Search Results (25)

The genus Dracocephalum (family Lamiaceae) comprises approximately 70 species, many of which have been traditionally used in various ethnomedical systems. The plants exhibit a broad distribution across steppe, semi-deserts, deserts, and alpine zones of temperate Eurasia, with isolated endemic species occurring in North America and North Africa. The traditional medicinal uses of the Dracocephalum species encompass the treatment of respiratory diseases, colds and fever, gastrointestinal disorders, liver and gallbladder ailments, musculoskeletal conditions, cardiovascular diseases, diabetes, gynecological and urological disorders, as well as ailments of the ears, throat, mouth, and eyes, as well as various dermatological conditions. The plants are rich sources of polyphenolic compounds, including flavonoids and phenolic acids, which contribute to their diverse pharmacological activities. The flavonoid profile of the Dracocephalum species is dominated by luteolin and apigenin derivatives, supplemented by mono-, di-, tri-, tetra-, and pentamethoxylated flavones. The predominant phenolic acids are chlorogenic acid, coumaric acid, rosmarinic acid, and their derivatives. Other phenolic compounds have also been identified in the genus: anthocyanins, lignans, phenylethanoids, phenylacetamide glycosides, flavonoid alkaloids, gingerols, coumarins, furanocoumarins, and cyanogenic glucosides. Despite growing scientific interest in this genus, a comprehensive review of its polyphenolic constituents, their structures, and associated biological activities remains lacking. To bridge this gap, this review presents an analysis of the polyphenolic profile of the Dracocephalum species, their ethnomedicinal uses, and the latest findings on their biological potential. Full article

The cyanogenic glucoside dhurrin is found in sorghum and has been reported for its role in defense against biotic and abiotic stresses, both involving hydrogen cyanide (HCN) release. The fungus Sporisorium reilianum f. sp. reilianum (SRS) causes sorghum head smut and the infection occurs at the seedling stage, later resulting in panicle loss. Here, the focus was to determine the role of dhurrin in sorghum’s reaction against SRS infection. We investigated the genomic basis of HCN potential (HCNp) variation and its relationship with seedlings’ response to SRS inoculation, along with other sorghum traits, and the expression of dhurrin biosynthetic genes in SRS-inoculated young sorghum. Genome-wide association studies (GWAS) using HCNp scores showed significant single nucleotide polymorphisms (SNPs) on chromosomes harboring the dhurrin biosynthetic and catabolic genes but not in proximity. Significant hits were also detected in or near genes encoding proteins involved in plant defense/resistance against biotic stresses. Correlation analyses showed a strong positive relationship between average HCNp scores and latent period in SRS-inoculated sorghum seedlings. RT-qPCR revealed that the dhurrin biosynthetic genes were upregulated in the leaves of the head smut resistant line BTx635 up to two days after SRS inoculation. Our results suggest the involvement of dhurrin in sorghum’s protection against SRS. Full article

Cyanogenic glucosides are specialized metabolites produced by over 3000 species of higher plants from more than 130 families. The deployment of cyanogenic glucosides is influenced by biotic and abiotic factors in addition to being developmentally regulated, consistent with their roles in plant defense and stress mitigation. Despite their ubiquity, very little is known regarding the molecular mechanisms that regulate their biosynthesis. The biosynthetic pathway of dhurrin, the cyanogenic glucoside found in the important cereal crop sorghum (Sorghum bicolor (L.) Moench), was described over 20 years ago, and yet no direct regulator of the biosynthetic genes has been identified. To isolate regulatory proteins that bind to the promoter region of the key dhurrin biosynthetic gene of sorghum, SbCYP79A1, yeast one-hybrid screens were performed. A bait fragment containing 1204 base pairs of the SbCYP79A1 5′ regulatory region was cloned upstream of a reporter gene and introduced into Saccharomyces cerevisiae. Subsequently, the yeast was transformed with library cDNA representing RNA from two different sorghum developmental stages. From these screens, we identified SbGATA22, an LLM domain B-GATA transcription factor that binds to the putative GATA transcription factor binding motifs in the SbCYP79A1 promoter region. Transient assays in Nicotiana benthamiana show that SbGATA22 localizes to the nucleus. The expression of SbGATA22, in comparison with SbCYP79A1 expression and dhurrin concentration, was analyzed over 14 days of sorghum development and in response to nitrogen application, as these conditions are known to affect dhurrin levels. Collectively, these findings suggest that SbGATA22 may act as a negative regulator of SbCYP79A1 expression and provide a preliminary insight into the molecular regulation of dhurrin biosynthesis in sorghum. Full article

