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Table 1 LC-MS/MS identified compounds present in anti-malarial active methanol extract of Andrographis paniculata

From: Secondary metabolite profiling and characterization of diterpenes and flavones from the methanolic extract of Andrographis paniculata using HPLC-LC-MS/MS

S. No. RT (Min) Purity percentage (%) Molecular weight (g/mol) Molecular formula Class of identified compounds LC-MS (Obtained mass, m/z) Predicted structure
Positive mode (ES+)
 1 1.13 5 358.346 5-Hydroxy-7,8,2',5'tetramethoxyflavone (C19H18O7) Flavone 381.1 (M+Na)
 2 3.83 7 332.44 14-Deoxy-11,12-didehydroandrographolide (C20H28O4) Diterpenoid 355.1 (M+Na)
 3 4.28 8 328.32 5-Hydroxy-2',7,8-trimethoxyflavone (C18H16O6) Flavone 329.1 (M+1)
 4 8.32 12 296.41 Andrographolactone (C20H24O2) Diterpenoid 297.2 (M+1)
 5 8.32 8 314.29 Skullcapavone I (C17H14O6) Flavone 315.2 (M+1)
 6 8.82 7 364.43 Andrographic acid (C20H28O6) Diterpenoid 447.1 (M+1+2ACN)
 7 9.49 15 350.455 Andrographolide (C20H30O5) Diterpenoid 351.2 (M+1)
 8 10.71 1 350.455 Andrographolide (C20H30O5)
(diastereomers)
Diterpenoid 701.5 (2M+1)
 9 10.71 2 332.44 14-Deoxy-11,12-didehydroandrographolide (C20H28O4) (diastereomers) Diterpenoid 333.2 (M+1)
 10 11.16 4 496.597 Andropanoside (C26H40O9) Diterpenoid 993.6 (2M+1)
 11 11.79 1 300.266 5,8,2'-Trihydroxy-7-methoxyflavone (C16H12O6) Flavone 301.1 (M+1)
 12 12.01 1 298.29 7-O-Methylwogonin (C17H14O5) Flavone 299.1 (M+1)
 13 13.18 3 318.457 Andrograpanin (C20H30O3) Diterpenoid 319.3 (M+1),
 14 13.18 9 480.598 Neoandrographolide (C26H40O8) Diterpenoid 481.3 (M+1)
 15 13.18 1 480.598 Neoandrographolide (C26H40O8)
(diastereomers)
Diterpenoid 499.3 (M+1+H2O)
 16 13.67 2 318.457 Andrograpanin (C20H30O3) (diastereomers) Diterpenoid 584.3, 319.2 (M+1)
 17 13.96 3 334.456 14-Deoxyandrographiside (C20H30O4) Diterpenoid 669.4 (2M+1)
 18 14.07 5 664.88 Bisandrographolide A (C40H56O8) Diterpenoid 665.4 (M+1)
 19 16.29 1 300.266 5,8,2'-Trihydroxy-7-methoxyflavone
(C16H12O6) (diastereomers)
Flavone 301.1 (M+1)
 20 16.66 1 358.346 5-Hydroxy-7,8,2',5'tetramethoxyflavone (C19H18O7) (diastereomers) Flavone 359.2 (M+1)
 21 20.58 1 350.455 Andrographolide (C20H30O5) (diastereomers) Diterpenoid 723.6 (2M+Na)
 22 20.74 1 611.70 19-O-[β-D-Apiofuranosyl(1f2)-β-D-glucopyranoyl]-3,14-dideoxyandrographolide (C31H47O12) Diterpenoid 634.5 (M+Na) -
 23 29.70 1 351.20 3,15,19-trihydroxy-ent-labda-8(17),13-dien-16-oicacid (C20H30O5) Diterpenoid 352.3 (M+1) -
