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result(s) for
"Sinigrin"
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Identification of a gustatory receptor tuned to sinigrin in the cabbage butterfly Pieris rapae
by
Wang, Chen-Zhu
,
van Loon, Joop J. A.
,
Guo, Hao
in
Adults
,
Biology and Life Sciences
,
Caffeine
2021
Glucosinolates are token stimuli in host selection of many crucifer specialist insects, but the underlying molecular basis for host selection in these insects remains enigmatic. Using a combination of behavioral, electrophysiological, and molecular methods, we investigate glucosinolate receptors in the cabbage butterfly Pieris rapae . Sinigrin, as a potent feeding stimulant, elicited activity in larval maxillary lateral sensilla styloconica, as well as in adult medial tarsal sensilla. Two P . rapae gustatory receptor genes PrapGr28 and PrapGr15 were identified with high expression in female tarsi, and the subsequent functional analyses showed that Xenopus oocytes only expressing PrapGr28 had specific responses to sinigrin; when ectopically expressed in Drosophila sugar sensing neurons, PrapGr28 conferred sinigrin sensitivity to these neurons. RNA interference experiments further showed that knockdown of PrapGr28 reduced the sensitivity of adult medial tarsal sensilla to sinigrin. Taken together, we conclude that PrapGr28 is a gustatory receptor tuned to sinigrin in P . rapae , which paves the way for revealing the molecular basis of the relationships between crucifer plants and their specialist insects.
Journal Article
Functional analysis of a bitter gustatory receptor highly expressed in the larval maxillary galea of Helicoverpa armigera
by
Wang, Chen-Zhu
,
Huang, Ling-Qiao
,
Wang, Pei-Chao
in
Amino acids
,
Biology and Life Sciences
,
Caffeine
2022
Many plant secondary substances are feeding deterrents for insects and play a key role in the selection of host plants. The taste sensilla of phytophagous insects contain gustatory sensory neurons sensitive to deterrents but the molecular basis of deterrent chemoreception remains unknown. We investigated the function of Gr180, the most highly expressed bitter gustatory receptor in the maxillary galea of Helicoverpa armigera larvae. Functional analyses using the Xenopus oocyte expression system and two-electrode voltage clamp revealed that the oocytes expressing Gr180 responded to coumarin. Tip recording results showed that the medial sensilla styloconica of the maxilla of fifth instar larvae exhibited electrophysiological responses to coumarin. Two-choice feeding bioassays confirmed that coumarin inhibited larval feeding. A homozygous mutant strain of H . armigera with truncated Gr180 proteins ( Gr180 −/− ) was established using the CRISPR-Cas9 system. The responses of the medial sensilla styloconica in Gr180 −/− to coumarin were almost abolished, and the responses to sinigrin and strychnine were also significantly decreased. Knockout of Gr180 alleviated the feeding deterrent effects of coumarin, sinigrin, and strychnine. Thus, we conclude that Gr180 is a receptor responding to coumarin,and also participates in sensing sinigrin and strychnine. These results enhance our understanding of the gustatory sensing mechanisms of phytophagous insects to deterrents.
