes them highly vulnerable to physical harvest weed seed control strategies, with small amounts of damage resulting in their full decay.

Antioxidant activity and sensory evaluation of a rosmarinic acid-enriched extract of Salvia officinalis.

An extract of Salvia officinalis (garden sage) was prepared using supercritical carbon dioxide (SC-CO2 ) extraction, followed by hot water extraction. The resulting extract was enriched in polyphenols, including rosmarinic acid (RA), which has shown promising health benefits in animals. The extract contained RA at a concentration of 28.4 mg/g, representing a significant enrichment from the RA content in sage leaves. This extract was incorporated into oil-in-water emulsions as a source of lipid antioxidants and compared to emulsions containing pure rosmarinic acid. Both treatments were effective in suppressing lipid oxidation. The extract was evaluated by a trained sensory panel in a tea formulation. While the panel could discriminate among extract-treated and control samples, panelists demonstrated high acceptability of the sage extract in a tea.

Camelina sativa defatted seed meal contains both alkyl sulfinyl glucosinolates and quercetin that synergize bioactivity.

Camelina sativa L. Crantz is under development as a novel oilseed crop, yet bioefficacy of camelina phytochemicals is unknown. Defatted camelina seed meal contains two major aliphatic glucosinolates (GSLs), glucoarabin (9-(methylsulfinyl)nonylglucosinolate; GSL 9) and glucocamelinin (10-(methylsulfinyl)decylglucosinolate; GSL 10), with traces of a third, 11(methylsulfinyl)undecylglucosinolate and several flavonoids, mostly quercetin glycosides. In Hepa1c1c7 cells, hydrolyzed GSLs (hGSLs) 9 and 10 upregulated the phase II detoxification enzyme quinone reductase (NQO1), with no effect on cytochrome P450 (CYP) 1A1 activity. Isobologram graphs revealed synergy of NQO1 induction for a combination of hGSL 9 and quercetin. These findings suggest that defatted camelina seed meal should be evaluated for anticancer activity, similar to broccoli and other Brassicaceae family members. Interestingly, synergy of NQO1 induction was also seen for physiologically relevant doses of sulforaphane (SF) and quercetin, two key bioactives present in broccoli. This suggests that SF within broccoli may be more potent than purified SF.

Bioactive compounds from culinary herbs inhibit a molecular target for type 2 diabetes management, dipeptidyl peptidase IV.

Greek oregano (Origanum vulgare), marjoram (Origanum majorana), rosemary (Rosmarinus officinalis), and Mexican oregano (Lippia graveolens) are concentrated sources of bioactive compounds. The aims were to characterize and examine extracts from greenhouse-grown or commercially purchased herbs for their ability to inhibit dipeptidyl peptidase IV (DPP-IV) and protein tyrosine phosphatase 1B (PTP1B), enzymes that play a role in insulin secretion and insulin signaling, respectively. Greenhouse herbs contained more polyphenols (302.7-430.1 µg of gallic acid equivalents/mg of dry weight of extract (DWE)) and flavonoids (370.1-661.4 µg of rutin equivalents/mg of DWE) compared to the equivalent commercial herbs. Greenhouse rosemary, Mexican oregano, and marjoram extracts were the best inhibitors of DPP-IV (IC50=16, 29, and 59 µM, respectively). Commercial rosemary, Mexican oregano, and marjoram were the best inhibitors of PTP1B (32.4-40.9% at 500 µM). The phytochemicals eriodictyol, naringenin, hispidulin, cirsimaritin, and carnosol were identified by LC-ESI-MS as being present in greenhouse-grown Mexican oregano and rosemary. Computational modeling indicated that hispidulin, carnosol, and eriodictyol would have the best binding affinities for DPP-IV. Biochemically, the best inhibitors of DPP-IV were cirsimaritin (IC50=0.43±0.07 µM), hispidulin (IC50=0.49±0.06 µM), and naringenin (IC50=2.5±0.29 µM). Overall, herbs contain several flavonoids that inhibit DPP-IV and should be investigated further regarding their potential in diabetes management.