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Copyright of Journal of Food Safety & Quality is the property of Journal of Food Safety & Quality Editorial Department and its content may not be copied or emailed to multiple sites or posted to a listserv without the copyright holder's express written permission. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)

Copyright of China Condiment is the property of China Condiment and its content may not be copied or emailed to multiple sites or posted to a listserv without the copyright holder's express written permission. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)

As an important spice species in Rutaceae, the Sichuan pepper (Zanthoxylum armatum) can provide pungent and numbing taste, as well as aroma in its mature fruit. Here we assembled a chromosome-level genome of green prickly ash which was widely cultivated in a major production area including Chongqing and Sichuan province, China. We generated 712 Gb (∼112 × ) PacBio long reads and 511 Gb (∼82 × ) Hi-C data, and yielded an assembly of 99 pseudochromosomes with total size of 5.32 Gb and contig N50 of 796 kb. The genomic analyses and cytogenetic experiments both indicated that the cultivar ‘Zhuye Huajiao’ was a triploid. We identified a Zanthoxylum-specific whole genome duplication event emerging about 24.8 million years ago (Mya). We also detected a transposition burst event (0.3–0.4 Mya) responsible for the large genome size of Z. armatum. Metabolomic analysis of the Zanthoxylum fruits during development stages revealed profiles of 39 volatile aroma compounds and 528 secondary metabolites, from which six types of sanshools were identified. Based on metabolomic and transcriptomic network analysis, we screened candidate genes encoding long chain acyl-CoA synthetase, fatty acid desaturase, branched-chain amino acid aminotransferase involved in sanshool biosynthesis and three genes encoding terpene synthase during fruit development. The multi-omics data provide insights into the evolution of Zanthoxylum and molecular basis of numbing and aroma flavor of Sichuan pepper.

Natural evolution has nurtured a series of active molecules that play vital roles in physiological systems, but their further applications have been severely limited by rapid deactivation, short cycle time, and potential toxicity after isolation. For instance, the instability of structures and properties has greatly descended when sanshool is derived from Zanthoxylum xanthoxylum. Herein, natural polyphenols are employed to boost the key properties of sanshool by fabricating a series of nanoparticles (NPs). The intracellular evaluation and in vivo animal model are conducted to demonstrate the decreased photodamage score and skin‐fold thickness of prepared NPs, which can be attributed to the better biocompatibility, improved free radical scavenging, down‐regulated apoptosis ratios, and reduced DNA double‐strand breaks compared to naked sanshool. This work proposes a novel strategy to boost the key properties of naturally occurring active molecules with the assistance of natural polyphenol‐based platforms. [ABSTRACT FROM AUTHOR]

The objective of the present study was to evaluate structure-activity relationships of four sanshools on antioxidant activities. In vitro, hydroxy-a-sanshool (HAS), hydroxy-ß-sanshool (HBS), and hydroxy-γ-sanshool (HRS) had stronger antioxidant capacities than hydroxy-γ-sanshool (RS), attributed to the hydroxyl group. Furthermore, HRS had the greatest oxygen radical absorbance capacities (ORAC) and free radical scavenging (DPPH and ABTS) capacities, attributed to more cis-double bonds. Sanshools could effectively decrease the level of oxidative stress in colonic tissue and HCT-116 cells, including increased enzyme activities of catalase (CAT), superoxide dismutase (SOD), and glutathione peroxidase (GSH-Px) and decreased concentrations of malondialdehyde (MDA). After intragastric administration of sanshool, HRS increased the the level of hepatic Total antioxidant capacity (T-AOC) and colon GSH-Px and SOD. Moreover, sanshools significantly increased Nrf2, HO-1 proteins and decreased Keap1 protein. The protective effect of HRS was much higher than HAS, HBS, and RS, apparently due to its amide and hydroxyl groups. The binding energies of Nrf2 with HAS, HBS, HRS, and RS were -5.17, -5.11, -5.75, and -4.16 kcal/mol, respectively. HRS is more easily combine with Nrf2. In summary, sanshools acted as substitutes for natural antioxidants, in which HRS has the greatest antioxidant activity. This study provided a basis for future research on relationships between structure and activity. [ABSTRACT FROM AUTHOR]

