The Phytochemical Profile and Anticancer Activity of Anthemis tinctoria and Angelica sylvestris Used in Estonian Ethnomedicine
Abstract
:1. Introduction
2. Results
2.1. Chemical Composition
2.1.1. Content and Chemical Composition of Essential Oils
2.1.2. Identification of Polyphenolic Compounds
2.1.3. Total Content of Different Compounds
2.1.4. Anticancer Activity of Essential Oils and Methanolic Extracts
3. Discussion
4. Materials and Methods
4.1. Plant Material
4.2. Hydrodistillation of Essential Oil
4.3. Making of Methanolic Dry Extracts
4.4. Gas-Chromatografic Analysis of the Essential Oils
4.5. High-Performance Liquid Chromatography of Polyphenolic Compounds
4.5.1. Evaluation of Phenolic Profile of Plant Samples by MS Spectrum and MS/MS Fragment Analysis by LC–MS/MS Chromatography
4.5.2. Reagents
4.5.3. Evaluation of Phenolic Compound Profile by UPLC–MS/MS Conditions
4.6. Cytotoxicity
5. Conclusions
Supplementary Materials
Author Contributions
Funding
Data Availability Statement
Conflicts of Interest
References
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Compound | RI * (DB-5) | Content in Essential Oil (%) |
---|---|---|
Sabinene | 972 | 0.7 |
β-Pinene | 975 | 2.7 |
Myrcene | 983 | 1.0 |
p-Cymene | 1019 | 12.6 |
(Z)-β-Ocimene | 1040 | 4.3 |
(E)-β-Ocimene | 1048 | 2.6 |
Isoborneol | 1147 | 2.1 |
Terpinen-4-ol | 1174 | 4.0 |
Crysanthenyl acetate | 1260 | 3.6 |
δ-Cadinene | 1520 | 1.6 |
Caryophyllene oxide | 1572 | 2.8 |
Isocaryophyllene oxide/caryophyllenol | 1577 | 3.9 |
Humulene epoxide | 1603 | 2.9 |
δ-Cadinol | 1638 | 6.6 |
α-Muurolene | 1648 | 12.5 |
2-Pentadecanone | 1680 | 2.5 |
Nerolidol acetate | 1720 | 2.5 |
n-Hexadecanal | 1814 | 2.5 |
Palmitic acid | 1967 | 15.3 |
Unknown | 2534 | 12.6 |
Total | 99.3 | |
Monoterpenes | 15.5 | |
Cyclic monoterpenes | 5.5 | |
Bicyclic sesquiterpenes | 6.7 | |
Sesquiterpenes | 24.5 | |
Other compounds | 47.1 |
Compound | RI * (DB-5) | Content in Essential Oils (%) | |
---|---|---|---|
Aerial Parts | Roots | ||
α-Pinene | 933 | 45.4 | 12.4 |
Camphene | 946 | 4.6 | nf |
Sabinene | 971 | 1.1 | nf |
β-Pinene | 974 | 2.0 | nf |
β-Myrcene | 990 | 13.3 | nf |
α-Terpinen | 1014 | 0.4 | 0.7 |
p-Cymene | 1018 | 15.5 | 8.2 |
β-Phellandrene | 1030 | 1.3 | nf |
(Z)-β-Ocimene | 1040 | 1.1 | 0.9 |
(E)-β-Ocimene | 1048 | 0.7 | nf |
Terpinolene | 1085 | 1.2 | nf |
n-Nonanal | 1108 | nf | 1.3 |
α-Terpineol | 1188 | nf | 1.2 |
(E)-Verbenyl acetate | 1301 | 1.4 | nf |
β-Elemene | 1391 | nf | 1.2 |
(E)-β-Caryophyllene | 1416 | 0.8 | nf |
β-Copaene | 1424 | nf | 2.7 |
α-Humulene | 1450 | 1.0 | nf |
β-Farnesene | 1456 | nf | 2.2 |
Germacrene D | 1477 | 3.2 | nf |
β-Bisabolene | 1501 | nf | 1.5 |
γ-Cadinene | 1507 | 0.8 | nf |
Cadina-1,4-diene | 1536 | nf | 2.3 |
Elemol | 1546 | nf | 3.4 |
Caryophyllene oxide | 1573 | nf | 2.4 |
Isocaryophyllene oxide/caryophyllenol | 1582 | nf | 31.9 |
Epiglobulol/humulene epoxide | 1614 | nf | 1.4 |
α-Muurolene | 1648 | nf | 4.2 |
