Table 1 MS/MS-based characterization of R. sinensis compounds extracted with different solvents

Tentative identification

Chemical formula of [M-H]⁻

R_t (min)

Calculated mass

[M-H]⁻ m/z

MS² ions

Type of extract

Structure

Acetone

Methanol

Chromones

 6-Hydroxymethyl eugenitin

C₁₂H₁₁O₅

11.80

235.0606

235

235, 232, 220, 207, 190, 164, 148, 137, 83, 79, 73

 + 

-

 Lepraric acid

C₁₈H₁₇O₈

13.10

361.0923

361

235, 220, 207, 191

 + 

-

Depsides

 Ramalinaic acid

C₁₈H₁₅O₈

11.90

359.0766

359

343, 326, 323, 301, 283, 275, 257, 229, 215, 83

 + 

-

 Subsekikaic acid

C₂₀H₂₁O₈

15.16

389.1236

389

389, 343, 328, 325, 315, 301, 299, 286, 259, 231, 220, 180, 139, 95, 83

 + 

-

 2-O-Methyldivaricatic acid

C₂₂H₂₅O₇

12.94

401.1600

401

356, 342, 325, 282, 270, 226, 218, 181, 96, 68

-

 + 

 Stenosporic acid

C₂₃H₂₇O₇

13.54

415.1756

415

370, 355, 343, 338, 326, 314, 231, 160

 + 

 + 

 Perlatolic acid

C₂₅H₃₁O₇

14.43

443.2069

443

398, 366, 357, 339, 326, 313, 297, 259, 258, 218

 + 

-

 2'-O-Methylperlatolic acid

C₂₆H₃₃O₇

15.00

457.2226

457

412, 397, 386, 354, 340, 314, 297, 239, 214, 180, 94

-

 + 

 Squamatic acid

2 M-2H + Na

15.10

801.164

802

412, 391, 389

-

-

Tentative identification

Chemical formula of [M-H]⁻

R_t (min)

Calculated mass

[M-H]⁻ m/z

MS² ions, m/z

Type of extract

Structure

Acetone

Methanol

Dibenzofurans

 Isousnic acid

13.58

342

312, 286, 231, 82

 + 

-

 Usnic acid

C₁₈H₁₅O₇

15.44

343.0817

343

328, 313, 299, 259, 231, 215, 189, 83

 + 

 + 

 Placodiolic acid

C₁₉H₁₉O₈

14.47

375.1079

375

375, 373, 357, 343, 328, 315, 299, 255, 247, 234, 231, 215, 180, 83

 + 

-

 Usnic acid

2 M-2H + Na

15.42

709.153

710

343, 328

 + 

 + 

 Pseudoplacodiolic acid

2 M-2H + Na

14.51

773.206

774

774, 375, 233

-

 + 

Depsidones

 Virensic acid

12.95

356

341, 326, 313, 311, 299, 297, 284, 272, 267, 243, 231, 177, 163, 96, 59

-

 + 

 Norstictic acid

C₁₈H₁₁O₉

13.49

371.0403

371

369, 340, 338, 326, 323, 313, 309, 299, 231, 216, 207, 110, 79

-

 + 

 Conprotocetraric acid

C₁₈H₁₆O₉

14.47

376.0794

376

343, 328, 315, 301, 299, 291, 286, 283, 271, 259, 256, 244, 231, 227, 196, 187, 180, 95, 82, 55

-

 + 

Tentative identification

Chemical formula of [M-H]⁻

R_t (min)

Calculated mass

[M-H]⁻ m/z

MS² ions, m/z (relative intensity)

Type of extract

Structure

Acetone

Methanol

Depsidones

 Methylstictic acid

C₂₀H₁₅O₉

11.18

399.0716

399

383, 368, 354, 325, 314, 300, 286, 256, 231, 225, 189, 94

 + 

 + 

 Gangaleoidin

C₁₈H₁₄Cl₂O₇

14.99

412.0116

412

395, 354, 326, 312, 310, 299, 164, 151, 136

-

 + 

Terpenoids

  (-)-ent-Kauran-16α-ol

(Ceruchinol)

C₂₀H₃₃O

11.06

289.2531

289

288, 260, 231, 182, 117

-

-

Fatty acids

 Nephrosterinic acid

C₁₇H₂₇O₄

14.19

295.1909

295

277 (100), 195 (21), 183 (37), 180 (9), 171 (23), 164 (11), 108 (12), 97 (14)

 + 

 + 

 Arachidonic acid

C₂₀H₃₁O₂

11.80

303.2324

304

259, 244, 231, 215, 203, 189, 161, 83

 + 

-

Monocyclic aromatic

 Atranol

C₈H₇O₃

1.58

151.0395

151

87, 71, 59, 55, 43, 41

 + 

 + 

 Olivetolic acid

C₁₂H₁₅O₄

12.55

223.0970

223

223, 207, 181, 163, 148, 137, 123, 121, 119, 95, 83, 79

 + 

-

Polyols

 meso-Erythritol

C₄H₁₀O₄

8.20

122.0579

121

121, 119, 92, 65

 + 

-

Pulvinic acid derivatives

 Leprapinic acid

C₂₀H₁₆O₆

11.97

352.094

351

288, 276, 259, 244, 231, 232, 216, 205, 158, 83, 68

 + 

-

 Leprapinic acid

2 M-2H + Na

8.80

725.163

725

679, 678, 677

-

 + 

Unknown compounds

 Unknown

-

9.20

-

187

187, 169, 151, 125, 123, 97, 95, 80, 57

 + 

-

 2-heptyl-4,6-dimethoxy-3-methylbenzoic acid

C₁₇H₂₆O₄

10.11

294.183

293

234, 250, 221, 207, 181, 178

 + 

-

 Trihydroxyoctadecenoic acid

C₁₈H₃₄O₅

10.72

330.240

330

329, 229, 211, 201, 171, 156, 139, 127

 + 

-

 Unknown

-

12.00

-

360

303, 302, 301

-

 + 

 Unknown

-

14.38

-

390

389, 387, 371, 369, 273, 201

 + 

 + 

 Unknown

-

8.67

-

742

-

-

 Unknown

-

13.10

-

746

745, 383, 361, 235

 + 

-