Benzoylcyclopropane Derivatives from Hypoxis hemerocallidea Corms

  • Planta Med. 2022 Jul;88(8):685-692. doi: 10.1055/a-1540-4978.
Fazila Zulfiqar  1 ,  Pankaj Pandey  1 ,  Siddharth K Tripathi  1 ,  Zulfiqar Ali  1 ,  Amar G Chittiboyina  1 ,  Ikhlas A Khan  1  2
Affiliations
  • 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.
PMID: 34331304 DOI: 10.1055/a-1540-4978
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.

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