α-Cadinol | 1663 | nf | 1.7 |
α-Bisabolol | 1680 | 1.4 | 17.5 |
Nerolidol acetate | 1721 | nf | 1.3 |
Unknown | 1857 | nf | 1.5 |
Palmitic acid | 1965 | 3.3 | nf |
Total | 99.9 | 99.9 | |
Monoterpenes | 16.7 | 2.8 | |
Cyclic monoterpenes | 49.8 | 12.4 | |
Bicyclic sesquiterpenes | 0.8 | 34.3 | |
Sesquiterpenes | 6.4 | 36.7 | |
Other compounds | 24.8 | 13.7 |
tR (min) | [M-H]− | MS/MS | Plant Material/Substance | ||
---|---|---|---|---|---|
Aerial Parts of A. tinctoria | Aerial Parts of A. sylvestris | Roots of A. sylvestris | |||
0.5 | 341 | 179, 161 | Caffeic acid glucosides | Caffeic acid glucosides | Caffeic acid glucosides |
1.7 | 315 | 225, 153, 109 | Protocatechuic or gentisic acid glucoside | Protocatechuic or gentisic acid glucoside | nf |
4.3 | 325 | 163; 119 | nf | nf | Coumaric acid glucoside |
5.1 | 299 | 137 | 4-Hydroxybenzoic acid glucoside | 4-Hydroxybenzoic acid glucoside | nf |
10.3 | 339 | 281, 251, 177, 135 | Daphnin = daphnetin glucoside | nf | nf |
12.5 | 353 | 191, 179, 173, 135 | Neochlorogenic acid | Neochlorogenic acid | Neochlorogenic acid |
15.2 | 385 | 223, 179, 163 | Sinapinic acid glucoside | nf | nf |
15.5 | 353 | 306, 191, 135 | nf | Chlorogenic acid | nf |
16.5 | 639 | 463, 301, 535 | Quercetin glucoside glucuronide | nf | nf |
16.7 | 337 | 191, 163, 173 | nf | Coumaroylquinic acid | Coumaroylquinic acid |
17.3 | 625 | 463, 301 | Quercetin diglucoside | nf | nf |
17.8 | 335 | 179, 135 | Caffeoylshikimic acid | nf | nf |
18.6 | 367 | 191, 173 | 5-Feruloylquinic acid | 5-Feruloylquinic acid | 5-Feruloylquinic acid |
19.8? | 479 | 317 | Myricetin glucoside | nf | nf |
20.9 | 625 | 301 | nf | Quercetinlucoside-glucoside | nf |
21.3 | 655 | 493, 331 | Patuletin diglucoside | nf | nf |
22.0 | 449 | 287, 151 | Eriodictyol glucoside | nf | nf |
22.2 | 741 | 609, 475, 343, 301 | Quercetin rutinoside pentoside | nf | nf |
22.6 | 477 | 301, 373 | Quercetin glucuronide | nf | nf |
22.8 | 463 | 301, 179, 343 | Quercetin galactoside | Quercetin galactoside | nf |
23.2 | 609 | 301, 343, 271 | Rutin | Rutin | Rutin, traces |
23.3 | 463 | 301 | Quercetin glucoside | Quercetin glucoside | Quercetin glucoside |
24.0 | 493 | 331, 373 | Patuletin glucoside | nf | nf |
24.9 | 477 | 315, 433 | Isorhamnetin glucoside | nf | nf |
24.9 | 505 | 463, 301, 179, 151 | Quercetin acetyl glucoside | nf | nf |
25.4 | 515 | 353, 191 | Dicaffeoylquinic acid 1 | Dicaffeoylquinic acid 1 | nf |
26.4 | 493 | 331, 287 | Patuletin-7-glucoside | nf | nf |
26.4 | 373 | 211, 193 | Pinosylvin glucoside | nf | nf |
26.7 | 477 | 315, 357, 300 | Isorhamnetin glucoside | Isorhamnetin glucoside | nf |
27.3 | 607 | 299, 284 | Diosmetin rutinoside = diosmin | Diosmetin rutinoside = diosmin | nf |
27.4 | 515 | 191, 179, 255, 299, 353 | 3,4-Dicaffeoylquinic acid-2 | 3,4-Dicaffeoylquinic acid-2 | 3,4-Caffeoylquinic acid |
27.7 | 489 | 285 | Kaempferol acetylglucoside | nf | nf |