Apricot is a widely cultivated fruit tree of the drupe family, and its sweet/bitter kernel traits are important indicators of the quality and merchantability of apricots. The sweetness/bitterness traits were mainly determined by amygdalin content. However, the lack of high-quality genomes has limited insight into the traits. In this study, a high-quality genome of ‘Xiaobaixing’ was obtained by using single-molecule sequencing and chromosome-conformation capture techniques, with eight chromosomes of 0.21 Gb in length and 52.80% repetitive sequences. A total of 29,157 protein-coding genes were predicted with contigs N50 = 3.56 Mb and scaffold N50 = 26.73 Mb. Construction of phylogenetic trees of 15 species of Rosaceae fruit trees, with ‘Xiaobaixing’ differentiated by 5.3 Ma as the closest relative to ‘Yinxiangbai’. GO functional annotation and KEGG enrichment analysis identified 227 specific gene families to ‘Xiaobaixing’, with 569 expansion-gene families and 1316 contraction-gene families, including the significant expansion of phenylalanine N-monooxygenase and β-glucosidase genes associated with amygdalin synthesis, significant contraction of wild black cherry glucoside β-glucosidase genes, amygdalin β-glucosidase genes, and β-glucosidase genes, and significant enrichment of positively selected genes in the cyanogenic amino acid metabolic pathway. The 88 bHLH genes were identified in the genome of ‘Xiaobaixing’, and ParbHLH66 (rna-Par24659.1) was found to be a key gene for the identification of sweet/bitter kernels of apricots. The amino acid sequence encoded by its gene is highly conserved in the species of Prunus mume, Prunus dulcis, Prunus persica, and Prunus avium and may be participating in the regulation of amygdalin biosynthesis, which provides a theoretical foundation for the molecular identification of sweet/bitter kernels of apricots. Full article

Plants and phytophagous arthropods have coevolved in a long battle for survival. Plants respond to phytophagous feeders by producing a battery of antiherbivore chemical defences, while herbivores try to adapt to their hosts by attenuating the toxic effect of the defence compounds. Cyanogenic glucosides are a widespread group of defence chemicals that come from cyanogenic plants. Among the non-cyanogenic ones, the Brassicaceae family has evolved an alternative cyanogenic pathway to produce cyanohydrin as a way to expand defences. When a plant tissue is disrupted by an herbivore attack, cyanogenic substrates are brought into contact with degrading enzymes that cause the release of toxic hydrogen cyanide and derived carbonyl compounds. In this review, we focus our attention on the plant metabolic pathways linked to cyanogenesis to generate cyanide. It also highlights the role of cyanogenesis as a key defence mechanism of plants to fight against herbivore arthropods, and we discuss the potential of cyanogenesis-derived molecules as alternative strategies for pest control. Full article

