Oxypeucedanin: Chemotaxonomy, Isolation, and Bioactivities
Abstract
:1. Introduction
2. Phytochemical Studies of Oxypeucedanin
2.1. Preparative Analysis of Oxypeucedanin
2.1.1. Isolation and Purification of Oxypeucedanin from the Apiaceae Family
2.1.2. Isolation and Purification of Oxypeucedanin from the Rutaceae Family
Plant Family | Plant Species | Subjected Plant Part/Soluble Extract | Method of Isolation/Purification | Reference |
---|---|---|---|---|
Apiaceae | Anethum graveolens | WP/NHEX | VLC [NHEX‒EtOAc 100:0 to 90:10], VLC [NHEX–EtOAc 50:50], RP-PTLC [NHEX–EtOAc 60:40] | [12] |
Angelica archangelica | R/CHCl3 | MPLC [butanone‒CHCl3‒DEE‒NHEX 6.9:1:1.4;90.7% to 48:6.8:10:35.2%], MPLC [THF–Propanol–MeCN–H2O 7.5:1.3:1.7:89.5 to 45.1:7.5:10:37.4] | [13] | |
Angelica dahurica | R/MeOH | CC [NHEX–EtOH–MeOH], CC [NHEX–EtOH], CC[NHEX–EtOH– MeOH 5:1:1], CC [NHEX–EtOH 1:1] | [16] | |
R/MeOH | CC [NHEX–EtOAc–MeOH], CC [NHEX–EtOAc–MeOH 5:1:1], CC [NHEX–EtOAc 1:1] | [17] | ||
R/MeOH | CC [NHEX–EtOAc 5:1, 1:1, 0:1], CC [NHEX–EtOAc 5:1] | [18] | ||
R/EtOH | CC [NHEX–Me2CO 20:1, 15:1, 10:1, 7:1, 4:1, 2:1, 1:1; CHCl3–MeOH 10:1, 8:1, 6:1, 4:1, 2:1, 1:1], CC [NHEX–Me2CO 20:1, 15:1, 10:1, 8:1, 6:1, 4:1, 2:1], CC [NHEX–Me2CO 14:1, 4:1] | [19] | ||
R/n-BuOH | CC [NHEX‒Me2CO 20:1 to 2:1], RP-CC [MeOH‒H2O 75:25], RP-HPLC [MeCN‒H2O 40:60], recrys. | [20] | ||
R/CHCl3 | CC | [21] | ||
R/CHCl3 | CC [CHCl3‒Me2CO 1:0, 0:1], CC [NHEX-EtOAc], recrys. [DEE‒CH2Cl2] | [22] | ||
R/CH2Cl2 | CC [NHEX–EtOAc 5:1 to 0:1] | [23] | ||
R/CH2Cl2 | CC [NHEX–EtOAc], CC [NHEX–EtOAc 3:1] | [24] | ||
R/EtOAc | CC [NHEX–EtOAc 3:2] | [26,27] | ||
R/EtOAc | CC [CH2Cl2‒MeOH 100:0 to 0:100], ODS-CC [MeOH‒H2O 50:50 to 95:5], SLH [MeOH] | [28] | ||
R/EtOAc | HSCCC [NHEX–EtOAc–MeOH–H2O 5:5:4:6] | [31] | ||
R/EtOAc | HSCCC [NHEX–EtOAc–MeOH–H2O 1:1:1:1, 5:5:4.5:5.5] | [32] | ||
R/EtOAc | HSCCC [NHEX–EtOAc–MeOH–H2O 1:1:1:1, 5:5:4:6] | [33] | ||
R/EtOAc | CC [NHEX–EtOAc 20:80 to 0:100], CC [EtOAc–MeOH 100:0 to 0:100], recrys. | [29] | ||
R/PET | CCC [NHEX–MeOAc–MeCN–H2O 4:3:4:4], HPLC | [34] | ||
R/NHEX | CC [NHEX–EtOAc], ODS-CC [MeOH–H2O 80:20] | [35] | ||
R/nd | nd | [15] | ||
Angelica furcijuga | Fl/EtOAc | CC [NHEX–EtOAc 10:1 to 5:1 to 1:1, to MeOH 100%], RP-CC [MeOH–H2O 70:30 to 80:20 to 90:10 to MeOH 100%], RP-CC [MeOH–H2O 60:40 to 75:25, 0:100], HPLC [MeOH–H2O 75:25] | [36] | |
Angelica koreana | R/EtOAc | HPLC [MeCN–H2O 30:70] | [37] | |
Angelica pancicii | R/MeOH R/CH2Cl2 | FC [petrol; DEE], HPLC [MeCN–H2O (HCO2H 2%) 50:50, 65:35] HPLC [MeCN–H2O (HCO2H 2%) 50:50, 65:35] | [38] | |
