ACS Publications. Most Trusted. Most Cited. Most Read

OR SEARCH CITATIONS

My Activity
Publications
CONTENT TYPES

Figure 1Loading Img
Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Agric. Food Chem. 2007, 55, 21, 8390-8397
RETURN TO ISSUEPREVArticleNEXT

Ginger and Its Bioactive Component Inhibit Enterotoxigenic Escherichia coli Heat-Labile Enterotoxin-Induced Diarrhea in Mice

View Author Information
Graduate Institute of Chinese Pharmaceutical Sciences, Graduate Institute of Pharmaceutical Chemistry, Department of Biochemistry, Graduate Institute of Chinese Medical Science, Department of Microbiology, China Medical University, Taichung 40402, Taiwan
* To whom correspondence should be addressed. Tel.: +886 4 22053366 ext. 2163 (C.-Y.H.); +886 4 22053366 ext. 3302 (T.-Y.H.). Fax: +886 4 22053764 (C.-Y.H.); +886 4 22032295 (T.-Y.H.). E-mail: [email protected] (C.-Y.H.); [email protected] (T.-Y.H.).
†Graduate Institute of Chinese Pharmaceutical Sciences.
‡Graduate Institute of Pharmaceutical Chemistry.
§Department of Biochemistry.
∥Graduate Institute of Chinese Medical Science.
⊥Department of Microbiology.
Cite this: J. Agric. Food Chem. 2007, 55, 21, 8390–8397
Publication Date (Web):September 20, 2007
https://doi.org/10.1021/jf071460f
Copyright © 2007 American Chemical Society
Request reuse permissions

    Article Views

    4653

    Altmetric

    -

    Citations

    55
    LEARN ABOUT THESE METRICS
    Read OnlinePDF (1 MB)
    Get e-Alerts
    Supporting Info (1)»
    SUBJECTS:

    Abstract

    Ginger is one of the most commonly used fresh herbs and spices. Enterotoxigenic Escherichia coli heat-labile enterotoxin (LT)-induced diarrhea is the leading cause of infant death in developing countries. In this study, we demonstrated that ginger significantly blocked the binding of LT to cell-surface receptor GM1, resulting in the inhibition of fluid accumulation in the closed ileal loops of mice. Biological-activity-guided searching for active components showed that zingerone (vanillylacetone) was the likely active constituent responsible for the antidiarrheal efficacy of ginger. Further analysis of chemically synthesized zingerone derivatives revealed that compound 31 (2-[(4-methoxybenzyl)oxy]benzoic acid) significantly suppressed LT-induced diarrhea in mice via an excellent surface complementarity with the B subunits of LT. In conclusion, our findings provide evidence that ginger and its derivatives may be effective herbal supplements for the clinical treatment of enterotoxigenic Escherichia coli diarrhea.

    KEYWORDS:

    Supporting Information

    ARTICLE SECTIONS
    Jump To

    Solid-phase synthesis of 1-phenyl-3,5-dodecenediones and 3-phenyl-acrylaldehydes, the superimposition of cocrystal and docking structures of MNPG around the receptor-binding domain of LTB, X-Score results of MNPG and compound 31, and spectral characteristics of benzyloxybenzene compounds. This material is available free of charge via the Internet at http://pubs.acs.org.

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    This article is cited by 55 publications.