Hydroxy-α-sanshool (HAS), hydroxy-β-sanshool (HBS), hydroxy-γ-sanshool (HRS), and γ-sanshool (RS) are the key components from the Zanthoxylum genus, processing a range of pharmacological activities. The present study investigated the protective capacities of four sanshools on a dextran sulfate sodium (DSS)-induced model of ulcerative colitis (UC). The results showed that sanshool administration alleviated the colitis symptoms by reducing body weight loss and disease activity index (DAI) score, increasing the colon length, and improving colonic injury and the change in immune organ weight. Furthermore, sanshools enhanced the antioxidant enzyme activities, and RS exhibited the lowest effect on the improvement in total antioxidative capacity (T-AOC) and antioxidant abilities compared to the other three sanshools. The p65 nuclear factor κB (p65 NFκB) signaling pathway was inhibited to prevent hyperactivation and decreased the production of inflammatory factors. The gut barrier function in DSS-induced mice was restored by increasing goblet cell number and levels of tight junction proteins (zonula occludens-1, occludin, and claudin-1), and the levels of protein in HAS and HRS groups were higher than that in the HBS group, significantly. The analysis of gut microbiota suggested that sanshool administration significantly boosted the abundance of Lachnospiraceae, Muribaculaceae, Oscillospiraceae, and Alistipes and reduced the level of Buchnera in colitis mice. Collectively, the sanshool treatment could ameliorate colitis by resisting colon injury and regulating intestinal barrier dysfunction and gut microbiota dysbiosis; meanwhile, HRS and HAS have better improvement effects. [ABSTRACT FROM AUTHOR]

Abstract Natural evolution has nurtured a series of active molecules that play vital roles in physiological systems, but their further applications have been severely limited by rapid deactivation, short cycle time, and potential toxicity after isolation. For instance, the instability of structures and properties has greatly descended when sanshool is derived from Zanthoxylum xanthoxylum. Herein, natural polyphenols are employed to boost the key properties of sanshool by fabricating a series of nanoparticles (NPs). The intracellular evaluation and in vivo animal model are conducted to demonstrate the decreased photodamage score and skin‐fold thickness of prepared NPs, which can be attributed to the better biocompatibility, improved free radical scavenging, down‐regulated apoptosis ratios, and reduced DNA double‐strand breaks compared to naked sanshool. This work proposes a novel strategy to boost the key properties of naturally occurring active molecules with the assistance of natural polyphenol‐based platforms.

Copyright of Chinese Journal of Applied Entomology is the property of Chinese Journal of Applied Entomology, Editorial Department and its content may not be copied or emailed to multiple sites or posted to a listserv without the copyright holder's express written permission. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)

Three kinds of sanshools were separated from Zanthoxylum bungeanum oleoresin by high‐speed countercurrent chromatography. Sanshools are a series of amide compounds extracted from the Zanthoxylum bungeanum. Due to similar structures, polarities, and dissociation constants, it was challenging to select an appropriate solvent system for their complete separation by countercurrent chromatography. To address this challenge, a solvent‐system‐selection strategy was proposed to identify a relatively suitable solvent system. Additionally, a separation procedure incorporating multi‐elution modes selection was established to separate similar compounds in a logical order. Ultimately, a solvent system comprising n‐hexane:ethyl acetate:methanol:water in a ratio of 19:1:1:5.67 was selected. Three amide compounds with high purity were obtained through the use of recycling elution mode to improve separation resolution: hydroxy‐ε‐sanshool (8.4 mg; purity: 90.64%), hydroxy‐α‐sanshool (326.4 mg; purity: 98.96%), and hydroxy‐β‐sanshool (71.8 mg; purity: 98.26%) were obtained from 600 mg sanshool crude extract. The summarized solvent‐system‐selection strategy and separation procedure incorporating multi‐elution modes may instruct countercurrent chromatography users, particularly novices, seeking to separate compounds with highly similar chemical properties. [ABSTRACT FROM AUTHOR]

