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Planta Med 2022; 88(08): 685-692
DOI: 10.1055/a-1540-4978
Biological and Pharmacological Activity
Original Papers

Benzoylcyclopropane Derivatives from Hypoxis hemerocallidea Corms

Fazila Zulfiqar 
1   National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS, USA
,
Pankaj Pandey
1   National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS, USA
,
Siddharth K. Tripathi
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
,
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   Division of Pharmacognosy, Department of BioMolecular Sciences, School of Pharmacy, University of Mississippi, University, MS, USA
› Author AffiliationsSupported by: U.S. Department of Agriculture 58-6060-6-015
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Abstract

Two monobenzoylcyclopropane (hypoxhemerol A (1) and hypoxhemeroloside G (2)) and three dibenzoylcyclopropane (hypoxhemerol B (3), hypoxhemeroloside H (4), and hypoxhemeroloside I (5)) derivatives were isolated from the hydro-alcoholic extract of Hypoxis hemerocallidea corms. This is the first instance where benzoylcyclopropane analogs were isolated from any natural source. Structure elucidation was mainly based on 1D- and 2D-NMR and HRESIMS data. The absolute configuration (2R, 4R) of 1 was determined via NOESY NMR and experimental and calculated ECD data analyses. Compounds 1–5 and 11 recently reported metabolites (hypoxoside, obtuside A, interjectin, acuminoside, curcapicycloside, and hypoxhemerolosides A – F) were screened for in vitro antimicrobial activity against various bacterial and fungal strains. Curcapicycloside and acuminoside exhibited antibacterial activity against Escherichia coli with 78 and 79% inhibition at 20 µg/mL, respectively. Hypoxhemeroloside A showed mild antifungal activity against Cryptococcus neoformans with 63% inhibition at 20 µg/mL.

Key words

Hypoxis hemerocallidea - hypoxidaceae - benzoylcyclopropane - hypoxhemerol - hypoxhemeroloside - antimicrobial

Supporting Information

    The HRESIMS and NMR spectra for compounds 1–5 and antimicrobial data of extract and compounds are available as Supporting Information.

  • Supporting Information


Publication History

Received: 10 February 2021

Accepted after revision: 25 June 2021

Article published online:
30 July 2021

© 2021. Thieme. All rights reserved.

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