- An Electrophilic Natural Product Provides a Safe and Robust Odor Neutralization Approach To Counteract Malodorous Organosulfur Metabolites Encountered in Skunk Spray. [Journal Article]
- JNJ Nat Prod 2019 Jul 05
- The anal secretions of skunks comprise several types of malodorous organosulfur compounds. The pungent metabolites are used defensively by skunks to repel threats posed by predators, and in many part…
The anal secretions of skunks comprise several types of malodorous organosulfur compounds. The pungent metabolites are used defensively by skunks to repel threats posed by predators, and in many parts of the world, those perceived threats include humans and their pets. The extremely low thresholds for detection of the organosulfur metabolites make efforts to "de-skunk" people, animals, and clothing a process fraught with many challenges. The fungal-derived metabolite pericosine A (4) is a promiscuous yet stabile electrophilic compound that we propose is used by some fungi as a novel form of chemical defense. Our investigations have indicated that pericosine A readily reacts with skunk-spray secretions to transform them into odorless products. Mechanistic and computational studies suggested that pericosine A and its synthetic analogues react via SN2'-type mechanisms with thiols and thioacetates under aqueous conditions to generate stable thioethers. Testing revealed that pericosine A did not cause skin or eye irritation and was highly effective at deodorizing skunk anal gland secretions when formulated to include adjunctive cosmetic ingredients.
- Evaluating the role of dithiolane rich fraction of Ferula asafoetida (apiaceae) for its antiproliferative and apoptotic properties: in vitro studies. [Journal Article]
- EOExp Oncol 2019; 41(2):90-94
- CONCLUSIONS: Further elucidation of bioactive molecules and underlying mechanisms could lead to potential intervention in liver cancer in animal models. The safety and efficacy as well as the mode of EO action in animal models would be highly crucial.
- Induction of apoptosis by piperine in human cervical adenocarcinoma via ROS mediated mitochondrial pathway and caspase-3 activation. [Journal Article]
- EJEXCLI J 2019; 18:154-164
- Piperine (1-piperoylpeperdine), a nitrogenous pungent substance, is present in the fruits of black pepper (Piper nigrum Linn.) and long pepper (Piper longum Linn.). It possesses several pharmacologic…
Piperine (1-piperoylpeperdine), a nitrogenous pungent substance, is present in the fruits of black pepper (Piper nigrum Linn.) and long pepper (Piper longum Linn.). It possesses several pharmacological properties and has been extensively explored for its anti-cancerous activities. The mechanism underlying its anti-cancer potential in human cervical adenocarcinoma (HeLa) cells is not well interpreted. The anti-proliferative effect and the mode of action of piperine were investigated through some potent markers of apoptosis viz.reactive oxygen species (ROS) generation, cellular apoptosis and loss of mitochondrial membrane potential (MMP). DNA fragmentation, cell cycle kinetics, caspase-3 activity and cell migration assays were also conducted to observe the efficacy of piperine against HeLa cells. The results showed that piperine exposure induces apoptosis significantly in a dose-dependent manner and inhibits the growth of HeLa cells with an increase in ROS generation, nuclear condensation and delayed wound healing. In addition, piperine also encourages cell death by the loss of MMP, DNA fragmentation and the activation of caspase-3. Growth inhibition of HeLa cells was found to be associated with G2/M phase arrest and sub-G1 accumulation. The present study provides useful insight into the apoptotic potential of piperine and further in vivo and clinical studies will be needed for its validation and in the finding of more effective and least toxic regimens against cervical cancer.
