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. 2012, 60, 1, 108-111
RETURN TO ISSUEPREVArticleNEXT

Sesamolinol Glucoside, Disaminyl Ether, and Other Lignans from Sesame Seeds

View Author Information
† Laboratoire de Pharmacognosie, UMR CNRS 8638, Université Paris Descartes, Sorbonne Paris cité, Faculté de Pharmacie, 4 Avenue de l’Observatoire, F-75006 Paris, France
‡ Department of Pharmacognosy and Natural Products Chemistry, Faculty of Pharmacy, University of Athens, Panepistimiopolis Zografou, GR-15771 Athens, Greece
§ Laboratory of Animal Physiology, School of Biology, Aristotle University, GR-54006 Thessaloniki, Greece
*Telephone: +30-210-7274052. Fax: +30-210-7274594. E-mail: [email protected]
Cite this: J. Agric. Food Chem. 2012, 60, 1, 108–111
Publication Date (Web):December 7, 2011
https://doi.org/10.1021/jf2040687
Copyright © 2011 American Chemical Society
Request reuse permissions

    Article Views

    1170

    Altmetric

    -

    Citations

    32
    LEARN ABOUT THESE METRICS
    Other access options
    Get e-Alerts
    SUBJECTS:

    Abstract

    The application of a procedure based on XAD-4 adsorption resin permitted the obtainment of an enriched polyphenolic extract from Sesamum indicum seeds. Chemical analysis of the obtained extract led to the identification of 12 lignans. Among them, 2 lignans, (+)-sesamolinol-4′-O-β-d-glucoside and disaminyl ether, are reported for the first time as natural compounds. Their structure has been determined by spectroscopic methods, mainly by the application of one-dimensional (1D) and two-dimensional (2D) nuclear magnetic resonance (NMR) techniques [heteronuclear multiple-quantum coherence (HMQC), heteronuclear multiple-bond correlation (HMBC), and nuclear Overhauser effect spectrometry (NOESY)] and mass spectroscopy. The isolated compounds were evaluated for their antimutagenic activity. Among the tested lignans, the most active lignan was found to be sesamolin, followed by sesamolinol and samin, against H2O2. Additionally, some of the tested lignans showed desmutagenic activity against benzo[a]pyrene (BaP).

    KEYWORDS:

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. You can change your affiliated institution below.

    Cited By

    This article is cited by 32 publications.