Angelica purpurascens | Fr/NHEX | CC [NHEX–EtOAc 100:0 to 0:100], CC [NHEX–EtOAc 80:20] | [39] | |
Diplolophium buchanani | L/CH2Cl2 | CPC [NHEX–EtOAc–MeOH–H2O 10:5:5:1], recrys. [NHEX–EtOAc] | [40] | |
Ducrosia anethifolia | AP/CHCl3 | CC [CHCl3–MeOH 100:0 to 20:80], MPLC [NHEX–CH2Cl2 50:50 to 0:100, CH2Cl2–MeOH 100:0 to 100:0], MPLC [NHEX–EtOAc 95:5 to 0:100], CPTLC [NHEX–EtOAc 95:5 to 0:100] | [41] | |
Ferulago angulate (syn. F. trifida) | R/NHEX | PTLC [CHCl3–Me2CO 95:5] | [44] | |
R/CHCl3 | CC [CHCl3‒EtOAc 10:0, 5:5], CC [CHCl3‒EtOAc 9:1] | [45,46] | ||
Ferulogo bernardii | AP/NHEX | CC [PET‒EtOAc‒MeOH 60:40], recrys. [EtOH‒H2O] | [47] | |
Ferulago capillaris | AP, R/NHEX | CC [NHEX–EtOAc] | [48] | |
Ferulago humulis | Rhizome/PET | CC [NHEX‒EtOAc; EtOAc‒MeOH], PTLC [cyclohexane‒EtOAc 2:1] | [42] | |
Ferulago subvelutina | R/EtOAc | CC [NHEX‒CHCl3, CHCl3, CHCl3‒EtOAc], CC [CHCl3‒EtOAc 9:1, EtOAc], recrys. | [49] | |
Harbouria trachypleura | AP/MeOH | VLC [NHEX‒EtOAc], FC [CH2Cl2–Me2CO 97:3], CC [CH2Cl2–Me2CO 97:3 to 4:1], RP-VLC [MeOH‒H2O 50:50 to 100:0], PTLC [CH2Cl2–Me2CO 97:3] | [50] | |
Levisticum officinale | R/EtOAc | CC [NHEX–EtOAc 100:0 to 0:100; EtOAc–MeOH 100:0 to 80:20] | [42] | |
Ostericum koreanum | R/CHCl3 | CC [Bz‒EtOAc 9:1] | [51] | |
R/EtOAc | CC [NHEX–EtOAc] | [52,53] | ||
Petroselinurn crispurn | flake/DEE | RP-CC [MeCN–H2O 3:2], HPLC [MeCN–H2O 37:63], HPLC [CHCl3‒MeOH 99.9:0.1] | [54] | |
L/DEE | CC [NHEX–DEE 1:1], HPLC [MeCN–H2O 35:65] | [55] | ||
L/EtOAc | nd | [57] | ||
L/CH2Cl2 | CC [PET–EtOAc 1:0, 9:1, 8:2], CC [CH2Cl2–EtOAc 9:1], CC [CH2Cl2–MeOH 9:1, 8:2, 0:1], SLH [PE–CH2Cl2–MeOH 3:2:1], SLH [PET–CH2Cl2–MeOH 4:2:1], PTLC [PET–EtOAc 7:3] | [56] | ||
Peucedanum cervaria | Fr/CH2Cl2 | CCC [heptane–EtOAc–MeOH–H2O 3:2:3:2] | [58] | |
Peucedanum ostruthium | R/EtOAc | HPLC [MeOH–H2O (HOAc 0.1%) 0:100 to 100:0] | [59] | |
Prangos ferulacea | R/Me2CO | VLC [heptane–EtOAc 10:0 to 0:10], MPLC [heptane–EtOAc 7:3 to 5:5] | [61] | |
Prangos pabularia | R/CHCl3 | CC [NHEX–EtOAc 20:1; 10:1 to 0:1; EtOAc–MeOH 15:1 to 2:1], CC [NHEX–EtOAc 15:1] | [62] | |
Prangos uloptera | L/NHEX | CC [NHEX–EtOAc 100:0, 1:99, 5:95, 10:99, 20:80, 40:60, 60:40, 80:20, 100:0, MeOH 100], CC [NHEX–EtOAc 20:80, 0:100, MeOH 100%], PTLC [Me2CO–CHCl3 5:95] | [63] | |
Rutaceae | Citrus hystrix | Fr/EtOAc | ODS-CC [MeOH–H2O 50:50], PTLC [EtOAc–NHEX 4:1] | [64] |
Citrus limon | peel/EO | PTLC [EtOAc–Me2CO 95:5], HPLC | [65] | |
peel/EO | CC [PET–EtOAc 80:20], recrys. | [66] | ||
Citrus aurantifolia & C. latifolia | nd/EO | HSCCC [NHEX–EtOAc–MeOH–H2O 6:4:5:5] | [67] | |
