Molecules (Nov 2023)

Salazinic Acid and Norlobaridone from the Lichen <i>Hypotrachyna cirrhata</i>: Antioxidant Activity, α-Glucosidase Inhibitory and Molecular Docking Studies

  • Tatapudi Kiran Kumar,
  • Bandi Siva,
  • Basani Kiranmai,
  • Vidya Jyothi Alli,
  • Surender Singh Jadav,
  • Araveeti Madhusudana Reddy,
  • Joël Boustie,
  • Françoise Le Devehat,
  • Ashok Kumar Tiwari,
  • Katragadda Suresh Babu

DOI
https://doi.org/10.3390/molecules28237840
Journal volume & issue
Vol. 28, no. 23
p. 7840

Abstract

Read online

The present study was intended for the identification of secondary metabolites in acetone extract of the lichen Hypotrachyna cirrhata using UPLC-ESI-QToF-MS/MS and the detection of bioactive compounds. This study led to the identification of 22 metabolites based on their MS/MS spectra, accurate molecular masses, molecular formula from a comparison of the literature database (DNP), and fragmentation patterns. In addition, potent antioxidant and α-glucosidase inhibitory potentials of acetone extract of H. cirrhata motivated us to isolate 10 metabolites, which were characterized as salazinic acid (11), norlobaridone (12), atranorin (13), lecanoric acid (14), lichesterinic acid (15), protolichesterinic acid (16), methyl hematommate (17), iso-rhizonic acid (18), atranol (19), and methylatratate (20) based on their spectral data. All these isolates were assessed for their free radicals scavenging, radical-induced DNA damage, and intestinal α-glucosidase inhibitory activities. The results indicated that norlobaridone (12), lecanoric acid (14), methyl hematommate (17), and atranol (19) showed potent antioxidant activity, while depsidones (salazinic acid (11), norlobaridone (12)) and a monophenolic compound (iso-rhizonic acid, (18)) displayed significant intestinal α-glucosidase inhibitory activities (p 12) is hooked into the finger-like cavity of the allosteric pocket; moreover, it also established Van der Waals interactions with hydrophobic residues of the allosteric pocket. Thus, the potency of norlobaridone to inhibit α-glucosidase enzyme might be associated with its allosteric binding. Also, MM-GBSA (Molecular Mechanics-Generalized Born Surface Area) binding free energies of salazinic acid (11) and norlobaridone (12) were superior to acarbose and may have contributed to their high activity compared to acarbose.

Keywords