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  1. Comparative Trap Catches of Male Bactrocera, Dacus, and Zeugodacus Fruit Flies (Diptera: Tephritidae) With Four Floral Phenylbutanoid Lures (Anisyl Acetone, Cue-Lure, Raspberry Ketone, and Zingerone) in Queensland, Australia
    Royer JE, Tan KH, Mayer DG
    Environ Entomol, 2020 08 20;49(4):815-822.
    PMID: 32514581 DOI: 10.1093/ee/nvaa056
    The male fruit fly attractants, cue-lure (CL) and raspberry ketone (RK), are important in pest management. These volatile phenylbutanoids occur in daciniphilous Bulbophyllum Thouar (Orchidaceae: Asparagales) orchids, along with zingerone (ZN) and anisyl acetone (AA). While these four compounds attract a similar range of species, their relative attractiveness to multiple species is unknown. We field tested these compounds in two fruit fly speciose locations in north Queensland, Australia (Lockhart and Cairns) for 8 wk. Of 16 species trapped in significant numbers, 14 were trapped with CL and RK, all in significantly greater numbers with CL traps than RK traps (at least in higher population locations). This included the pest species Bactrocera tryoni (Froggatt) (Diptera: Tephritidae) (CL catches ca. 5× > RK), Bactrocera neohumeralis (Hardy) (Diptera: Tephritidae) and Bactrocera bryoniae (Tryon) (Diptera: Tephritidae) (CL catches ca. 3× > RK), and Bactrocera frauenfeldi (Schiner) (Diptera: Tephritidae) (in Cairns-CL catches ca. 1.6× > RK). Seven species were trapped with AA, and all were also caught in CL and RK traps in significantly greater numbers, with the exception of B. frauenfeldi. For this species, catches were not statistically different with CL, RK, and AA in Lockhart, and RK and AA in Cairns. Seven species were trapped with ZN, two at this lure only, and the remainder also with CL or RK but in significantly greater numbers. This is the first quantitative comparison of the relative attractiveness of CL, RK, AA, and ZN against multiple species, and supports the long-held but untested assumption that CL is broadly more attractive lure than RK.
    Matched MeSH terms: Guaiacol/analogs & derivatives
  2. Fulltext Male-lure type, lure dosage, and fly age at feeding all influence male mating success in Jarvis' fruit fly
    Wee SL, Clarke AR
    Sci Rep, 2020 09 14;10(1):15004.
    PMID: 32929156 DOI: 10.1038/s41598-020-72209-x
    Males of certain Dacini fruit flies are strongly attracted to, and feed upon, plant secondary compounds such as methyl eugenol, raspberry ketone and zingerone. The consumed lure is generally found to induce physiological and behavioural changes that enhance the mating performance of lure-fed males. Male Bactrocera jarvisi respond strongly to zingerone from a young age, but only weakly respond to raspberry ketone. We hypothesized that this selective lure-response would be reflected in the physiological importance of the lure to the fly. We found that zingerone feeding by young males resulted in significantly greater mating success in competitive mating trials with lure-deprived flies, but the mating advantage was lost in older males. Lure dosage had a significant effect on the duration of the mating advantage, for example when fed 20 µg of zingerone, the advantage lasted only 1 day post-feeding, but when fed of 50 µg zingerone the advantage lasted 7 days. Raspberry ketone feeding did not confer any mating advantage to males except at one dosage (50 µg) for 1 day after feeding. When given a choice, B. jarvisi females preferred to mate with zingerone-fed versus to raspberry ketone-fed males. This study revealed lure, dosage and age of fly at time of lure administration are all important factors for maximising lure-enhanced fruit fly mating performance. These findings contribute to a better theoretical understanding of the evolution of fruit fly-lure interactions and may help improve fruit fly pest management via the Sterile Insect Technique through semiochemical-mediated enhancement of sterile male mating performance.
    Matched MeSH terms: Guaiacol/administration & dosage; Guaiacol/analogs & derivatives; Guaiacol/pharmacology
  3. Diaminobenzene schiff base, a novel class of DNA minor groove binder
    Helal MH, Al-Mudaris ZA, Al-Douh MH, Osman H, Wahab HA, Alnajjar BO, et al.
    Int J Oncol, 2012 Aug;41(2):504-10.
