Table 3.
Chromatographic (tR), mass-spectrometric data (ESI-MS), and seasonal presence/content of compounds 1–60 found in the Agrimonia asiatica herb.
| No | tR, min | ESI-MS, [M–H]– | Group a | Compound b | Content, mg/g Dry Plant Weight ± S.D. | ||
|---|---|---|---|---|---|---|---|
| May | July | September | |||||
| 1 | 1.38 | 341 | S | Hexosyl-O-hexose L | tr. | tr. | tr. |
| 2 | 1.52 | 331 | GT | 1-O-Galloyl-glucose S | tr. | n.f. | n.f. |
| 3 | 1.88 | 331 | GT | O-Galloyl-glucose L | tr. | n.f | n.f. |
| 4 | 1.94 | 331 | GT | O-Galloyl-glucose L | tr. | tr. | n.f. |
| 5 | 2.11 | 331 | GT | O-Galloyl-glucose L | tr. | n.f. | n.f. |
| 6 | 2.36 | 183 | V | 2-Pyrone-4,6-dicarboxylic acid S | 1.42 ± 0.03 | 2.05 ± 0.04 | 2.11 ± 0.03 |
| 7 | 2.67 | 783 | ET | Pedunculagin S | tr. | tr. | tr. |
| 8 | 2.91 | 353 | HC | 4-O-Caffeoylquinic acid S | 15.63 ± 0.32 | 18.59 ± 0.37 | 16.37 ± 0.31 |
| 9 | 3.22 | 783 | ET | Casuariin S | tr. | tr. | tr. |
| 10 | 4.01 | 577 | P | Procyanidin B1 S | tr. | tr. | tr. |
| 11 | 4.26 | 785 | ET | Tellimagrandin I1 S | tr. | tr. | n.f. |
| 12 | 4.51 | 577 | P | Procyanidin B3 S | tr. | tr. | tr. |
| 13 | 4.76 | 289 | C | Catechin S | 20.19 ± 0.41 | 22.27 ± 0.45 | 11.63 ± 0.19 |
| 14 | 5.31 | 353 | HC | 5-O-Caffeoylquinic acid S | tr. | tr. | tr. |
| 15 | 5.51 | 305 | C | Epigallocatechin S | 27.02 ± 0.54 | 65.15 ± 1.30 | 36.11 ± 0.72 |
| 16 | 6.09 | 577 | P | Procyanidin B2 S | tr. | tr. | tr. |
| 17 | 6.33 | 447 | V | Ellagic acid-O-methyl ester-O-pentoside L | n.f. | tr. | tr. |
| 18 | 6.59 | 937 | ET | Tri-O-galloyl-O-hexahydroxydiphenoyl-glucose L | tr. | tr. | n.f. |
| 19 | 6.92 | 785 | ET | Tellimagrandin I2 S | tr. | tr. | n.f. |
| 20 | 7.54 | 577 | P | Procyanidin B (dimer) L | tr. | tr. | tr. |
| 21 | 8.03 | 783 | ET | Bis-O-hexahydroxydiphenoyl-glucose L | tr. | tr. | n.f. |
| 22 | 8.20 | 785 | ET | Di-O-galloyl-O-hexahydroxydiphenoyl-glucose L | tr. | tr. | n.f. |
| 23 | 8.49 | 289 | C | Epicatechin S | tr. | tr. | tr. |
| 24 | 8.71 | 337 | ET | Hexahydroxydiphenic acid L | tr. | tr. | n.f. |
| 25 | 9.08 | 785 | ET | Di-O-galloyl-O-hexahydroxydiphenoyl-glucose L | tr. | tr. | n.f. |
| 26 | 9.46 | 515 | HC | 1,3-Di-O-caffeoyquinic acid S | tr. | tr. | tr. |
| 27 | 9.54 | 783 | ET | Bis-O-hexahydroxydiphenoyl-glucose L | tr. | tr. | n.f. |
| 28 | 9.69 | 463 | F | 6-Hydroxyluteolin-7-O-Glc S | n.f. | tr. | n.f. |
| 29 | 10.02 | 783 | ET | Bis-O-hexahydroxydiphenoyl-glucose L | tr. | tr. | n.f. |
| 30 | 10.27 | 577 | P | Procyanidin B (dimer) L | n.f. | tr. | tr. |
| 31 | 10.42 | 937 | ET | Tellimagrandin II1 S | tr. | tr. | n.f. |
| 32 | 10.71 | 935 | ET | Potentillin S | tr. | tr. | tr. |
| 33 | 11.01 | 1103 | ET | Agrimonic acid A S | tr. | tr. | n.f. |