    1. Derek A. Jackson and Andrew P. Dicks . The Five Senses of Christmas Chemistry. Journal of Chemical Education 2012, 89 (10) , 1267-1273. https://doi.org/10.1021/ed300231z
    2. Mona N. BinMowyna. Zingerone attenuates intestinal injury and colitis caused by a high-fat diet through Nrf2 signaling regulation. Saudi Journal of Biological Sciences 2023, 30 (10) , 103775. https://doi.org/10.1016/j.sjbs.2023.103775
    3. Shahnam Shamsabadi, Yazdan Nazer, Javad Ghasemi, Erfan Mahzoon, Vafa Baradaran Rahimi, Basiru O. Ajiboye, Vahid Reza Askari. Promising influences of zingerone against natural and chemical toxins: A comprehensive and mechanistic review. Toxicon 2023, 233 , 107247. https://doi.org/10.1016/j.toxicon.2023.107247
    4. Fatimah I. Qassadi, Zheying Zhu, Tanya M. Monaghan. Plant-Derived Products with Therapeutic Potential against Gastrointestinal Bacteria. Pathogens 2023, 12 (2) , 333. https://doi.org/10.3390/pathogens12020333
    5. Mehdi Goudarzi, Zahra Basir, Alireza Malayeri, Ali Nesari, Narjes Zaeemzadeh. Zingerone Attenuates Methotrexate-Induced Hepatotoxicity in Rats. Jundishapur Journal of Natural Pharmaceutical Products 2021, 17 (3) https://doi.org/10.5812/jjnpp.118745
    6. M. Zakir Hosen, Anirban Biswas, M. Rabiul Islam, Sheikh Julfikar Hossain. Anti-Bacterial, Anti-Diarrheal, and Cytotoxic Activities of Edible Fruits in the Sundarbans Mangrove Forest of Bangladesh. Preventive Nutrition and Food Science 2021, 26 (2) , 192-199. https://doi.org/10.3746/pnf.2021.26.2.192
    7. Hegde Veena, Sandesh K. Gowda, Rajeshwara N. Achur, Nayaka Boramuthi Thippeswamy. Molecular mechanism of Escherichia coli H10407 induced diarrhoea and its control through immunomodulatory action of bioactives from Simarouba amara (Aubl.). Journal of Microbiology 2021, 59 (4) , 435-447. https://doi.org/10.1007/s12275-021-0423-2
    8. T. Kaewkod, R. Tobe, Y. Tragoolpua, H. Mihara. Medicinal plant extracts protect epithelial cells from infection and DNA damage caused by colibactin‐producing Escherichia coli , and inhibit the growth of bacteria. Journal of Applied Microbiology 2021, 130 (3) , 769-785. https://doi.org/10.1111/jam.14817
    9. Mohamad Kazem Momeni, , Omid Bameri, , Mehrangiz Ghafari, , Sima Saravani, , Fereshteh Javadian, . Evaluation of Antifungal Activity of Medicinal Plant Extracts on Candida albicans. Journal of Obstetrics, Gynecology and Cancer Research 2021, 6 (2) , 50-56. https://doi.org/10.30699/jogcr.6.2.50
    10. Young-Ju Lim, Hyeon-Young Min, Won-Gu Jang. Zingerone Attenuates Pi-induced Vascular Calcification via AMPK-mediated TIMP4 Expression. Journal of Lipid and Atherosclerosis 2021, 10 (1) , 62. https://doi.org/10.12997/jla.2021.10.1.62
    11. P. A. Chistyakova, A. V. Chistyakov, M. V. Tsodikov. Heterogeneous Catalytic Synthesis of Zingerone and Dehydrozingerone. Petroleum Chemistry 2020, 60 (9) , 1080-1086. https://doi.org/10.1134/S0965544120090066
    12. Denise Cavuoto, Federica Zaccheria, Marcello Marelli, Claudio Evangelisti, Oreste Piccolo, Nicoletta Ravasio. The Role of Support Hydrophobicity in the Selective Hydrogenation of Enones and Unsaturated Sulfones over Cu/SiO2 Catalysts. Catalysts 2020, 10 (5) , 515. https://doi.org/10.3390/catal10050515
    13. Han-Bi Kim, Sang-Chul Kwon, Xiao Sun, Mahbuba Akther, Jun-Hyuk Han, Tae-Yeon Kim, Tae-Bong Kang, Kwang-Ho Lee. Vanillylacetone attenuates NLRP3 inflammasome mediated immune responses in murine bone marrow derived macrophages via NLRP3 alkylation. Journal of Functional Foods 2020, 64 , 103655. https://doi.org/10.1016/j.jff.2019.103655
    14. T. M. Agbede. Influence of Five Years of Tillage and Poultry Manure Application on Soil Properties and Ginger (Ziginber officinale Roscoe) Productivity. Journal of Crop Science and Biotechnology 2019, 22 (2) , 91-99. https://doi.org/10.1007/s12892-018-0155-0
