Phytochemical Investigation of New Algerian Lichen Species: Physcia Mediterranea Nimis
Abstract
:1. Introduction
2. Results and Discussion
2.1. GC-MS Analysis
2.2. HPLC-ESI-MS-MS Analysis
2.2.1. WA-hex Extract Analysis of Physcia mediterranea
2.2.2. ME-hex Extract Analysis of Physcia mediterranea
2.3. NMR Analysis
3. Materials and Methods
3.1. Lichen Material
3.2. Sample Preparation
3.3. Preparation of Physcia mediterranea Extracts
3.4. Instrumentation and Analysis Parameters
3.4.1. GC-MS Analysis
3.4.2. NMR Analysis
3.4.3. HPLC-ESI-MS-MS
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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N° | RT | Compound | Mass | % | Synonyms | |
---|---|---|---|---|---|---|
1 | 19:56 | Methyl 2-hydroxy-4-methoxy-6-methylbenzoate | 196 | 0.3 | Orsellinic Acid Methyl Ester 4-Methyl Ether (Sparassol) | C10H12O4 |
2 | 20:01 | Methyl 2,4-dihydroxy-3,5,6-trimethylbenzoate | 210 | 52.3 | Derivatives of methylbenzoic acids | C11H14O4 |
3 | 20:43 | Methyl 4-hydroxy-2-methoxy-3,6-dimethylbenzoate | 210 | 1.1 | 2-metoxy-Atraric acid | C10H12O4 |
4 | 20:64 | Methyl 2,4-dihydroxy-3,6-dimethylbenzoate | 196 | 2.3 | Atraric acid | C10H12O4 |
5 | 22:55 | Methyl hexadecanoate | 270 | 24.2 | Palmitic acid | C16H32O2 |
6 | 23:53 | 13-Methyl-17-norkaur-15-ene | 272 | 2.4 | Linoleic acid | C18H32O2 |
7 | 24:19 | Methyl cis, cis-9,12-octadecadienoate | 294 | 3.2 | Oleic acid | C18H34O2 |
8 | 24:25 | Methyl (Z)-9-octadecenoate | 296 | 4.9 | Stearic acid | C18H34O2 |
9 | 24:48 | Methyloctadecanoate | 298 | 3.8 | (−)-ent-Kauran-16α-ol | C2OH34O |
10 | 26:21 | Unknown | 376 | 2.2 | Unknown | |
T% | 95.5 |
N° | RT | [M − H]− | TM | MM | MT | Compounds Identification |
---|---|---|---|---|---|---|
1 | 0.03 | 146.9397 | 147.9475 | C4H4O6 | A | Dihydroxyfumaric acid |
2 | 1.80 | 116.9276 | 117.9354 | C4H6O4 | A | Butendioic acid |
3 | 2.72 | 187.0971 | 188.1049 | C9H16O2 | A | 3,5-dimethoxyciclohexanecarboxylic acid |
4 | 5.51 | 163.0395 | 164.0473 | C9 H8 O3 | B | p-Coumaric acid |
5 | 6.57 | 227.1286 | 228.1364 | C12H20O4 | A | Trans-dodec-2-enedioic acid (traumatic acid) |
6 | 7.46 | 282.2077 | 283.2155 | C16 H29 NO3 | A | N-dodecanoyl-l-Homoserine lactone |
7 | 8.09 | 174.9556 | 175.9634 | C5 H4 O7 | A | 2-Hydroxy-3,4-dioxopentanedioc acid |
8 | 8.15 | 293.1762 | 294.1840 | C17H26O4 | B | Gingerol |
9 | 14.37 | 295.2280 | 296.2358 | C18 H32 O3 | A | 18-Hydroxylinoleic acid |
10 | 15.36 | 177.0186 | 178.0264 | C9 H6 O4 | B | 6,7-Dihydroxycoumarin (esculetin) |
11 | 15.44 | 373.0929 | 374.1007 | C19 H18 O8 | C | Atranorin |
12 | 16.47 | 407.0539 | 408.0617 | C19 H17 O8Cl | C | Chloroatranorin |
13 | 17.57 | 277.2175 | 278.2203 | C18H30O2 | A | Octadeca-9,12,15-trienoic acid (linolenelaidic acid) |
