Search Results (14)

Zanthoxylum armatum DC. (Z. armatum) is a versatile plant species valued for its aroma oil and nutritional components. However, the variability of chemical composition in Z. armatum fruits in the field remains largely unknown, and it is still unclear how harvest parameters affect the aroma and nutritional quality of the fruits. To address this gap, Z. armatum fruits from varying harvest times, tree ages, and fruiting positions were analyzed for physicochemical properties, nutrients, minerals, aroma profiles, and antioxidant activity. A quality assessment method was developed based on key Z. armatum fruit parameters. Results showed significant differences in the size, weight, total phenol, flavonoid and sanshool content of Z. armatum fruit from different harvest parameters. Z. armatum fruits contained abundant minerals, showing diverse harvest-condition variations. In vitro antioxidant assays showed higher ABTS/DPPH scavenging activity and reducing capacity (23–54 mg/g). HS-SPME-GC-MS identified 64 aroma compounds, encompassing terpenes, alcohols, etc. Linalool was the predominant constituent (46.65%). PLS-DA and Volcano plot analyses highlighted significant differences in VOCs among harvest times and tree ages, while fruit positions showed minimal impact. The Mantel test identified aroma-active compounds associated with antioxidant activity. These findings facilitate a science-based harvesting strategy to standardize Z. armatum fruit quality and marketability. Full article

Investigations into human longevity are increasingly focusing on healthspan enhancement, not just lifespan extension. Lifestyle modifications and nutritional choices, including food supplements, can significantly affect aging and general health. Phytochemicals in centenarians’ diets, such as those found in Timut pepper, a Nepalese spice with various medicinal properties, may contribute to their longevity. Similarly, Sichuan pepper, a related species, has demonstrated anti-inflammatory and neuroprotective activities. With the broader purpose of uncovering a novel treatment to address aging and its comorbidities, this study aims to investigate the potential lifespan- and healthspan-promoting effects of Timut pepper using the model organism Caenorhabditis elegans. We show that Timut pepper extract extends C. elegans’ lifespan at different maintenance temperatures and increases the proportion of active nematodes in their early adulthood. In addition, we show that Timut pepper extract enhances speed and distance moved as the nematodes age. Finally, Timut pepper extract assures extracellular matrix homeostasis by slowing the age-dependent decline of collagen expression. Full article

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. Full article

Hydroxy-α-sanshool (HAS) is the predominant active compound in Zanthoxylum bungeanum Maxim (ZBM). Our present work was aimed to explore the in vitro metabolism characteristics, and in vivo pharmacokinetic (PK) profile of HAS. Plasma (human), liver microsomes, and hepatocytes (human, monkey, dog, mouse, and rat) were collected for HAS metabolism studies in vitro and HAS elimination rates in liver microsomes and hepatocytes of different species were investigated. In addition, five recombinant human CYP enzymes were used to identify CYP isoforms of HAS. Finally, the PK properties of HAS in rats in vivo were studied by oral administration (p.o.). The results showed that HAS stably metabolized in human and rat liver microsomes and human hepatocytes, and the binding of HAS to human plasma proteins was nonspecific; HAS has strong inhibitory effects on CYP2C9 and CYP2D6 of human liver microsomes. In addition, in vivo PK study, HAS is rapidly absorbed in rats after oral administration. In conclusion, the in vivo and in vitro metabolic studies of HAS in this study provide data support for its further development and application, and the metabolic profiles of different species can be used as a reference for its safety evaluation. Full article

Zanthoxylum oleoresin, a concentrated extract derived from Zanthoxylum bungeanum, is rich in non-volatile, intensely flavorful substances and amide compounds, such as hydroxy-α-sanshool, hydroxy-β-sanshool, and hydroxy-ε-sanshool. The production process of Zanthoxylum oleoresin remains unstandardized, and there is still a lack of research on the precise classification and quantification of its key chemical constituents, as well as the stability of these compounds when produced using different extraction methods. This study utilized preparative liquid chromatography to extract and purify amide compounds from Zanthoxylum oleoresin, successfully isolating three sanshools: hydroxy-α-sanshool, hydroxy-β-sanshool, and hydroxy-ε-sanshool. The stability of three these sanshools under UVB irradiation in different solvents was explored in UVB-simulated sunlight conditions to investigate the degradation or transformation mechanism of Zanthoxylum alkylamides under UVB irradiation. The findings indicate a rapid decrease in the hydroxy-α-sanshool content under UVB ultraviolet light, aligning with the second-order kinetics. This study revealed alterations in the contents of hydroxy-α-sanshool, hydroxy-β-sanshool, and hydroxy-ε-sanshool and the formation of a new compound following exposure to UVB light. This new compound, along with the three sanshools, possesses a uniform m/z 264 and shares similar chemical structures. Further analysis also uncovered that these compounds are capable of undergoing isomerization reactions under UVB irradiation. This demonstrates that UVB irradiation of certain intensities can modify the concentrations and chemical structures of these Zanthoxylum alkylamides. These insights offer crucial guidance for future studies on the processing and preservation of Zanthoxylum alkylamides and their derivatives. Full article

