Table 3 Identification of compounds present in anti-malarial active extract of Andrographis paniculata by LC-MS/MS analysis
From: Diterpenoids as potential anti-malarial compounds from Andrographis paniculata
Peak No. | RT (Min) | Molecular weight (g/mol) | Molecular formula | Class of identified compounds | LC-MS (obtained mass, m/z) |
|---|---|---|---|---|---|
Positive mode (ES+) | |||||
 1 | 6.58 | 480.598 | Neoandrographolide (C26H40O8) | Diterpenoid | 481.6 (M+1) |
 2 | 9.49 | 350.455 | Andrographolide (C20H30O5) | Diterpenoid | 351.3(M+1) |
 3 | 10.73 | 350.455 | Andrographolide (C20H30O5) | Diterpenoid | 701.5 (2 M+1) |
 4 | 11.29 | 368.46 | 12S-Hydroxyandrographolide (C20H32O6Na) | Diterpenoid | 451.2 (M+1+2ACN) |
 5 | 11.50 | 332.44 | 14-Deoxy-11,12-didehydroandrographolide (C20H28O4) | Diterpenoid | 333.5 (M+1) |
 6 | 11.62 | 484.6 | Ent-Labda-8(17), 13Z-diene-15, 16, 19-triol 19-O-glucoside (C26H44O8) | Diterpenoid | 485.3 (M+1) |
 7 | 12.01 | 300.266 | 5,8,2′-Trihydroxy-7-methoxyflavone (C16H12O6) | Flavone | 301.1 (M+1) |
 8 | 13.18 | 318.457 | Andrograpanin (C20H30O3) | Diterpene | 319.2 (M+1) |
 9 | 13.18 | 497.60 | Andrographatoside (C26H42O9) | Diterpenoid | 498.3 (M+1) |
 10 | 13.66 | 522.63 | 6-acetylneoandrographolide (C28H42O9) | Diterpenoid | 523.3 (M+1) |
 11 | 13.67 | 520.482 | 5-Hydroxy-7,8,2′,5′- tetra- Methoxyflavone 5-O-glucoside (C25H28O12) | Flavone | 584.3 (M+Na+ACN) |
 12 | 13.96 | 334.456 | 14-Deoxyandrographiside (C20H30O4) | Diterpenoid | 691.5 (2M+Na) |
 13 | 14.07 | 664.88 | Bisandrographolide A (C40H56O8 ) | Diterpenoid | 687.5 (M+Na) |
 14 | 14.07 | 350.455 | Andrographolide (C20H30O5) | Diterpenoid | 433.1 (M+1+2ACN) |
 15 | 14.69 | 314.3 | Skullcapflavone I (C17H14O6) | Flavone | 315.2 (M+1) |
 16 | 15.23 | 296.41 | Andrographolactone (C20H24O2) | Diterpenoid | 297.2 (M+1) |
 17 | 15.44 | 352.42 | 7-Hydroxy-14-deoxyandrographolide (C19H28O6) | Diterpenoid | 353.4 (M+1) |
 18 | 15.44 | 664.88 | Bisandrographolide A (C40H56O8 ) | Diterpenoid | 665.5 (M+1) |
 19 | 15.83 | 318.457 | Andrograpanin (C20H30O3) | Diterpenoid | 659.6 (2 M+Na) |
 20 | 16.66 | 358.346 | 5-hydroxy-7,8,2′,5′tetramethoxyflavone glucoside (C19H18O7) | Flavone | 359.2 (M+1) |
 21 | 18.71 | 664.88 | Bisandrographolide A (C40H56O8 ) | Diterpenoid | 665.5(M+1) |
 22 | 18.82 | 298.29 | 7-O-Methylwogonin (C17H14O5) | Flavone | 623.5 (2M+Na) |
 23 | 19.06 | 532.586 | 3-Oxo-14-deoxy-11,12-Didehydroandrographolide (C28H36O10) | Diterpenoid | 533.5 (M+1) |
 24 | 19.79 | 664.88 | Bisandrographolide A (C40H56O8 ) | Diterpenoid | 687.5 (M+Na) |
 25 | 20.25 | 512.596 | Andrographiside (C26H40O10) | Diterpenoid | 513.4 (M+1) |
 26 | 20.60 | 350.455 | Andrographolide (C20H30O5) | Diterpenoid | 723.5 (2 M+Na) |
 27 | 20.76 | 611.70 | 19-O-[β-D-Apiofuranosyl(1f2)-β-D-glucopyranoyl]-3,14-dideoxyandrographolide (C31H47O12) | Diterpenoid | 634.5 (M+Na) |
 28 | 21.03 | 611.70 | 19-O-[β-D-Apiofuranosyl(1f2)-β-D-glucopyranoyl]-3,14-dideoxyandrographolide (C31H47O12) | Diterpenoid | 634.7 (M+Na) |
 29 | 21.16 | 522.63 | 6-acetylneoandrographolide (C28H42O9) | Diterpenoid | 545.4 (M+Na) |
