Phytochemistry and Allelopathic Properties of Invasive Heracleum sosnowskyi Aqueous Extracts Against Lettuce (Lactuca sativa L.), Perennial Ryegrass (Lolium perenne L.), Timothy (Phleum pratense L.) and White Clover (Trifolium repens L.)
Abstract
1. Introduction
2. Results
2.1. Chemical Composition of Volatile Organic Compounds (VOCs) in Heracleum sosnowskyi Extracts
2.2. Chemical Composition of Heracleum sosnowskyi Aqueous Extracts Revealed Using the HPLC/DAD/TOF Technique
2.3. Allelopathic Effects of Heracleum sosnowskyi Aqueous Extracts on Different Plant Seeds
3. Discussion
4. Materials and Methods
4.1. Plant Material
4.2. Preparation of H. sosnowskyi Aqueous Extracts for HPLC/DAD/TOF Analysis and Allelopathic Tests
4.3. Preparation of H. sosnowskyi Extracts for Analysis of Volatile Organic Compounds (VOCs)
4.4. GC-MS Analysis
4.5. HPLC-DAD-MS (TOF) Analysis
4.6. Seed Germination Bioassay
4.7. Statistical Data Analyses
5. Conclusions
Supplementary Materials
Author Contributions
Funding
Data Availability Statement
Conflicts of Interest
Abbreviations
| GC/MS | Gas Chromatography/Mass Spectrometry |
| HPLC/DAD/TOF | High Performance Liquid Chromatography/Diode Array Detection/Time-of-Flight-Mass Spectrometry |
| VOC | Volatile Organic Compounds |
| GR | Germination Rate |
| VI | Vigor index |
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| No. | Compound | RI | Flowers | Leaves | Roots |
|---|---|---|---|---|---|
| 1. | Isopsoralen (2H-Furo[2,3-h]chromen-2-one; Furo(2,3-h)coumarin) (syn. Angelecin) | 1810 | 55.4 ± 4.3 | 47.3 ± 3.1 | 9.1 ± 2.0 |
| 2. | Ficusin (7H-Furo[3,2-g][1]benzopyran-7-one; Furo[4′,5′:6,7]coumarin; 7H-Furo[3,2-g]chromen-7-one) (syn. Psoralen) | 1842 | 3.6 ± 1.0 | 5.3 ± 1.7 | 1.9 ± 0.8 |
| 3. | Isobergapten (2H-Furo[2,3-h]-1-benzopyran-2-one, 5-methoxy; 5-Methoxy-2H-furo[2,3-H]chromen-2-one) | 2016 | 1.7 ± 0.4 | 0.1 ± 0.1 | 8.0 ± 2.2 |
| 4. | Methoxsalen (7H-Furo[3,2-g][1]benzopyran-7-one; 9-Methoxy-7H-furo[3,2-g]chromen-7-one) (syn. Ammoidin; Meladinin; Meloxine; Oxsoralen; Xanthotoxin) | 2032 | 14.7 ± 4.3 | 30.1 ± 5.8 | 3.7 ± 0.9 |
| 5. | Bergapten (7H-Furo[3,2-g][1]benzopyran-7-one, 4-methoxy; 5-Methoxypsoralen) (syn. Bergaptan; Heraclin) | 2056 | 6.6 ± 2.5 | 11.2 ± 3.3 | 12.4 ± 3.3 |
| 6. | Pimpinellin (5,6-Dimethoxy-2H-furo[2,3-H]chromen-2-one; 2H-Furo[2,3-h]-1-benzopyran-2-one, 5,6-dimethoxy) | 2118 | 13.8 ± 4.0 | 0.2 ± 0.1 | 44.9 ± 5.1 |
| 7. | Isopimpinellin (7H-Furo[3,2-g][1]benzopyran-7-one, 4,9-dimethoxy; 4,9-Dimethoxy-7H-furo[3,2-g]chromen-7-one) (syn. 5,8-Dimethoxypsoralen; 5,8-Dimethoxy-6,7- furanocoumarin) | 2248 | 1.2 ± 0.3 | 2.9 ± 0.0 | 14.9 ± 1.7 |