    1. Titiruetai Doungwichitrkul, Thanakorn Damsud, Preecha Phuwapraisirisan. α-Glucosidase Inhibitors from Cold-Pressed Black Sesame (Sesamum indicum) Meal: Characterization of New Furofuran Lignans, Kinetic Study, and In Vitro Gastrointestinal Digestion. Journal of Agricultural and Food Chemistry 2024, 72 (2) , 1044-1054. https://doi.org/10.1021/acs.jafc.3c04159
    2. Yuan Chi, Hong-Wei He, Cai-Yun Chen, Si-Ying Zhao, Huan Zhou, Dan Xu, Xili Liu, Gong Xu. Furofuran Lignans for Plant Protection: Discovery of Sesamolin and Its Derivatives as Novel Anti-Tobacco Mosaic Virus and Antibacterial Agents. Journal of Agricultural and Food Chemistry 2023, 71 (28) , 10798-10808. https://doi.org/10.1021/acs.jafc.3c03257
    3. Shu-Ming Huang, Cheng-Yang Hsieh, Jasmine U. Ting, Kathlia A. De Castro-Cruz, Ching-Chiung Wang, Chia-Jung Lee, Po-Wei Tsai. Anti-COVID-19, Anti-Inflammatory, and Anti-Osteoarthritis Activities of Sesamin from Sesamum indicum L.. Bioengineering 2023, 10 (11) , 1263. https://doi.org/10.3390/bioengineering10111263
    4. Shu-Ming Huang, Cheng-Hung Chuang, Christine Joyce F. Rejano, Lemmuel L. Tayo, Cheng-Yang Hsieh, Steven Kuan-Hua Huang, Po-Wei Tsai. Sesamin: A Promising Therapeutic Agent for Ameliorating Symptoms of Diabetes. Molecules 2023, 28 (21) , 7255. https://doi.org/10.3390/molecules28217255
    5. Bishoy Abib, Sherif M. Afifi, Mohamed G. Sharaf El-Din, Mohamed A. Farag. How do cultivar origin and stepwise industrial processing impact Sesamum indicum seeds’ metabolome and its paste and in relation to their antioxidant effects? A case study from the sesame industry. Food Chemistry 2023, 420 , 136134. https://doi.org/10.1016/j.foodchem.2023.136134
    6. Gyeong Han Jeong, Tae Hoon Kim. New Anti-Glycative Lignans from the Defatted Seeds of Sesamum indicum. Molecules 2023, 28 (5) , 2255. https://doi.org/10.3390/molecules28052255
    7. Xiaoyue Zhang, Longqin Wang, Bowen Li, Jiayan Shi, Jia Xu, Minlan Yuan. Targeting Mitochondrial Dysfunction in Neurodegenerative Diseases: Expanding the Therapeutic Approaches by Plant-Derived Natural Products. Pharmaceuticals 2023, 16 (2) , 277. https://doi.org/10.3390/ph16020277
    8. Reham Hassan Mekky, Mostafa M. Hegazy, María de la Luz Cádiz-Gurrea, Álvaro Fernández-Ochoa, Antonio Segura Carretero. Bioactive Phytochemicals from Sesame Oil Processing By-products. 2023, 155-194. https://doi.org/10.1007/978-3-030-91381-6_9
    9. Andrescia Ferreira de Carvalho, Marcos Jácome de Araújo, Santos Jeovanny Aguilera Vallecillo, José Pires Carvalho Neto, Alex Rodrigues de Souza, Ricardo Loiola Edvan, Tairon Pannunzio Dias-Silva, Leilson Rocha Bezerra. Tissue composition and meat quality of lambs fed diets containing whole-plant sesame silage as a replacement for whole-plant corn silage. Small Ruminant Research 2022, 216 , 106799. https://doi.org/10.1016/j.smallrumres.2022.106799
    10. Andrzej Patyra, Małgorzata Kołtun-Jasion, Oktawia Jakubiak, Anna Karolina Kiss. Extraction Techniques and Analytical Methods for Isolation and Characterization of Lignans. Plants 2022, 11 (17) , 2323. https://doi.org/10.3390/plants11172323
    11. Jianjun Wang, Taixiang Chen, James F. White, Xuekai Wei, Xiuzhang Li, Chunjie Li. Pantoea agglomerans, a seed-borne plant pathogenic bacterium, decreased seed germination, seedling growth and seed quality of oat. European Journal of Plant Pathology 2022, 162 (3) , 667-679. https://doi.org/10.1007/s10658-021-02430-5
    12. Larissa Kom Ma’mag, Auguste Abouem A. Zintchem, Alex de Théodore Atchadé, Théodora Kopa Kowa, Alembert Tchinda Tiabou, Dominique Serge Ngono Bikobo, Dieudonné Emmanuel Pegnyemb. Antileishmanial activity of long chain alkyl benzene and other constituents from seeds of Sesamum indicum. L (Pedaliaceae). Natural Product Research 2021, 35 (23) , 5535-5539. https://doi.org/10.1080/14786419.2020.1793147
    13. Anuj Kumar, Dwijesh Chandra Mishra, Ulavappa Basavanneppa Angadi, Rashmi Yadav, Anil Rai, Dinesh Kumar. Inhibition Potencies of Phytochemicals Derived from Sesame Against SARS-CoV-2 Main Protease: A Molecular Docking and Simulation Study. Frontiers in Chemistry 2021, 9 https://doi.org/10.3389/fchem.2021.744376
    14. Reny Rosalina, Natthida Weerapreeyakul. An Insight into Sesamolin: Physicochemical Properties, Pharmacological Activities, and Future Research Prospects. Molecules 2021, 26 (19) , 5849. https://doi.org/10.3390/molecules26195849
