Spicy Compounds Research Articles

Taste traces: Capsaicin and sweeteners as anthropogenic markers in municipal wastewater

Dietary-derived substances possess significant potential as anthropogenic markers owing to the large consumption and different intake habit. To investigate and evaluate such markers, wastewater samples from 35 wastewater treatment plants across 29 Chinese cities were collected to analyze artificial sweeteners (acesulfame and cyclamate) and natural spicy compounds (capsaicin and dihydrocapsaicin). Acesulfame (mean: 14.6 μg/L), cyclamate (mean: 24.3 μg/L), and capsaicin (mean: 101 ng/L) can be further investigated as anthropogenic markers due to their high detection frequency at high concentrations. Spatial use patterns revealed that acesulfame (5.31 g/d/1000 inhabitants (inh)) and cyclamate (8.16 g/d/1000 inh) use in northern China notably surpassed that in southern China (1.79 g/d/1000 inh and 3.23 g/d/1000 inh, p < 0.05). Conversely, chili pepper use was significantly higher (p < 0.05) in southern China (6702 g/d/1000 inh) than in northern China (2751 g/d/1000 inh), signifying a preference for sweetness in the northern regions and a predilection for spiciness in the southern regions. The total annual use of acesulfame (1842 t), cyclamate (3110 t), and chili (18.4 million tonnes) in China was estimated by this study, which was close to the national statistical production. In addition, sweetener use was negatively associated with the elderly population ratio, suggesting that the elderly population might not consume sweet foods. This study reveals the dietary sources of anthropogenic markers, highlighting the need for further research on the environmental implications of such markers.

Formulation and evaluation of herbal syrup of ginger extract

Zingiber officinale is a plant found locally in India that is widely used as a flavoring agent in savory dishes such as curries and sweets such as cakes and biscuits, alcoholic beverages as well. like in tea. Ginger is a well-known herb, commonly used in traditional medicine all over the world. Ginger has been used for thousands of years to treat colds, nausea, arthritis, migraines, and high blood pressure. The many pharmacological activities of ginger are antiemetic, antidiabetic, analgesic, anti-arthritis, anticancer, antioxidant, anti-ulcer, antibacterial, anti-inflammatory, estrogenic and cardiovascular. A chemical stimulant and an unsaturated liquid phenolic ketone C17H24O3 are responsible for the pungent taste of ginger. The main components of ginger are aromatic essential oils, antioxidants and pungent oleoresin. These aromatic or spicy compounds have been identified as C6H5C(O)CH3, known as a chemical stimulant, phenolic ketone unsaturated liquid C17H24O3 and Vanillylacetone. Lab-scale formulation is made with herbal syrup and evaluated for several parameters such as pH, viscosity, density, stability testing during formulation evaluation. is a stable and ready-to-know formula. F1, F2, F3 and F4 have been prepared with different amounts of ingredients such as alcohol, sugar and a final amount of syrup. Results show that Herbal Syrup Formula 4 (F4) is more stable than other forms.

Evaluation of oral cancer-induced chemosensitivity

<h3>Introduction</h3> Oral cancer patients experience severe function related pain that impacts quality of life. Some patients report sensitivity to spicy food. Pain is attributed to neuronal sensitization by the release of chemical mediators from the cancer and cancer microenvironment that activate TRPV1 (transient receptor potential cation channel subfamily V member 1). To better understand the underlying mechanisms of oral cancer pain, this study was designed to evaluate cancer-induced chemosensitivity in oral cancer preclinical models. <h3>Materials and Methods</h3> A two-bottle preference test was used to measure aversion to the TRPV1 agonist, capsaicin, the spicy compound in chili peppers. Naïve wild type mice (C57BL/6) were housed two to five mice per cage. Liquid intake over 5-7 day periods was measured from two drinking bottles one with water and capsaicin (0.25 µM – 1 µM) and the other vehicle (0.1% ethanol). Positions of the bottles were exchanged daily to avoid habituation. <h3>Results</h3> Female C57BL/6 mice drank less water with capsaicin for all tested concentrations of capsaicin, demonstrating aversion. Male C57BL/6 mice demonstrated aversion to capsaicin concentrations greater than 0.25 µM. Aversion increased in successive trials, suggesting conditioning or sensitization. Male mice that did not show aversion to 0.25 µM capsaicin over three successive trials demonstrated aversion to 0.25 µM capsaicin after injection in the tongue with complete Freund's adjuvant (20 µl) to generate inflammatory pain. <h3>Conclusions</h3> Female mice showed greater sensitivity to capsaicin than male mice. Aversion to a non-aversive concentration of capsaicin was demonstrated in male mice with inflammatory pain. The lowest dose of capsaicin is expected identify the change in chemosensitivity and difference between sensitive vs. non sensitive cancers.