| No. | Compound | Formula | Molecular Weight | m/z ESI+ (Da) | m/z ESI− (Da) |
|---|---|---|---|---|---|
| Acids | |||||
| 1. | Glutaric acid L,F,R | C5H8O4 | 132.11 | 132.100 | |
| 2. | p-Anisic (4-Methoxybenzoic) acid F | C8H8O3 | 152.15 | 151.004 | |
| 3. | Suberic (Octanedioic) acid F | C8H14O4 | 174.19 | 173.083 | |
| 4. | Quinic acid L,F | C7H12O6 | 192.17 | 191.020 | |
| 5. | Phenyloctanoic acid F | C14H20O2 | 220.31 | 221.049 | |
| 6. | Linolenic acid (9,12,15-Octadecatrienoic) acid L,F,R | C18H30O2 | 278.45 | 279.157 | |
| 7. | Oleic (cis-9-Octadecenoic) acid F | C18H34O2 | 282.47 | 281.124 | |
| 8. | Chlorogenic (caffeoylquinic) acid L,R | C16H18O9 | 354.31 | 355.099 | 353.086 |
| 9. | 3-O-Feruloylquinic acid L | C17H20O9 | 368.31 | 367.101 | |
| 10. | Isochlorogenic (3,4-dicaffeoylquinic) acid L,R | C25H24O12 | 516.45 | 515.139 | |
| 11. | Chrysophanic acid (Chrysophanol; 1,8-Dihydroxy-3-methylanthraquinone) R | C15H10O4 | 254.24 | 253.143 | |
| 12. | Gelseminic (Chrysatropic) acid R (Scopoletin; 7-Hydroxy-6-methoxy-2H-chromen-2-one) | C10H8O4 | 192.16 | 191.018 | |
| 13. | Indole-3-acetyl-L-aspartic acid (Indoleacetylaspartate) F | C14H14N2O5 | 290.27 | 289.034 | |
| Esters | |||||
| 14. | Isoamyl butyrate L,F | C9H18O2 | 158.24 | 158.995 | |
| 15. | Hexyl hexanoate L | C12H24O2 | 200.32 | 199.097 | |
| Terpenoids | |||||
| 16–19. | Monoterpenes (Limonene, Ocimene, Terpinene or Terpinolene) L | C10H16 | 136.24 | 135.030 | 135.019 |
| 20. | Germacrene D L,F | C15H24 | 204.35 | 205.095 | |
| 21. | Neophytadiene F | C20H38 | 278.52 | 279.036 | 277.033 |
| Flavonoids | |||||
| 22. | Quercetin 7,3,4-trimethyl ether L,F,R | C18H16O7 | 344.3 | 343.035 | |
| 23. | Astragalin (Kaempferol 3-O-glucoside) L,F | C21H20O11 | 448.38 | 449.105 | 447.091 |
| 24. | Baicalin (7-D-Glucuronic acid-5,6-dihydroxyflavone) R | C21H18O11 | 446.36 | 447.120 | |
| 25. | Nicotiflorin (Kaempferol-3-O-rutinoside) L,F | C27H30O15 | 594.50 | 595.159 | 593.148 |
| 26. | Rutin (Quercetin-3-O-rutinoside) L,F | C27H30O16 | 610.52 | 611.155 | 609.145 |
| Furano-derivatives | |||||
| 27. | Coumaran L,F,R | C8H8O | 120.15 | 121.050 | |
| 28. | 5,6,7,7a-Tetrahydro-4,4,7a-trimethyl-2(4h)-benzofuran L,F,R | C11H18O | 166.26 | 166.085 | 165.055 |
| 29. | Isopsoralen L,F,R | C11H6O3 | 186.16 | 187.038 | |
| 30. | Ficusin L,F,R | C11H6O3 | 186.16 | 187.098 | |
| 31. | Methoxsalen F,R | C12H8O4 | 216.19 | 217.046 | |
| 32. 33. | Bergapten/Isobergapten L,F,R | C12H8O4 | 216.19 | 217.002 | |
| 34. 35. | Pimpinellin/Isopimpinellin L,F,R | C13H10O5 | 246.21 | 247.058 | |