Skimmia japonica | L/EtOAc | PTLC [CHCl3–EtOAc 8:2], PTLC [NHEX–CHCl3–EtOAc 7:2:1], CC [NHEX–CHCl3–EtOAc 8:1:1, 7:2:1, 6:3:1] | [68] | |
Zanthoxylum flavum | R/MeOH | RP-SPE [MeOH–H2O 6:4] | [69] |
2.2. Structural Identification of Oxypeucedanin
2.3. Analytical Investigations of Oxypeucedanin
2.3.1. Identification of Oxypeucedanin in the Apiaceae Family
Plant Family/Herbal Product | Plant Species | Subjected Plant Part/Soluble Extract | Analytical Instrument | Eluent System for Chromatography | Quantity | Reference |
---|---|---|---|---|---|---|
Apiaceae | Angelica archangelica | Fr/hydro-ethanolic (96%) | HPLC-UV | H2O‒MeOH [40:60 to 5:95] | 0‒6.45 mg/g | [71] |
R, L/MeOH | HPLC-MS | H2O (1% HCO2H)‒MeOH [40:60]; H2O (0.1% HCO2H)‒MeOH [100:0 to 70:30, 40:60, 0:100, 100:0] | na | [72] | ||
Angelica dahurica | Radix/MeOH | RRLC | H2O‒MeOH [55:45, 50:50, 42:58, 36:64, 30:70, 20:80] | 0.066‒1.45 mg/g | [14] | |
Radix/MeOH | HPLC-UV | H2O (0.2% H3PO4)‒MeOH [52:48, 40:60, 55:45, 48:52, 25:75] | 0.816 µg/mL (by IL-DLLME) | [73] | ||
Radix/MeOH | HPLC-UV | H2O‒MeCN [70:30, 40:60, 30:70, 40:60, 70:30] | 22.30 µg/g | [74] | ||
R/MeOH | HPLC-DAD | H2O‒MeOH [40:60, 20:80, 10:90, 0:100] | 1.5–3.0 mg/g | [75] | ||
R/MeOH | HPLC-DAD | H2O‒MeOH [40:60, 20:80, 10:90, 0:100] | 36.95 ± 1.45 (freeze dried) 24.96 ± 0.75 (shade dried) 24.22 ± 1.75 (40 °C) 32.13 ± 1.42 (70 °C) | [76] | ||
R/MeOH | SFC | CO2‒MeOH (0.1% DEA) [100:0, 97:3, 90:10] | 1.54–2.93 g/100 g (0.16‒0.77%) | [77] | ||
nd/MeOH | 1H-qNMR | solvent: DMSO-d6 | 6.38–6.39 ppm (0.17–0.35%) | [78] | ||
Radix/hydro-ethanolic (70%) | HPLC-DAD | H2O (0.1% HCO2H)‒MeOH [95:5, 35:65, 5:95] (for qualification) H2O (0.1% HCO2H)‒MeOH [70:30, 40:60, 40, 5:95] (for quantification) | 1.24–4.98 mg/g | [79] | ||
Radix/hydro-ethanolic (70%) | HPLC-UV | H2O‒MeCN [30:70] | 0.063 ± 0.01 % (collected from Korea) 0.024 ± 0.02 % (collected from China) | [80] | ||
R/EtOH | LC-NMR-MS | H2O‒MeCN [40:60] | na | [81] | ||
R/H2O (for boiled sample) and soybean oil, MeOH (for fried sample) | HPLC-DAD-ESI-MS | H2O (0.1% HCO2H)‒MeOH [for boiled sample: 95:5, 75:25, 26:64, 95:5] [for fried sample: 95:5, 85:15, 77:23, 47:53, 20:80, 95:5] | 15 µg/mL (for boiled sample) 8 µg/mL (for fried sample) | [82] | ||
Ostericum koreanum | R/MeOH | HPLC-UV | H2O‒MeCN [65:35 to 25:75] | 0.57 ± 0.26 0.99 ± 0.89 | [83] | |
nd/hydro-ethanolic (70%) | HPLC-UV | H2O‒MeCN [40:60] | 0.70 ± 0.02–21.11 ± 0.07% (Korean samples) 1.02 ± 0.01–12.60 ± 0.10% (Chinese samples) | [53] | ||
Petroselinum crispum | AP/MeOH | HPLC-QTOF-MS | H2O (0.1% HCO2H)‒MeCN [90:10, 60:40, 20:80, 10:90, 0:100, 90:10] | 46.04 ± 5.50 mg/kg | [84] | |
