Scrophularia peyronii Post. from Jordan: Chemical Composition of Essential Oil and Phytochemical Profiling of Crude Extracts and Their In Vitro Antioxidant Activity
Abstract
:1. Introduction
2. Materials and Methods
2.1. Instrumentation
2.2. Chemical Reagents
2.3. Plant Material and Fractionations
2.4. Extraction of Essential Oils
2.5. Phytochemical Analysis
2.6. GC/MS Analysis of Essential Oils
Identification of the Chemical Constituents
2.7. Determination of Antioxidant Activity
2.7.1. DPPH Free Radical Scavenging Activity
2.7.2. ABTS Radical Scavenging Assay
2.8. Statistical Analysis
3. Results and Discussion
3.1. Chemical Composition of S. peyronii EO
3.2. Phytochemical Analysis
3.3. Phytochemical Profiling of Crude Extracts by Using LC-MS/MS
No. | Rt (min) | m/z Meas. | MM Calculated | Name | Structure | Molecular Formula | Fractions | Classification | |
---|---|---|---|---|---|---|---|---|---|
Sp-M | Sp-B | ||||||||
1 | 0.99 | 117.0176 | 118.049 | Succinic acid | C4H6O4 | + | + | Aliphatic acid | |
2 | 2.14 | 375.1257 | 376.133 | 3,4-Dihydro-methyl catalpol | C16H24O10 | + | + | Iridoid | |
3 | 3.45 | 625.1359 | 626.1432 | Isorhamnetin-3-O-rutinoside | C28H32O16 | + | + | Flavonoid | |
4 | 3.81 | 811.2823 | 812.2896 | Scropolioside B | C41H46O17 | − | + | Iridoid | |
5 | 4.15 | 179.0325 | 180.0398 | Caffeic acid | C9H8O4 | + | + | Phenolic acid | |
6 | 4.49 | 163.0379 | 164.0452 | p-Coumaric acid | C9H8O3 | + | + | Phenolic acid | |
7 | 5.41 | 609.1411 | 610.1484 | Rutin | C27H30O16 | + | + | Flavonoid | |
8 | 5.61 | 609.1395 | 610.1467 | 3-Glu-7-Rha Quercetin | C27H30O16 | + | + | Flavonoid | |
9 | 5.76 | 495.203 | 496.2103 | 6′-O-cinnamoylharpagide | C24H30O11 | − | + | Iridoid | |
10 | 5.78 | 175.0377 | 194.0554 | Isoferulic acid | C10H10O4 | − | + | Phenolic acid | |
11 | 5.78 | 463.0837 | 464.0909 | Hyperoside | C21H20O12 | + | + | Flavonoid | |
12 | 6.35 | 593.1463 | 594.1535 | 3-O-Neohesperidoside Kaempferol | C27H30O15 | + | + | Flavonoid | |
13 | 6.56 | 447.0892 | 448.0965 | Kaempferol-3-O-glucoside | C21H20O11 | + | + | Flavonoid | |
14 | 6.57 | 495.3129 | 496.3202 | Nepitrin | C22H22O13 | + | + | Flavonoid | |
15 | 7.96 | 377.0807 | 756.1759 | 6-O-Methylcatapol | C16H24O10 | − | + | Iridoid | |
16 | 8.72 | 147.0427 | 148.05 | Cinnamic acid | C9H8O2 | + | + | Phenolic acid | |
17 | 11.09 | 751.2377 | 752.2449 | Scropolioside A | C35H44O18 | + | + | Iridoid | |
18 | 13.67 | 752.2377 | 753.245 | Scrovalentinoside | C35H44O18 | + | + | Iridoid | |
19 | 27.05 | 478.3855 | 479.3928 | Homoplantaginin | C22H22O11 | + | + | Flavonoid | |
20 | 29.97 | 351.2467 | 352.254 | Ningposide C | C17H20O8 | + | + | Phenolic acid | |
21 | 30.07 | 339.3222 | 340.3295 | 3-O-trans-Feruloylrhamnopyranose | C16H20O8 | + | + | Phenolic acid |
3.4. Total Phenolic Content, Total Flavonoid Content, and Antioxidant Activity