Journal Article
Critical Review on Nutritional, Bioactive, and Medicinal Potential of Spices and Herbs and Their Application in Food Fortification and Nanotechnology
Medicinal or herbal spices are grown in tropical moist evergreen forestland, surrounding most of the tropical and subtropical regions of Eastern Himalayas in India (Sikkim, Darjeeling regions), Bhutan, Nepal, Pakistan, Iran, Afghanistan, a few Central Asian countries, Middle East, USA, Europe, South East Asia, Japan, Malaysia, and Indonesia. According to the cultivation region surrounded, economic value, and vogue, these spices can be classified into major, minor, and colored tropical spices. In total, 24 tropical spices and herbs (cardamom, black jeera, fennel, poppy, coriander, fenugreek, bay leaves, clove, chili, cassia bark, black pepper, nutmeg, black mustard, turmeric, saffron, star anise, onion, dill, asafoetida, celery, allspice, kokum, greater galangal, and sweet flag) are described in this review. These spices show many pharmacological activities like anti-inflammatory, antimicrobial, anti-diabetic, anti-obesity, cardiovascular, gastrointestinal, central nervous system, and antioxidant activities. Numerous bioactive compounds are present in these selected spices, such as 1,8-cineole, monoterpene hydrocarbons, γ-terpinene, cuminaldehyde, trans-anethole, fenchone, estragole, benzylisoquinoline alkaloids, eugenol, cinnamaldehyde, piperine, linalool, malabaricone C, safrole, myristicin, elemicin, sinigrin, curcumin, bidemethoxycurcumin, dimethoxycurcumin, crocin, picrocrocin, quercetin, quercetin 4’-O-β-glucoside, apiol, carvone, limonene, α-phellandrene, galactomannan, rosmarinic acid, limonene, capsaicinoids, eugenol, garcinol, and α-asarone. Other than that, various spices are used to synthesize different types of metal-based and polymer-based nanoparticles like zinc oxide, gold, silver, selenium, silica, and chitosan nanoparticles which provide beneficial health effects such as antioxidant, anti-carcinogenic, anti-diabetic, enzyme retardation effect, and antimicrobial activity. The nanoparticles can also be used in environmental pollution management like dye decolorization and in chemical industries to enhance the rate of reaction by the use of catalytic activity of the nanoparticles. The nutritional value, phytochemical properties, health advantages, and both traditional and modern applications of these spices, along with their functions in food fortification, have been thoroughly discussed in this review
Journal Article
Isothiocyanates, Nitriles, and Epithionitriles from Glucosinolates Are Affected by Genotype and Developmental Stage in Brassica oleracea Varieties
2017
Vegetables of the
group, such as broccoli, cauliflower, and cabbage, play an important role for glucosinolate consumption in the human diet. Upon maceration of the vegetable tissue, glucosinolates are degraded enzymatically to form volatile isothiocyanates, nitriles, and epithionitriles. However, only the uptake of isothiocyanates is linked to the cancer-preventive effects. Thus, it is of great interest to evaluate especially the isothiocyanate formation. Here, we studied the formation of glucosinolates and their respective hydrolysis products in sprouts and fully developed vegetable heads of different genotypes of the five
varieties: broccoli, cauliflower as well as white, red, and savoy cabbages. Further, the effect of ontogeny (developmental stages) during the head development on the formation of glucosinolates and their respective hydrolysis products was evaluated at three different developmental stages (mini, fully developed, and over-mature head). Broccoli and red cabbage were mainly rich in 4-(methylsulfinyl)butyl glucosinolate (glucoraphanin), whereas cauliflower, savoy cabbage and white cabbage contained mainly 2-propenyl (sinigrin) and 3-(methylsulfinyl)propyl glucosinolate (glucoiberin). Upon hydrolysis, epithionitriles or nitriles were often observed to be the main hydrolysis products, with 1-cyano-2,3-epithiopropane being most abundant with up to 5.7 μmol/g fresh weight in white cabbage sprouts. Notably, sprouts often contained more than 10 times more glucosinolates or their hydrolysis products compared to fully developed vegetables. Moreover, during head development, both glucosinolate concentrations as well as hydrolysis product concentrations changed and mini heads contained the highest isothiocyanate concentrations. Thus, from a cancer-preventive point of view, consumption of mini heads of the
varieties is recommended.
Journal Article
Stressful conditions reveal decrease in size, modification of shape but relatively stable asymmetry in bumblebee wings
by
Fullgrabe, Lovina
,
Gerard, Maxence
,
Smagghe, Guy
in
631/158/2458
,
631/601/1466
,
Animal biology
2018
Human activities can generate a wide variety of direct and indirect effects on animals, which can manifest as environmental and genetic stressors. Several phenotypic markers have been proposed as indicators of these stressful conditions but have displayed contrasting results, depending, among others, on the phenotypic trait measured. Knowing the worldwide decline of multiple bumblebee species, it is important to understand these stressors and link them with the drivers of decline. We assessed the impact of several stressors (i.e. natural toxin-, parasite-, thermic- and inbreeding- stress) on both wing shape and size and their variability as well as their directional and fluctuating asymmetries. The total data set includes 650 individuals of
Bombus terrestris
(Hymenoptera: Apidae). Overall wing size and shape were affected by all the tested stressors. Except for the sinigrin (e.g. glucosinolate) stress, each stress implies a decrease of wing size. Size variance was affected by several stressors, contrary to shape variance that was affected by none of them. Although wing size directional and fluctuating asymmetries were significantly affected by sinigrin, parasites and high temperatures, neither directional nor fluctuating shape asymmetry was significantly affected by any tested stressor. Parasites and high temperatures led to the strongest phenotype modifications. Overall size and shape were the most sensitive morphological traits, which contrasts with the common view that fluctuating asymmetry is the major phenotypic marker of stress.