Grapholita molesta (Busck) (Lepidoptera: Tortricidae), Oriental fruit moth (OFM), attacks fruits and shoots of the economically important trees in Rosaceae. Amygdalin is a cyanogenic glucoside of rosaceous plants that may be related to the seasonal patterns of infestation in many pests. The amygdalin concentration of fruits and shoots of peach, pear, and apple varies over the growing season. However, the relationship between the amygdalin concentration and G. molesta performance has not been reported. Here, we measured the performance (feeding, growth, development, and fecundity) of G. molesta larvae (as subsequent adults) reared on artificial diets with six amygdalin concentrations (0, 3, 6, 12, 24, and 48 mg/g), and we then calculated the population parameters. We found that these different concentrations of amygdalin affected the developmental time and fecundity, except for the proportion of larvae feeding on the diet and the survival rates of larvae and pupae. When compared with the control diet without amygdalin, diets with 3 or 6 mg/g (low and moderate concentrations) of amygdalin shortened developmental times and increased the number of eggs laid by females; however, a diet with 12 mg/g (moderate concentration) of amygdalin only increased the number of eggs laid by females and did not affect the larval and pupal developmental rate. A diet with 48 mg/g (high concentration) of amygdalin prolonged developmental times and reduced the number of eggs laid by females when compared with the control diet without amygdalin. Furthermore, the intrinsic rate of increase (r_m) for insects reared on diets with 3 or 6 mg/g (low and moderate concentrations) of amygdalin versus the control diet without amygdalin showed a slightly improved population growth. However, this increase in the r_m value did not persist over ten successive generations of rearing on the same diet. We concluded that the diet with 6 mg of amygdalin per g of diet can enhance the performance and population growth of G. molesta, but the effects of amygdalin are concentration-dependent. Full article

Dairy production is a pivotal economic sector of Austrian and European agriculture. Dietary toxins and endocrine disruptors of natural origin such as mycotoxins and phytoestrogens can affect animal health, reproduction, and productivity. This study characterized the profile of a wide spectrum of fungal, plant, and unspecific secondary metabolites, including regulated, emerging, and modified mycotoxins, phytoestrogens, and cyanogenic glucosides, in complete diets of lactating cows from 100 Austrian dairy farms. To achieve this, a validated multi-metabolite liquid chromatography/electrospray ionization–tandem mass spectrometric (LC/ESI–MS/MS) method was employed, detecting 155 of >800 tested metabolites. Additionally, the most influential dietary and geo-climatic factors related to the dietary mycotoxin contamination of Austrian dairy cattle were recognized. We evidenced that the diets of Austrian dairy cows presented ubiquitous contamination with mixtures of mycotoxins and phytoestrogens. Metabolites derived from Fusarium spp. presented the highest concentrations, were the most recurrent, and had the highest diversity among the detected fungal compounds. Zearalenone, deoxynivalenol, and fumonisin B1 were the most frequently occurring mycotoxins considered in the EU legislation, with detection frequencies >70%. Among the investigated dietary factors, inclusion of maize silage (MS) and straw in the diets was the most influential factor in contamination with Fusarium-derived and other fungal toxins and metabolites, and temperature was the most influential among the geo-climatic factors. Full article

This study was carried out to develop a green approach to synthesising sodium cyanide (NaCN) using hydrogen cyanide (HCN) extracted from cassava (Manihot esculenta Crantz) leaves after 120 min of maceration at 30 °C and 45 min of recovery under vacuum at 35–40 °C. The CN^- ion released via autolysis was reacted with the Na⁺ ion following vacuum extraction of the former to produce NaCN by saturating the absorbing sodium hydroxide (NaOH) solution. This specific extraction method avoided direct contact between the cassava leaves homogenate and the absorbing solution. NaCN was crystallised by drying the NaCN slurry at 100 °C in an air oven. A total of 15.70 kg of fresh cassava leaves was needed to produce 32.356 g of NaCN (green-NaCN) (% NaCN yield = 0.21%). The results of X-ray diffraction, attenuated total reflectance–Fourier transform infrared spectroscopy and scanning electron microscopy with energy-dispersive X-ray spectroscopy, show that NaCN was successfully prepared using the proposed method. These spectral techniques showed that the control and green-NaCN contained sodium carbonate impurities. The latter was quantified by the titration experiments and was found to be 0.61% and 2.29% in the control and green-NaCN, respectively. Furthermore, the titration experiments revealed that the residual NaOH content was 1.63% in control NaCN and 4.68% in green-NaCN. The aim of modifying the green synthesis route for producing NaCN from cassava, developed by the Attahdaniel research group in 2013 and 2020, was achieved. Full article