14 | 17.77 | 265.1480 | 266.1558 | C15 H22 O4 | A | (4E,6E,9E)-Pentadeca-4,6,9-trienedioic acid |
15 | 18.03 | 253.2331 | 254.2249 | C16 H30 O2 | A | Palmitoleic acid |
16 | 18.34 | 241.2173 | 242.2251 | C15H30O2 | A | Pentadecanoic acid |
17 | 18.50 | 279.0936 | 280.2409 | C18 H32 O2 | A | Linoleic acid |
18 | 18.91 | 267.2331 | 268.2409 | C17 H32 O2 | A | cis-9-Heptadecenoic acid (margaroleic acid) |
19 | 19.15 | 255.2329 | 256.2407 | C16 H32 O2 | A | Palmitic acid |
20 | 19.35 | 459.3271 | 460.3349 | C25H48O7 | Unknown | Unknown |
21 | 19.51 | 281.2487 | 282.2565 | C18 H34 O2 | A | Oleic acid |
22 | 19.75 | 459.3272 | 460.3350 | C25 H48 O7 | A | Methyl glucose isostearate |
23 | 19.89 | 269.2488 | 270.2566 | C17 H34 O2 | A | Heptadecanoic acid (margaric acid) |
24 | 19.99 | 307.2645 | 308.2723 | C20 H36 O2 | A | 11,14-Eicosadienoic acid |
25 | 20.07 | 457.3722 | 458.3800 | C27 H54 O5 | Unknown | Unknown |
26 | 20.18 | 295.2645 | 296.2723 | C19H36O2 | A | 10E-nonadecenoic acid |
27 | 20.54 | 283.2643 | 284.2721 | C18 H36 O2 | A | Stearic acid (octadecanoic acid) |
28 | 20.82 | 309.2800 | 310.2878 | C20 H38 O2 | A | Eicosenoic acid (gondoic acid) |
29 | 21.71 | 311.2957 | 312.3035 | C20H40O2 | A | Arachidic acid (eicosanoic acid) |
30 | 22.62 | 297.1532 | 298.1610 | C12H26O8 | Unknown | Unknown |
31 | 22.77 | 339.3268 | 340.3346 | C22H44O2 | A | Docosanoic acid (behenic acid) |
32 | 23.08 | 309.1743 | 310.1821 | C17 H26 O5 | D | Portentol |
33 | 23.58 | 353.2003 | 354.2081 | C19H30O6 | Unknown | Unknown |
34 | 23.81 | 311.1689 | 312.1767 | C13 H30 O8 | Unknown | Unknown |
35 | 23.89 | 367.3579 | 368.3657 | C24H48O2 | A | Lignoceric acid (tetracosanoic acid) |
36 | 24.01 | 397.2266 | 398.2344 | C21H34O7 | D | Stephanol |
37 | 24.60 | 293.1793 | 294.1871 | C17H26O4 | A | Heptadecatrienedioic acid |
38 | 24.94 | 325.1844 | 326.1922 | C14 H30 O8 | Unknown | Unknown |
39 | 25.33 | 395.3895 | 396.3973 | C26H52O2 | A | Hexacosanoic acid or cerotic acid |
40 | 25.89 | 337.2055 | 338.2133 | C19 H30 O5 | A | 6-Oxononadeca-8,11-dienedioic acid |
41 | 26.10 | 339.2000 | 340.2078 | C15 H32 O8 | Unknown | Unknown |
42 | 26.24 | 381.2317 | 382.2395 | C21 H34 O6 | A | 19-Acetoxylichesterinic acid |
43 | 26.75 | 425.2581 | 426.2659 | C23H38O7 | E | Asebotoxin I |
44 | 27.53 | 321.2106 | 322.2184 | C19H30O4 | A | Nonadecatrienedioic acid |
45 | 27.85 | 304.9143 | 305.9221 | Unknown | Unknown | Unknown |
N° | RT | [M – H]− | TM | MM | MT | Compounds | MS2 Ions |
---|---|---|---|---|---|---|---|
1 | 2.72 | 187.0970 | 188.1043 | C9H16O4 | A | 3,5-Dimethoxyciclohexanecarboxylic acid | 141.8670; 123.0807 |