The pungent component of sansho (Japanese pepper, Zanthoxylum pipritum) is sanshool, which is easily oxidized and decomposed. We have previously reported several sanshool stabilizers, such as α-tocopherol (α-Toc). Sansho pericarp powder treated with middle-chain triglycerides (MCTs) can be used to obtain extracts containing hydroxy-α-sanshool (HαS). Although HαS is stabilized when α-Toc is added to the MCT extracts, the loss of HαS is accelerated when it is mixed with a powder such as lactose. The separation of α-Toc from sanshools was thought to inevitably lead to their oxidation. Therefore, using sansho pericarp MCT extracts with or without α-Toc, oil/water (o/w) emulsions were prepared by adding a surfactant, glycerin, and water to these extracts. In both emulsions, HαS was stable in accelerated tests at 50 °C. However, when lactose powder was added to the emulsions and an accelerated test was performed, HαS in the emulsion containing α-Toc was stable, but HαS in the emulsion without α-Toc was unstable. These results highlight the importance of maintaining the close proximity of HαS and α-Toc in the emulsion. The stabilization of sanshools using emulsion technology can facilitate the production of various processed beverages, foods, cosmetics, and pharmaceuticals containing Japanese pepper. Full article

Japanese pepper (sansho, Zanthoxylum piperitum) contains several types of sanshools belonging to N-alkylamides. Because of the long-chain unsaturated fatty acids present in their structure, sanshools are prone to oxidative deterioration, which poses problems in processing. In this paper, we evaluated the effects of antioxidants from the genus Zanthoxylum in preventing sanshool degradation using accelerated tests. An ethanolic extract of segment membranes of the sansho fruit pericarp was incubated at 70 °C for 7 days with different antioxidants to determine the residual amount of hydroxy-α-sanshool (HαS) in the extract. α-Tocopherol (α-Toc) showed excellent HαS-stabilizing activity at low concentrations. Among phenolic acids, we noted that the HαS-stabilizing activity increased with the number of hydroxy groups per molecule. For example, gallic acid and its derivatives exhibited excellent sanshool-stabilizing activity. Quercetin was found to be a superior HαS stabilizer compared with hesperetin and naringenin. However, the effective concentration was much higher for phenolic compounds than for α-Toc. These substances are believed to play a role in preventing the decomposition of sanshools in the pericarp of sansho. These sanshool stabilizers should be useful in the development of new beverages, foods, cosmetics, and pharmaceuticals that take advantage of the taste and flavor of sansho. Full article

Background: Hydroxy-α-Sanshool (HAS) possesses various pharmacological properties, such as analgesia and regulating gastrointestinal function. However, the low oral bioavailability of HAS has limited its oral delivery in clinical application. Methods and Results: To enhance its oral bioavailability, a nanocomposite delivery system based on chitosan (CH, as the polycation) and sodium alginate (SA, as the polyanion) was prepared using a layer-by-layer coating technique. The morphology, thermal behavior and Fourier transform infrared spectrum (FTIR) showed that the obtained sodium alginate/chitosan-coated HAS-loaded liposomes (SA/CH-HAS-LIP) with core-shell structures have been successfully covered with polymers. When compared with HAS-loaded liposomes (HAS-LIP), SA/CH-HAS-LIP displayed obvious pH sensitivity and a sustained-release behavior in in vitro studies, which fitted well to Weibull model. In vivo, the half-life of HAS from SA/CH-HAS-LIP remarkably extended after oral administration compared to the free drug. Additionally, it allowed a 4.6-fold and 4.2-fold increase in oral bioavailability, respectively, compared with free HAS and HAS-LIP. Conclusions: SA/CH-HAS-LIP could be a promising release vehicle for the oral delivery of HAS to increase its oral bioavailability. Full article