L, R, flake/EtOAc | HPLC-UV | cyclohexane‒isopropyl ether‒n-amyl alcohol [15:4:0.5] | 102.87 ± 14.08 µg/g (curled L) 88.68 ± 6.04 µg/g (curled R) 88.60 ± 17.90 µg/g (flake) | [55] | ||
Peucedanum alsaticum | Fr/PET | UPLC | H2O‒MeCN [74:26 to 55:45] | na | [85] | |
Peucedanum ostruthium | Rh/CH2Cl2 | HPLC-DAD-MS | H2O (0.01% HOAc)‒MeCN (0.01% HOAc) [75:25 to 63:37 to 55:45 to 35:65 to 5:95] | 1.58 ± 0.03–25.05 ± 0.11 mg/g | [86] | |
R/EtOAc | HPLC-DAD (RP-C30) HPLC-UV-ESI-MS | H2O (0.1% HOAc)‒MeOH [100:0 to 0:100] | na | [59] | ||
Peucedanum palustre | R, St, L, umbel/MeOH | HPLC-DAD-ESI-HR-MS | H2O (0.01 M HCO2H)‒MeCN [100:0 to 40:60, 10:90] | 24.3 ± 14.0 mg/g (in R) 2.62 ± 1.56 mg/g (in St) 2.25 ± 1.28 mg/g (in L) 22.8 ± 30.9 mg/g (in umbel) | [87] | |
R, umbel/MeOH | HPLC-MS | H2O (1% HCO2H)‒MeOH [40:60] H2O‒MeOH (1% HCO2H) [71:29, 0:100], H2O‒MeOH (1% HCO2H) [100:0 to 70:30, 40:60, 0:100, 100:0] | nd | [72] | ||
R/NHEX | HPLC-DAD | THF‒MeCN‒MeOH‒H2O [3.1:35:5.4:56.5] | 0.16–0.44 mg/100 g | [88] | ||
Prangos ferulacea | R/NHEX, hydro-ethanolic (95%), MeOH | HPLC-UV | H2O‒MeOH [30:70] | 59.38 ± 0.007 mg/g (extraction with Soxhlet, NHEX) 79.27 ± 0.22 mg/g (extraction with UAE, hydro-ethanolic 95%) 55.29 ± 0.01 mg/g (extraction with maceration, MeOH) | [89] | |
Rutaceae | Atalantia ceylanica | Se/MeOH | HPLC-UV | nd | na | [90] |
Citrus spp. | EO | HPLC-UV | NHEX‒isopropanol [98:2] | 0.7–1.65 g/L (Lemon EO from Sicily) 0.95 g/L (Lemon EO from Spain) 2.02 g/L (Lemon EO from Argentina) 0.49 g/L (Lime EO from Mexican 1) 0.96 g/L (Lime EO from Mexican 2) 0.68 g/L (Lime EO from Iran) | [91] | |
EO | HPTLC | CH2Cl2‒DEE [100:3], CHCl3‒heptane [95:5] | na | [92] | ||
EO | HPLC-UV | NHEX + EtOAc (92:8)‒NHEX + EtOH (90:10) | 1.55 ± 0.38 g/kg (extracted EO by Sfumatrice technology) 2.2 ± 0.41 g/kg (extracted EO by Pelatrice technology) 1.9 ± 0.45 g/kg (extracted EO by FMC technology) 0.86 ± 0.26 g/kg (extracted EO by Torchi technology) | [93] | ||
Citrus aurantifolia & C. latifolia | EO | HPLC-DAD | H2O + MeOH + THF (85:10:5)‒MeOH + THF (95:5) [100:0, 60:40, 10:90, 100:0] | 4.09–10.54 g/L (C. aurantifolia) 0.27–10.72 g/L (C. latifolia) | [94] | |
EO | HPLC-UV | NHEX + EtOAc (93:7)‒NHEX + EtOH (90:10) [100:0 to 5:95, 100:0] | 144 mg/100 g (C. aurantifolia) 210–328 mg/100 g (C. latifolia) | [95] | ||
Citrus aurantifolia & C. latifolia & C. paradisi | EO | HPLC-DAD | H2O‒MeCN [70:30 to 60:40] | na | [67] | |
Citrus limon | Wax/EO | UHPLC-DAD | H2O (0.1% HCO2H)‒MeCN [25:75, 100:0, 50:50, 30:70] | 62 ± 0.8 mg/kg | [96] | |
EO | HPLC-DAD | NHEX + EtOAc (92:8)‒NHEX + EtOH (90:10) [100:0 to 0:100] | 89–157 mg/100 g | [66] | ||