 24 33.78 1 352.42 7-Hydroxy-14-deoxyandrographolide (C19H28O6) Diterpenoid 353.4 (M+1)
 25 33.99 1 352.42 7-Hydroxy-14-deoxyandrographolide (C19H28O6) (diastereomers) Diterpenoid 353.3 (M+1)
Negative Mode (ES-)
 1 1.12 1 342.347 Tetramethoxyflavone (C19H18O6) Flavone 341.2 (M-1)
 2 1.12 2 342.347 Tetramethoxyflavone (C19H18O6) (diastereomers) Flavone 377.1 (M+Cl)
 3 1.43 3 364.47 14-deoxy-12-methoxyandrographolide (C21H32O5) (diastereomers) Diterpenoid 363.2 (M-1) -
 4 2.94 4 476 Skullcapavone I 2'-O-b-D-glucopyranoside Flavone 443.3 (M-1-MeOH) -
 5 3.84 1 352.46 14-Deoxy-17β-hydroxyandrographolide (C20H32O5) (diastereomers) Diterpenoid 351.1(M-1) -
 6 4.29 1 484.6 Ent-Labda-8(17), 13Z-diene-15, 16, 19-triol 19-O-glucoside (C26H44O8) Diterpenoid 505.0 (M+Na-2) -
 7 4.29 1 484.6 Ent-Labda-8(17), 13Z-diene-15, 16, 19-triol 19-O-glucoside (C26H44O8) (diastereomers) Diterpenoid 451.2 (M-1-MeOH) -
 8 5.35 2 388.115 Serpyllin (C20H20O8) Flavone 433.2 (M+formic acid-1) -
 9 5.97 3 332.44 14-Deoxy-11,12-didehydroandrographolide (C20H28O4) (diastereomers) Diterpenoid 367.1 (M+Cl)
 10 6.34 4 368.46 12S-Hydroxyandrographolide (C20H32O6Na) Diterpenoid 413.1 (M+formic acid-1)
 11 6.97 3 522.63 6-acetylneoandrographolide (C28H42O9) Diterpenoid 557.3 (M+Cl)
 12 7.09 15 350.455 Andrographolide (C20H30O5) (diastereomers) Diterpenoid 349.2 (M-1)
 13 7.80 2 350.455 Andrographolide (C20H30O5) (diastereomers) Diterpenoid 349.2 (M-1)
 14 8.11 1 388.115 Serpyllin (C20H20O8) (diastereomers) Flavone 423.2 (M+Cl) -
 15 8.31 3 332.44 14-Deoxy-11,12-didehydroandrographolide (C20H28O4) (diastereomers) Diterpenoid 331.2 (M-1)
 16 9.04 5 480.598 Neoandrographolide (C26H40O8) (diastereomers) Diterpenoid 515.2 (M+Cl)
 17 9.25 1 350.455 Andrographolide(C20H30O5) (diastereomers) Diterpenoid 395.2 (M+formic acid-1)
 18 9.74 3 480.598 Neoandrographolide (C26H40O8) (diastereomers) Diterpenoid 461.1 (M-1-H2O)
 19 9.85 5 364.43 Andrographic acid (C20H28O6) Diterpenoid 363.1 (M-1)
 20 10.06 1 350.455 Andrographolide (C20H30O5) (diastereomers) Diterpenoid 363.2 (M+formic acid-1)
 21   2 664.88 Bisandrographolide A (C40H56O8) (diastereomers) Diterpenoid 685.5 (M+Na-2)
 22 10.24 1 494.57 14-deoxy-11,12-dihydroandrographiside (C26H38O9) Diterpenoid 529.3 (M+Cl)  
 23 10.53 1 497.60 Deoxyandrographiside (C26H41O9) Diterpenoid 542.2 (M+formic acid-1) -
 24 10.72 2 350.455 Andrographolide (C20H30O5) (diastereomers) Diterpenoid 745.5 (2M+formic acid-1)
 25 11.15 1 497.60 Deoxyandrographiside (C26H41O9) (diastereomers) Diterpenoid 542.3 (M+formic acid-1) -