The investigation of detection and sensing mechanism of spicy substance based on human TRPV1 channel protein-cell membrane biosensor

The transient receptor potential vanilloid 1 (TRPV1) is a key target for the spicy taste sensor and analgesic drug development. However, the human TRPV1-associated signaling remains to be obscure. In this study, we overexpressed human TRPV1 (hTRPV1) in HEK293T cells and explored its signaling activated by spicy substances. A cell membrane biosensor was constructed by using the cells highly expressed hTRPV1 through a layer-by-layer assembly. Our results showed that the activation constants by capsaicin, allicin and sanshool, the active components of chili pepper, garlic and mountain pepper, were Ka, capsaicin = 3.5206 × 10-16 mol/L, Ka, allicin = 5.0227 × 10-15 mol/L, Ka, sanshool = 1.7832 × 10-15 mol/L. Obviously, the order of the sensitivity mediated by hTRPV1 was capsaicin > sanshool > allicin. The affinity values of the three spicy substances with hTRPV1 analyzed by molecular docking simulation also displayed the same law. Most importantly, some amide bonds and their similar groups and even benzene rings of spicy compounds were fund to be critical in the spicy sensing process. In addition, Glu570 in the active pocket of hTRPV1 plays an important role in identifying spicy substances. The elucidation of the detailed mechanism mediated by hTRPV1 in spicy sensing will lay a theoretical foundation to design rational strategies for screening of potential analgesics.

A rapid GC-FID method for determination of sabinene, β-pinene, α-thujone and β-thujone in the essential oil of Kitchen Sage (Salvia officinalis L.)

Terpenes and terpenoids are dominant fragrances in the essential oils of many economically important fruits and vegetables. Hence, content and variation are important factors in the evaluation and common perception of food quality. Sabinene, β-pinene, α-thujone and β-thujone are examples of such compounds found in the different species of Sage. Sabinene and β-pinene are spicy compounds much used by the fragrance industry while the two thujones are highly toxic. Here, we report a rapid method for quantification of these compounds in the essential oil of Sage. The total analytical time is approx. 7,5 min in contrast to approx. 30 min for similar gas chromatographic methods. The analytical method had a linear range of 28–342 mg L−1 for the different compounds, with an analytical precision of 0,6–0,9% for standards. Correlation coefficients were 0,9993–1,0000. The Limit of Detection of all compounds were 0,02–0,9 mg L−1 and the Limit of Quantification were 0,08–3,0 mg L−1. The technique was used for quantification of the compounds in seven commercial essential Sage oils and in a pilot study of the effect of ozone on the terpenes and terpenoids in fresh Sage leaves. Large variation was observed between the different commercial samples, of which some were thujone dominant and some did not have any content of thujone at all. Treatment of fresh Sage leaves with ozone caused degradation of the terpenes sabinene and β-pinene whereas the terpenoids α/β-thujone were more resistant to degradation.

Fungal Seed Pathogens of Wild Chili Peppers Possess Multiple Mechanisms To Tolerate Capsaicinoids.