- TRPA1 Channel as a Regulator of Neurogenic Inflammation and Pain: Structure, Function, Role in Pathophysiology, and Therapeutic Potential of Ligands. [Review]
- BBiochemistry (Mosc) 2019; 84(2):101-118
- TRPA1 is a cation channel located on the plasma membrane of many types of human and animal cells, including skin sensory neurons and epithelial cells of the intestine, lungs, urinary bladder, etc. TR…
TRPA1 is a cation channel located on the plasma membrane of many types of human and animal cells, including skin sensory neurons and epithelial cells of the intestine, lungs, urinary bladder, etc. TRPA1 is the major chemosensor that also responds to thermal and mechanical stimuli. Substances that activate TRPA1, e.g., allyl isothiocyanates (pungent components of mustard, horseradish, and wasabi), cinnamaldehyde from cinnamon, organosulfur compounds from garlic and onion, tear gas, acrolein and crotonaldehyde from cigarette smoke, etc., cause burning, mechanical and thermal hypersensitivity, cough, eye irritation, sneezing, mucus secretion, and neurogenic inflammation. An increased activity of TRPA1 leads to the emergence of chronic pruritus and allergic dermatitis and is associated with episodic pain syndrome, a hereditary disease characterized by episodes of debilitating pain triggered by stress. TRPA1 is now considered as one of the targets for developing new anti-inflammatory and analgesic drugs. This review summarizes information on the structure, function, and physiological role of this channel, as well as describes known TRPA1 ligands and their significance as therapeutic agents in the treatment of inflammation-associated pain.
- A distinct structural mechanism underlies TRPV1 activation by piperine. [Journal Article]
- BBBiochem Biophys Res Commun 2019 Aug 20; 516(2):365-372
- Piperine, the principle pungent compound in black peppers, is known to activate the capsaicin receptor TRPV1 ion channel. How piperine interacts with the channel protein, however, remains unclear. He…
Piperine, the principle pungent compound in black peppers, is known to activate the capsaicin receptor TRPV1 ion channel. How piperine interacts with the channel protein, however, remains unclear. Here we show that piperine binds to the same ligand-binding pocket as capsaicin but in different poses. There was no detectable detrimental effect when T551 and E571, two major sites known to form hydrogen bond with capsaicin, were mutated to a hydrophobic amino acid. Computational structural modeling suggested that piperine makes interactions with multiple amino acids within the ligand binding pocket, including T671 on the pore-forming S6 segment. Mutations of this residue could substantially reduce or even eliminate piperine-induced activation, confirming that T671 is an important site. Our results suggest that the bound piperine may directly interact with the pore-forming S6 segment to induce channel opening. These findings help to explain why piperine is a weak agonist, and may guide future efforts to develop novel pharmaceutical reagents targeting TRPV1.
- Contaminants migrating from crossed-linked polyethylene pipes and their effect on drinking water odour. [Journal Article]
- WRWater Res 2019 Sep 15; 161:341-353
- The formation potential of contaminants diffusing from cross-linked polyethylene (PE-X) pipes and their impact on the odour of drinking water was determined. Three types of PE-X material, Pe-Xa, PE-X…
The formation potential of contaminants diffusing from cross-linked polyethylene (PE-X) pipes and their impact on the odour of drinking water was determined. Three types of PE-X material, Pe-Xa, PE-Xb and PE-Xc, were extensively assessed by performing migration tests following EN 1420 and EN 12873-1. Migration waters were analysed for their threshold odour number (TON). The same samples were investigated by two gas chromatography-mass spectrometry methods: screening and olfactometry. Most of the PE-X materials failed the German regulation of TON <2 for cold water and TON ≤4 for warm water. PE-Xb material caused the strongest odour and also released the highest amount of contaminants. Metilox, 7,9-di-tert-butyl-1-oxaspiro(4,5)deca-6,9-diene-2,8-dione, 3,5-di-tert-butyl-4-hydroxybenzaldehyde and 2,6-di-tert-butyl-p-benzoquinone (2,6-DtBQ) were the most often detected substances leaching from the tested plastic materials. However, no odour was perceived for most of these substances. Methyl tert-butyl ether (MtBE) and 2-tert-butylphenol are believed to contribute to the sensory problem in the migration water among other substances such as tert-amyl methyl ether, 2,2,2,5-tetramethyltetrahydrofuran, toluene or xylene. In total ten specific descriptions characterized the odour of the individual contaminants: ethereal, fresh, solvent, sweet, fruity, floral, unsavoury, pungent, aromatic and chemical.