    15. Vishvanath Tiwari. Molecular insight into the therapeutic potential of phytoconstituents targeting protein conformation and their expression. Phytomedicine 2019, 52 , 225-237. https://doi.org/10.1016/j.phymed.2018.09.214
    16. Niloufar Roshan, Thomas V. Riley, Daniel R. Knight, Katherine A. Hammer. Effect of natural products on the production and activity of Clostridium difficile toxins in vitro. Scientific Reports 2018, 8 (1) https://doi.org/10.1038/s41598-018-33954-2
    17. Jakob Cervin, Amberlyn M. Wands, Anna Casselbrant, Han Wu, Soumya Krishnamurthy, Aleksander Cvjetkovic, Johanna Estelius, Benjamin Dedic, Anirudh Sethi, Kerri-Lee Wallom, Rebecca Riise, Malin Bäckström, Ville Wallenius, Frances M. Platt, Michael Lebens, Susann Teneberg, Lars Fändriks, Jennifer J. Kohler, Ulf Yrlid, . GM1 ganglioside-independent intoxication by Cholera toxin. PLOS Pathogens 2018, 14 (2) , e1006862. https://doi.org/10.1371/journal.ppat.1006862
    18. Niloufar Roshan, Katherine A. Hammer, Thomas V. Riley. Non-conventional antimicrobial and alternative therapies for the treatment of Clostridium difficile infection. Anaerobe 2018, 49 , 103-111. https://doi.org/10.1016/j.anaerobe.2018.01.003
    19. Usana Chatturong, Tanwarat Kajsongkram, Sakara Tunsophon, Rachanee Chanasong, Krongkarn Chootip. Ginger Extract and [6]-Gingerol Inhibit Contraction of Rat Entire Small Intestine. Journal of Evidence-Based Integrative Medicine 2018, 23 , 2515690X1877427. https://doi.org/10.1177/2515690X18774273
    20. Vijay Mani, Sivaranjani Arivalagan, Aktarul Islam Siddique, Nalini Namasivayam. Antihyperlipidemic and antiapoptotic potential of zingerone on alcohol induced hepatotoxicity in experimental rats. Chemico-Biological Interactions 2017, 272 , 197-206. https://doi.org/10.1016/j.cbi.2017.04.019
    21. Victor Antony Santiago Jesudoss, Sundari Victor Antony Santiago, Karthikkumar Venkatachalam, Partiban Subramanian. Zingerone (Ginger Extract). 2017, 289-297. https://doi.org/10.1016/B978-0-12-805377-5.00021-7
    22. Woom-Yee Bae, Jae-Sun Choi, Ja-Eun Kim, Chan Park, Joo-Won Jeong. Zingerone suppresses angiogenesis via inhibition of matrix metalloproteinases during tumor development. Oncotarget 2016, 7 (30) , 47232-47241. https://doi.org/10.18632/oncotarget.10030
    23. Abhinav Upadhyay, Shankumar Mooyottu, Hsinbai Yin, Meera Nair, Varunkumar Bhattaram, Kumar Venkitanarayanan. Inhibiting Microbial Toxins Using Plant-Derived Compounds and Plant Extracts. Medicines 2015, 2 (3) , 186-211. https://doi.org/10.3390/medicines2030186
    24. Kamaljeet Kaur, Arpit Saxena, Raghavendra Haniadka, Elroy Saldanha, Prajnya D’Silva, Venkatesh Ponemone, Raja Fayad, Manjeshwar Shrinath Baliga. Medicinal Benefits of Ginger in Various Gastrointestinal Ailments. 2015, 51-61. https://doi.org/10.1016/B978-0-12-418680-4.00006-3
    25. Bilal Ahmad, Muneeb U. Rehman, Insha Amin, Ahmad Arif, Saiema Rasool, Showkat Ahmad Bhat, Insha Afzal, Ishraq Hussain, Sheikh Bilal, Manzoor ur Rahman Mir. A Review on Pharmacological Properties of Zingerone (4-(4-Hydroxy-3-methoxyphenyl)-2-butanone). The Scientific World Journal 2015, 2015 , 1-6. https://doi.org/10.1155/2015/816364
    26. Zheng-Xu Cai. Effect of gingerol on colonic motility via inhibition of calcium channel currents in rats. World Journal of Gastroenterology 2015, 21 (48) , 13466. https://doi.org/10.3748/wjg.v21.i48.13466
    27. Faoziyat A. Sulaiman, Muinat O. Kazeem, Ahmed M. Waheed, Simisade O. Temowo, Idris O. Azeez, Faridat I. Zubair, Temitope A. Adeyemi, Azido Nyang, Oluyomi S. Adeyemi. Antimicrobial and toxic potential of aqueous extracts of Allium sativum , Hibiscus sabdariffa and Zingiber officinale in Wistar rats. Journal of Taibah University for Science 2014, 8 (4) , 315-322. https://doi.org/10.1016/j.jtusci.2014.05.004
    28. Katie Walsh, Helen F. Sneddon, Christopher J. Moody. Sustainable, mild and efficient p-methoxybenzyl ether deprotections utilizing catalytic DDQ. Tetrahedron 2014, 70 (40) , 7380-7387. https://doi.org/10.1016/j.tet.2014.07.003