29.1 | 529 | 353, 191 | Feruloylquinic acid glucoside | Feryloylquinic acid glucoside | nf |
30.4 | 535 | 331, 316 | Patuletin acetylglucoside | nf | nf |
31.0 | 331 | 316, 209 | Patuletin | nf | nf |
31.8 | 315 | 300 | Iso-rhamnetin | nf | nf |
32.6 | 271 | 151, 177, 119 | nf | Naringenin | Naringenin |
32.8 | 609 | 285 | Kaempferol rutinoside | nf | nf |
33.0 | 345 | 330, 315 | Spinacetin | nf | nf |
34.1 | 677 | 515, 353, 255, 191 | Tricaffeoylquinic acid | Tricaffeoylquinic acid | nf |
34.3 | 271 | 107, 119, 151 | nf | nf | Naringenin chalcone |
35.3 | 299 | 284 | Diosmetin | nf | nf |
35.7 | 315 | 300, 251 | Nepetin | nf | nf |
36.6 | 329 | 314, 171 | Jaceosidin | nf | nf |
38.1 | 359 | 344, 329 | Jaceidin | nf | nf |
38.3 | 593 | 447; 301 | nf | Quercetin dirhamnoside | nf |
38.4 | 593 | 285 | nf | Luteolin rutinoside | nf |
tR (min) | Precursor Ion (m/z) [M-H]− | Product Ion (m/z) MS/MS | Aerial Parts of A. tinctoria | Aerial Parts of A. sylvestris | Roots of A. sylvestris |
---|---|---|---|---|---|
0.46 | 191 | 85 | Quinic acid | Quinic acid | Quinic acid |
2.80 | 353 | 191 | Neochlorogenic acid | Neochlorogenic acid | Neochlorogenic acid |
3.75 | 353 | 191 | Chlorogenic acid | Chlorogenic acid | Chlorogenic acid |
3.98 | 179 | 107 | Caffeic acid | Caffeic acid | nf |
5.06 | 609 | 300 | Rutin | Rutin | nf |
5.15 | 593 | 285 | Luteolin 7-rutinoside | Luteolin 7-rutinoside | Luteolin 7-rutinoside |
5.18 | 193 | 134 | Ferulic acid | Ferulic acid | Ferulic acid |
5.39/5.55/5.76 | 515 | 353 | Dicaffeoylquinic acids | Dicaffeoylquinic acids | Dicaffeoylquinic acids |
5.22 | 463 | 301 | Hyperoside | nf | nf |
5.26 | 447 | 285 | Luteolin-7-glucoside | nf | nf |
5.28 | 463 | 301 | Isoquercitrin | Isoquercitrin | Isoquercitrin |
5.52 | 623 | 315 | Isorhamnetin 3-rutinoside | nf | nf |
5.70 | 447 | 300 | Quercitrin | Quercitrin | Quercitrin |
5.70 | 447 | 285 | Luteolin 4-glucoside | nf | nf |
6.79 | 285 | 133 | Luteolin | nf | nf |
6.86 | 301 | 151 | nf | Quercetin | nf |
7.22 | 271 | 151 | nf | Naringenin | Naringenin |
7.38 | 269 | 117 | Apigenin | Apigenin | Apigenin |
7.57 | 299 | 284 | nf | Diosmetin | Diosmetin |
7.60 | 315 | 300 | nf | Isorhamnetin | nf |
Plant Part | Total Phenolics | Total Chlorogenic Acids | Total Flavonols, 360 nm |
---|---|---|---|
A. tinctoria, herb | 14.7 | 12.7 | 11,471 |
A. sylvestris, herb | 5.5 | 4.9 | 2629 |
A. sylvestris, root | 2.3 | 2.1 | 0 |
Plant Part | Total Quinic Acid Derivatives |
---|---|
A. tinctoria, herb | 320,218 |
A. sylvestris, herb | 259,839 |
A. sylvestris, root | 105,600 |
Concentration (µg/mL) | % Inhibition | ||||
---|---|---|---|---|---|
Essential oil of A. tinctoria (Aerial Parts) | |||||
HepG2 | MKN7 | SW480 | LNCaP | KB | |
100 | 91.80 | 97.07 | 81.11 | 93.85 | 96.32 |
20 | 25.33 | 28.47 | 23.85 | 38.51 | 40.18 |
4 | 12.88 | 19.99 | 17.81 | 28.31 | 25.99 |
0.8 | 0.13 | 8.81 | 8.59 | 12.23 | 10.03 |
IC50 | 44.98 ± 2.96 | 43.04 ± 4.50 | 55.45 ± 5.70 | 29.96 ± 2.25 | 27.75 ± 1.86 |