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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No. | Rt (min) | RI (exp) | Compound | % Peak Area | Method of Identification |
---|---|---|---|---|---|
1 | 3.676 | 877 | (4Z)-Hexenol | 0.56 | MS, RI |
2 | 5.847 | 954 | (2E)-Heptenal | 0.47 | MS, RI |
3 | 5.955 | 960 | Benzaldehyde | 0.94 | MS, RI |
4 | 6.48 | 998 | n-Octanal | 5.98 | MS, RI |
5 | 6.698 | 1004 | ρ-Mentha-1(7),8-diene | 0.47 | MS, RI |
6 | 6.819 | 1007 | (2E,4E)-Heptadienal | 0.99 | MS, RI, RC |
7 | 7.168 | 1013 | (2E)-Hexenyl acetate | 0.90 | MS, RI |
8 | 8.035 | 1029 | Limonene | 4.10 | MS, RI |
9 | 8.431 | 1039 | Lavender lactone | 0.55 | MS, RI, RC |
10 | 8.522 | 1042 | Benzene acetaldehyde | 0.52 | MS, RI, RC |
11 | 9.086 | 1059 | trans-Decahydro-naphthalene | 0.77 | MS, RI |
12 | 9.364 | 1065 | Acetophenone | 0.52 | MS, RI |
13 | 9.579 | 1081 | cis-Vertocitral | 0.48 | MS, RI |
14 | 9.598 | 1088 | Camphenilone | 0.81 | MS, RI |
15 | 10.184 | 1096 | Linalool | 0.49 | MS, RI |
16 | 10.46 | 1103 | 2,2-Dimethyl-3,4-Octadienal | 0.62 | MS, RI |
17 | 10.662 | 1120 | Dehydro-Sabina ketone | 3.76 | MS, RI |
18 | 10.796 | 1125 | 1-Undecyne | 2.24 | MS, RI, RC |
19 | 10.917 | 1126 | α-Campholenal | 1.02 | MS, RI |
20 | 12.526 | 1146 | Menthone | 0.48 | MS, RI |
21 | 13.073 | 1162 | iso-Menthone | 0.68 | MS, RI |
22 | 13.336 | 1169 | Borneol | 0.89 | MS, RI |
23 | 13.488 | 1177 | Santalone | 2.02 | MS, RI |
24 | 13.652 | 1177 | cis-Pinocarveol | 0.48 | MS, RI |
25 | 13.801 | 1189 | trans-ρ-Mentha-1(7),8-dien-2-ol | 0.86 | MS, RI |
26 | 14.392 | 1199 | γ-Terpineol | 1.57 | MS, RI |
27 | 14.699 | 1217 | 4-Methylene-Isophorone | 0.62 | MS, RI |
28 | 14.982 | 1225 | Citronellol | 0.92 | MS, RI |
29 | 15.589 | 1237 | Pulegone | 1.06 | MS, RI |
30 | 17.386 | 1263 | (2E)-Decenal | 1.47 | MS, RI |
31 | 17.502 | 1269 | n-Decanol | 0.54 | MS, RI |
32 | 18.007 | 1286 | 5-Undecanol | 0.49 | MS, RI |
33 | 18.407 | 1294 | Camphorquinone | 0.71 | MS, RI |
34 | 18.914 | 1305 | iso-Menthyl acetate | 0.86 | MS, RI, RC |
35 | 19.597 | 1314 | 2,3,4-Trimethyl benzaldehyde | 1.67 | MS, RI |
36 | 19.747 | 1324 | trans-(E)-Jasmonol | 1.11 | MS, RI |
37 | 20.824 | 1352 | Citronellyl acetate | 2.07 | MS, RI |
38 | 21.755 | 1375 | Linalool isobutanoate | 1.29 | MS, RI |
39 | 22.565 | 1393 | β-Elemene | 6.36 | MS, RI |
40 | 22.861 | 1407 | Longifolene | 4.30 | MS, RI |
41 | 23.487 | 1408 | Dodecanal | 0.69 | MS, RI |
42 | 24.003 | 1433 | β-Gurjunene | 4.16 | MS, RI, RC |
43 | 24.549 | 1439 | α-Guaiene | 0.48 | MS, RI |
44 | 25.428 | 1459 | trans-Prenyl limonene | 0.99 | MS, RI |
45 | 25.606 | 1460 | allo-Aromadendrene | 0.53 | MS, RI |
46 | 25.869 | 1466 | (2E)-Dodecenal | 1.31 | MS, RI |
47 | 26.764 | 1488 | (E)-β-Ionone | 2.06 | MS, RI |
48 | 27.158 | 1502 | trans-β-Guaiene | 0.61 | MS, RI |
49 | 27.714 | 1513 | γ-Cadinene | 1.84 | MS, RI |
50 | 28.269 | 1534 | trans-Cadina-1,4-diene | 0.50 | MS, RI |