    PMID: 22614449 DOI: 10.3892/ijo.2012.1491
    Molecules that target the deoxyribonucleic acid (DNA) minor groove are relatively sequence specific and they can be excellent carrier structures for cytotoxic chemotherapeutic compounds which can help to minimize side effects. Two novel isomeric derivatives of diaminobenzene Schiff base [N,N'-bis (2-hydroxy-3-methoxybenzylidene)-1,2-diaminobenzene (2MJ) and N,N'-bis(2-hydroxy-3-methoxybenzylidene)-1,3-diaminobenzene (2MH)] were analyzed for their DNA minor groove binding (MGB) ability using viscometry, UV and fluorescence spectroscopy, computational modeling and clonogenic assay. The result shows that 2MJ and 2MH are strong DNA MGBs with the latter being more potent. 2MH can form interstrand hydrogen bond linkages at its oxygens with N3 of adenines. Changing the 2-hydroxy-3-methoxybenzylidene binding position to the 1,3 location on the diaminobenzene structure (2MJ) completely removed any viable hydrogen bond formation with the DNA and caused significant decrease in binding strength and minor groove binding potency. Neither compound showed any significant cytotoxicity towards human breast, colon or liver cancer cell lines.
    Matched MeSH terms: Guaiacol/analogs & derivatives*; Guaiacol/pharmacology; Guaiacol/chemistry
  4. Zingerone improves mating performance of Zeugodacus tau (Diptera: Tephritidae) through enhancement of male courtship activity and sexual signaling
    Shamshir RA, Wee SL
    J Insect Physiol, 2019 09 26;119:103949.
    PMID: 31563620 DOI: 10.1016/j.jinsphys.2019.103949
    Certain male fruit flies from the genera Bactrocera and Zeugodacus (Diptera: Tephritidae) actively forage for floral semiochemicals produced by some endemic Bulbophyllum orchids found in tropical and subtropical forests. These floral semiochemicals are largely classified as either phenylbutanoids (e.g., raspberry ketone (RK)) or phenylpropanoids (e.g., methyl eugenol (ME)). Zingerone (ZN) is a phenylbutanoid recently found that structurally resembles ME and RK, both of which are phytochemicals commonly used as male attractants in fruit fly control programmes. It was previously shown that feeding on ME and RK increased the mating success of certain tephritid fruit flies, specifically in B. dorsalis and B. tryoni males, respectively, through enhancement of sexual signaling. However, ZN, which acts as a metabolic enhancer to increase male courtship activity in B. tryoni, did not show the same effect. As fruit fly-phytochemical lure interactions are unique and species-specific phenomena, this study seeks to elucidate the ecological significance of ZN feeding to Zeugodacus tau in terms of sexual signaling. We demonstrate here that ZN feeding by Z. tau males enhanced female attraction and subsequent mating success by increasing male courtship, and the attractiveness of the sexual signals in both wind tunnel and semi-field cage bioassays. In addition, we also demonstrated temporal effects on male behaviour in relation to the amount of lure intake. However, feeding on ZN did not appear to affect the total time spent in copula for Z. tau. This is the first report showing an important role of ZN in increasing courtship activity as well as enhancement of sexual signaling in Z. tau males.
    Matched MeSH terms: Guaiacol/analogs & derivatives*; Guaiacol/pharmacology
  5. An Optical Biosensor based on Immobilization of Laccase and MBTH in Stacked Films for the Detection of Catechol
    Abdullah J, Ahmad M, Heng LY, Karuppiah N, Sidek H
    Sensors (Basel), 2007 Oct 11;7(10):2238-2250.
