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FOOD CHEMISTRY · 2014 · IF 3.259

Development of a rapid, simple and sensitive HPLC-FLD method for determination of rhodamine B in chili-containing products

Ping Qi,Zhihao Lin,Jiaxu Li,ChengLong Wang,WeiWei Meng,Hong Hong,Xuewu Zhang

In this work, a simple, rapid and sensitive analytical method for the determination of rhodamine B in chili-containing foodstuffs is described. The dye is extracted from samples with methanol and analysed without further cleanup procedure by high-performance liquid chromatography (HPLC) coupled to fluorescence detection (FLD). The influence of matrix fluorescent compounds (capsaicin and dihydrocapsaicin) on the analysis was overcome by the optimisation of mobile-phase composition. The limit of determination (LOD) and limit of quantification (LOQ) were 3.7 and 10   μg/kg, respectively. Validation data show a good repeatability and within-lab reproducibility with relative standard deviations <10%. The overall recoveries are in the range of 98–103% in chili powder and in the range of 87–100% in chili oil depending on the concentration of rhodamine B in foodstuffs. This method is suitable for the routine analysis of rhodamine B due to its sensitivity, simplicity, reasonable time and cost.

CAS / MDL: 404-86-4 19408-84-5
研究领域: 食品科学 · 分析化学
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JOURNAL OF SEPARATION SCIENCE · 2014 ·Vol. 38 ·期 1 ·100-107 · IF 2.594

Molecularly imprinted polymers with synthetic dummy templates for the preparation of capsaicin and dihydrocapsaicin from chili peppers

Xiuli Ma,Wenhua Ji,Lingxiao Chen,Xiao Wang,Jianhua Liu,Xueyong Wang

In this work, dummy molecularly imprinted polymers with high selectivity and affinity to capsaicin and dihydrocapsaicin are designed using N -vanillylnonanamide as a dummy template. The performance of dummy molecularly imprinted polymers and nonimprinted polymers was evaluated using adsorption isotherms, adsorption kinetics, and selective recognition capacity. Dummy molecularly imprinted polymers were found to exhibit good site accessibility, taking just 20 min to achieve adsorption equilibrium; they were also highly selective toward capsaicin and dihydrocapsaicin. We successfully used dummy molecularly imprinted polymers as a specific sorbent for selectively enriching capsaicin and dihydrocapsaicin from chili pepper samples. In a scaled-up experiment, the selective recovery of capsaicinoids was calculated to be 77.8% using solid-phase extraction. To the best of our knowledge, this is the first example of the use of N -vanillylnonanamide as a dummy template in molecularly imprinted polymers to simultaneously enrich capsaicin and dihydrocapsaicin.

研究领域: 食品科学 · 分析化学
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CHINESE JOURNAL OF ANALYTICAL CHEMISTRY · 2022 · IF 1.193

Effect of hapten structures on development of novel antibody against capsaicin and dihydrocapsaicin

Jia-Li ZHANG,Fei MA,Chuan-Yun ZHA,Qing-Qing YANG,Qi ZHANG,Wen ZHANG,Pei-Wu LI,Xia SUN

Capsaicinoids content as a basis for the evaluation of spicy taste has attracted much attention. Antibody, as an important component of immunoassay, plays an important role in the detection of capsaicinoids levels. The molecular structure of the hapten is the key factor affecting the quality of small molecule antibodies. In our study, six capsaicinoids haptens were selected with different junction arm of length and structure to analyzed immune effect by geometric structure and electrostatic potential (ESP). Among them, three haptens were capsaicinoids structural analogues, and others were designed and synthesized. The results showed that the retention of amide bond (–NH–CO–) and hydroxyl group in the benzene ring of capsaicinoids hapten as well as rigid spacer arm that linked proteins to hapten had a positive effect on the affinity of the antibody. It provided a theoretical basis for rapid screening of small molecular substance haptens. To test our hypothesis, four kinds of haptens were used to synthesize antigens and immunize animals. Comparing 28 antiserum/coating conjugates combinations tested by indirect competitive enzyme-linked immunosorbent assay (icELISA) method for capsaicinoids (i.e., capsaicin and dihydrocapsaicin), the homologous combination of Pa-B2/OVA-hapten B had been shown to be most suitable for the determination of capsaicin and dihydrocapsaicin, which was consistent with the ESP analysis. In short, ESP analysis can speed up haptens screening and reduce the workload while producing high-quality antibodies. Thus, an icELISA based on hapten B polyclonal antibody was developed with IC 50 value of 0.36 μg mL −1 and the limit of detections (LODs) of 20 µg kg −1 in spicy food samples. Moreover, these results were also validated by high performance liquid chromatography (HPLC), and showed good agreements.