Hydroxy-α-sanshool (HAS), hydroxy-β-sanshool (HBS), hydroxy-γ-sanshool (HRS), and γ-sanshool (RS) are the key components from the Zanthoxylum genus, processing a range of pharmacological activities. The present study investigated the protective capacities of four sanshools on a dextran sulfate sodium (DSS)-induced model of ulcerative colitis (UC). The results showed that sanshool administration alleviated the colitis symptoms by reducing body weight loss and disease activity index (DAI) score, increasing the colon length, and improving colonic injury and the change in immune organ weight. Furthermore, sanshools enhanced the antioxidant enzyme activities, and RS exhibited the lowest effect on the improvement in total antioxidative capacity (T-AOC) and antioxidant abilities compared to the other three sanshools. The p65 nuclear factor κB (p65 NFκB) signaling pathway was inhibited to prevent hyperactivation and decreased the production of inflammatory factors. The gut barrier function in DSS-induced mice was restored by increasing goblet cell number and levels of tight junction proteins (zonula occludens-1, occludin, and claudin-1), and the levels of protein in HAS and HRS groups were higher than that in the HBS group, significantly. The analysis of gut microbiota suggested that sanshool administration significantly boosted the abundance of Lachnospiraceae, Muribaculaceae, Oscillospiraceae, and Alistipes and reduced the level of Buchnera in colitis mice. Collectively, the sanshool treatment could ameliorate colitis by resisting colon injury and regulating intestinal barrier dysfunction and gut microbiota dysbiosis; meanwhile, HRS and HAS have better improvement effects.

Sanshool compounds are the trigeminal active compounds in andaliman (Zanthoxylum acantho-podium DC) with a numbing and tingling sensation. The analysis of such compounds is usually done through HPLC approach; however, limited studies have reported that the analysis of such compounds could be conducted with Gas Chromatography-Mass Spectrometry (GC-MS). This method could save research time and funding by analyzing both sanshools and volatiles simultaneously, which would describe the complete profile of andaliman flavor compounds. This study aimed to confirm the potency of GC-MS in analyzing sanshool compounds and to utilize this method in studying the impact of different drying methods towards andaliman trigeminal active compounds. Andaliman was dried with five drying methods (sun, sunshade, air, oven, and freeze-drying) and was macerated with chloroform, concentrated, and analyzed with GC-MS. The results of this study showed that GC-MS was able to analyze sanshool compounds efficiently. Drying had no statistically significant impact on sanshool quantities extracted from andaliman. Fresh andaliman contained 0.69 % (dry weight basis) of α-sanshool, the main sanshool in andaliman. On the other hand, dried andaliman contained 0.80-1.08% of α-sanshool (dry weight basis). As oven drying managed to produce andaliman with a similar concentration of α-sanshool at a faster time and more affordable cost than other drying methods, oven drying was suggested as the ideal drying method to extend the shelf life of andaliman.

Summary: The nutritional, flavour and metabolite properties of Zanthoxylum schinifolium in 10–145 days postanthesis (P10‐P145) were comprehensively investigated. With increasing maturity, fruit volume and weight significantly increased, moisture content decreased. Amino acids in Z. schinifolium are mainly composed of arginine, proline, tryptophan and glutamic acid. Total amino acid content reached the highest level of 31.153 mg/g at P130. Total phenols and flavonoids contents reached the highest level at P100. The content of sanshool and volatile oil reached the highest level of 123.76 mg/g and 12.79 mL/100 g, respectively, at P100 and P115. In addition, linalool, as the characteristic aroma component of Z. schinifolium, was the most abundant at P100. Z. schinifolium at P100 is considered to be the most edible and economic value. P100 is therefore considered to be the suitable picking stage for consumption and processing of Z. schinifolium. Meanwhile, metabolomics is performed to quickly identify the maturity of Z. schinifolium in this study. The present results can be used to optimise harvest timing and promote the development of Z. schinifolium industry. [ABSTRACT FROM AUTHOR]

Sanshool compounds are the trigeminal active compounds in andaliman (Zanthoxylum acanthopodium DC) with a numbing and tingling sensation. The analysis of such compounds is usually done through HPLC approach; however, limited studies have reported that the analysis of such compounds could be conducted with Gas Chromatography-Mass Spectrometry (GC-MS). This method could save research time and funding by analyzing both sanshools and volatiles simultaneously, which would describe the complete profile of andaliman flavor compounds. This study aimed to confirm the potency of GC-MS in analyzing sanshool compounds and to utilize this method in studying the impact of different drying methods towards andaliman trigeminal active compounds. Andaliman was dried with five drying methods (sun, sunshade, air, oven, and freeze-drying) and was macerated with chloroform, concentrated, and analyzed with GC-MS. The results of this study showed that GC-MS was able to analyze sanshool compounds efficiently. Drying had no statistically significant impact on sanshool quantities extracted from andaliman. Fresh andaliman contained 0.69 % (dry weight basis) of α-sanshool, the main sanshool in andaliman. On the other hand, dried andaliman contained 0.80-1.08% of α-sanshool (dry weight basis). As oven drying managed to produce andaliman with a similar concentration of α-sanshool at a faster time and more affordable cost than other drying methods, oven drying was suggested as the ideal drying method to extend the shelf life of andaliman. [ABSTRACT FROM AUTHOR]