    PMID: 28903224 DOI: 10.3390/s7102238
    The fabrication of an optical biosensor by using stacked films where 3-methyl-2-benzothiazolinone hydrazone (MBTH) was immobilized in a hybrid nafion/sol-gelsilicate film and laccase in a chitosan film for the detection of phenolic compounds wasdescribed. Quinone and/or phenoxy radical product from the enzymatic oxidation ofphenolic compounds was allowed to couple with MBTH to form a colored azo-dye productfor spectrophometric detection. The biosensor demonstrated a linear response to catecholconcentration range of 0.5-8.0 mM with detection limit of 0.33 mM and response time of10 min. The reproducibility of the fabricated biosensor was good with RSD value of 5.3 %(n = 8) and stable for at least 2 months. The use of the hybrid materials of nafion/sol-gelsilicate to immobilize laccase has altered the selectivity of the enzyme to various phenoliccompounds such as catechol, guaicol, o-cresol and m-cresol when compared to the non-immobilized enzyme. When immobilized in this hybrid film, the biosensor response onlyto catechol and not other phenolic compounds investigated. Immobilization in this hybridmaterial has enable the biosensor to be more selective to catechol compared with the non-immobilized enzyme. This shows that by a careful selection of different immobilizationmatrices, the selectivity of an enzyme can be modified to yield a biosensor with goodselectivity towards certain targeted analytes.
    Matched MeSH terms: Guaiacol
  6. Quantitation of Protein Cysteine-Phenol Adducts in Minced Beef Containing 4-Methyl Catechol
    Arsad SS, Zainudin MAM, De Gobba C, Jongberg S, Larsen FH, Lametsch R, et al.
    J Agric Food Chem, 2020 Feb 26;68(8):2506-2515.
    PMID: 32013414 DOI: 10.1021/acs.jafc.9b07752
    Thiol groups of cysteine (Cys) residues in proteins react with quinones, oxidation products of polyphenols, to form protein-polyphenol adducts. The aim of the present work was to quantify the amount of adduct formed between Cys residues and 4-methylcatechol (4MC) in minced beef. A Cys-4MC adduct standard was electrochemically synthesized and characterized by liquid chromatography-mass spectrometry (LC-MS) as well as NMR spectroscopy. Cys-4MC adducts were quantified after acidic hydrolysis of myofibrillar protein isolates (MPIs) and LC-MS/MS analysis of meat containing either 500 or 1500 ppm 4MC and stored at 4 °C for 7 days under a nitrogen or oxygen atmosphere. The concentrations of Cys-4MC were found to be 2.2 ± 0.3 nmol/mg MPI and 8.1 ± 0.9 nmol/mg MPI in meat containing 500 and 1500 ppm 4MC, respectively, and stored for 7 days under oxygen. The formation of the Cys-4MC adduct resulted in protein thiol loss, and ca. 62% of the thiol loss was estimated to account for the formation of the Cys-4MC adduct for meat containing 1500 ppm 4MC. Furthermore, protein polymerization increased in samples containing 4MC as evaluated by sodium dodecyl sulfate-polyacrylamide gel electrophoresis (SDS-PAGE), and the polymerization was found to originate from protein-polyphenol interactions as evaluated by a blotting assay with staining by nitroblue tetrazolium.
    Matched MeSH terms: Guaiacol/chemistry*
  7. Fulltext A Review on Pharmacological Properties of Zingerone (4-(4-Hydroxy-3-methoxyphenyl)-2-butanone)
    Ahmad B, Rehman MU, Amin I, Arif A, Rasool S, Bhat SA, et al.
    ScientificWorldJournal, 2015;2015:816364.
    PMID: 26106644 DOI: 10.1155/2015/816364
    Humans have been using natural products for medicinal use for ages. Natural products of therapeutic importance are compounds derived from plants, animals, or any microorganism. Ginger is also one of the most commonly used condiments and a natural drug in vogue. It is a traditional medicine, having some active ingredients used for the treatment of numerous diseases. During recent research on ginger, various ingredients like zingerone, shogaol, and paradol have been obtained from it. Zingerone (4-(4-hydroxy-3-methoxyphenyl)-2-butanone) is a nontoxic and inexpensive compound with varied pharmacological activities. It is the least pungent component of Zingiber officinale. Zingerone is absent in fresh ginger but cooking or heating transforms gingerol to zingerone. Zingerone closely related to vanillin from vanilla and eugenol from clove. Zingerone has potent anti-inflammatory, antidiabetic, antilipolytic, antidiarrhoeic, antispasmodic, and so forth properties. Besides, it displays the property of enhancing growth and immune stimulation. It behaves as appetite stimulant, anxiolytic, antithrombotic, radiation protective, and antimicrobial. Also, it inhibits the reactive nitrogen species which are important in causing Alzheimer's disease and many other disorders. This review is written to shed light on the various pharmacological properties of zingerone and its role in alleviating numerous human and animal diseases.