CAS / MDL: 108-31-6 108-30-5
研究领域: 免疫学 · 分析化学 · 食品科学
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PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY · 2019 · IF 2.87

Capsaicinoid metabolism by the generalist Helicoverpa armigera and specialist H. assulta: Species and tissue differences

Jiang Zhu,Kai Tian,Christopher A. Reilly,Xinghui Qiu

Helicoverpa armigera and H. assulta are two of the few insects that can feed on hot pepper fruits. Capsaicin and dihydrocapsaicin ( i.e. , capsaicinoids) are the principal pungent compounds in hot peppers. To explore possible molecular mechanisms of adaptation that allow these two species to consume capsaicinoids, the capacity of the three detoxification tissues (fat body, midgut, and Malpighian tubule) of the two pests, to metabolically degrade capsaicin and dihydrocapsaicin, was compared. The results showed that capsaicin and dihydrocapsaicin were metabolized by crude enzyme preparations from all three tissues of the two pests. Five metabolites of capsaicin, and five metabolites of dihydrocapsaicin were identified. Tissue and species differences in the degree of capsaicin and dihydrocapsaicin metabolism were observed. The specialist H. assulta had an overall greater capacity to degrade the capsaicinoids compared to the generalist H. armigera. Further, the midgut was the most significant contributor to capsaicinoid metabolism. The notably high specific activity in Malpighian tubules of H. armigera also further highlights the significance of this organ in xenobiotic detoxification. Alkyl hydroxylation and dehydrogenation were the main pathways for the oxidative biotransformation of both capsaicin and dihydrocapsaicin by cytochrome P450s. This study provides evidence that enhanced metabolic decomposition of capsaicinoids may be an adaptation explaining dietary preferences for Capsicum fruits by these two pests.

研究领域: 昆虫学 · 植物化学 · 分子生物学
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POLYMER TESTING · 2021 · IF 4.282

Synthesis of highly efficient non-lethal repellent for rats from natural capsaicin and its influence on properties of EVA

Xuechao Wang,Haibing Wei,Hongmei Xu,Xueliang Li,Guobing Zhang,Sheng Cheng,Chenxi Wang,Gang Ruan,Yiyang Zhou,Yunsheng Ding

A repellent for rats named DC has been successfully synthesized from natural capsaicin and 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO) via a one-pot procedure. The chemical structure of obtained DC is confirmed by Fourier transform infrared (FTIR), Raman and nuclear magnetic resonance (NMR). Then DC was incorporated into ethylene vinyl acetate copolymer (EVA) by blending, to endow EVA with rat proof property and present the advantage of non-lethal. The influence of DC on the structure and properties of EVA is investigated systematically by theoretical calculations and various measurements. Thermogravimetric analysis (TGA) reveals that the incorporation of 4 wt% DC into EVA can significantly enhance the char residue yield from 2.80 wt% to 6.84 wt%. In addition, limiting oxygen index (LOI) and the char residues analysis suggest that DC could facilitate the formation of char layers, resulting in the improvement of synergistic flame retardancy for EVA/DC compounds. This work provided novel insights into the preparation of highly efficient non-lethal repellent for rats and its potential application for polymer materials.

