Restricted accessResearch articleFirst published online 2024-4
Liquid chromatography-electrospray ionization-mass spectrometry/mass spectrometry characterization of depsides and depsidones from the Chilean lichen Parmotrema perlatum
Lichens are recognized by their unique compounds and diverse applications in food, medicines, and cosmetics. Using ultra-high pressure liquid chromatography, coupled with a high-resolution mass spectrometer, metabolomic profiling of the lichen Parmotrema perlatum, from a methanolic extract, was performed. Based on characteristic fragmentation patterns, twenty-five lichenic substances were tentatively identified including 5 depsides, 12 depsidones, 2 diphenyl ethers, 1 aromatic considered as possible artifact, 1 dibenzofuran, 1 carbohydrate, 1 organic acid, and 2 undefined compounds. To the best of our knowledge, this is a more complete report of their phytochemistry from P perlatum. Our findings of the P perlatum profile may contribute and complement the current data of the Parmotrema genus.
HawksworthDL. Lichenization: the origin of a fungal life-style. In: UpretiDKDivakarPKShuklaV, etal (eds) Recent Advances in Lichenology, vol. 2. New Delhi: Springer, 2015, pp.1–10.
2.
SpribilleTReslPStantonDE, et al.Evolutionary biology of lichen symbioses. New Phytol2022; 234: 1566–1582.
3.
ZhaoYWangMXuBA. Comprehensive review on secondary metabolites and health-promoting effects of edible lichen. J Funct Foods2021; 80: 104283.
4.
ElkhateebWAElnahasMODabaG. Lichentherapy: Highlights on the pharmaceutical potentials of lichens. J Microbiol Biotechnol2021; 6: 1–10.
5.
WijayawardeneNNHydeKDAl-AniLKT, et al.Outline of fungi and fungus-like taxa. Mycosphere2020; 11: 1060–1456.
6.
Torres-BenítezARivera-MontalvoMSepúlvedaB, et al.Metabolomic analysis of two parmotrema lichens: P. robustum (degel.) hale and P. andinum (mull. Arg.) hale using UHPLC-ESI-OT-MS-MS. Molecules2017; 22: 1861.
7.
KumarKSivaBSarmaVUM, et al.UPLC–MS/MS quantitative analysis and structural fragmentation study of five Parmotrema lichens from the Eastern Ghats. J Pharm Biomed Anal2018; 156: 45–57.
8.
StelateADel-PradoRAlorsD, et al.Resolving the phylogenetic relationship between Parmotrema crinitum and Parmotrema perlatum populations. Lichenologist2022; 54: 183–194.
9.
PereiraIErrazúrizIGarridoP, et al.Lichen diversity associated with native forest of the Achibueno river ravine, Maule region, Chile. Gayana—Botanica2021; 78: 200–207.
10.
Candotto CarnielFZanelliDBertuzziS, et al.Desiccation tolerance and lichenization: a case study with the aeroterrestrial microalga Trebouxia sp.(chlorophyta). Planta2015; 242: 493–505.
11.
DwarakanathPRAbinayaKNagasathyaK, et al.Profiling secondary metabolites from lichen “Parmotrema perlatum (huds.) M.choisy” and antibacterial and antioxidant potentials. Biomass Convers Bior2022. https://doi.org/10.1007/s13399-022-03572-0
12.
RavichandranNSBhaskarA. Invitro antioxidant and antibacterial activity of edible lichen: parmotrema Perlatum. Euro J Mol Clin Med2020; 7: 10.
13.
HussainMBakhshHSyedSK, et al.The spasmolytic, bronchodilator, and vasodilator activities of parmotrema perlatum are explained by anti-muscarinic and calcium antagonistic mechanisms. Molecules2021; 26: 6348.
14.
DeviKVJyothiMV. Exploration of phytoconstituents, antitubercular & antimicrobial potential of acclaimed spices-Ceiba pentandra and Parmotrema perlatum. In: ElshimaliJYI (ed.) Current overview on pharmaceutical science. vol. 7. B P International, India, 2023, pp. 37–46.
15.
SieteiglesiasVGonzález-BurgosEBermejo-Bescós, et al.Lichens of parmelioid clade as promising multitarget neuroprotective agents. Chem Res Toxicol2019; 32: 1165–1177.
16.
Olivier-JimenezDChollet-KruglerMRondeauD, et al.A database of high-resolution MS/MS spectra for lichen metabolites. Sci Data2019; 6: 694.
17.
ThadhaniVMMusharrafSGAliA. Sensitive analysis of secondary metabolites in different lichen species using liquid chromatography–mass spectrometry: a review. In: Studies in natural product chemistry. vol. 70. Amsterdam, Netherlands: Elsevier, 2021, pp. 23–49.
18.
Eifler-LimaVLSperryASinbandhitS, et al.NMR Spectral data of salazinic acid isolated from some species of parmotrema. Magn Reson Chem2000; 38: 472–474.
19.
AlbornozLTorres-BenítezAMoreno-PalaciosM, et al.Phylogenetic studies and metabolite analysis of Sticta Species from Colombia and Chile by ultra-high performance liquid chromatography-high resolution-Q-orbitrap-mass spectrometry. Metabolites2022; 12: 156.