2 | 2.75 | 293.0669 | 294.0741 | C14H14O7 | A | 6-(Hydroxymethyl)-3,5-bis(methoxycarbonyl)-2,4-dimethylcyclohex-1-ene-1-carboxylic acid | 234.0530; 207.0695 |
3 | 3.08 | 243.1239 | 244.1311 | C12H20O5 | A | 3,5,6-Hydroxymethyl-2,4-dimethylcyclohex-1-ene-1-carboxylic acid | 183.1025; 176.6474 |
4 | 3.15 | 151.0393 | 152.0465 | C8H8O3 | B | Atranol | 123.0444; 105.0335; 81.0335 |
5 | 3.20 | 225.1129 | 226.1201 | C12H18O4 | A | 5-Formyl-3-hydroxymethyl-2,4,6-trimethylcyclohex-1-ene-1-carboxylic acid | 207.1023; 97.0284 |
6 | 3.47 | 199.0973 | 200.1046 | C10H16O4 | A | 3,5-Dihydroxy-2,4,6-trimethylciclohexenecarboxilic acid | 183.4492; 162.8385; 114.9508 |
7 | 3.58 | 149.0237 | 150.0310 | C8H6O3 | C | 4-Formylbenzoic acid | − |
8 | 3.82 | 241.1081 | 242.1153 | C12H18O5 | A | 5-Formyl-3,6-dihydroxymethyl-2,4-dimethylcyclohex-1-enecarboxylic acid | 218.816; 172.6485 |
9 | 4.10 | 201.1129 | 202.1202 | C10H18O4 | A | 2,4-Dihydroxy-3,5,6-trimethylcyclohexane-1-carboxylic acid | 197.6263; 164.8350; 139.1124 |
10 | 4.95 | 199.1337 | 200.1409 | C11H20O3 | A | 2-Hydroxy-10-undecenoic acid | − |
11 | 5.00 | 185.0006 | 186.0079 | C8H7ClO3 | B | Chloroatranol | − |
12 | 5.21 | 169.0863 | 170.0936 | C9H14O3 | A | 4-Hydroxy-2,5-dimethylcyclohex-1-ene-1-carboxylic acid | 124.9796; 104.4180 |
13 | 5.49 | 163.0392 | 164.0470 | C9H8O3 | D | p-Coumaric acid | − |
14 | 5.60 | 209.1181 | 210.1253 | C12H18O3 | A | 6-(1-Oxopentyl)-1-cyclohexene-1-carboxylic acid | 146.9850; 105.0336 |
15 | 5.87 | 215.1286 | 216.1359 | C11H20O4 | A | Undecanedioic acid | − |
16 | 6.57 | 227.1288 | 228.1360 | C12H20O4 | A | trans-Dodec-2-enedioic acid | − |
17 | 7.44 | 282.2078 | 283.2150 | C16H29NO3 | A | N-Dodecanoyl-l-Homoserine lactone | − |
18 | 9.53 | 243.1601 | 244.1675 | C13H24O4 | A | Tridecanedioic acid | − |
19 | 10.59 | 311.2230 | 312.2302 | C18H32O4 | A | 9Z-Octadecenedioic acid | − |
20 | 10.87 | 233.1547 | 234.1619 | C15H22O2 | E | Fukinanolide | − |
21 | 10.89 | 323.2230 | 324.2303 | C19H32O4 | F | allo-Protolichesterinic acid | − |
22 | 12.28 | 313,2388 | 314.2266 | C18H34O4 | A | Octadecanedioic acid | − |
23 | 13.04 | 389.1245 | 390.1315 | C20H22O8 | B | 8-Hydroxydiffractaic acid | − |
24 | 13.34 | 293.2124 | 294.2202 | C18H30O3 | A | 2-Hydroxylinolenic acid | − |
25 | 13.58 | 291.1968 | 292.2041 | C18H28O3 | A | α-Licanic acid | − |
26 | 14.38 | 295.2279 | 296.2351 | C18H32O3 | A | 2-Hydroxylinoleic acid | − |
27 | 14.40 | 295,2278 | 296,2352 | C18H32O3 | A | 18-hydroxylinoleic acid | − |
28 | 15.19 | 297.2436 | 298.2508 | C18H34O3 | A | 9-Oxooctadecanoic acid | − |
29 | 15.25 | 295.2280 | 296.2351 | C18H32O3 | A | Coriolic acid | − |
30 | 15.36 | 297.2435 | 298.2508 | C18H34O3 | A | Ricinoleic acid | − |
31 | 15.43 | 177.0187 | 178.0259 | C9H6O4 | D | 6,7-Dihydroxycoumarin | − |