Journal Article
Characterization of a Novel Myrosinase with High Activity from Marine Bacterium Shewanella baltica Myr-37
2022
Myrosinase can hydrolyze glucosinolates to generate isothiocyanates, which have cancer prevention and anti-cancer properties. The main sources of myrosinase are cruciferous plants. To further improve the efficiency of isothiocyanates preparation, it is necessary to explore novel sources of myrosinases. In this study, we described a bacterium, Shewanella baltica Myr-37, isolated from marine mud, capable of producing a novel myrosinase (Smyr37) with a molecular weight of 100 kDa. The crude enzyme of Smyr37 showed the highest activity at 50 °C and pH 8.0. The sinigrin- and glucoraphanin-hydrolyzing activities of Smyr37 were 6.95 and 5.87 U/mg, respectively. Moreover, when the reaction temperature was 40 °C and pH was 7.0, the crude enzyme of Smyr37 could efficiently degrade glucoraphanin into sulforaphane within 25 min with a yield of 0.57 mg/mL. The corresponding conversion efficiency of sulforaphane from glucoraphanin was 89%. In summary, S. baltica Myr-37 myrosinase Smyr37, a novel myrosinase, can be used in the preparation of isothiocyanates.
Journal Article
Enzyme systems involved in glucosinolate metabolism in Companilactobacillus farciminis KB1089
by
Morisaka, Hironobu
,
Kishino, Shigenobu
,
Osada, Kengo
in
6-Phospho-β-glucosidase
,
631/326/2522
,
631/326/41
2021
Cruciferous vegetables are rich sources of glucosinolates (GSLs). GSLs are degraded into isothiocyanates, which are potent anticarcinogens, by human gut bacteria. However, the mechanisms and enzymes involved in gut bacteria-mediated GSL metabolism are currently unclear. This study aimed to elucidate the enzymes involved in GSL metabolism in lactic acid bacteria, a type of gut bacteria.
Companilactobacillus farciminis
KB1089 was selected as a lactic acid bacteria strain model that metabolizes sinigrin, which is a GSL, into allylisothiocyanate. The sinigrin-metabolizing activity of this strain is induced under glucose-absent and sinigrin-present conditions. A quantitative comparative proteomic analysis was conducted and a total of 20 proteins that were specifically expressed in the induced cells were identified. Three candidate proteins, β-glucoside-specific IIB, IIC, IIA phosphotransferase system (PTS) components (
Cf
PttS), 6-phospho-β-glucosidase (
Cf
PbgS) and a hypothetical protein (
Cf
NukS), were suspected to be involved in sinigrin-metabolism and were thus investigated further. We hypothesize a pathway for sinigrin degradation, wherein sinigrin is taken up and phosphorylated by
Cf
PttS, and subsequently, the phosphorylated entity is degraded by
Cf
PbgS. As expression of both
pttS
and
pbgS
genes clearly gave
Escherichia coli
host strain sinigrin converting activity, these genes were suggested to be responsible for sinigrin degradation. Furthermore, heterologous expression analysis using
Lactococcus lactis
suggested that
Cf
PttS was important for sinigrin degradation and
Cf
PbgS degraded phosphorylated sinigrin.
Journal Article
Turning glucosinolate into allelopathic fate: investigating allyl isothiocyanate variability and nitrile formation in eco-friendly Brassica juncea from South Korea
2024
Leaf mustard (
Brassica juncea
L.) is explored for its biofumigant properties, derived from its secondary metabolites, particularly allyl isothiocyanate (AITC), produced during the enzymatic breakdown of glucosinolates like sinigrin. The research examines eight leaf mustard cultivars developed in Yeosu city, South Korea, focusing on their genetic characteristics, AITC concentration and nitriles formation rates from glucosinolates. Results indicate that the allelopathic effects, largely dependent on AITC concentration and enzymatic activity, vary across cultivar. Sinigrin and AITC constitute 79% and 36%, respectively, of glucosinolate and its hydrolysis products. The cultivar 'Nuttongii' demonstrates significant potential for inhibiting weeds, exhibiting the highest AITC concentration at 27.47 ± 6.46 µmole g
−1
These outcomes highlight the importance of selecting mustard cultivars for biofumigation based on their glucosinolate profiles and hydrolysis product yields. The study also identifies a significant genetic influence on AITC and nitrile formation, suggesting that epithiospecifier protein modulation could enhance both allelopathic and other beneficial effects. Collectively, the research underscores the promise of mustard as a sustainable, environmentally friendly alternative to traditional herbicides.