CAS / MDL: 35948-25-5
研究领域: 材料科学 · 化学合成 · 生物学
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CHEMISTRY & BIODIVERSITY · 2021 ·Vol. 18 ·期 4 ·e2000910 · IF 2.408

Hydroxylation, Epoxidation, and Dehydrogenation of Capsaicin by a Microbial Promiscuous Cytochrome P450 105D7

Bingbing Ma,Qianwen Wang,Bing-Nan Han,Haruo Ikeda,Chunfang Zhang,Lian-Hua Xu

Cytochrome P450 enzymes (P450s) are versatile biocatalysts, which insert a molecular oxygen into inactivated C−H bonds under mild conditions. CYP105D7 from Streptomyces avermitilis has been reported as a bacterial substrate-promiscuous P450 which catalyzes the hydroxylation of 1-deoxypentalenic acid, diclofenac, naringenin, compactin and steroids. In this study, CYP105D7 catalyzes hydroxylation, epoxidation and dehydrogenation of capsaicin, a pharmaceutical agent, revealing its functional diversity. The kinetic parameters of the CYP105D7 oxidation of capsaicin were determined as K m =311.60±87.30 μM and k cat =2.01±0.33 min −1 . In addition, we conducted molecular docking, mutagenesis and substrate binding analysis, indicating that Arg81 plays crucial role in the capsaicin binding and catalysis. To our best knowledge, this study presents the first report to illustrate that capsaicin can be catalyzed by prokaryotic P450s.

研究领域: 生物化学 · 药物代谢
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PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY · 2019 · IF 2.87

Capsaicin is efficiently transformed by multiple cytochrome P450s from Capsicum fruit-feeding Helicoverpa armigera

Kai Tian,Jiang Zhu,Mei Li,Xinghui Qiu

Capsaicin (8-methyl- N -vanillyl-6-nonenamide) is the most abundant capsaicinoids found in hot peppers ( Capsicum annum and Capsicum frutescens ). It has been well documented that capsaicin plays an important role in the defense against the attack of herbivores or pathogens on Capsicum plants. A few insect herbivores such as Helicoverpa armigera and Helicoverpa assulta have been recorded to be capable of feeding on hot pepper fruits, suggesting that these insects evolve mechanisms against the toxicity of capsaicin. Although cytochrome P450-meidated detoxification is considered to be an important mechanism by which cotton bollworms cope with capsaicin, experimental evidence is lacking. In this study, we compared the capacity of four H. armigera P450s (CYP6B6, CYP9A12, CYP9A14 and CYP9A17) in capsaicin metabolism, and the capsaicin metabolites were screened and tentatively identified by liquid chromatography–tandem mass spectrometry (LC–MS/MS). HPLC analyses showed that depletion rates of capsaicin were 21.9 ± 0.1, 11.9 ± 1.5, 16.3 ± 1.4 and 14.8 ± 0.2 min −1 for CYP6B6, CYP9A12, CYP9A14 and CYP9A17 respectively. The transformation of capsaicin was inhibited by the P450 inhibitor piperonyl butoxide . A total of seven products were detected, and hydroxylation (aromatic and aliphatic) and dehydrogenation were found to be two main pathways in capsaicin metabolism. In addition, capsaicin metabolism was enzyme selective: M1 (ω-hydroxylated N-macrocyclic metabolite) and M3 (ω-hydroxylated metabolite) were uniquely detected in the CYP6B6 catalytic reaction, while M4 (ω-n hydroxylated capsaicin), M5 (diene of capsaicin) and M6 (doubly oxidized metabolite of dehydrogenated capsaicin) were only detectable in CYP9A metabolisms. A capsaicin dimer (5, 5′-dicapsaicin) was found to be the major metabolite of CYP9A reactions, but the minor product produced by CYP6B6. An overall more similar behavior in capsaicin metabolism was observed among CYP9As than between CYP6B6 and CYP9As. Our data demonstrate that CYP6B6 and CYP9As have a potent capability to transform capsaicin, and individual P450 produce unique metabolite profile. These findings help us to understand the molecular basis of capsaicin adaptation in H. armigera .