32 | 15.46 | 365.2330 | 366.2403 | C21H34O5 | G | Muronic acid | − |
33 | 16.37 | 471.3481 | 472.3553 | C30H48O4 | Unknown | Unknown | − |
34 | 16.47 | 210.9834 | 211.9873 | C9H5ClO4 | H | 7-chloro-3-oxo-1,3-dihydroisobenzofuran-5-carboxylic acid | 138.9948, 103.0180 |
35 | 16.51 | 407.0540 | 408.0611 | C19H17ClO8 | B | Chloroatranorin | − |
36 | 17.59 | 387.2544 | 388.2616 | C24H36O4 | Unknown | Unknown | − |
37 | 17.68 | 389.1242 | 390.1314 | C20H22O8 | I | Leprolomin | − |
38 | 18.04 | 253.2173 | 254.2244 | C16H30O2 | A | Palmitoleic acid | − |
39 | 18.33 | 241.2172 | 242.2245 | C15H30O2 | A | Pentadecanoic acid | − |
40 | 18.35 | 455.3531 | 456.3605 | C30H48O3 | G | Ursolic acid | − |
41 | 18.50 | 279.2330 | 280.2403 | C18H32O2 | A | Linoleic acid | − |
42 | 18.66 | 299.2595 | 300.2667 | C18H36O3 | A | 2-Hydroxyoctadecanoic acid | − |
43 | 18.78 | 279.2332 | 280.2403 | C18H32O2 | A | Linoleic acid | − |
44 | 19.16 | 255.2329 | 256.2401 | C16H32O2 | A | Palmitic acid | − |
45 | 19.49 | 281.2485 | 282.2559 | C18H34O2 | A | Oleic acid | − |
46 | 19.62 | 269.2488 | 270.2561 | C17H34O2 | A | 15-Methylhexadecanoic acid | − |
47 | 19.89 | 269.2488 | 270.2561 | C17H34O2 | A | Heptadecanoic acid | − |
48 | 20.07 | 327.2543 | 328.2616 | C20H40O3 | A | 2-Hydroxyeicosanoic acid | − |
49 | 20.54 | 283.2643 | 284.2716 | C18H36O2 | A | Stearic acid (octadecanoic acid) | − |
50 | 20.74 | 309.2801 | 310.2875 | C20H38O2 | A | Eicosenoic acid (Gondoic acid) | − |
51 | 21.14 | 297.2801 | 298.2873 | C19H38O2 | A | Nonadecanoic acid | − |
52 | 21.70 | 311.2957 | 312.3029 | C20H40O2 | A | Arachidic acid (Eicosanoic acid) | − |
53 | 22.68 | 637.4841 | 638.4908 | C41 H66 O5 | Unknown | Unknown | − |
54 | 24.51 | 605.3483 | 606. 3561 | C37H50O7 | Unknown | Unknown | − |
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Kerboua, M.; Ahmed, M.A.; Samba, N.; Aitfella-Lahlou, R.; Silva, L.; Boyero, J.F.; Raposo, C.; Lopez Rodilla, J.M. Phytochemical Investigation of New Algerian Lichen Species: Physcia Mediterranea Nimis. Molecules 2021, 26, 1121. https://doi.org/10.3390/molecules26041121
Kerboua M, Ahmed MA, Samba N, Aitfella-Lahlou R, Silva L, Boyero JF, Raposo C, Lopez Rodilla JM. Phytochemical Investigation of New Algerian Lichen Species: Physcia Mediterranea Nimis. Molecules. 2021; 26(4):1121. https://doi.org/10.3390/molecules26041121
Chicago/Turabian StyleKerboua, Marwa, Monia Ali Ahmed, Nsevolo Samba, Radhia Aitfella-Lahlou, Lucia Silva, Juan F. Boyero, Cesar Raposo, and Jesus Miguel Lopez Rodilla. 2021. "Phytochemical Investigation of New Algerian Lichen Species: Physcia Mediterranea Nimis" Molecules 26, no. 4: 1121. https://doi.org/10.3390/molecules26041121