    Matched MeSH terms: Guaiacol/analogs & derivatives*; Guaiacol/pharmacology; Guaiacol/therapeutic use; Guaiacol/chemistry
  8. Fulltext Classification of different pineapple varieties grown in Malaysia based on volatile fingerprinting and sensory analysis
    Lasekan O, Hussein FK
    Chem Cent J, 2018 Dec 19;12(1):140.
    PMID: 30569201 DOI: 10.1186/s13065-018-0505-3
    BACKGROUND: Pineapple is highly relished for its attractive sweet flavour and it is widely consumed in both fresh and canned forms. Pineapple flavour is a blend of a number of volatile and non-volatile compounds that are present in small amounts and in complex mixtures. The aroma compounds composition may be used for purposes of quality control as well as for authentication and classification of pineapple varieties.

    RESULTS: The key volatile compounds and aroma profile of six pineapple varieties grown in Malaysia were investigated by gas chromatography-olfactometry (GC-O), gas-chromatography-mass spectrometry and qualitative descriptive sensory analysis. A total of 59 compounds were determined by GC-O and aroma extract dilution analysis. Among these compounds, methyl-2-methylbutanoate, methyl hexanoate, methyl-3-(methylthiol)-propanoate, methyl octanoate, 2,5-dimethyl-4-methoxy-3(2H)-furanone, δ-octalactone, 2-methoxy-4-vinyl phenol, and δ-undecalactone contributed greatly to the aroma quality of the pineapple varieties, due to their high flavour dilution factor. The aroma of the pineapples was described by seven sensory terms as sweet, floral, fruity, fresh, green, woody and apple-like.

    CONCLUSION: Inter-relationship between the aroma-active compounds and the pineapples revealed that 'Moris' and 'MD2' covaried majorly with the fruity esters, and the other varieties correlated with lesser numbers of the fruity esters. Hierarchical cluster analysis (HCA) was used to establish similarities among the pineapples and the results revealed three main groups of pineapples.

    Matched MeSH terms: Guaiacol
  9. Fulltext Formation of 6-, 8- and 10-Shogaol in Ginger through Application of Different Drying Methods: Altered Antioxidant and Antimicrobial Activity
    Ghasemzadeh A, Jaafar HZE, Baghdadi A, Tayebi-Meigooni A
    Molecules, 2018 07 05;23(7).
    PMID: 29976903 DOI: 10.3390/molecules23071646
    Gingerols and shogaols are compounds found in ginger (Zingiber officinale Roscoe); shogaols are found in lower concentration than gingerols but exhibit higher biological activities. This work studied the effects of different drying methods including open sun drying (OSD) solar tunnel drying (STD) and hot air drying (HAD) with various temperature on the formation of six main active compounds in ginger rhizomes, namely 6-, 8-, and 10-gingerols and 6-, 8-, and 10-shogaols, as well as essential oil content. Antioxidant and antimicrobial activity of dried ginger was also evaluated. High performance liquid chromatography (HPLC) analysis showed that after HAD with variable temperature (120, 150 and 180 °C), contents of 6-, 8-, and 10-gingerols decreased, while contents of 6-, 8-, and 10-shogaol increased. High formation of 6-, 8-, and 10-shogaol contents were observed in HAD (at 150 °C for 6 h) followed by STD and OSD, respectively. OSD exhibited high content of essential oil followed by STD and HAD method. Ginger-treated with HAD exhibited the highest DPPH (IC50 of 57.8 mg/g DW) and FRAP (493.8 µM of Fe(II)/g DM) activity, compared to STD and OSD method. HAD ginger exhibited potent antimicrobial activity with lower minimum inhibition concentration (MIC) value against bacteria strains followed by STD and OSD, respectively. Ginger extracts showed more potent antimicrobial activity against Gram positive bacteria than Gram negative bacteria strains. Result of this study confirmed that conversion of gingerols to shogaols was significantly affected by different drying temperature and time. HAD at 150 °C for 6 h, provides a method for enhancing shogaols content in ginger rhizomes with improving antioxidant and antimicrobial activities.