In 2009, Food Standards Australia New Zealand set a total cyanide content limit of 10 ppm for ready-to-eat cassava products to address food safety concerns about cyanogenic glucosides in cassava. This study surveys a range of cassava food products available in Melbourne, Australia, ten years after the implementation of these regulations. Of all the products tested, the mean cyanide content was greatest in ready-to-eat cassava chips (48.4 ppm), although imported ready-to-eat products had a higher mean cyanide content (95.9 ppm) than those manufactured in Australia (1.0 ppm). Cyanide was detected in frozen cassava products (grated mean = 12.9 ppm; whole root mean = 19.8 ppm), but was significantly reduced through processing according to packet instructions in both product types. Three methods were used to quantify total cyanide content: the evolved cyanide method, the picrate absorbance method and the picrate chart method, with satisfactory agreement between methods. The picrate absorbance and chart methods reported mean cyanide contents 13.7 ppm and 23.1 ppm higher, respectively, than the evolved cyanide method. Our results reaffirm the need for the ongoing testing of cassava food products, especially ready-to-eat products whose cyanide content will not be reduced before consumption. Full article

In plants, aldoximes per se act as defense compounds and are precursors of complex defense compounds such as cyanogenic glucosides and glucosinolates. Bacteria rarely produce aldoximes, but some are able to transform them by aldoxime dehydratase (Oxd), followed by nitrilase (NLase) or nitrile hydratase (NHase) catalyzed transformations. Oxds are often encoded together with NLases or NHases in a single operon, forming the aldoxime–nitrile pathway. Previous reviews have largely focused on the use of Oxds and NLases or NHases in organic synthesis. In contrast, the focus of this review is on the contribution of these enzymes to plant-bacteria interactions. Therefore, we summarize the substrate specificities of the enzymes for plant compounds. We also analyze the taxonomic and ecological distribution of the enzymes. In addition, we discuss their importance in selected plant symbionts. The data show that Oxds, NLases, and NHases are abundant in Actinobacteria and Proteobacteria. The enzymes seem to be important for breaking through plant defenses and utilizing oximes or nitriles as nutrients. They may also contribute, e.g., to the synthesis of the phytohormone indole-3-acetic acid. We conclude that the bacterial and plant metabolism of aldoximes and nitriles may interfere in several ways. However, further in vitro and in vivo studies are needed to better understand this underexplored aspect of plant-bacteria interactions. Full article

Papaya fruit is one of economic crops in Taiwan, mostly eaten as table fruits. In some Asian countries, unripe papaya fruit is eaten as salad and this led to trends in Taiwan as well. However, unripe papaya fruit may taste bitter during cool seasons. Glucosinolate and cyanogenic glucoside are among the substances that cause bitter taste in many plants, which can also be found in papaya. However, there is still no report about the relationship between seasons and bitter taste in papaya fruits. Thus, the purpose of this study is to investigate the glucosinolate biosynthesis and its correlation between bitterness intensity during cool and warm seasons. The bitterness intensity was highest at the young fruit stage and decreased as it developed. In addition, the bitterness intensity in cool season fruits is higher than in warm season fruits. Cyanogenic glucoside and BITC content showed negative correlation with bitterness intensity (r = −0.54 ***; −0.46 ***). Phenylalanine showed positive correlation with bitterness intensity (r = 0.35 ***), but its content did not reach the bitterness threshold concentration, which suggested that phenylalanine only acts as cyanogenic glucoside and glucosinolate precusors. Glucosinolate content showed positive correlation with bitterness intensity at different developmental stages (r = 0.805 ***). However, the correlation value in different lines/cultivars decreased (0.44 ***), suggesting that glucosinolate was not the only substance that caused bitter taste in immature papaya fruits. Full article

Domestication has resulted in a loss of genetic diversity in our major food crops, leading to susceptibility to biotic and abiotic stresses linked with climate change. Crop wild relatives (CWR) may provide a source of novel genes potentially important for re-gaining climate resilience. Sorghum bicolor is an important cereal crop with wild relatives that are endemic to Australia. Sorghum bicolor is cyanogenic, but the cyanogenic status of wild Sorghum species is not well known. In this study, leaves of wild species endemic in Australia are screened for the presence of the cyanogenic glucoside dhurrin. The direct measurement of dhurrin content and the potential for dhurrin-derived HCN release (HCNp) showed that all the tested Australian wild species were essentially phenotypically acyanogenic. The unexpected low dhurrin content may reflect the variable and generally nutrient-poor environments in which they are growing in nature. Genome sequencing of six CWR and PCR amplification of the CYP79A1 gene from additional species showed that a high conservation of key amino acids is required for correct protein function and dhurrin synthesis, pointing to the transcriptional regulation of the cyanogenic phenotype in wild sorghum as previously shown in elite sorghum. Full article