| 35. | Imperatorin F,R | C16H14O4 | 270.28 | 271.225 | |
| 37. | L-Arabinofuranose L | C5H10O5 | 150.13 | 149.109 | |
| 38. | Bakuchicin (Furo[2,3-f]chromen-7-one; 7H-Furo(2,3-f)(1)benzopyran-7-one) R | C11H6O3 | 186.16 | 187.037 | |
| 39. | Hermandiol ((8S)-8-(1,2-dihydroxypropan-2-yl)-8,9-dihydrofuro[2,3-h]chromen-2-one) R | C14H14O5 | 262.26 | 263.058 | |
| 40. | Byakangelicol (9-[[(2R)-3,3-dimethyloxiran-2-yl]methoxy]-4-methoxyfuro[3,2-g]chromen-7-one) F | C17H16O6 | 316.30 | 315.071 | |
| 41. | Apterin F | C20H24O10 | 424.40 | 423.067 | |
| 42. | Candinol A R | C21H16O6 | 364.35 | 365.133 | |
| 43. | Candinol C R | C32H32O12 | 608.60 | 607.102 | |
| 44. | Candibirin F R | C34H34O11 | 618.64 | 617.187 | |
| Coumarins | |||||
| 45. | Limettin (5,7-Dimethoxycoumarin) F | C11H10O4 | 206.19 | 205.050 | |
| 46. | Umbelliferone (7-Hydroxycoumarin; 7-Hydroxy-2H-chromen-2-one) F,R | C9H6O3 | 162.14 | 161.024 | |
| 47. | Yunngnin A R | C12H10O6 | 250.05 | 248.956 | |
| 48. | Yunngnin B R | C11H8O5 | 220.04 | 221.048 |
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Judžentienė, A.; Kundrotaitė, A.; Charkova, T.; Nedveckytė, I. Phytochemistry and Allelopathic Properties of Invasive Heracleum sosnowskyi Aqueous Extracts Against Lettuce (Lactuca sativa L.), Perennial Ryegrass (Lolium perenne L.), Timothy (Phleum pratense L.) and White Clover (Trifolium repens L.). Plants 2026, 15, 346. https://doi.org/10.3390/plants15030346
Judžentienė A, Kundrotaitė A, Charkova T, Nedveckytė I. Phytochemistry and Allelopathic Properties of Invasive Heracleum sosnowskyi Aqueous Extracts Against Lettuce (Lactuca sativa L.), Perennial Ryegrass (Lolium perenne L.), Timothy (Phleum pratense L.) and White Clover (Trifolium repens L.). Plants. 2026; 15(3):346. https://doi.org/10.3390/plants15030346
Chicago/Turabian StyleJudžentienė, Asta, Aistė Kundrotaitė, Tatjana Charkova, and Irena Nedveckytė. 2026. "Phytochemistry and Allelopathic Properties of Invasive Heracleum sosnowskyi Aqueous Extracts Against Lettuce (Lactuca sativa L.), Perennial Ryegrass (Lolium perenne L.), Timothy (Phleum pratense L.) and White Clover (Trifolium repens L.)" Plants 15, no. 3: 346. https://doi.org/10.3390/plants15030346
APA StyleJudžentienė, A., Kundrotaitė, A., Charkova, T., & Nedveckytė, I. (2026). Phytochemistry and Allelopathic Properties of Invasive Heracleum sosnowskyi Aqueous Extracts Against Lettuce (Lactuca sativa L.), Perennial Ryegrass (Lolium perenne L.), Timothy (Phleum pratense L.) and White Clover (Trifolium repens L.). Plants, 15(3), 346. https://doi.org/10.3390/plants15030346

