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New Tetracyclic Sesterterpenes from Cydonia vulgaris

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    New Tetracyclic Sesterterpenes from Cydonia vulgaris
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    Facoltà di Farmacia, Università di Salerno, Piazza V. Emanuele 9, 84084 Penta di Fisciano, Salerno, Italy
    Dipartimento di Chimica delle Sostanze Naturali, Università degli Studi di Napoli, via D. Montesano 49, 80131 Napoli, Italy
    MRC, Collaborative centre 1-3 Burtanhole Lane, Mill Hill, London NW7 1AD England
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    Journal of Natural Products

    Cite this: J. Nat. Prod. 1996, 59, 3, 267–270
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    https://doi.org/10.1021/np9600513
    Published March 22, 1996
    Copyright © 1996 American Chemical Society and American Society of Pharmacognosy
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    Abstract

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    The CHCl3−MeOH extract of Cydonia vulgaris Pers. (Rosaceae) was shown to contain four new sesterterpene esters, namely 24,25-O-diacetylvulgaroside (1), 25-O-acetylvulgaroside (2), 24-O-acetyl-25-O-cinnamoylvulgaroside (3), and 25-O-cinnamoylvulgaroside (4). The structure elucidation of these compounds was accomplished using homonuclear and heteronuclear 2D-NMR experiments and FABMS.

    Copyright © 1996 American Chemical Society and American Society of Pharmacognosy

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     To whom correspondence should be addressed. Phone:  39/81/7486540. Fax:  39/81/7486552.

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     Abstract published in Advance ACS Abstracts, January 15, 1996.

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    This article is cited by 21 publications.