Copyright of Shipin Kexue/ Food Science is the property of Food Science Editorial Department and its content may not be copied or emailed to multiple sites or posted to a listserv without the copyright holder's express written permission. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)

An efficient and practical route for the synthesis of α-sanshools and spilanthol is described herein. Several modifications of an existing method enabled the preparation of the (2E,6Z,8E,10E)-tetraene precursor of hydroxy-α-sanshool in good yield. A highly selective Wittig reaction employing newly synthesized phosphonium salt with low deliquescence and long-term stability yielded the desired Z-form tetraene. This improved methodology was shown to be applicable to the efficient synthesis of α-sanshool and spilanthol.

[Display omitted] • Structural and energetic properties of 16 hydroxy-α-sanshool conformers were studied. • The relative energetic difference between conformers were explored. • The intermolecular isomerization would be much easier after they are excited. • The cis/trans- C C bonds and solvent change their photochemical stability. • The possible degradation mechanism of hydroxy-α-sanshool is proposed. To better understand the structural changes of sanshool pungent dietary components during the process and preservation of Sichuan pepper and pungent foods, the mechanistic insights into the intrinsic degradation and transformation of 16 hydroxy-α-sanshool conformers have been explored computationally. Our results have revealed that increasing the cis -C C bond numbers in the most stable all-trans hydroxy-β-sanshool structure causes the maximum 34.21 kJ/mol conformational energetic difference, and the existent probability of C2nnn would be lower than that of C1nnn (n = 1,2). The isomerization between the conformers could be much easier when they are excited by light radiation, as the strength of the C C bonds and their connected C C bonds becomes significantly close, and the relative energies among conformers are largely reduced. Besides, the different combination of cis/trans -C C bonds changes the delocalization degree of molecular Frontier orbitals, which consequently causes the different photochemical stability. Finally, the possible molecular oxidation degradation mechanism is proposed. [ABSTRACT FROM AUTHOR]

[Display omitted] • The difference in the geometrical parameters of sanshools were compared. • The conformational energies and their experimental distributions were correlated. • The overall and local chemical reactive sites or areas of sanshools were revealed. • The autoxidation, photochemical stability and electrostatic potentials were evaluated. • The effect of molecular electrostatic/spatial parameters on pungency were studied. The structural basis behind the pungency of sanshools remains largely unknown at present. Herein, the crucial geometrical, electronic and energetic properties of sanshools have been explored and correlated with the pungency computationally. Our results have revealed the preferred reactive sites or area in sanshools responsible for their degradation, as well as their probable electrostatic and hydrophobic interaction patterns with the pungent receptors. Increasing the solvent polarity in the calculations or the conjugated C C numbers increase their chemical instability. The correlation between the polar/nonpolar/negative/positive surface area and pungency indicates the necessity of the amide, C C bonds, HO groups and carbon chains. The autoxidation may occur more probably through the radical addition than hydrogen abstraction during their applications like the process of relevant foods, and increasing the conjugated C C numbers weakens the corresponding allylic C H bonds. This study would benefit the mature pungent mechanistic understanding and practical applications in the pungent foods. [ABSTRACT FROM AUTHOR]

[Display omitted] • HaSS had the greatest impact on Zanthoxylum pungency. • The higher the HγSS content, the longer the tingling duration. • The most influential factor on sanshool tingling was the cis -double bonds. • Tingling and numbing were not perceived by HβSS (200 μg/mL). Huajiao (Zanthoxylum) from different regions varies in pungency features. The objective of this study was to explore the reasons for the differences. Temporal check-all-that-apply (TCATA) and time-intensity (TI)) were used to determine time-related pungency features of huajiao and sanshools. The compositions of sanshools in huajiao were measured by high-performance liquid chromatograph (HPLC). TI results revealed that hydroxy-γ-sanshool tingling and numbing duration (1332.00 ± 50.91 and 1020.00 ± 61.19 s, respectively) were about twice that of hydroxy-α-sanshool (720.00 ± 25.92 and 584.00 ± 22.63 s, respectively). Tingling and numbing were not perceived by hydroxy-β-sanshool and hydroxy-γ-isosanshool. HPLC results showed that HαSS was the main component of huajiao sanshools, representing 71.06 % to 92.90 %. TCATA results revealed the pungency sensations appearance sequence: tingling, salivating, cooling, and burning appeared first, followed by vibrating, and numbing was perceived last. These findings revealed the relationship between the compositions of sanshool and the pungency features of huajiao. [ABSTRACT FROM AUTHOR]