Hydroxyl-α-sanshool is the main alkylamide produced by Zanthoxylum armatum DC., and it is responsible for numbness after consuming Z. armatum-flavored dishes or food products. The present study deals with the isolation, enrichment, and purification of hydroxyl-α-sanshool. The results indicated that the powder of Z. armatum was extracted with 70% ethanol and then filtrated; the supernatant was concentrated to get pasty residue. Petroleum ether (60–90 °C) and ethyl acetate at a 3:2 ratio, with an Rf value of 0.23, were chosen as the eluent. Petroleum ether extract (PEE) and ethyl acetate–petroleum ether extract (E-PEE) were used as the suitable enriched method. Afterward, the PEE and E-PEE were loaded onto silica gel for silica gel column chromatography. Preliminary identification was carried out by TLC and UV. The fractions containing mainly hydroxyl-α-sanshool were pooled and dried by rotary evaporation. Lastly, all of the samples were determined by HPLC. The yield and recovery rates of hydroxyl-α-sanshool in the p-E-PEE were 12.42% and 121.65%, respectively, and the purity was 98.34%. Additionally, compared with E-PEE, the purity of hydroxyl-α-sanshool in the purification of E-PEE (p-E-PEE) increased by 88.30%. In summary, this study provides a simple, rapid, economical, and effective approach to the separation of high-purity hydroxyl-α-sanshool. Full article

To explore the hydroxy-alpha-sanshool (HAS) effects on the intestinal metabolites of insulin-resistant mice, the blank group (BG), model group (MG), and HAS dose group (DG) were designed. The insulin resistance (IR) model was induced through streptozotocin (STZ) combined with a high-fat and high-sugar diet. Based on the availability of the model, the HAS dose was given by gavage for 28 days. The determination of cecum and key serum indexes was made, including the contents of insulin (INS), triglycerides (TG), total cholesterol (TC), glycosylated serum protein (GSP), and glycosylated hemoglobin (GHb). The changes in gut microbiota and metabolites in cecal contents were detected by 16S rRNA gene amplicon sequencing and UPLC/HRMS technology, respectively. The results that the levels of GSP, GHb, TG, and TC were significantly increased; this was not the case for INS; or for the changes in the gut microbiota and metabolites in MG. However, the intervention of HAS effectively reversed these changes, for instance, it decreased levels of GSP, GHb, TG, TC, and alterations of metabolite composition for linoleic acid and tyrosine metabolism and recovered trends of declining species diversity and richness of the gut microbiota in MG. It was indicated that HAS alleviated IR by regulating the gut microbiota and metabolites and affecting lipid and amino acid metabolism pathways. Full article

To evaluate the storage stability and flavor changes of marinated pork treated with chili and pepper essential oils, the contents of total sulfhydryl, malondialdehyde, total volatile base nitrogen (TVBN), Ca²⁺ATPase activity, and total viable counts of marinated pork were determined. Further, the non-volatile (umami, numb, and spicy) and volatile flavor compounds of marinated pork were analyzed. Based on the results, the chili and pepper essential oils had limited effects on the storage stability of marinated pork. However, these essential oils could inhibit the oxidation of lipids and proteins and reduce the number of microorganisms and TVBN in marinated pork within 6 days. The non-volatile flavors of the marinated pork decreased as the refrigeration time increased. It was concluded that the decomposition of umami-enhancing nucleotides (GMP, IMP, XMP), the number of flavor substances (hydroxyl-α-sanshool, hydroxyl-β-sanshool), and spicy (capsaicin) tasting compounds caused the decrease in non-volatile flavors. Full article