    1. Andreia P. Oliveira, José A. Pereira, Paula B. Andrade, Patrícia Valentão, Rosa M. Seabra and Branca M. Silva. Phenolic Profile of Cydonia oblonga Miller Leaves. Journal of Agricultural and Food Chemistry 2007, 55 (19) , 7926-7930. https://doi.org/10.1021/jf0711237
    2. Cosimo Pizza, , Aurora Bellino and, Pietro Venturella. Triterpenoid Saponins from Schefflera divaricata. Journal of Natural Products 1997, 60 (7) , 663-668. https://doi.org/10.1021/np9605807
    3. Nunziatina De Tommasi,, Sonia Piacente,, Francesco De Simone, and, Cosimo Pizza. Constituents of Cydonia vulgaris:  Isolation and Structure Elucidation of Four New Flavonol Glycosides and Nine New α-Ionol-Derived Glycosides. Journal of Agricultural and Food Chemistry 1996, 44 (7) , 1676-1681. https://doi.org/10.1021/jf950547a
    4. Shan-Shan Jiao, Rui-Feng Ding, Xin Yuan, Xiao-Ping He, Yan Liu, Kai Guo, Sheng-Hong Li. Megastigmane glycosides from the traditional Uighur medicine Cydonia oblonga Mill.. Phytochemistry 2024, 225 , 114188. https://doi.org/10.1016/j.phytochem.2024.114188
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    6. Hari Prasad Devkota, Amina Ibrahim Dirar, Md. Mahadi Hassan, Rajan Logesh. Cydonia oblonga Mill. 2023, 91-99. https://doi.org/10.1016/B978-0-323-85591-4.00026-X
    7. Atefeh Amerizadeh, Golnaz Vaseghi, Nazgol Esmaeilian, Sedigheh Asgary, . Cardiovascular Effects of Cydonia oblonga Miller (Quince). Evidence-Based Complementary and Alternative Medicine 2022, 2022 , 1-7. https://doi.org/10.1155/2022/3185442
    8. Kai Guo, Yan Liu, Sheng-Hong Li. The untapped potential of plant sesterterpenoids: chemistry, biological activities and biosynthesis. Natural Product Reports 2021, 38 (12) , 2293-2314. https://doi.org/10.1039/D1NP00021G
    9. Qingwen Chen, Jianxu Li, Yihua Ma, Weiliang Yuan, Peng Zhang, Guodong Wang. Occurrence and biosynthesis of plant sesterterpenes (C25), a new addition to terpene diversity. Plant Communications 2021, 2 (5) , 100184. https://doi.org/10.1016/j.xplc.2021.100184
    10. Jiao-Jiao Wei, Wen-Qiong Wang, Wei-Bin Song, Li-Jiang Xuan. Three new dibenzofurans from Cydonia oblonga Mill. Natural Product Research 2020, 34 (8) , 1146-1151. https://doi.org/10.1080/14786419.2018.1553877
    11. Katerina Cvetkovska, Biljana Bauer. Ethnopharmacological and toxicological review of Cydonia oblonga M.. Macedonian Pharmaceutical Bulletin 2018, 64 (02) , 3-16. https://doi.org/10.33320/maced.pharm.bull.2018.64.02.001
    12. Ishwar Prakash Sharma. Wild Fruits of Uttarakhand (India): Ethnobotanical and Medicinal Uses. International Journal of Complementary & Alternative Medicine 2017, 8 (3) https://doi.org/10.15406/ijcam.2017.08.00260
    13. Muhammad U. Ashraf, Gulzar Muhammad, Muhammad A. Hussain, Syed N. A. Bukhari. Cydonia oblonga M., A Medicinal Plant Rich in Phytonutrients for Pharmaceuticals. Frontiers in Pharmacology 2016, 7 https://doi.org/10.3389/fphar.2016.00163
    14. Sidra Sabir, Rahmatullah Qureshi, Muhammad Arshad, Muhammad Shoaib Amjad, Sammer Fatima, Maria Masood, Saboon, Sunbal Khalil Chaudhari. Pharmacognostic and clinical aspects of Cydonia oblonga: A review. Asian Pacific Journal of Tropical Disease 2015, 5 (11) , 850-855. https://doi.org/10.1016/S2222-1808(15)60934-3
    15. Joanna Kolniak-Ostek, Jan Oszmiański, Aneta Wojdyło. Effect of apple leaves addition on physicochemical properties of cloudy beverages. Industrial Crops and Products 2013, 44 , 413-420. https://doi.org/10.1016/j.indcrop.2012.12.003
    16. Andreia P. Oliveira, Rossana M. Costa, Ana S. Magalhães, José A. Pereira, Márcia Carvalho, Patrícia Valentão, Paula B. Andrade, Branca M. Silva. Targeted metabolites and biological activities of Cydonia oblonga Miller leaves. Food Research International 2012, 46 (2) , 496-504. https://doi.org/10.1016/j.foodres.2010.10.021
    17. T. K. Lim. Cydonia oblonga. 2012, 371-380. https://doi.org/10.1007/978-94-007-4053-2_45
    18. Nicon Ungur, Veaceslav Kulciţki. Occurrence, biological activity and synthesis of cheilanthane sesterterpenoids. Tetrahedron 2009, 65 (19) , 3815-3828. https://doi.org/10.1016/j.tet.2009.02.001
    19. Andreia P. Oliveira, José A. Pereira, Paula B. Andrade, Patrícia Valentão, Rosa M. Seabra, Branca M. Silva. Organic acids composition of Cydonia oblonga Miller leaf. Food Chemistry 2008, 111 (2) , 393-399. https://doi.org/10.1016/j.foodchem.2008.04.004
    20. J. Buckingham. V. 1998, 339-341. https://doi.org/10.1007/978-1-4899-3314-0_22
    21. Rokia Sanogo, Maria Paola Germano, Nunziatina de Tommasi, Cosimo Pizza, Rita Aquino. Vernoniosides and an androstane glycoside from Vernonia kotschyana. Phytochemistry 1998, 47 (1) , 73-78. https://doi.org/10.1016/S0031-9422(97)00477-9
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    Journal of Natural Products

    Cite this: J. Nat. Prod. 1996, 59, 3, 267–270
    Click to copy citationCitation copied!
    https://doi.org/10.1021/np9600513
    Published March 22, 1996
    Copyright © 1996 American Chemical Society and American Society of Pharmacognosy
    Request reuse permissions

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