    Matched MeSH terms: Guaiacol/analogs & derivatives; Guaiacol/analysis; Guaiacol/pharmacology
  10. Pyroligneous acid-the smoky acidic liquid from plant biomass
    Mathew S, Zakaria ZA
    Appl Microbiol Biotechnol, 2015 Jan;99(2):611-22.
    PMID: 25467926 DOI: 10.1007/s00253-014-6242-1
    Pyroligneous acid (PA) is a complex highly oxygenated aqueous liquid fraction obtained by the condensation of pyrolysis vapors, which result from the thermochemical breakdown or pyrolysis of plant biomass components such as cellulose, hemicellulose, and lignin. PA produced by the slow pyrolysis of plant biomass is a yellowish brown or dark brown liquid with acidic pH and usually comprises a complex mixture of guaiacols, catechols, syringols, phenols, vanillins, furans, pyrans, carboxaldehydes, hydroxyketones, sugars, alkyl aryl ethers, nitrogenated derivatives, alcohols, acetic acid, and other carboxylic acids. The phenolic components, namely guaiacol, alkyl guaiacols, syringol, and alkyl syringols, contribute to the smoky odor of PA. PA finds application in diverse areas, as antioxidant, antimicrobial, antiinflammatory, plant growth stimulator, coagulant for natural rubber, and termiticidal and pesticidal agent; is a source for valuable chemicals; and imparts a smoky flavor for food.
    Matched MeSH terms: Guaiacol/chemistry
  11. Stacked films immobilization of MBTH in nafion/sol-gel silicate and horseradish peroxidase in chitosan for the determination of phenolic compounds
    Abdullah J, Ahmad M, Heng LY, Karuppiah N, Sidek H
    Anal Bioanal Chem, 2006 Nov;386(5):1285-92.
    PMID: 17031625
    The stacked-film immobilization of 3-methyl-2-benzothiazolinone hydrazone (MBTH) in hybrid nafion/sol-gel silicate film and horseradish peroxidase (HRP) in chitosan, performed in order to allow the determination of phenolic compounds, was investigated via an optical method. The stacked films were deposited onto a microscope glass slide by a spin-coating technique. The quinone or free radical product formed by the enzymatic reactions of phenolic compounds interacts with MBTH to form azo-dye products, which can be measured spectrophotometrically at a wavelength of 500 nm. The color intensity of the product was found to increase in proportion to the phenolic concentration after 5 min of exposure. The response of the biosensor was linear over concentration ranges of 0.025-0.500, 0.010-0.070 and 0.050-0.300 mM for guaiacol, resorcinol and o-cresol, respectively, and gave detection limits of 0.010, 0.005 and 0.012 mM. The sensor exhibited good sensitivity and stability for at least two months.
    Matched MeSH terms: Guaiacol/analysis
  12. Zingerone (4-(4-hydroxy-3-methylphenyl)butan-2-one) ameliorates renal function via controlling oxidative burst and inflammation in experimental diabetic nephropathy
    Rehman MU, Rashid SM, Rasool S, Shakeel S, Ahmad B, Ahmad SB, et al.
    Arch Physiol Biochem, 2019 Jul;125(3):201-209.
    PMID: 29537332 DOI: 10.1080/13813455.2018.1448422
    Development of diabetic nephropathy (DN) is directly linked to oxidative stress and inflammation. In this context, inflammatory and oxidative markers have gained much attention as targets for therapeutic intervention. We studied the effect of zingerone in a streptozotocin/high fat diet (STZ/HFD)-induced type 2 diabetic Wistar rat model. Zingerone also known as vanillyl acetone is a pharmacologically active compound present usually in dry ginger. STZ/HFD caused excessive increase in ROS and inflammation in experimental animals. The treatment with zingerone markedly abrogated ROS levels, inhibited the NF-кB activation and considerably reduced level of other downstream inflammatory molecules (TNF-α, IL-6, IL-1β), furthermore, zingerone treatment improved renal functioning by significantly decreasing the levels of kidney toxicity markers KIM-1, BUN, creatinine, and LDH and suppressed TGF-β. Collectively, these findings indicate that zingerone treatment improved renal function by anti-hyperglycaemic, anti-oxidant, and anti-inflammatory effects, suggesting the efficacy of zingerone in the treatment of DN.
    Matched MeSH terms: Guaiacol
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