 30 | 21.95 | 294.38 | 3,19-dihydroxy-14,15,16-trinor-ent-labda-8(17),11-dien-13-oic acid (C17H26O4) | Diterpenoid | 311.3 (M+1+O2) |
 31 | 22.88 | 334.456 | 14-Deoxyandrographiside (C20H30O4) | Diterpenoid | 352.3 (M+NH4) |
 32 | 24.50 | 511.58 | 3-O-β-D-Glucopyranosyandrographolide (C26H39O10) | Diterpenoid | 528.5 (M+1+O2) |
 33 | 25.93 | 300.266 | 5,8,2′-Trihydroxy-7-methoxyflavone (C16H12O6) | Flavone | 601.5 (2M+1) |
 34 | 26.69 | 352.42 | 7-Hydroxy-14-deoxyandrographolide (C19H28O6) | Diterpenoid | 354.3 (M+2) |
 35 | 27.46 | 330.42 | 19-hydroxy-3-oxo-ent-labda-8(17),11,13-trien-16,15-olide (C20H26O4) | Diterpenoid | 678.5 (2 M+NH4) |
Negative mode (ES−) | |||||
 1 | 9.50 | 350.455 | Andrographolide (C20H30O5) | Diterpenoid | 349.2 (M−1) |
 2 | 10.72 | 350.455 | Andrographolide (C20H30O5) | Diterpenoid | 395.3 (M+formic acid-1) |
 3 | 11.18 | 496.597 | Andropanoside (C26H40O9) | Diterpenoid | 541.3 (M+formic acid-1) |
 4 | 11.57 | 494.57 | 19-[(b-D-Glucopyranosyl)oxy-19-oxo-entlabda-8(17),13-dien-16,15-olide (C26H38O9) | Diterpenoid | 539.5 (M+formic acid-1) |
 5 | 11.82 | 494.57 | 19-[(b-D-Glucopyranosyl)oxy-19-oxo-entlabda-8(17),13-dien-16,15-olide (C26H38O9) | Diterpenoid | 461.2 (M−1−MeOH) |
 6 | 12.36 | 332.44 | 14-Deoxy-11,12-didehydroandrographolide (C20H28O4) | Diterpenoid | 331.2 (M−1) |
 7 | 13.19 | 480.598 | Neoandrographolide (C26H40O8) | Diterpenoid | 525.3(M+formic acid-1) |
 8 | 13.33 | 330.42 | 19-hydroxy-3-oxo-ent-labda-8(17),11,13-trien-16,15-olide (C20H26O4) | Diterpenoid | 329.3 (M−1) |
 9 | 13.66 | 522.63 | 6-acetylneoandrographolide (C28H42O9) | Diterpenoid | 521.3 (M−1) |
 10 | 13.87 | 332.44 | 14-Deoxy-11,12-didehydroandrographolide (C20H28O4) | Diterpenoid | 331.2 (M−1) |
 11 | 14.08 | 318.457 | Andrograpanin (C20H30O3) | Diterpenoid | 377.3 (M+acetic acid-1) |
 12 | 14.39 | 334.456 | 14-Deoxyandrographolide (C20H30O4 ) | Diterpenoid | 369.1 (M+Cl) |
 13 | 14.39 | 532.586 | 3-Oxo-14-deoxy-11,12-Didehydroandrographolide (C28H36O10) | Diterpenoid | 567.3 (M+Cl) |
 14 | 15.32 | 664.88 | Bisandrographolide A (C40H56O8 ) | Diterpenoid | 663.5 (M−1), |
 15 | 16.52 | 512.596 | Andrographiside (C26H40O10) | Diterpenoid | 557.2 ( M+formic acid-1) |
 16 | 17.35 | 294.38 | 3,19-dihydroxy-14,15,16-trinor-ent-labda-8(17),11-dien-13-oic acid (C17H26O4) | Diterpenoid | 293.3 (M−1) |
 17 | 18.20 | 294.38 | 3,19-dihydroxy-14,15,16-trinor-ent-labda-8(17),11-dien-13-oic acid (C17H26O4) | Diterpenoid | 293.3 (M−1) |
 18 | 18.56 | 294.38 | 3,19-dihydroxy-14,15,16-trinor-ent-labda-8(17),11-dien-13-oic acid (C17H26O4) | Diterpenoid | 339.3 (M+formic acid-1) |
 19 | 21.60 | 296.41 | Andrographolactone (C20H24O2) | Diterpenoid | 295.2 (M−1) |
 20 | 24.55 | 334.456 | 14-Deoxyandrographolide (C20H30O4 ) | Diterpenoid | 311.3 (M−Na) |
 21 | 26.99 | 454.563 | 19-Benzyl isoandrographolide (C27H34O6) | Diterpenoid | 453.5 (M−1) |
 22 | 27.20 | 454.563 | 19-Benzyl isoandrographolide (C27H34O6) | Diterpenoid | 453.4 (M−1) |
 23 | 30.77 | 368.46 | 12S-Hydroxyandrographolide (C20H32O6Na) | Diterpenoid | 367.1 (M−1) |
 24 | 31.14 | 294.38 | 3,19-dihydroxy-14,15,16-trinor-ent-labda-8(17),11-dien-13-oic acid (C17H26O4) | Diterpenoid | 293.1 (M−1) |