    29. Udoamaka F. Ezuruike, Jose M. Prieto. The use of plants in the traditional management of diabetes in Nigeria: Pharmacological and toxicological considerations. Journal of Ethnopharmacology 2014, 155 (2) , 857-924. https://doi.org/10.1016/j.jep.2014.05.055
    30. Ajit Kumar Prasad, P. C. Mishra. Study of scavenging action of zingerone towards the OH radical: formation of vanillin and ferulic acid. Journal of Physical Organic Chemistry 2014, 27 (1) , 18-26. https://doi.org/10.1002/poc.3200
    31. J. Dubreuil. Antibacterial and Antidiarrheal Activities of Plant Products against Enterotoxinogenic Escherichia coli. Toxins 2013, 5 (11) , 2009-2041. https://doi.org/10.3390/toxins5112009
    32. Mahmoud Bahmani, Hannaneh Golshahi, Ava Mohsenzadegan, Majid Ghollami Ahangarani, Elmira Ghasemi. Comparative assessment of the anti-Limnatis nilotica activities of Zingiber officinale methanolic extract with levamisole. Comparative Clinical Pathology 2013, 22 (4) , 667-670. https://doi.org/10.1007/s00580-012-1463-0
    33. Claudia Sanfilippo, Angela Patti, Maria Antonietta Dettori, Davide Fabbri, Giovanna Delogu. Lipase behavior in the stereoselective transesterification of zingerol-like derivatives and related biphenyls. Journal of Molecular Catalysis B: Enzymatic 2013, 90 , 107-113. https://doi.org/10.1016/j.molcatb.2013.01.007
    34. Mohammad Fahim Kadir, Muhammad Shahdaat Bin Sayeed, M.M.K. Mia. Ethnopharmacological survey of medicinal plants used by traditional healers in Bangladesh for gastrointestinal disorders. Journal of Ethnopharmacology 2013, 147 (1) , 148-156. https://doi.org/10.1016/j.jep.2013.02.023
    35. Helle Wangensteen, Line Klarpås, Mahiuddin Alamgir, Anne Samuelsen, Karl Malterud. Can Scientific Evidence Support Using Bangladeshi Traditional Medicinal Plants in the Treatment of Diarrhoea? A Review on Seven Plants. Nutrients 2013, 5 (5) , 1757-1800. https://doi.org/10.3390/nu5051757
    36. Fulton P. Rivera, Anicia M. Medina, Sandra Bezada, Roberto Valencia, María Bernal, Rina Meza, Ryan C. Maves, Theresa J. Ochoa, . Bovine Lactoferrin Decreases Cholera-Toxin-Induced Intestinal Fluid Accumulation in Mice by Ganglioside Interaction. PLoS ONE 2013, 8 (4) , e59253. https://doi.org/10.1371/journal.pone.0059253
    37. Elizabeth A. Townsend, Matthew E. Siviski, Yi Zhang, Carrie Xu, Bhupinder Hoonjan, Charles W. Emala. Effects of Ginger and Its Constituents on Airway Smooth Muscle Relaxation and Calcium Regulation. American Journal of Respiratory Cell and Molecular Biology 2013, 48 (2) , 157-163. https://doi.org/10.1165/rcmb.2012-0231OC
    38. M.S. Baliga, A.R. Shivashankara, R. Haniadka, P.L. Palatty, R. Arora, R. Fayad. Ginger (Zingiber officinale Roscoe). 2013, 187-199. https://doi.org/10.1016/B978-0-12-397154-8.00189-5
    39. Chien-Yun Hsiang, Hsin-Yi Lo, Hui-Chi Huang, Chia-Cheng Li, Shih-Lu Wu, Tin-Yun Ho. Ginger extract and zingerone ameliorated trinitrobenzene sulphonic acid-induced colitis in mice via modulation of nuclear factor-κB activity and interleukin-1β signalling pathway. Food Chemistry 2013, 136 (1) , 170-177. https://doi.org/10.1016/j.foodchem.2012.07.124
    40. Jiaojiao Zheng, Yicun Chen, Fen Yao, Weizhou Chen, Ganggang Shi. Chemical Composition and Antioxidant/Antimicrobial Activities in Supercritical Carbon Dioxide Fluid Extract of Gloiopeltis tenax. Marine Drugs 2012, 10 (12) , 2634-2647. https://doi.org/10.3390/md10122634
    41. I. Rahath Kubra, L. Jagan Mohan Rao. An Impression on Current Developments in the Technology, Chemistry, and Biological Activities of Ginger ( Zingiber officinale Roscoe). Critical Reviews in Food Science and Nutrition 2012, 52 (8) , 651-688. https://doi.org/10.1080/10408398.2010.505689