- Structural Mechanism Underlying TRPV1 Activation by Pungent Compounds in Gingers. [Journal Article]
- BJBr J Pharmacol 2019 Jun 17
- CONCLUSIONS: Mechanistic insights on ginger compound-TRPV1 interactions should help guide pharmaceutic efforts to regulate nociception.
- Innovative technologies in virgin olive oil extraction process: influence on volatile compounds and organoleptic characteristics. [Journal Article]
- JSJ Sci Food Agric 2019 Jun 17
- CONCLUSIONS: The introduction of ultrasound, coupled with heat exchanger and microwave, seemed not to modify the behaviour of enzymes of the LOX pathway, and the obtained virgin olive oils showed volatiles and organoleptic characteristics not significantly different from those obtained by the traditional olive oil extraction process. These findings provided the first insights into the effect of the combination of innovative technologies in the olive oil extraction process on virgin olive oil volatiles and sensory characteristics. © 2019 Society of Chemical Industry.
- Non-Pungent n-3 Polyunsaturated Fatty Acid (PUFA)-Derived Capsaicin Analogues as Potential Functional Ingredients with Antioxidant and Carbohydrate-Hydrolysing Enzyme Inhibitory Activities. [Journal Article]
- AAntioxidants (Basel) 2019 Jun 05; 8(6)
- N-Eicosapentaenoyl vanillylamine (EPVA) and N-docosahexaenoyl vanillylamine (DHVA), derived from n-3 polyunsaturated eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), respectively, were stu…
N-Eicosapentaenoyl vanillylamine (EPVA) and N-docosahexaenoyl vanillylamine (DHVA), derived from n-3 polyunsaturated eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), respectively, were studied for their potential antioxidant and carbohydrate-hydrolysing enzyme inhibitory activities together with capsaicin and the corresponding n-3 polyunsaturated fatty acids (PUFAs). The antioxidant potential was evaluated by 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay, 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid (ABTS) assay, β-carotene bleaching test, and ferric reducing ability power (FRAP). In the ABTS assay the following trend of potency could be observed EPVA > DHVA ≥ capsaicin. In addition, except for the FRAP test, all samples showed a greater activity than the positive controls used as reference compounds in the antioxidant assays. Both EPVA and DHVA showed half maximal inhibitory concentration (IC50) values much lower than acarbose, which was used as the reference drug in the carbohydrate-hydrolysing enzyme inhibitory activity assays. It is interesting to note that structural changes in capsaicin derivatives had higher impacts on α-glucosidase than on α-amylase inhibition. Taken together, our data suggest that both EPVA and DHVA, which are not limited in compliance-related considerations with respect to capsaicin, due to absence of pungency, could be proposed as functional ingredients for the development of products for the management of type II diabetes and border-line hyperglycaemic patients.
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- Voltammetric and spectroscopic determination of polyphenols and antioxidants in ginger (Zingiber officinale Roscoe). [Journal Article]
- HHeliyon 2019; 5(5):e01717
- Ginger (Zingiber officinale) is widely consumed as an important spice or a common condiment in food and beverages. This study focuses on the determination of pungent and bioactive components in ginge…
Ginger (Zingiber officinale) is widely consumed as an important spice or a common condiment in food and beverages. This study focuses on the determination of pungent and bioactive components in ginger and their antioxidant activity using voltammetric and spectroscopic methods. Gas chromatography-mass spectroscopy analysis revealed that the major components of the pungent compounds were zingerone, shogaols, gingerols, paradols, wikstromol, and carinol. Using spectroscopic methods, the antioxidant capacity of ginger aqueous extract was found to be 16.0 μmol gallic acid equivalent (GAE) per gram of ginger extract, and the total phenolic and flavonoid content was estimated to be 7.8 mg GAE/g ginger extract and 15.4 mg Quercetin equivalent (QE) per gram of ginger extract, respectively. Electroanalytical quantification estimated the antioxidant capacity of the ginger infusion to be 23.5 μmol GAE/g ginger extract, which is slightly higher than that estimated using chemical assay. The results may provide useful information for the development of ginger processing and utilization as a flavoring agent, and for our understanding of ginger as a source of natural antioxidants.