Concentration (µg/mL) | Essential oil of A. sylvestris (aerial parts) | ||||
HepG2 | MKN7 | SW480 | LNCaP | KB | |
100 | 87.08 | 88.79 | 103.03 | 90.21 | 96.76 |
20 | 33.14 | 32.31 | 38.47 | 42.23 | 52.30 |
4 | 11.61 | 15.34 | 13.35 | 20.35 | 18.36 |
0.8 | −2.02 | 1.93 | 4.45 | 7.21 | 4.92 |
IC50 | 37.46 ± 2.33 | 38.06 ± 2.09 | 30.72 ± 1.81 | 27.78 ± 1.28 | 19.84 ± 2.35 |
Concentration (µg/mL) | Essential oil of A. sylvestris (roots) | ||||
HepG2 | MKN7 | SW480 | LNCaP | KB | |
100 | 97.82 | 99.34 | 75.35 | 95.08 | 97.22 |
20 | 44.11 | 36.14 | 40.70 | 39.34 | 49.19 |
4 | 20.33 | 12.44 | 27.66 | 21.86 | 28.60 |
0.8 | 5.14 | 6.00 | 16.85 | 10.53 | 14.28 |
IC50 | 24.69 ± 1.96 | 34.09 ± 2.08 | 33.36 ± 2.25 | 30.37 ± 2.35 | 19.73 ± 2.18 |
Concentration (µg/mL) | Methanolic extract of A. tinctoria (aerial parts) | ||||
HepG2 | MKN7 | SW480 | LNCaP | KB | |
100 | 21.29 | 30.50 | 29.89 | 29.83 | 25.36 |
20 | 14.28 | 8.76 | 5.09 | 8.83 | 10.46 |
IC50 | >100 | >100 | >100 | >100 | >100 |
Concentration (µg/mL) | Methanolic extract of A. sylvestris (aerial parts) | ||||
HepG2 | MKN7 | SW480 | LNCaP | KB | |
100 | 14.50 | 29.69 | 20.61 | 36.32 | 19.62 |
20 | 2.91 | 9.65 | 7.00 | 7.85 | 8.12 |
IC50 | >100 | >100 | >100 | >100 | >100 |
Concentration (µg/mL) | Methanolic extract of A. sylvestris (roots) | ||||
HepG2 | MKN7 | SW480 | LNCaP | KB | |
100 | 67.48 | 68.94 | 63.43 | 76.48 | 73.07 |
20 | 26.01 | 25.71 | 22.73 | 34.81 | 36.29 |
4 | 12.11 | 7.09 | 11.76 | 17.33 | 19.60 |
0.8 | −0.60 | 0.66 | −1.11 | 4.57 | 8.14 |
IC50 | 57.37 ± 3.57 | 58.52 ± 3.52 | 66.06 ± 2.74 | 40.08 ± 2.22 | 40.60 ± 1.85 |
Concentration (µg/mL) | Ellipticine * | ||||
HepG2 | MKN7 | SW480 | LNCaP | KB | |
10 | 103.80 | 97.28 | 87.44 | 93.85 | 99.82 |
2 | 86.90 | 88.59 | 78.68 | 80.01 | 78.04 |
0.4 | 49.17 | 47.09 | 48.76 | 49.33 | 51.45 |
0.08 | 22.02 | 20.66 | 21.11 | 24.57 | 28.34 |
IC50 | 0.38 ± 0.04 | 0.41 ± 0.05 | 0.48 ± 0.05 | 0.40 ± 0.04 | 0.35 ± 0.02 |
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Raal, A.; Jaama, M.; Utt, M.; Püssa, T.; Žvikas, V.; Jakštas, V.; Koshovyi, O.; Nguyen, K.V.; Thi Nguyen, H. The Phytochemical Profile and Anticancer Activity of Anthemis tinctoria and Angelica sylvestris Used in Estonian Ethnomedicine. Plants 2022, 11, 994. https://doi.org/10.3390/plants11070994
Raal A, Jaama M, Utt M, Püssa T, Žvikas V, Jakštas V, Koshovyi O, Nguyen KV, Thi Nguyen H. The Phytochemical Profile and Anticancer Activity of Anthemis tinctoria and Angelica sylvestris Used in Estonian Ethnomedicine. Plants. 2022; 11(7):994. https://doi.org/10.3390/plants11070994
Chicago/Turabian StyleRaal, Ain, Marel Jaama, Meeme Utt, Tõnu Püssa, Vaidotas Žvikas, Valdas Jakštas, Oleh Koshovyi, Khan Viet Nguyen, and Hoai Thi Nguyen. 2022. "The Phytochemical Profile and Anticancer Activity of Anthemis tinctoria and Angelica sylvestris Used in Estonian Ethnomedicine" Plants 11, no. 7: 994. https://doi.org/10.3390/plants11070994