The wild chili pepper Capsicum chacoense produces the spicy defense compounds known as capsaicinoids, including capsaicin and dihydrocapsaicin, which are antagonistic to the growth of fungal pathogens. Compared to other microbes, fungi isolated from infected seeds of C. chacoense possess much higher levels of tolerance of these spicy compounds, having their growth slowed but not entirely inhibited. Previous research has shown capsaicinoids inhibit microbes by disrupting ATP production by binding NADH dehydrogenase in the electron transport chain (ETC) and, thus, throttling oxidative phosphorylation (OXPHOS). Capsaicinoids may also disrupt cell membranes. Here, we investigate capsaicinoid tolerance in fungal seed pathogens isolated from C. chacoense We selected 16 fungal isolates from four ascomycete genera (Alternaria, Colletotrichum, Fusarium, and Phomopsis). Using relative growth rate as a readout for tolerance, fungi were challenged with ETC inhibitors to infer whether fungi possess alternative respiratory enzymes and whether effects on the ETC fully explained inhibition by capsaicinoids. In all isolates, we found evidence for at least one alternative NADH dehydrogenase. In many isolates, we also found evidence for an alternative oxidase. These data suggest that wild-plant pathogens may be a rich source of alternative respiratory enzymes. We further demonstrate that these fungal isolates are capable of the breakdown of capsaicinoids. Finally, we determine that the OXPHOS theory may describe a weak primary mechanism by which dihydrocapsaicin, but not capsaicin, slows fungal growth. Our findings suggest that capsaicinoids likely disrupt membranes, in addition to energy poisoning, with implications for microbiology and human health.IMPORTANCE Plants make chemical compounds to protect themselves. For example, chili peppers produce the spicy compound capsaicin to inhibit pathogen damage and animal feeding. In humans, capsaicin binds to a membrane channel protein, creating the sensation of heat, while in microbes, capsaicin limits energy production by binding respiratory enzymes. However, some data suggest that capsaicin also disrupts membranes. Here, we studied fungal pathogens (Alternaria, Colletotrichum, Fusarium, and Phomopsis) isolated from a wild chili pepper, Capsicum chacoense By measuring growth rates in the presence of antibiotics with known respiratory targets, we inferred that wild-plant pathogens might be rich in alternative respiratory enzymes. A zone of clearance around the colonies, as well as liquid chromatography-mass spectrometry data, further indicated that these fungi can break down capsaicin. Finally, the total inhibitory effect of capsaicin was not fully explained by its effect on respiratory enzymes. Our findings lend credence to studies proposing that capsaicin may disrupt cell membranes, with implications for microbiology, as well as human health.

Detection of Spicy Compounds Using the Electronic Tongue

The consumption of spicy food products has increased, resulting in an increased demand for these products. The sensory evaluation of foods containing spicy compounds provides challenges due to their trigeminal innervation and associated sensory fatigue. Thus, for the routine evaluation of spices, a need exists for rapid and objective methods of analysis; the electronic tongue (e-tongue) provides a potential solution. The objective of this study was to evaluate the ability of the e-tongue to distinguish among spicy compounds at varying concentrations. Due to the diversity of spicy compounds, seven spicy compounds were selected: capsaicin, thymol, piperine, zingerone, p-cymene, menthol, and eugenol. For each of these compounds, a low concentration (1.427 × 10-5 to 0.85 mg/L), medium concentration (2.854 × 10-5 to 1.49 mg/L), and high concentration (0.0133 to 30.5 mg/L) were analyzed by the e-tongue. For each compound, the e-tongue discriminated among the concentrations with discrimination indices between 72% to 84%. Based on the responses of the e-tongue sensors, the samples formed three clusters. Cluster 1 contained menthol, eugenol, and p-cymene, cluster 2 contained capsaicin and thymol, and cluster 3 contained piperine and zingerone. Same-different sensory testing was completed on a representative sample from each cluster. Untrained consumers (n = 80) distinguished among the three clusters, verifying the clusters identified by the e-tongue. These results demonstrated that the e-tongue could be applicable in product development and the routine evaluation of spicy products. PRACTICAL APPLICATION: As the e-tongue differentiated among spicy compounds in an effective manner, it could be used instead of or alongside sensory evaluation when evaluating spicy compounds to reduce sensory fatigue associated with routine testing. Utilizing the e-tongue for spicy products will be an important area of research as the market for such products continues to grow.

6-shogaol, a active constiuents of ginger prevents UVB radiation mediated inflammation and oxidative stress through modulating NrF2 signaling in human epidermal keratinocytes (HaCaT cells)

Disclosure of ultraviolet (UV) radiation is the key feature from environment to cause redness of the skin, inflammation, photoaging and skin cancer. 6-Shogaol, a spicy compound secluded from ginger, which shows anti-inflammatory effects. Present study was demonstrated the role of 6-Shogaol on UVB induced oxidative stress and photoaging signaling in human epidermal keratinocytes (HaCaT cells). In this study, UVB-irratiation (180 mJ/cm2) significantly elevated the intracellular ROS levels, depletion of antioxidants resulted in apoptotic HaCaT cells. MAPKs signaling are concerned in oxidative stress; these signaling events are measured as differentiation. We found that 6-shogaol prevents over expression of MAPKs (ERK1, JNK1 & p38), in disclosure of UVB in HaCaT cells. Moreover, 6-shogaol infringed Bax and Bcl-2 in which 20 μg 6-shogaol influenced apoptosis in HaCaT cells by investigating augmented appearance of Bax and condensed appearance of Bcl-2 in contrast to control HaCaT cells. These results suggest that 6-shogaol could be a successful healing agent provides fortification against UVB-induced provocative and oxidative skin reimbursement.

