Two New Fumarprotocetraric Acid Lactones Identified and Characterized by UHPLC-PDA/ESI/ORBITRAP/MS/MS from the Antarctic Lichen Cladonia metacorallifera

Abstract

Lichens are symbiotic organisms between algae and fungi, which are makers of secondary compounds named as lichen substances. Hyphenated techniques have significantly helped natural product chemistry, especially UHPLC/ESI/MS/MS in the identification, separation, and tentative characterization of secondary metabolites from natural sources. Twenty-five compounds were detected from the Antarctic lichen Cladonia metacorallifera for the first time using UHPLC-PDA/ESI/Orbitrap/MS/MS. Compounds 5 and 7 are reported as new compounds, based on their MS/MS fragmentation routes, and considered as fumarprotocetraric acid derivatives. Besides, ten known phenolic identified as orsellinic acid, ethyl 4-carboxyorsellinate, psoromic acid isomer, succinprotocetraric acid, siphulellic acid, connorstictic acid, cryptostictic acid, lecanoric acid, lobaric acid and gyrophoric acid are noticed for the first time in the Cladonia genus.

Antioxidant and antidiabetic activity and phytoconstituents of lichen extracts with temperate and polar distribution

“…Aromatic derivatives: Peaks 3, 4, 5, 6, 7, 8, 10, and 12 were identified as hypoxyphenone (C 10 H 9 O 5 ), prephenic acid (C 10 H 9 O 6 ), In recent years, metabolomic studies have intensified in lichenic species of tropical and, especially, temperate distribution and polar territories, strengthening the bank of reported compounds that make up chemotaxonomic variables for the differentiation of species and their complexes (Torres-Benítez et al, 2017). Likewise, the use of robust state-of-the-art techniques such as ultra-high performance liquid chromatography with a diode array (UHPLC-DAD) coupled to an electrospray ionization tandem mass spectrometer (ESI-MS-MS) traditionally used in plant extracts has also allowed greater precision in the identification and elucidation of bioactive compounds in lichens (Sepúlveda et al, 2022;Torres-Benítez et al, 2023b). Compounds present in the species O. frigida, P. contortuplicata, and U. antarctica are shared with other Antarctic species such as Lecania brialmontii, Pseudephebe pubescens, Sphaerophorus globosus (Torres-Benítez et al, 2022), Cladonia gracilis, Cladonia chlorophaea (Torres-Benítez et al, 2023a), and Himantormia lugubris (Areche et al, 2022), including carbohydrates, phenolic compounds (such as lecanoric acid, orselinic acid, and orcinol derivatives), and lipids.…”

Recent advances on natural depsidones: sources, biosynthesis, structure-activity relationship, and bioactivities

“…Other reported halogenated derivatives were biosynthesized as a result of modification of the culture media using KBr, NaBr, or porcine.NaBr ( Guo et al, 2022 ; Morshed et al, 2018 ; Sureram et al, 2013 ). These metabolites were principally encountered in fungi, lichens, and plants and were rarely reported from marine sources ( Hartati, Megawati & Antika, 2022 ; Sepúlveda et al, 2022 ; Ismed et al, 2021 ). Naturally occurring depsidones have been reported to display a span of bioactivities including antimicrobial, antimalarial, cytotoxic, anti- Trypanosoma , anti-inflammatory, anti- Helicobacter pylori , antimycobacterial, antihypertensive, anti-diarrheal, larvicidal, antidiabetic, herbicidal, antileishmanial, phytotoxic, anti-HIV, anti-osteoclastogenic, and butyrylcholinesterase, aromatase, tyrosinase, hyaluronidase, and acetylcholinesterase inhibition ( Addo et al, 2021 ; Ibrahim et al, 2018 ).…”