| 34 | 11.12 | 1871 | ET | Gemin A S | tr. | tr. | tr. |
| 35 | 11.48 | 1103 | ET | Agrimonic acid B S | tr. | tr. | n.f. |
| 36 | 11.63 | 1869 | ET | Agrimoniin S | 82.59 ± 1.67 | 114.18 ±2.37 | 27.32 ± 0.54 |
| 37 | 11.97 | 441 | C | Epicatechin gallate S | tr. | tr. | tr. |
| 38 | 12.27 | 301 | V | Ellagic acid S | 3.60 ± 0.06 | 5.31 ± 0.12 | 34.62 ± 0.69 |
| 39 | 12.51 | 609 | F | Quercetin-3-O-(6″-O-rhamnosyl)-glucoside S | 8.06 ± 0.17 | 16.32 ± 0.31 | 17.83 ± 0.35 |
| 40 | 12.98 | 937 | ET | Tellimagrandin II2 S | tr. | tr. | n.f. |
| 41 | 13.41 | 463 | F | Quercetin-3-O-glucoside S | 9.53 ± 0.17 | 29.80 ± 0.61 | 24.18 ± 0.48 |
| 42 | 13.50 | 477 | F | Quercetin-3-O-glucuronide S | tr. | tr. | tr. |
| 43 | 13.89 | 447 | F | Luteolin-7-O-glucoside S | tr. | tr. | tr. |
| 44 | 14.21 | 461 | F | Luteolin-7-O-glucuronide S | 2.16 ± 0.04 | 4.21 ± 0.09 | 4.69 ± 0.08 |
| 45 | 15.20 | 549 | F | Quercetin-3-O-(6″-O-malonyl)-glucoside S | 6.37 ± 0.12 | 4.14 ± 0.08 | 0.92 ± 0.02 |
| 46 | 15.67 | 515 | HC | 3,5-Di-O-caffeoyquinic acid S | 2.40 ± 0.04 | 2.59 ± 0.05 | 0.31 ± 0.01 |
| 47 | 16.01 | 593 | F | Kaempferol-3-O-(6″-O-rhamnosyl)-glucoside S | 7.53 ± 0.15 | 9.27 ± 0.19 | 11.36 ± 0.21 |
| 48 | 16.20 | 447 | F | Quercetin-3-O-rhamnoside S | tr. | tr. | tr. |
| 49 | 16.51 | 447 | F | Kaempferol-3-O-glucoside S | tr. | tr. | tr. |
| 50 | 16.55 | 431 | F | Apigenin-7-O-glucoside S | tr. | 0.75 ± 0.02 | 0.82 ± 0.02 |
| 51 | 17.08 | 445 | F | Apigenin-7-O-glucuronide S | 22.18 ± 0.44 | 47.22 ± 0.94 | 56.14 ± 1.14 |
| 52 | 17.27 | 533 | F | Kaempferol-O-malonyl-O-hexoside L | tr. | tr. | tr. |
| 53 | 17.91 | 533 | F | Luteolin-3-O-(6″-O-malonyl)-glucoside S | 2.10 ± 0.04 | 0.85 ± 0.02 | n.f. |
| 54 | 18.23 | 431 | F | Kaempferol-3-O-rhamnoside S | 0.21 ± 0.00 | 0.59 ± 0.01 | 0.73 ± 0.01 |
| 55 | 19.43 | 609 | F | Quercetin-3-O-(6″-O-p-coumaroyl)-glucoside S | tr. | tr. | tr. |
| 56 | 20.01 | 593 | F | Kaempferol-3-O-(6″-O-p-coumaroyl)-glucoside S | tr. | tr. | tr. |
| 57 | 20.87 | 329 | V | Ellagic acid di-O-methyl ester L | tr. | tr. | tr. |
| 58 | 21.63 | 593 | F | Luteolin-7-O-(6″-O-p-coumaroyl)-glucoside S | tr. | tr. | n.f. |
| 59 | 22.24 | 517 | F | Apigenin-7-O-(6″-O-p-malonyl)-glucoside S | tr. | tr. | tr. |
| 60 | 24.43 | 577 | F | Apigenin-7-O-(6″-O-p-coumaroyl)-glucoside S | tr. | tr. | tr. |
a Chemical group of compound: C—catechins, ET—ellagitannins, F—flavones/flavonols, GT—gallotannins, HC—hydroxycinnamates, P—procyanidins, S—sugars, V—various compounds. b The identification of compounds was realized on comparison of retention time, UV and MS spectral data with a reference standard (S) or interpretation of UV and MS spectral data and comparison with literature data (L). tr.—trace, n.f.—not found.