Journal Article
Overexpression of the MYB29 transcription factor affects aliphatic glucosinolate synthesis in Brassica oleracea
by
Zuluaga, Diana L
,
Wagstaff, Carol
,
A E Elaine van Ommen Kloeke
in
Biosynthesis
,
Brassica oleracea
,
Colon
2019
Key messageOverexpression of BoMYB29 gene up-regulates the aliphatic glucosinolate pathway in Brassica oleracea plants increasing the production of the anti-cancer metabolite glucoraphanin, and the toxic and pungent sinigrin.Isothiocyanates, the bio-active hydrolysis products of glucosinolates, naturally produced by several Brassicaceae species, play an important role in human health and agriculture. This study aims at correlating the content of aliphatic glucosinolates to the expression of genes involved in their synthesis in Brassica oleracea, and perform functional analysis of BoMYB29 gene. To this purpose, three genotypes were used: a sprouting broccoli, a cabbage, and a wild genotype (Winspit), a high glucosinolate containing accession. Winspit showed the highest transcript level of BoMYB28, BoMYB29 and BoAOP2 genes, and BoAOP2 expression was positively correlated with that of the two MYB genes. Further analyses of the aliphatic glucosinolates also showed a positive correlation between the expression of BoAOP2 and the production of sinigrin and gluconapin in Winspit. The Winspit BoMYB29 CDS was cloned and overexpressed in Winspit and in the DH AG1012 line. Overexpressing Winspit plants produced higher quantities of alkenyl glucosinolates, such as sinigrin. Conversely, the DH AG1012 transformants showed a higher production of methylsulphinylalkyl glucosinolates, including glucoraphanin, and, despite an up-regulation of the aliphatic glucosinolate genes, no increase in alkenyl glucosinolates. The latter may be explained by the absence of a functional AOP2 gene in DH AG1012. Nevertheless, an extract of DH AG1012 lines overexpressing BoMYB29 provided a chemoprotective effect on human colon cells. This work exemplifies how the genetic diversity of B. oleracea may be used by breeders to select for higher expression of transcription factors for glucosinolate biosynthesis to improve its natural, health-promoting properties.
Journal Article
The Effect of the Glucosinolate Sinigrin on Alterations in Molecular Biomarkers of the Myocardium in Swiss Mice
by
Beletić, Anđelo
,
Odeh, Dyana
,
Đikić, Domagoj
in
Animal welfare
,
Aqueous solutions
,
Atrial natriuretic peptide
2025
Glucosinolates are chemically stable compounds that exhibit biological activity in the body following hydrolysis catalyzed by the enzyme myrosinase. While existing in vitro and in vivo studies suggest that the hydrolysis products of glucosinolates predominantly exert beneficial effects in both human and animal organisms, some studies have found that the excessive consumption of glucosinolates may lead to toxic and anti-nutritional effects. Given that glucosinolates are primarily ingested in the human diet through dietary supplements and commercially available cruciferous vegetables, we investigated the in vivo effects of the glucosinolate sinigrin on molecular markers in the myocardia of healthy Swiss mice. This study aims to elucidate whether sinigrin induces positive or negative physiological effects in mammals following consumption. The alterations in myocardial parameters were assessed by measuring metabolic, inflammatory, structural, and antioxidant markers. Our findings revealed that subchronic exposure to sinigrin in the myocardia of female mice resulted in a significant increase (p ≤ 0.05) in the levels of the myokine irisin, matrix metalloproteinases (MMP-2, MMP-9), catalase (CAT), and total glutathione (tGSH), alongside a marked decrease (p ≤ 0.05) in the levels of atrial natriuretic peptide (ANP), compared to the control group consisting of both female and male mice. These results suggest that the hydrolysis products of sinigrin may exert a potentially toxic effect on the myocardial tissue of female mice and possess the capability to modulate transcription factors in vivo in a sex-dependent manner. This observation calls for further investigation into the mechanisms regulating the actions of glucosinolate hydrolysis products, their interactions with sex hormones, and the determination of permissible intake levels associated with both beneficial and adverse outcomes.
Journal Article