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Acrotrione: An Oxidized Xanthene from the Roots of Acronychia pubescens
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    Acrotrione: An Oxidized Xanthene from the Roots of Acronychia pubescens
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    • Luke P. Robertson
      Luke P. Robertson
      Environmental Futures Research Institute, Griffith University, Gold Coast Campus, Southport 4222, Australia
      Griffith Institute for Drug Discovery, Griffith University, Nathan Campus, Brisbane 4111, Australia
    • Leonardo Lucantoni
      Leonardo Lucantoni
      Griffith Institute for Drug Discovery, Griffith University, Nathan Campus, Brisbane 4111, Australia
    • Sandra Duffy
      Sandra Duffy
      Griffith Institute for Drug Discovery, Griffith University, Nathan Campus, Brisbane 4111, Australia
      More by Sandra Duffy
    • Vicky M. Avery
      Vicky M. Avery
      Griffith Institute for Drug Discovery, Griffith University, Nathan Campus, Brisbane 4111, Australia
    • Anthony R. Carroll*
      Anthony R. Carroll
      Environmental Futures Research Institute, Griffith University, Gold Coast Campus, Southport 4222, Australia
      Griffith Institute for Drug Discovery, Griffith University, Nathan Campus, Brisbane 4111, Australia
      *Tel.: +61 7 55529187. Fax: +61 7 55529047. E-mail: [email protected]
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    Journal of Natural Products

    Cite this: J. Nat. Prod. 2019, 82, 4, 1019–1023
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    https://doi.org/10.1021/acs.jnatprod.8b00956
    Published March 13, 2019
    Copyright © 2019 American Chemical Society and American Society of Pharmacognosy

    Abstract

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    A new oxidized xanthene, acrotrione (1), and two known acetophenones (2 and 3) were isolated from a methanol extract of the roots of Acronychia pubescens. The structure of 1 was elucidated on the basis of its (+)-HRESIMS, 2D NMR, and ECD data. Acritrione (1) contains an unusual oxidized furo[2,3-c]xanthene moiety that has not been previously reported. Moderate antiplasmodial activity for these natural products against chloroquine-sensitive (3D7) and chloroquine-resistant (Dd2) Plasmodium falciparum was determined with IC50 values ranging from 1.7 to 4.7 μM.

    Copyright © 2019 American Chemical Society and American Society of Pharmacognosy

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    Supporting Information

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jnatprod.8b00956.

    • 1D and 2D NMR spectra for acrotrione (1) (PDF)

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    Cited By

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    This article is cited by 14 publications.