CAS / MDL: 367-93-1 53-59-8
研究领域: 昆虫学 · 植物化学 · 分子生物学
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FOOD CHEMISTRY · 2023 · IF 8.8

Multi-dimensional pungency and sensory profiles of powder and oil of seven chili peppers based on descriptive analysis and Scoville heat units

Yiwen Zhu,Xiang Li,Shui Jiang,Yin Zhang,Lihua Zhang,Yuan Liu

The pungency and flavor experience of peppers determines their economic benefits and consumption; thus, a systematic sensory evaluation of peppers is essential to monitor their production. Here the Scoville heat units (SHUs) of powders and oils of seven commercial peppers in China (i.e., Indian, Erjintiao, Shizhuhong, Zidantou, Xinyidai, Mantianxing and Denglong) were derived based on concentrations of capsaicin and dihydrocapsaicin. Then, the pungency and sensory profiles of pepper products were investigated by 11 trained panelists. The potential indicators for predicting perceived pungency in peppers were found based on correlation analysis. The Indian pepper stood out for its highest SHU (85909), bright redness, peppery, and bitterness, but lacked herb/woody flavor. But other species had more varied flavor profiles and gentler mouth-feelings. SHU and capsaicin were more recommended in predicting the perceived pungency in pepper powder and pepper oil. This study offers a framework for evaluating the sensory characteristics of pepper products.

CAS / MDL: 404-86-4
研究领域: 食品科学 · 感官评价 · 化学 · 农业
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ECOTOXICOLOGY AND ENVIRONMENTAL SAFETY · 2025 · IF 6.1

Beneficial effects of dihydrocapsaicin on paraquat-induced acute kidney injury: role of Sox9/Sesn2 axis-mediated autophagy

Siqi Yu,Fudong Wang,Yuan Zhang,Xiaofeng Wang,Hongyu Zhao,Qiang Zheng

Autophagy inhibition induced by paraquat (PQ) poisoning is an important factor causing multi-organ damage, including renal tissue. Dihydrocapsaicin (DHC), the main active ingredient in chili peppers, was reported to induce autophagy, but its effect on PQ-induced AKI remains unclear. Rats were intraperitoneally injected with 25 mg/kg PQ to establish AKI rat model followed immediately by DHC administration (2.5, 5, or 10 mg/kg, i.p.). Rat renal tubular epithelial cells were exposed to PQ (300 μM) in combination with DHC (25, 50, or 100 μM) for 24 h. The results showed that DHC treatment attenuated PQ-induced renal injury and dysfunction while suppressing apoptosis and oxidative stress in vivo and in vitro . Furthermore, DHC administration induced autophagy—a protective mechanism against oxidative stress and apoptosis—as demonstrated by: 1) increased autophagosome/autophagolysosome formation, 2) upregulated LC3-II and autophagy-related gene 7 expressions and reduced p62 protein level. Blocking of autophagy by 3-methyladenine (3-MA) reversed the effects of DHC. Interestingly, transcription factor sex determining region Y-box 9 (Sox9) and autophagy inducer Sestrin2 RNA levels were increased by DHC treatment. Sox9 activated Sestrin2 transcription through direct binding to its promoter region. Sox9 or Sestrin2 silencing reversed the effects of DHC. Collectively, our findings demonstrate that DHC attenuates PQ-induced AKI via Sox9/Sestrin2 axis-mediated autophagy, indicating therapeutic utility of DHC against AKI.

研究领域: 药理学 · 毒理学 · 分子生物学 · 肾脏病学
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JOURNAL OF DRUG DELIVERY SCIENCE AND TECHNOLOGY · 2025 · IF 4.9

Highly Concentrated Eutectic Creams of Capsaicin for Long-term Analgesia

Xinru Zhu,Yulin Chen,Yumeng Li,Wenwen Cui,Xiaoying Wang,Lele Mao,Yue Li,Letian Zhang,Ying Chen,Mei Dong,Qingsong Wang