Capsaicin synergizes with camptothecin to induce increased apoptosis in human small cell lung cancers via the calpain pathway

Small cell lung cancer (SCLC) is characterized by excellent initial response to chemotherapy and radiation therapy with a majority of the patients showing tumor shrinkage and even remission. However, the challenge with SCLC therapy is that patients inevitably relapse and subsequently do not respond to the first line treatment. Recent clinical studies have investigated the possibility of camptothecin-based combination therapy as first line treatment for SCLC patients. Conventionally, camptothecin is used for recurrent SCLC and has poor survival outcomes. Therefore, drugs which can improve the therapeutic index of camptothecin should be valuable for SCLC therapy. Extensive evidence shows that nutritional compounds like capsaicin (the spicy compound of chili peppers) can improve the anti-cancer activity of chemotherapeutic drugs in both cell lines and animal models. Statistical analysis shows that capsaicin synergizes with camptothecin to enhance apoptosis of human SCLC cells. The synergistic activity of camptothecin and capsaicin is observed in both classical and variant SCLC cell lines and, in vivo, in human SCLC tumors xenotransplanted on chicken chorioallantoic membrane (CAM) models. The synergistic activity of capsaicin and camptothecin are mediated by elevation of intracellular calcium and the calpain pathway. Our data foster hope for novel nutrition based combination therapies in SCLC.

Integrated Process for Production of Galangal Acetate, the "Wasabi-Like" Spicy Compound, and Analysis of Essential Oils of Rhizoma Alpinia officinarum (Hance) Farw.

Rhizoma Alpinia officinarum (Hance) Farw, Zingiberaceae (AO), a ginger family herb exhibiting stimulant and a carminative bioactivity, is widely used in European and Asian countries as spicy condiment and medicinal uses. Allyl isothiocyanate (AITC) is the main pungent taste of native Wasabi (Wasabia japonica). The cytotoxicity of AITC has been implicated in thymus, adrenals, and white blood cells. Considering food safety, apparently a safer substitute for wasabi is worthy commercialized. Previously, we found AO crude paste to be rather feasible for use as a "Wasabi-substitute" in fresh meat and cold salads. A process linking cold ethyl acetate (EtAc) extraction with silica gel adsorption and reversed phase high-performance liquid chromatography (RP-HPLC) (mobile phase, 75% methanol) was used to isolate galangal acetate, the Wasabi-like taste constituent. AO contained abundant galangal acetate (3.84 ± 0.07%) compared to A. galangal (0.57 ± 0.16%), and as already confirmed by thin layer chromatography (TLC), gas chromatography (GC)/mass spectrometry (MS)/MS and Nuclear Magnetic Resonance Spectroscopy (NMR), galangal acetate was particularly thermally labile. The steam distilled essential oil (SDEO) of AO (0.14% on wet basis) contained 80 compounds (number of component, %): monoterpene hydrocarbon (21, 13.83%); oxygenated monoterpene (17, 27.08%); sesquiterpene hydrocarbon (20, 31.03%), and oxygenated sesquiterpene (20, 21.85%), respectively. However, no spicy wasabi-like constituent remained in SDEO. Alternatively, n-hexane, EtAc, and methanol extracts of AO all showed potent DPPH- and superoxide anion-scavenging activity. Conclusively, SDEO although contains 80 volatiles, galangal acetate is absent due to thermal instability. Galangal acetate exhibits pleasant "Wasabi-like taste" for which we have successively developed an integrated process for mass production.