    15. Reham Hassan Mekky, Mostafa M. Hegazy, María de la Luz Cádiz-Gurrea, Álvaro Fernández-Ochoa, Antonio Segura Carretero. Bioactive Phytochemicals from Sesame Oil Processing By-products. 2021, 1-40. https://doi.org/10.1007/978-3-030-63961-7_9-1
    16. Jicheng Chen, Yazhen Chen, Xianjiang Ye. Lignans in Diets. 2021, 1687-1708. https://doi.org/10.1007/978-981-15-4148-3_38
    17. Sahar S. El Souda. Mutagenesis and chemoprotective role of natural products. 2021, 345-379. https://doi.org/10.1016/B978-0-12-819489-8.00012-0
    18. Lucy Sun Hwang, Min‐Hsiung Lee, Nan‐Wei Su. Sesame Oil. 2020, 1-39. https://doi.org/10.1002/047167849X.bio031.pub2
    19. Jicheng Chen, Yazhen Chen, Xianjiang Ye. Lignans in Diets. 2020, 1-22. https://doi.org/10.1007/978-981-13-1745-3_38-1
    20. Ming-Shun Wu, Levent Bless B. Aquino, Marjette Ylreb U. Barbaza, Chieh-Lun Hsieh, Kathlia A. De Castro-Cruz, Ling-Ling Yang, Po-Wei Tsai. Anti-Inflammatory and Anticancer Properties of Bioactive Compounds from Sesamum indicum L.—A Review. Molecules 2019, 24 (24) , 4426. https://doi.org/10.3390/molecules24244426
    21. Saber Eweda, Al Newairy, Heba Abdou, Assmaa Gaber. Bisphenol A‑induced oxidative damage in the hepatic and cardiac tissues of rats: The modulatory role of sesame lignans. Experimental and Therapeutic Medicine 2019, 24 https://doi.org/10.3892/etm.2019.8193
    22. Reham Hassan Mekky, Essam Abdel-Sattar, Antonio Segura-Carretero, María del Mar Contreras. Phenolic Compounds from Sesame Cake and Antioxidant Activity: A New Insight for Agri-Food Residues’ Significance for Sustainable Development. Foods 2019, 8 (10) , 432. https://doi.org/10.3390/foods8100432
    23. Eleni V. Mikropoulou, Eleftherios A. Petrakis, Aikaterini Argyropoulou, Sofia Mitakou, Maria Halabalaki, Leandros A. Skaltsounis. Quantification of bioactive lignans in sesame seeds using HPTLC densitometry: Comparative evaluation by HPLC-PDA. Food Chemistry 2019, 288 , 1-7. https://doi.org/10.1016/j.foodchem.2019.02.109
    24. Dimitris Michailidis, Apostolis Angelis, Nektarios Aligiannis, Sofia Mitakou, Léandros Skaltsounis. Recovery of Sesamin, Sesamolin, and Minor Lignans From Sesame Oil Using Solid Support-Free Liquid–Liquid Extraction and Chromatography Techniques and Evaluation of Their Enzymatic Inhibition Properties. Frontiers in Pharmacology 2019, 10 https://doi.org/10.3389/fphar.2019.00723
    25. Makoto Naoi, Yuqiu Wu, Masayo Shamoto-Nagai, Wakako Maruyama. Mitochondria in Neuroprotection by Phytochemicals: Bioactive Polyphenols Modulate Mitochondrial Apoptosis System, Function and Structure. International Journal of Molecular Sciences 2019, 20 (10) , 2451. https://doi.org/10.3390/ijms20102451
    26. Ji Yoon Yi, Hui Ju Kim, Myong-Soo Chung, . Manufacture of low-benzo(a)pyrene sesame seed (Sesamum indicum L.) oil using a self-designed apparatus. PLOS ONE 2017, 12 (3) , e0173585. https://doi.org/10.1371/journal.pone.0173585
    27. Paola Manoukian, Eleni Melliou, Maria Liouni, Prokopios Magiatis. Identification and quantitation of benzoxazinoids in wheat malt beer by qNMR and GC–MS. LWT - Food Science and Technology 2016, 65 , 1133-1137. https://doi.org/10.1016/j.lwt.2015.10.014
    28. Tae-Shik Hahm, Chia-Yu Kuei. Present and Potential Industrial Applications of Sesame: A Mini Review. Journal of Food Processing and Preservation 2015, 39 (6) , 3137-3144. https://doi.org/10.1111/jfpp.12381
    29. Maribel Herrera-Ruiz, Ricardo López-Rodríguez, Gabriela Trejo-Tapia, Blanca Domínguez-Mendoza, Manases González-Cortazar, Jaime Tortoriello, Alejandro Zamilpa. A New Furofuran Lignan Diglycoside and Other Secondary Metabolites from the Antidepressant Extract of Castilleja tenuiflora Benth. Molecules 2015, 20 (7) , 13127-13143. https://doi.org/10.3390/molecules200713127
    30. Dorothea Bedigian. Systematics and evolution in Sesamum L. (Pedaliaceae), part 1: Evidence regarding the origin of sesame and its closest relatives. Webbia 2015, 70 (1) , 1-42. https://doi.org/10.1080/00837792.2014.968457
    31. Mohamed Elleuch, Dorothea Bedigian, Bouthaina Maazoun, Souhail Besbes, Christophe Blecker, Hamadi Attia. Improving halva quality with dietary fibres of sesame seed coats and date pulp, enriched with emulsifier. Food Chemistry 2014, 145 , 765-771. https://doi.org/10.1016/j.foodchem.2013.08.085
    32. Aejaz Ahmad Dar, Neelakantan Arumugam. Lignans of sesame: Purification methods, biological activities and biosynthesis – A review. Bioorganic Chemistry 2013, 50 , 1-10. https://doi.org/10.1016/j.bioorg.2013.06.009
    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