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Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Nat. Prod. 2021, 84, 4, 1163-1174
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Structure Elucidation and Confirmation of Phloroglucinols from the Roots of Garcinia dauphinensis by Comparison of Experimental and Calculated ECD Spectra and Specific Rotations

  • Kirk C. Pearce
    Kirk C. Pearce
    Department of Chemistry, Virginia Tech, Blacksburg, Virginia 24061, United States
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    Orcidhttp://orcid.org/0000-0001-8033-6310
  • , 
  • Rolly G. Fuentes
    Rolly G. Fuentes
    Department of Chemistry, Virginia Tech, Blacksburg, Virginia 24061, United States
    Virginia Tech Center for Drug Discovery, Virginia Tech, Blacksburg, Virginia 24061, United States
    Division of Natural Sciences and Mathematics, University of the Philippines Visayas Tacloban College, 6500 Tacloban City, Philippines
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  • , 
  • Susana Calderon
    Susana Calderon
    Department of Chemistry, Virginia Tech, Blacksburg, Virginia 24061, United States
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  • , 
  • Rageshwari Marolikar
    Rageshwari Marolikar
    Department of Chemistry, Virginia Tech, Blacksburg, Virginia 24061, United States
    More by Rageshwari Marolikar
  • , 
  • David G. I. Kingston
    David G. I. Kingston
    Department of Chemistry, Virginia Tech, Blacksburg, Virginia 24061, United States
    Virginia Tech Center for Drug Discovery, Virginia Tech, Blacksburg, Virginia 24061, United States
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    Orcidhttp://orcid.org/0000-0001-8944-246X
  • , and 
  • T. Daniel Crawford*
    T. Daniel Crawford
    Department of Chemistry, Virginia Tech, Blacksburg, Virginia 24061, United States
    Molecular Sciences Software Institute, 1880 Pratt Drive, Suite 1100, Blacksburg, Virginia 24060, United States
    *Email: [email protected]. Phone: +1 (540)231 7760.
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    Orcidhttp://orcid.org/0000-0002-7961-7016
Cite this: J. Nat. Prod. 2021, 84, 4, 1163–1174
Publication Date (Web):April 6, 2021
https://doi.org/10.1021/acs.jnatprod.0c01208
Copyright © 2021 American Chemical Society and American Society of Pharmacognosy
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    Abstract

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    Eight phloroglucinols from Garcinia dauphinensis were recently reported to have good to moderate antiplasmodial and anticancer activities, consistent with other phloroglucinol derivatives isolated from natural sources. Chiroptical properties were previously calculated and compared to experimental data for compound 2 as a means to deduce its absolute configuration. Tentative assignments for the remaining compounds were also reported based on these data. In order to arrive at stereochemical assignments for phloroglucinols 1 and 3–8, ECD spectra and specific rotations were computed for all stereoisomers of each compound. Molecular orbital analyses were also carried out for the most energetically favorable conformers of each compound. Absolute configurations are reported for all eight phloroglucinols for the first time.

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    • Comparison of experimental and calculated ECD spectra for all possible stereoiosmers of compounds 1 and 3–8, comparison of experimental and calculated specific rotations for all possible stereoiosmers of compounds 1 and 3–8, and characterisitic MO transitions for compounds 1 and 3–8 (PDF)

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    Cited By

    This article is cited by 2 publications.

    1. Ruifei Zhang, Zhuo Cheng, Qiong Fang, Edward J. Kennelly, Chunlin Long. Monoterpenoid acylphloroglucinols from Hypericum hengshanense W. T. Wang with antiproliferative activities. Phytochemistry 2023, 205 , 113500. https://doi.org/10.1016/j.phytochem.2022.113500
    2. Xing-Rong Peng, Qian Wang, Hui-Rong Wang, Kun Hu, Wen-Yong Xiong, Ming-Hua Qiu. FPR2-based anti-inflammatory and anti-lipogenesis activities of novel meroterpenoid dimers from Ganoderma. Bioorganic Chemistry 2021, 116 , 105338. https://doi.org/10.1016/j.bioorg.2021.105338
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