Identification of Significant Amino Acids in Multiple Transmembrane Domains of Human Transient Receptor Potential Ankyrin 1 (TRPA1) for Activation by Eudesmol, an Oxygenized Sesquiterpene in Hop Essential Oil

Transient receptor potential ankyrin 1 (TRPA1) is a calcium-permeable non-selective cation channel that is activated by various noxious or irritant substances in nature, including spicy compounds. Many TRPA1 chemical activators have been reported; however, only limited information is available regarding the amino acid residues that contribute to the activation by non-electrophilic activators, whereas activation mechanisms by electrophilic ligands have been well characterized. We used intracellular Ca(2+) measurements and whole-cell patch clamp recordings to show that eudesmol, an oxygenated sesquiterpene present at high concentrations in the essential oil of hop cultivar Hallertau Hersbrucker, could activate human TRPA1. Gradual activation of inward currents with outward rectification by eudesmol was observed in human embryonic kidney-derived 293 cells expressing human TRPA1. This activation was completely blocked by a TRPA1-specific inhibitor, HC03-0031. We identified three critical amino acid residues in human TRPA1 in putative transmembrane domains 3, 4, and 5, namely threonine at 813, tyrosine at 840, and serine at 873, for activation by β-eudesmol in a systematic mutational study. Our results revealed a new TRPA1 activator in hop essential oil and provide a novel insight into mechanisms of human TRPA1 activation by non-electrophilic chemicals.

New drugs from ancient natural foods. Oleocanthal, the natural occurring spicy compound of olive oil: a brief history

Extra-virgin olive oil (EVOO), a principal component of the Mediterranean diet (Med diet), is one of the most ancient known foods and has long been associated with health benefits. Many phenolic compounds extracted from Olea europea L. have attracted attention since their discovery. Among these phenolic constituents, oleocanthal has recently emerged as a potential therapeutic molecule for different diseases, showing relevant pharmacological properties in various pathogenic processes, including inflammation, cancers and neurodegenerative diseases. Here, we discuss and summarize the most recent pharmacological evidence for the medical relevance of oleocanthal, focusing our attention on its anti-inflammatory and chemotherapeutic roles.

A novel method for the identification of illegal cooking oil (1): detection of three capsaicinoids with liquid chromatography-mass spectrometry

Illegal cooking oil (ICO, also named swill-cooked dirty oil) has recently become a serious food safety problem in China. Now, the identification method of ICO is also a hot research area. Owning to the special eating habits of Chinese people, cayenne is widely used in catering business. Capsaicinoids are main spicy compounds in cayenne. So, they are potential evaluation indices for the identification of ICO. In this study, a solid phase extraction-liquid chromatography-mass spectrometry (SPE-LC-MS) method has been developed to detect the trace residues of three capsaicinoids (capsaicin, dihydrocapsaicin and nonylic acid vanillylamide) in cooking oil. The oil sample was first extracted with 20 g/L sodium hydroxide, the C18 SPE cartridge was then used to clean-up the sample and enrich the analytes before the liquid chromatography-mass spectrometry (LC-MS) detection. With this method, sixty seven blind samples provided by China National Center for Food Safety Risk Assessment were analyzed. The results showed that the capsaicinoids are good evaluation indices for the identification of ICO. In all the 48 ICO samples, 36 samples were successfully recognized. All the 19 normal oil samples were accurately identified. This method has been chosen and authorized as one of the four standard instrumental identification methods for ICO by the National Ministry of Health of China.

Studies on the Improvement of Antioxidant Effect of Tocopherols. XVI.

The synergistic antioxidant effects of d-tocopherol (Toc) and several spicy compounds on lard and plam oil were investigated by oven and AOM tests. The antioxidant effects of spicy compounds were also studied in the same manner.1) By the oven test, cinnamaldehyde, capsaicine and thymol showed weak antioxidant effect on lard, but spicy compounds which enhanced the antioxidant effect of Toc were capsaicine, cineol, camphene, phellandrene and geraniol. However, no effect was observed on palm oil.2) By the AOM test, only capsaicine showed antioxidant effect on lard, but none of the spicy compounds enhanced this effect of Toc.3) Remnant ratios of the spicy compounds after a month of the oven test were lower than 30%, except in the case of capsicine which may possibly volatilize after such a period of time. However, the ratios of capsaicine and thymol which had antioxidant effects were higher than those of other compounds on lard. The remnant ratio of total Toc in lard increased by the addition of capsaicine, cineol, camphene, phellandrene or geraniol, indicating these compounds to possibly protect Toc from oxidative decomposition.