 26 11.53 2 334.456 14-Deoxyandrographolide (C20H30O4) Diterpenoid 333.2 (M-1), 539.3
 27 11.76 2 332.44 14-Deoxy-11,12-didehydroandrographolide (C20H28O4) (diastereomers) Diterpenoid 331.2 (M-1)
 28 12.00 1 522.63 6-acetylneoandrographolide (C28H42O9) (diastereomers) Diterpenoid 567.5 (M+formic acid-1)
 29 12.32 1 332.44 14-Deoxy-11,12-didehydroandrographolide (C20H28O4) (diastereomers) Diterpenoid 331.2 (M-1)
 30 12.71 1 350.455 Andrographolide (C20H30O5) (diastereomers) Diterpenoid 349.2 (M-1)
 31 13.19 2 480.598 Neoandrographolide (C26H40O8) (diastereomers) Diterpenoid 525.3 (M+formic acid-1)
 32 13.33 1 330.42 19-hydroxy-3-oxo-ent-labda-8(17),11,13-trien-16,15-olide (C20H26O4) Diterpenoid 329.3 (M-1) -
 33 13.66 1 522.63 6-acetylneoandrographolide (C28H42O9) (diastereomers) Diterpenoid 521.3 (M-1)
 34 13.85 2 332.44 14-Deoxy-11,12-didehydroandrographolide (C20H28O4) (diastereomers) Diterpenoid 331.3 (M-1)
 35 14.06 1 332.44 14-Deoxy-11,12-didehydroandrographolide (C20H28O4) (diastereomers) Diterpenoid 709.5 (2M+formic acid-1)
 36 14.39 1 522.63 6-acetylneoandrographolide (C28H42O9) (diastereomers) Diterpenoid 567.4 (M+formic acid-1)
 37 15.34 2 664.88 Bisandrographolide A (C40H56O8) (diastereomers) Diterpenoid 663.5 (M-1)
 38 15.63 1 268.39 13,14,15,16-tetranor-ent-labd-8(17)-ene- 3,12,19-triol (C16H28O3) Diterpenoid 267.2 (M-1) -
 39 15.90 1 364.43 Andrographic acid (C20H28O6) (diastereomers) Diterpenoid 727.6 (2M-1)
 40 16.40 2 520.482 5-Hydroxy-7,8,2',5'- tetra- Methoxyflavone 5-O-glucoside (C25H28O12) Flavone 555.4 (M+Cl)
 41 16.81 1 352.42 7-Hydroxy-14-deoxyandrographolide (C19H28O6) (diastereomers) Diterpenoid 397.3 (M+formic acid-1)
 42 16.96 1 294.38 3,19-dihydroxy-14,15,16-trinor-ent-labda-8(17),11-dien-13-oic acid (C17H26O4) (diastereomers) Diterpenoid 293.3 (M-1) -
 43 17.50 1 364.43 Andrographic acid (C20H28O6) (diastereomers) Diterpenoid 325.1 (M-K)
 44 18.10 2 318.457 Andrograpanin (C20H30O3) Diterpenoid 339.2 (M+Na-2)
 45 18.56 1 296.41 Andrographolactone (C20H24O2) (diastereomers) Diterpenoid 295.3 (M-1)
 46 21.60 2 334.456 14-Deoxyandrographolide (C20H30O4) (diastereomers) Diterpenoid 311.3 (M-Na)
 46 24.55 1 300.266 5,8,2'-Trihydroxy-7-methoxyflavone (C16H12O6) Flavone 277.3 (M-Na)
 47 26.99 1 318.457 Andrograpanin (C20H30O3) (diastereomers) Diterpenoid 279.3 (M-K)
 48 30.79 1 294.38 3,19-dihydroxy-14,15,16-trinor-ent-labda-8(17),11-dien-13-oic acid (C17H26O4) (diastereomers) Diterpenoid 255.2 (M-K) -
 49 31.20 1 368.46 12S-Hydroxyandrographolide (C20H32O6Na) Diterpenoid 367.1 (M-1)