This study aimed to employ eutectic technology to formulate a stable, organic solvent-free and high-concentration capsaicin cream. Herein, menthol was selected to form a eutectic with capsaicin from ten compounds. The eutectic mixtures (EMs) were characterized by polarized optical microscopy (POM), differential scanning calorimetry (DSC), Fourier Transform Infrared (FT-IR) spectroscopy, and X-ray diffraction (XRD). The stability of the EMs in the cream was prolonged for over 8 months due to the interactions among capsaicin, menthol, Span 40, and polyvinyl alcohol (PVA). The rheological properties were further enhanced by incorporating white petrolatum and anhydrous calcium hydrogen phosphate into the eutectic cream, which indicated improved physical stability and spreadability. Moreover, the retention of capsaicin in porcine skin was comparable between the eutectic cream group (4% w/w capsaicin) and the Qutenza® group (8% w/w capsaicin). Once applied the capsaicin eutectic cream (4% w/w) to chronic constriction injury (CCI) model in mice, mechanical and thermal pain were alleviated in a manner similar to Qutenza®. Overall, the capsaicin eutectic cream was successfully prepared by combining eutectic, with a specific mixture of surfactant and PVA. Also, the cream showed excellent permeability and storage stability for topical application, which provided a promising potential for the development of long-acting analgesic drugs.

CAS / MDL: 75-05-8
研究领域: 药剂学 · 疼痛管理 · 药物递送系统
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PHARMAZIE · 2016 ·Vol. 71 ·期 5 ·269-273 · IF 1.264

Capsaicin induces metabolism of simvasatin in rat: involvement of upregulating expression of Ugt1a1

Zhu Chaoran,Zhai Xuejia,Chen Fen,Wang Nanxi,Zhang Xinlin,Lu Yongning

Capsaicin (CAP, trans-8-methyl-N-vanillyl-6-nonenamide) is a major pungent substance in hot pepper. However, little is known about the interactions between CAP and clinically used drugs. This study investigated the effect of acute and chronic ingestion of CAP on pharmacokinetics of simvastatin (SV) and the mechanism of this CAP–drug intercation. CAP was orally administered at doses of 3 and 8 mg·kg-1 for seven consecutive days once daily and on the 1st day and the 7th day, SV (8 mg·kg-1) was injected intravenously. Plasma concentrations of SV were determined using LC/MS/MS and expression of Ugt1a1 was analyzed by RT-qPCR and Western Blotting. We found that there were 78.0 % (P< 0.05) and 81.2% (P< 0.05) reduction in the AUC(0-∞) of SV, respectively, following pretreatment with two doses of CAP. The AUC(0-∞) of SV in the two dose group pretreated with CAP for 7 days were decreased significantly, compared to the group for 1 day. Both the RT-qPCR and Western Blotting data indicated that 7 days pretreatment with CAP increased the expression level of Ugt1a1 in liver. In conclusion, chronic ingestion of CAP enhanced the expression level of Ugt1a1 in liver, causing the food -drug interaction and decrease in SV exposure in rats to a significant extent.

CAS / MDL: 64-18-6
研究领域: 药理学 · 分子生物学 · 毒理学
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RSC Advances · 2022 ·Vol. 12 ·期 24 ·15613-15622 · IF 4.036

One-pot method for preparation of capsaicin-containing double-network hydrogels for marine antifouling

Pei Li,Xin Su,Dezhao Hao,Ming Yang,Taijiang Gui,Weiwei Cong,Wenqiang Jiang,Xiuli Ge,Xinglin Guo

Marine biofouling which interferes with normal marine operation and also causes huge economic loss has become a worldwide problem. With the development of society, there is an urgent need to develop non-toxic and efficient anti-fouling strategies. Capsaicin is an environmentally friendly antifouling agent, but controlling the stable release of capsaicin from the coating is still a challenge to be solved. To achieve long-lasting antifouling property, in this work, we incorporate a derivative of capsaicin N-(4-hydroxy-3-methoxybenzyl)acrylamide (HMBA) to prepare double network (DN) hydrogels and make HMBA a part of the polymer network. Polyvinyl alcohol (PVA) has good hydrophilicity, and as a soft and ductile network, acrylamide (AM) and HMBA can polymerize to generate a rigid and brittle network. By adjusting the content of HMBA in the DN hydrogels, we can obtain a PVA–PAHX hydrogel with high mechanical strength, low swelling rate, and excellent antifouling effect, which provides a feasible way for the practical application of a hydrogel coating in long-term marine antifouling.

研究领域: 材料科学 · 海洋生物学
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