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Planta Med 2024; 90(07/08): 631-640
DOI: 10.1055/a-2232-4755
Natural Product Chemistry and Analytical Studies
Original Papers

iso-Guttiferone J and Structure Revision of Guttiferone J from Garcinia gummi-gutta: A Combined Experimental and Integrated QM/NMR Approach[ # ]

Pankaj Pandey
1   National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS, USA
,
Mantasha Idrisi
1   National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS, USA
,
Zulfiqar Ali 
1   National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS, USA
,
Islam Husain
1   National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS, USA
,
William M. Neal
2   Department of Bio-Molecular Sciences, School of Pharmacy, University of Mississippi, University, MS, USA
,
Shabana I. Khan
1   National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS, USA
2   Department of Bio-Molecular Sciences, School of Pharmacy, University of Mississippi, University, MS, USA
,
Daneel Ferreira
1   National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS, USA
2   Department of Bio-Molecular Sciences, School of Pharmacy, University of Mississippi, University, MS, USA
,
Amar G. Chittiboyina
1   National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS, USA
,
Ikhlas A. Khan
1   National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS, USA
2   Department of Bio-Molecular Sciences, School of Pharmacy, University of Mississippi, University, MS, USA
› Author AffiliationsThis research is supported in part by the Center for Food Safety and Applied Nutrition, US Food and Drug Administration “Science-Based Authentication of Botanical Ingredients” Agreement No. 5U01FD004246.
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Abstract

Many polyprenylated acylphloroglucinols with fascinating chemical structures and intriguing biological activities have been identified as key to phytochemicals isolated from Garcinia, Hypericum, and related genera. In the present work, two chiral, tautomeric, highly-oxygenated polyprenylated acylphloroglucinols tethered with acyl and prenyl moieties on a bicyclo[3.3.1]nonanetrione core were isolated from the 95% ethanolic extract of Garcinia gummi-gutta fruit. The structures of both compounds were elucidated based on the NMR and MS data with ambiguity in the exact position of the enol and keto functions at C-1 and C-3 of the core structure. The structures of both polyprenylated acylphloroglucinols were established as a structurally revised guttiferone J and the new iso-guttiferone J with the aid of gauge-independent atomic orbital NMR calculations, CP3 probability analyses, specific rotation calculations, and electronic circular dichroism calculations in combination with the experimental data. The structures of both compounds resemble hyperforin, a potent activator of the human pregnane X receptor. As expected, both compounds showed strong pregnane X receptor activation at 10 µM [7.1-fold (guttiferone J) and 5.0-fold (iso-guttiferone J)], explained by a molecular docking study, necessitating further in-depth investigation to substantiate the herb-drug interaction potential of G. gummi-gutta upon co-administration with pharmaceutical drugs.

Key words

Garcinia gummi-gutta - Clusiaceae - polyprenylated acylphloroglucinols - structure revision - guttiferone J - iso-guttiferone J - QM/NMR

# This work is dedicated to Professors Rudolf Bauer, Chlodwig Franz, Brigitte Kopp, and Hermann Stuppner for their invaluable contributions and commitment to Austrian Pharmacognosy.


Supporting Information

    The NMR and HRESIMS spectra for compounds iso-guttiferone J and revised guttiferone J and computational NMR, DP4+, and CP3 data are available as Supporting Information.

  • Supporting Information


Publication History

Received: 03 October 2023

Accepted after revision: 13 December 2023

Article published online:
06 June 2024

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