Pests and diseases are responsible for most of the losses related to agricultural crops, either in the field or in storage. Moreover, due to indiscriminate use of synthetic pesticides over the years, several issues have come along, such as pest resistance and contamination of important planet sources, such as water, air and soil. Therefore, in order to improve efficiency of crop production and reduce food crisis in a sustainable manner, while preserving consumer’s health, plant-derived pesticides may be a green alternative to synthetic ones. They are cheap, biodegradable, ecofriendly and act by several mechanisms of action in a more specific way, suggesting that they are less of a hazard to humans and the environment. Natural plant products with bioactivity toward insects include several classes of molecules, for example: terpenes, flavonoids, alkaloids, polyphenols, cyanogenic glucosides, quinones, amides, aldehydes, thiophenes, amino acids, saccharides and polyketides (which is not an exhaustive list of insecticidal substances). In general, those compounds have important ecological activities in nature, such as: antifeedant, attractant, nematicide, fungicide, repellent, insecticide, insect growth regulator and allelopathic agents, acting as a promising source for novel pest control agents or biopesticides. However, several factors appear to limit their commercialization. In this critical review, a compilation of plant-derived metabolites, along with their corresponding toxicology and mechanisms of action, will be approached, as well as the different strategies developed in order to meet the required commercial standards through more efficient methods. Full article

Pastures are key feed sources for dairy production and can be contaminated with several secondary metabolites from fungi and plants with toxic or endocrine-disrupting activities, which possess a risk for the health, reproduction and performance of cattle. This exploratory study aimed to determine the co-occurrences and concentrations of a wide range of mycotoxins, phytoestrogens and other secondary metabolites in grazing pastures. Representative samples of pastures were collected from 18 Austrian dairy farms (one sample per farm) between April to October 2019. After sample preparation (drying and milling) the pastures were subjected to multi-metabolite analysis using LC-MS/MS. In total, 68 metabolites were detected, including regulated zearalenone and deoxynivalenol (range: 2.16–138 and 107–505 μg/kg on a dry matter (DM) basis, respectively), modified (3-deoxynivalenol-glucoside, HT-2-glucoside) and emerging Fusarium mycotoxins (e.g., enniatins), ergot alkaloids and Alternaria metabolites along with phytoestrogens and other metabolites. Aflatoxins, fumonisins, T-2 toxin, HT-2 toxin and ochratoxins were not detected. Of the geo-climatic factors and botanical diversity investigated, the environment temperature (average of 2 pre-sampling months and the sampling month) was the most influential factor. The number of fungal metabolites linearly increased with increasing temperatures and temperatures exceeding 15 °C triggered an exponential increment in the concentrations of Fusarium and Alternaria metabolites and ergot alkaloids. In conclusion, even though the levels of regulated mycotoxins detected were below the EU guidance levels, the long-term exposure along with co-occurrence with modified and emerging mycotoxins might be an underestimated risk for grazing and forage-fed livestock. The one-year preliminary data points out a dominant effect of environmental temperature in the diversity and contamination level of fungal metabolites in pastures. Full article

Amygdalin (d-Mandelonitrile 6-O-β-d-glucosido-β-d-glucoside) is a natural cyanogenic glycoside occurring in the seeds of some edible plants, such as bitter almonds and peaches. It is a medically interesting but controversial compound as it has anticancer activity on one hand and can be toxic via enzymatic degradation and production of hydrogen cyanide on the other hand. Despite numerous contributions on cancer cell lines, the clinical evidence for the anticancer activity of amygdalin is not fully confirmed. Moreover, high dose exposures to amygdalin can produce cyanide toxicity. The aim of this review is to present the current state of knowledge on the sources, toxicity and anticancer properties of amygdalin, and analytical methods for its determination in plant seeds. Full article