20.
Coassini-LokarLNimisPLGeattiM. Chemistry and chorology of the genus parmotrema massai (lichenes parmeliaceae) in Italy: Chemotassonomia e corologia del genere parmotrema (licheni parmeliacee) in italia. Webbia1987; 41: 125–142.
21.
HuneckSYoshimuraI. Identification of lichen substances. Berlin, Heidelberg: Springer, 1996.
22.
PapadopoulouPTzakouOVagiasC, et al. β-orcinol metabolites from the lichen Hypotrachyna revoluta. Molecules2007; 12: 997–1005.
23.
KerbouaMAhmedMASambaN, et al.Phytochemical investigation of new Algerian lichen Species: Physcia Mediterranea nimis. Molecules2021; 26: 1121.
24.
RajanVPGunasekaranSRamanathanS, et al.Biological activities of four Parmotrema species of Malaysian origin and their chemical constituents. J Appl Pharm Sci2016; 6: 36–43.
25.
KerbouaMMoniaAASambaN, et al.Phytochemical composition of lichen Parmotrema hypoleucinum (J. Steiner) hale from Algeria. Molecules2022; 27: 5229.
26.
MichelettiACBeatrizADe LimaDP, et al.Constituintes químicos de Parmotrema lichexanthonicum Eliasaro & Adler - isolamento, modificações estruturais e avaliação das atividades antibiótica e citotóxica. Quim Nova2009; 32: 12–20.
27.
MarcelliMPBenattiMNElixJA. New species of Parmotrema containing protocetraric or stictic acids from the coast of São Paulo state, southeastern Brazil. Mycotaxon2008; 105: 235–248.
28.
WhitePASOliveiraRCMOliveiraAP, et al.Antioxidant activity and mechanisms of action of natural compounds isolated from lichens: a systematic review. Molecules2014; 19: 14496–14527.
29.
SalgadoFAlbornozLCortézC, et al.Secondary metabolite profiling of Species of the genus Usnea by UHPLC-ESI-OT-MS-MS. Molecules2017; 23: 54.
30.
JayaprakashaGKRaoLJ. Phenolic constituents from the lichen Parmotrema stuppeum (Nyl.) hale and their antioxidant activity. Zeitschrift für Naturforschung C2000; 55: 1018–1022.
31.
LuXZhaoXBaiC, et al.LC–MS-based metabonomics analysis. J Chromatogr B2008; 866: 64–76.
32.
SegersKDeclerckSMangelingsD, et al.Analytical techniques for metabolomic studies: A review. Bioanalysis2019; 11: 2297–2318.
33.
ZekiÖCEylemCCReçberT, et al.Integration of GC–MS and LC–MS for untargeted metabolomics profiling. J Pharm Biomed Anal2020; 190: 113509.
34.
CalcottMJAckerleyDFKnightA, et al. Secondary metabolism in the lichen symbiosis. Chem Soc Rev2018; 47: 1730–1760.
35.
XuMHeidmarssonSThorsteinsdottirM, et al.Authentication of Iceland moss (Cetraria islandica) by UPLC-QToF-MS chemical profiling and DNA barcoding. Food Chem2018; 245: 989–996.
36.
Torres-BenítezAOrtega-ValenciaJESánchezM, et al.UHPLC-MS Chemical fingerprinting and antioxidant, enzyme inhibition, anti-inflammatory in silico and cytoprotective activities of Cladonia chlorophaea and C. gracilis (cladoniaceae) from Antarctica. Antioxidants2022; 12: 10.
37.
KonorevaLProkopievIFrolovI, et al.Metabolite profiling of the Cladonia lichens using gas chromatography-mass spectrometry. Biochem Syst Ecol2019; 85: 3–12.
38.
StaplesRLaDucaRLRozeLV, et al.Structure and chemical analysis of major specialized metabolites produced by the lichen Evernia prunastri. Chem Biodiversity2020; 17: e1900465.
39.
Torres-BenítezAOrtega-ValenciaJESanchezM, et al.Metabolomic profiling, antioxidant and enzyme inhibition properties and molecular docking analysis of antarctic lichens. Molecules2022; 27: 8086.
40.
ParrotDJanSBaertN, et al.Comparative metabolite profiling and chemical study of Ramalina siliquosa complex using LC–ESI-MS/MS approach. Phytochemistry2013; 89: 114–124.
41.
NorouziHAziziAGholamiM, et al.Chemotype variations among lichen ecotypes of Umbilicaria aprina as revealed by LC-ESI-MS/MS: A survey of antioxidant phenolics. Environ Sci Pollut Res2020; 27: 40296–40308.
42.
FarkasEKursinszkiLSzőkeÉ, et al.New chemotypes of the lichens Xanthoparmelia pulvinaris and X. Subdiffluens (Parmeliaceae, Ascomycota). Herzogia2015; 28: 679–689.
43.
MusharrafSGKanwalNThadhaniVM, et al.Rapid identification of lichen compounds based on structure-fragmentation relationship using ESI-MS/MS analysis. Anal Methods2015; 7: 6066–6076.
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