    42. Jaleel Kizhakkayil, B. Sasikumar. Diversity, characterization and utilization of ginger: a review. Plant Genetic Resources 2011, 9 (3) , 464-477. https://doi.org/10.1017/S1479262111000670
    43. . Phytochemicals Research—Emerging Concepts. 2011, 215-250. https://doi.org/10.1201/b10878-7
    44. Guang Gao , Feng‐Lei Gu , Jian‐Xiong Jiang, Kezhi Jiang, Chun‐Qi Sheng, Guo‐Qiao Lai, Li‐Wen Xu . Neighboring Lithium‐Assisted [1,2]‐Wittig Rearrangement: Practical Access to Diarylmethanol‐Based 1,4‐Diols and Optically Active BINOL Derivatives with Axial and sp 3 ‐Central Chirality. Chemistry – A European Journal 2011, 17 (9) , 2698-2703. https://doi.org/10.1002/chem.201003111
    45. Momoe Iwami, Takahiko Shiina, Haruko Hirayama, Takeshi Shima, Tadashi Takewaki, Yasutake Shimizu. Inhibitory effects of zingerone, a pungent component of Zingiber officinale Roscoe, on colonic motility in rats. Journal of Natural Medicines 2011, 65 (1) , 89-94. https://doi.org/10.1007/s11418-010-0463-0
    46. Momoe Iwami, Takahiko Shiina, Haruko Hirayama, Yasutake Shimizu. Intraluminal administration of zingerol, a non-pungent analogue of zingerone, inhibits colonic motility in rats. Biomedical Research 2011, 32 (2) , 181-185. https://doi.org/10.2220/biomedres.32.181
    47. C.-S. Hew, L.-H. Gam. The Identification of High Abundant Proteins in the Leaves of Gynura Procumbens. Biotechnology & Biotechnological Equipment 2010, 24 (4) , 2132-2136. https://doi.org/10.2478/v10133-010-0075-6
    48. Keith Singletary. Ginger. Nutrition Today 2010, 45 (4) , 171-183. https://doi.org/10.1097/NT.0b013e3181ed3543
    49. Wei Gao, Long Chen, Long Bing Xu, Xin Hua Huang. Specific IgG activity against diarrheagenic bacteria in bovine immune milk and effect of pH on its antigen-binding activity upon heating. Journal of Dairy Research 2010, 77 (2) , 220-224. https://doi.org/10.1017/S0022029910000014
    50. Shruti Chatterjee, Masahiro Asakura, Nityananda Chowdhury, Sucharit Basu Neogi, Norihiko Sugimoto, Soumya Haldar, Sharda Prasad Awasthi, Atsushi Hinenoya, Shunji Aoki, Shinji Yamasaki. Capsaicin, a potential inhibitor of cholera toxin production in Vibrio cholerae. FEMS Microbiology Letters 2010, 306 (1) , 54-60. https://doi.org/10.1111/j.1574-6968.2010.01931.x
    51. Adekanmi Hezekiah Adeniran, Sumbo Henrietta Abiose, Moses Terkula Ukeyima. Microbiological assessment of probioticated ginger‐based beverages. Nutrition & Food Science 2010, 40 (2) , 209-220. https://doi.org/10.1108/00346651011029246
    52. C.-S. Hew, L.-H. Gam. The Identification of High Abundant Proteins in the Leaves of Gynura Procumbens. Biotechnology & Biotechnological Equipment 2010, 24 (4) , 2132-2136. https://doi.org/10.1080/13102818.2010.10817791
    53. Jaw-Chyun Chen, Tin-Yun Ho, Yuan-Shiun Chang, Shih-Lu Wu, Chia-Cheng Li, Chien-Yun Hsiang. Identification of Escherichia coli enterotoxin inhibitors from traditional medicinal herbs by in silico, in vitro, and in vivo analyses. Journal of Ethnopharmacology 2009, 121 (3) , 372-378. https://doi.org/10.1016/j.jep.2008.11.011
    54. Xin Hua Huang, Long Chen, Wei Gao, Wei Zhang, Su Juan Chen, Long Bing Xu, Shuang Quan Zhang. Specific IgG activity of bovine immune milk against diarrhea bacteria and its protective effects on pathogen-infected intestinal damages. Vaccine 2008, 26 (47) , 5973-5980. https://doi.org/10.1016/j.vaccine.2008.08.040
    55. C‐Y Hsiang, T‐Y Ho. Emodin is a novel alkaline nuclease inhibitor that suppresses herpes simplex virus type 1 yields in cell cultures. British Journal of Pharmacology 2008, 155 (2) , 227-235. https://doi.org/10.1038/bjp.2008.242
    Download PDF

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    You’ve supercharged your research process with ACS and Mendeley!

    STEP 1:
    Click to create an ACS ID

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    MENDELEY PAIRING EXPIRED
    Your Mendeley pairing has expired. Please reconnect