Anti-proliferation and apoptosis induction activities of sanshool isolated from Zanthoxylum bungeanum (Rutaceae) in HepG2 cells were investigated. Cell proliferation was analyzed using MTT assays. Apoptotic bodies were observed under scanning electron microscopy. Nucleus staining using dichlorofluorescin diacetate (DAPI) was performed and the mitochondrial membrane potential (ΔΨm) using rhodamine-123 was observed under laser confocal microscopy. Sanshool inhibited cell proliferation in both a dose and time-dependent manner. The anti-proliferation activity was stimulated with apoptosis induction based on an increase in the sub-G1 cell population, DNA fragmentation, and typical apoptotic morphological changes. Sanshool also disrupted ΔΨm and up-regulated mRNA and protein expressions of p53 and caspase-3. Sanshool induced apoptosis via a mitochondrion-dependent pathway. Thus, sanshool is a potential anticancer medicine. [ABSTRACT FROM AUTHOR]

Sanshools are major active ingredients of Zanthoxylum piperitum and are used as food additives in East Asia. Sanshools cause irritant, tingling and sometimes paresthetic sensations on the tongue. However, the molecular mechanism underlying the pungent or tingling sensation induced by sanshools is not known. Because many transient receptor potential (TRP) channels are responsible for the sensations induced by various spices and food additives, we expressed 17 TRP channels in human embryonic kidney (HEK) cells and investigated their activation by hydroxy-α-sanshool (HαSS) or hydroxy-β-sanshool (HβSS) isolated from Zanthoxylum piperitum. It was found that HαSS, but not HβSS, depolarized sensory neurons with concomitant firing of action potentials and evoked inward currents. Among 17 TRP channels expressed in HEK cells, HαSS caused Ca2+ influx in cells transfected with TRPV1 or TRPA1, and evoked robust inward currents in cells transfected with TRPV1 or TRPA1. In primary cultured sensory neurons, HαSS induced inward currents and Ca2+ influx in a capsazepine-dependent manner. Moreover, HαSS-induced currents and Ca2+ influx were greatly diminished in TRPV1–/– mice. HαSS evoked licking behavior when injected into a single hind paw of wild-type mice, but this was much reduced in TRPV1-deficient mice. These results indicate that TRPV1 and TRPA1 are molecular targets of HαSS in sensory neurons. We conclude that the activations of TRPV1 and TRPA1 by HαSS explain its unique pungent, tingling sensation. [ABSTRACT FROM AUTHOR]

The article investigates the distribution of each sanshool in the Japanese pepper plant grown in various regions citing the change in composition of sanshools during maturation of the fruit. A quantitative analysis of sanshool compounds in Japanese pepper and their pungent characteristics were conducted. The study has calculated the degree of pungency and evaluated the pungent qualities of the products.

[Display omitted] The molecular basis of the pungency of sanshool dietary components from the Zanthoxylum species has been firstly addressed by constructing the statistically significant and highly predictive quantitative structure-pungency relationship models along with the pharmacophore models. The important pungent structural characters in the isobutylamide moiety and linear carbon chains were elucidated in this study that maintained the suitable spatial packing and electrostatic interactions with their receptors. Our results also revealed that the amide moiety, N -isobutyl moiety with suitable bulky and restricted electronegative substituents, and the relatively long straight carbon chains with suitable (conjugated) C C bonds or heteroatoms at regular intervals were essential for the high pungency. The pungency of 42 new sanshools was predicted, compared with the rough experimental data, and ultimately classified into weak, medium and strong types. Most of these sanshools were found to have good oral bioavailability and acceptable pharmacokinetic properties. [ABSTRACT FROM AUTHOR]

An efficient and practical route for the synthesis of α-sanshools and spilanthol is described herein. Several modifications of an existing method enabled the preparation of the (2 E ,6 Z ,8 E ,10 E )-tetraene precursor of hydroxy-α-sanshool in good yield. A highly selective Wittig reaction employing newly synthesized phosphonium salt with low deliquescence and long-term stability yielded the desired Z -form tetraene. This improved methodology was shown to be applicable to the efficient synthesis of α-sanshool and spilanthol., (Copyright © 2020 Nakamura, Mimaki, Tanigami and Maegawa.)