    1. Sushree Ranjan Sahoo, Vinod K. Singh. Brønsted Acid Catalyzed Friedel–Crafts Alkylation of Naphthols with In Situ Generated Naphthol-Derived ortho-Quinone Methides: Synthesis of Chiral and Achiral Xanthene Derivatives. The Journal of Organic Chemistry 2023, 88 (5) , 3159-3172. https://doi.org/10.1021/acs.joc.2c02939
    2. Zhen‐Zhen Yang, Ni‐Ping Li, Li‐Xia Lv, Yi‐Yi Li, Ge Ge, Yue Zhuo, Qi Wang, Ji‐Hong Gu, Yan Wu. Prenylated Acetophenone Derivatives from the Leaves of Acronychia pedunculata and Their Anti‐Proliferative Activities. Chemistry & Biodiversity 2024, 21 (11) https://doi.org/10.1002/cbdv.202401027
    3. Javier Cervantes-González, Salma E. Mora-Rodríguez, Gerardo Zepeda Vallejo, David Cruz Cruz, Miguel A. Vázquez, Selene Lagunas-Rivera. Xanthenes: Novelty and Green Photocatalysis for the Formation of Carbon-carbon or Carbon-heteroatom Bond. Current Organic Chemistry 2024, 28 (17) , 1346-1365. https://doi.org/10.2174/0113852728306831240516062222
    4. Ninh The Son. Genus Acronychia: An Extensive Review on Phytochemistry and Pharmacological Activities. Mini-Reviews in Organic Chemistry 2023, 20 (8) , 818-841. https://doi.org/10.2174/1570193X20666221026162904
    5. Awat Wisetsai, Ratsami Lekphrom, Thanapat Suebrasri, Sarawut Tontapha, Thanaset Senawong, Khanitha Pudhom, Siwattra Choodej, Florian T. Schevenels. Acrotrione B, a Prenylated and Highly Oxidized Xanthenoid with Antibacterial and Anti-proliferative Activities from the Roots of Acronychia pedunculata. Planta Medica 2023, 89 (04) , 416-422. https://doi.org/10.1055/a-1953-0479
    6. Li-Xia Lv, Yan Wu, Hao-Xuan He, Ni-Ping Li, Wei Zhao, Yun-Qi Fan, Xia Wei, Jun-Cheng Su, Qi Wang, Ji-Hong Gu. Acronyrones A–C, unusual prenylated acetophenones from Acronychia pedunculata. Fitoterapia 2022, 163 , 105303. https://doi.org/10.1016/j.fitote.2022.105303
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    8. Li-Xia Lv, Yan Wu, Hao-Xuan He, Ni-Ping Li, Wei Zhao, Yun-Qi Fan, Xia Wei, Jun-Cheng Su, Qi Wang, Ji-Hong Gu. Acronyrones A–C, Unusual Prenylated Acetophenones from Acronychia Pedunculata. SSRN Electronic Journal 2022, 26 https://doi.org/10.2139/ssrn.4188484
    9. Kim-Thao Le, Jan J. Bandolik, Matthias U. Kassack, Kenneth R. Wood, Claudia Paetzold, Marc S. Appelhans, Claus M. Passreiter. New Acetophenones and Chromenes from the Leaves of Melicope barbigera A. Gray. Molecules 2021, 26 (3) , 688. https://doi.org/10.3390/molecules26030688
    10. Luke P. Robertson, Vivek Makwana, Tanja M. Voser, Darren C. Holland, Anthony R. Carroll. Leptanoine D, a New Quinoline Alkaloid from the Australian Tree Pitaviaster haplophyllus (Rutaceae). Australian Journal of Chemistry 2021, 74 (3) , 173. https://doi.org/10.1071/CH20125
    11. Tülay Yıldız, İrem Baştaş, Hatice Başpınar Küçük. Transition-metal-free intramolecular Friedel–Crafts reaction by alkene activation: A method for the synthesis of some novel xanthene derivatives. Beilstein Journal of Organic Chemistry 2021, 17 , 2203-2208. https://doi.org/10.3762/bjoc.17.142
    12. Muthupandi Karthick, Edwin Konikkara Abi, Nagamalla Someshwar, Savarimuthu Philip Anthony, Chinnasamy Ramaraj Ramanathan. NaHSO 4 /SiO 2 catalyzed generation of o -quinone/ o -thioquinone methides: synthesis of arylxanthenes/ arylthioxanthenes via oxa-6π-electrocyclization. Organic & Biomolecular Chemistry 2020, 18 (42) , 8653-8667. https://doi.org/10.1039/D0OB01868F
    13. Anamika Prajapati, Mahendra Kumar, Ranjit Thakuria, Ashok K. Basak. Stereoselective synthesis of 9-vinyl substituted unsymmetrical xanthenes and thioxanthenes. Tetrahedron Letters 2020, 61 (37) , 152347. https://doi.org/10.1016/j.tetlet.2020.152347
    14. Ritesh Raju, Ahilya Singh, Dhanushka Gunawardena, Paul Reddell, Gerald Münch. Mulgravanols A and B, rare oxidized xanthenes and a new phloroglucinol isolated from the Australian rainforest plant Waterhousea mulgraveana (Myrtaceae). Fitoterapia 2020, 143 , 104595. https://doi.org/10.1016/j.fitote.2020.104595

    Journal of Natural Products

    Cite this: J. Nat. Prod. 2019, 82, 4, 1019–1023
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.jnatprod.8b00956
    Published March 13, 2019
    Copyright © 2019 American Chemical Society and American Society of Pharmacognosy

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