51 | 29.9 | 1578 | Spathulenol | 4.58 | MS, RI |
52 | 30.089 | 1580 | n-Hexyl benzoate | 0.54 | MS, RI |
53 | 30.368 | 1590 | β-Copaen-4-α-ol | 0.72 | MS, RI |
54 | 30.549 | 1604 | Khusimone | 1.52 | MS, RI |
55 | 31.757 | 1623 | 10-epi-γ-Eudesmol | 0.60 | MS, RI |
56 | 32.154 | 1641 | allo-Aromadendrene epoxide | 1.25 | MS, RI |
57 | 32.815 | 1646 | α-Muurolol | 3.15 | MS, RI |
58 | 33.313 | 1660 | neo-Intermedeol | 0.66 | MS, RI |
59 | 34.06 | 1679 | (Z)-Methyl epi-jasmonate | 1.07 | MS, RI, |
60 | 34.349 | 1688 | Eudesma-4(15),7-dien-1β-ol | 0.49 | MS, RI |
61 | 34.503 | 1699 | 11-αH-Himachal-4-en-1-β-ol | 0.48 | MS, RI |
62 | 38.085 | 1792 | Drimenone | 0.54 | MS, RI |
63 | 40.143 | 1856 | Z,Z-Farnesyl acetone | 11.04 | MS, RI |
64 | 41.642 | 1913 | (5E,9E)-Farnesyl acetone | 0.60 | MS, RI |
65 | 42.907 | 1942 | Callitrisin | 0.58 | MS, RI |
66 | 43.95 | 1971 | (Z)-Methyl-isoprenyl cinnamate | 0.53 | MS, RI |
Total identified | 98.16 |
Groups | Sp-M | Sp-B |
---|---|---|
Flavonoids | + | + |
Glycosides | + | + |
Alkaloids | + | − |
Tannins | − | − |
Saponins | + | + |
Anthraquinone | + | + |
Extract | TPC | TFC | IC50 (mg/mL) | |
---|---|---|---|---|
DPPH• | ABTS | |||
Sp-M | 45.44 ± 1.3 * | 25.74 ± 2.4 | (8.6 ± 0.09) × 10−2 | (26.0 ± 0.02) × 10−2 |
Sp-B | 51.90 ± 1.0 | 148.54 ± 1.0 | (8.0 ± 0.08) × 10−2 | (2.5 ± 0.02) × 10−2 |
EO | - | - | (4.84 ± 0.12) × 10−3 | (10.6 ± 0.08) × 10−3 |
Ascorbic acid | - | - | (1.8 ± 0.06) × 10−3 | (1.9 ± 0.04 ) × 10−3 |
α-tocopherol | - | - | (2.3 ± 0.04) × 10−3 | (1.8 ± 0.01) × 10−3 |
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Al-Dalahmeh, Y.; Almahmoud, S.A.J.; Al-Bataineh, N.; Alghzawi, T.A.; Alhamzani, A.G.; Al-Mutairi, A.A.; Al-Jaber, H.I.; Abu Orabi, S.T.; Bataineh, T.T.; Al-Sheraideh, M.S.; et al. Scrophularia peyronii Post. from Jordan: Chemical Composition of Essential Oil and Phytochemical Profiling of Crude Extracts and Their In Vitro Antioxidant Activity. Life 2023, 13, 1404. https://doi.org/10.3390/life13061404
Al-Dalahmeh Y, Almahmoud SAJ, Al-Bataineh N, Alghzawi TA, Alhamzani AG, Al-Mutairi AA, Al-Jaber HI, Abu Orabi ST, Bataineh TT, Al-Sheraideh MS, et al. Scrophularia peyronii Post. from Jordan: Chemical Composition of Essential Oil and Phytochemical Profiling of Crude Extracts and Their In Vitro Antioxidant Activity. Life. 2023; 13(6):1404. https://doi.org/10.3390/life13061404
Chicago/Turabian StyleAl-Dalahmeh, Yousef, Sondos Abdullah J. Almahmoud, Nezar Al-Bataineh, Taqwa A. Alghzawi, Abdulrahman G. Alhamzani, Aamal A. Al-Mutairi, Hala I. Al-Jaber, Sultan T. Abu Orabi, Tareq T. Bataineh, Mohammed S. Al-Sheraideh, and et al. 2023. "Scrophularia peyronii Post. from Jordan: Chemical Composition of Essential Oil and Phytochemical Profiling of Crude Extracts and Their In Vitro Antioxidant Activity" Life 13, no. 6: 1404. https://doi.org/10.3390/life13061404