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. 2022 Aug 16;27(16):5229.
doi: 10.3390/molecules27165229.

Phytochemical Composition of Lichen Parmotrema hypoleucinum (J. Steiner) Hale from Algeria

Marwa Kerboua  1 , Ali Ahmed Monia  1 , Nsevolo Samba  2   3 , Lúcia Silva  2   4 , Cesar Raposo  5 , David Díez  6 , Jesus Miguel Rodilla  2   4
Affiliations

Phytochemical Composition of Lichen Parmotrema hypoleucinum (J. Steiner) Hale from Algeria

Marwa Kerboua et al. Molecules. .

Abstract

In this work, we carried out studies of the chemical composition of hexane, chloroform and ethanol extracts from two samples of the lichen Parmotrema hypoleucinum collected in Algeria. Each sample of the lichen P. hypoleucinum was collected on two different supports: Olea europaea and Quercus coccifera. Hexane extracts were prepared, in Soxhlet; each hexane extract was fractionated by its solubility in methanol; the products soluble in methanol were separated (cold): 1-Hexane, 2-Hexane; and the products insoluble in methanol (cold): 1-Cires, 2-Cires. A diazomethane esterified sample of 1-Hexane, 2-Hexane, 1-Cires and 2-Cires was analyzed by GC-MS, and the components were identified as methyl esters. In the 1-Hexane and 2-Hexane fractions, the methyl esters of the predominant fatty acids in the lichen were identified: palmitic acid, linoleic acid, oleic acid and stearic acid; a hydrocarbon was also identified: 13-methyl-17-norkaur-15-ene and several derivatives of orsellinic acid. In the 1-Cires and 2-Cires fractions, the previous fatty acids were no longer observed, and only the derivatives of orsellinic acid were found. The analysis of the 1-Hexane, 2-Hexane fractions by HPLC-MS/MS allows us to identify different chemical components, and the most characteristic products of the lichen were identified, such as Atranol, Chloroatranol, Atranorin and Chloroatranorin. In the fractions of 1-Cires and 2-Cires, the HPLC-MS/MS analysis reveals that they are very similar in their chemical components; the characteristic products of this lichen in this fraction are Atranorin and Chloroatranorin. In the extracts of chloroform, 1-Chloroform and 2-Chloroform, the analysis carried out by HPLC-MS/MS shows small differences in their chemical composition at the level of secondary products; among the products to be highlighted for this work, we have chloroatranorin, the stictic acid, norstictic acid and other derivatives. In the analysis of the most polar extracts carried out in ethanol: 1-Ethanol and 2-Ethanol, HPLC-MS/MS analysis shows very similar chemical compositions in these two extracts with small differences. In these extracts, the following acids were identified as characteristic compounds of this lichen: constictic acid, stictic acid, substictic acid and methylstictic acid. In the HPLC-MS/MS analysis of all these extracts, alectoronic acid was not found.

Keywords: LC-MSD-Trap-XCT; Parmotrema hypoleucinum; lichen; norstictic acid and stictic acid; phytochemical composition.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Biosynthetic pathways of lichen secondary metabolites (Elix, 1996; Stocker wörgötter, 2008).
Figure 2
Figure 2
Chromatogram of Hexane extract part soluble in MeOH esterified with diazomethane, 1-Hexane.
Figure 3
Figure 3
Chromatogram of Hexane extract part soluble in MeOH esterified whit diazomethane, 2-Hexane.
Figure 4
Figure 4
Chromatogram of Hexane extract part insoluble in MeOH esterified whit diazomethane, 1-Cires.
Figure 5
Figure 5
Chromatogram of Hexane extract part insoluble in MeOH esterified whit diazometane, 2-Cires.
Figure 6
Figure 6
Chromatogram of Hexane extract part soluble in MeOH, 1-Hexane.
Figure 7
Figure 7
Chromatogram of Hexane extract part soluble in MeOH esterified whit diazomethane, 2-Hexane.
Figure 8
Figure 8
Chromatogram of Hexane extract part insoluble in MeOH, 1-Cires.
Figure 9
Figure 9
Chromatogram of Hexane extract part insoluble in MeOH, 2-Cires.
Figure 10
Figure 10
Chromatogram of 1-Chloroform extract from P. hypoleucinum.
Figure 11
Figure 11
Chromatogram of 2-Chloroform extract from P. hypoleucinum.
Figure 12
Figure 12
Chromatogram of 1-Ethanol extract from P. hypoleucinum.
Figure 13
Figure 13
Chromatogram of 2-Ethanol extract from P. hypoleucinum.
Figure 14
Figure 14
Location of El Kala National Park (P.N.E.K., 2010).
See this image and copyright information in PMC

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