The use of herbicide safeners can significantly alleviate herbicide injury to protect crop plants and expand the application scope of the existing herbicides in the field. Sanshools, which are well known as spices, are N-alkyl substituted compounds extracted from the Zanthoxylum species and have several essential physiological and pharmacological functions. Sanshools display excellent safener activity for the herbicide metolachlor in rice seedlings. However, the high cost of sanshools extraction and difficulties in the synthesis of their complicated chemical structures limit their utilization in agricultural fields. Thus, the present study designed and synthesized various N-alkyl amide derivatives via the scaffold-hopping strategy to solve the challenge of complicated structures and find novel potential safeners for the herbicide metolachlor. In total, 33 N-alkyl amide derivatives (2a–k, 3a–k, and 4a–k) were synthesized using amines and saturated and unsaturated fatty acids as starting materials through acylation and condensation. The identity of all the target compounds was well confirmed by ¹H-NMR, ¹³C-NMR, and high-resolution mass spectrometry (HRMS). The primary evaluation of safener activities for the compounds by the agar method indicated that most of the target compounds could protect rice seedlings from injury caused by metolachlor. Notably, compounds 2k and 4k displayed excellent herbicide safener activities on plant height and demonstrated relatively similar activities to the commercialized compound dichlormid. Moreover, we showed that compounds 2k and 4k had higher glutathione S-transferase (GST), superoxide dismutase (SOD), catalase (CAT), peroxidase (POD), and polyphenol oxidase (PPO) activities in rice seedlings, compared to the metolachlor treatment. In particular, 2k and 4k are safer for aquatic organisms than dichlormid. Results from the current work exhibit that compounds 2k and 4k have excellent crop safener activities toward rice and can, thus, be promising candidates for further structural optimization in rice protection. Full article

Background: Zanthoxylum armatum DC. (ZA) is a traditional Asian culinary spice and medicinal compound, which is rich in monoterpenes and hydroxy α-sanshool. Mechanistic interactions with the monoamine, cholinergic and cannabinoid neurotransmission systems, as well as transient receptor potential (TRP) and potassium ion channels, may predispose ZA to modulate human brain function. Objectives: To investigate the effects of a single dose and 56-days supplementation with a lipid extract of ZA on cognitive function, mood and cerebral blood-flow (CBF) parameters in the pre-frontal cortex during cognitive task performance. Design: Double-blind, randomized, parallel groups study with N = 82 healthy males and females between the ages of 30 and 55 years. Assessments were undertaken pre-dose and at 1, 3 and 5 h post-dose on the first (Day 1) and last (Day 56) days of supplementation. Results: A single dose of ZA (Day 1) resulted in acute improvements on a ‘Speed of Attention’ factor and the Rapid Visual Information Processing (RVIP) task, in comparison to placebo. However, following ZA participants were less accurate on the name-to-face recall task. After 56 days of ZA consumption (Day 56), speed was enhanced on a global ‘Speed of Performance’ measure, comprising data from all of the timed tasks in the computerized battery. Participants also completed more correct Serial 3s Subtractions at the 3 h assessment and were less mentally fatigued throughout the day than participants consuming placebo. These effects were complemented on both Day 1 and Day 56 by modulation of CBF parameters, as assessed by Near Infrared Spectroscopy (NIRS). The primary finding here was a reduced hemodynamic response during the RVIP task. Conclusion: ZA improves aspects of cognitive performance, in particular the speed of performing tasks, in healthy humans and results in concomitant reductions in hemodynamic responses in the frontal cortex during task performance. The findings suggest an increase in neural efficiency following ZA. Full article

Four new unsaturated aliphatic acid amides, named zanthoamides A–D (1–4), and eight known ones—tetrahydrobungeanool (5), ZP-amide A (6), ZP-amide B (7), ZP-amide C (8), ZP-amide D (9), ZP-amide E (10), bugeanumamide A (11), and (2E,7E,9E)-N-(2-hydroxy-2-methylpropyl)-6,11-dioxo-2,7,9-dodecatrienamide (12)—were isolated from the pericarps of Zanthoxylum bungeanum. The structures of these compounds were elucidated by extensive use of spectroscopic methods, including HRESIMS, 1D and 2D NMR analyses and comparison with previously reported data. Compound 4 contained a rare C₆ fatty acid unit with an acetal group. Results revealed that compounds 1, 5, 6, and 12 showed inhibitory effects on nitric oxide (NO) production in LPS-stimulated RAW 264.7 macrophages, with IC₅₀values of 48.7 ± 0.32, 27.1 ± 1.15, 49.8 ± 0.38, and 39.4 ± 0.63 µM, respectively, while the other compounds were inactive (IC₅₀ > 60 μM). They could contribute to the anti-inflammatory effects of Z. bungeanum by suppression of NO production. Full article