Citrus medica | Fr/EO | HPLC-DAD | H2O‒MeCN [70:30, 40:60, 0:100, 70:30] | 2.03–21.30 g/100 g | [97] | |
Eureka limon | peel/EO | GC-MS | - | na | [98] | |
Yuanhu zhitong (Chinese herbal drug) | Hydro-methanolic (75%) | UPLC-Q-TOF-MS | H2O (0.2% HCO2H)‒MeCN | na | [99] | |
Hydro-methanolic (75%) | RRLC-QQQ | H2O (0.3% HCO2H)‒MeCN [80:20, 60:40, 20:80] | 0.12–4.01 µg/g | [100] |
2.3.2. Characterization of Oxypeucedanin in the Rutaceae Family
2.3.3. Identification of Oxypeucedanin from Other Natural Sources
3. Biological Activities of Oxypeucedanin
3.1. Antiallergic Activity
3.2. Antiarrhythmic Activity
3.3. Anticonvulsant Activity
3.4. Antifeedant Activity
3.5. Antigenotoxic Activity
3.6. Anti-Inflammatory Activity
3.7. Antimalarial Activity
3.8. Antimicrobial Activity
3.9. Antioxidant Activity
3.10. Antiproliferative Activity
3.11. Antiviral Activity
3.12. Calcium Antagonistic Activity
3.13. Cytotoxic Activity
3.14. Enzyme Inhibitory Activity
3.15. Insecticidal Activity
3.16. Phytotoxic Activity
4. Pharmacokinetic Analysis of Oxypeucedanin
5. Conclusions and Perspectives
Supplementary Materials
Funding
Institutional Review Board Statement
Informed Consent Statement
Conflicts of Interest
References
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Plant Species/Purchased | Analytical Instrument | Method of Assessment | Concentration in Living Organisms | Reference |
---|---|---|---|---|
Angelica dahurica | UHPLC‒ELSD | AF (0.1% HCO2H)‒MeCN (0.1% HCO2H) [95:5, 86:14, 78:22, 70:30, 66:34, 62:38, 56:44, 16:84, 5:95, 95:5] | C: 0.05 µg/g in lung C: 0.013 µg/g in liver | [113] |
HPLC–ESI–MS | H2O (0.1% HCO2H)‒MeOH [28:72] | 0.177% (in bile) ‒ 0.082% (in rat urine) | [114] | |
UHPLC-MS/MS | H2O (0.1% HCO2H)‒MeCN [65:35, 40:60] | 6.67% Cmax: 38.5 ± 1.6 ng/mL at 0.5 g/kg (in normal rats) Cmax: 101.2 ± 21.2 ng/mL at 1.0 g/kg (in normal rats) Cmax: 29.0 ± 4.0 ng/mL at 0.5 g/kg (in TNBS-treated rats) Cmax: 61.2 ± 11.9 ng/mL at 1.0 g/kg (in TNBS-treated rats) | [115] | |
GC-MS | - | Cmax: 0.46 ± 0.01 µg/mL Tmax: 0.51 h | [116] | |
LC-MS/MS | H2O (0.1% HCO2H)‒MeCN [65:35, 53:47, 15:85, 65:35] | Cmax: 111 ± 25 ng/mL at 4.5 g/kg extract/5.2 mg/kg OP (in rat plasma) Tmax: 12 ± 0 h | [118] | |
Glehnia littoralis | HPLC-ESI-MS/MS | H2O (1 mmol AAc)‒MeOH [60:40, 10:90, 60:40] | 19.0 µg/mL (in plant sample) 13 ng (in rat urine after 72 h oral administration) 18 ng (in rat bile after 72 h oral administration) | [117] |
Purchased | LC-MS/MS | H2O (0.1% HCO2H)‒MeCN [70:30, 52:48, 30:70, 70:30] | Cmax: 118.40 ± 10.93 µg/L (docetaxel in rat plasma) Cmax: 178.80 ± 8.81 µg/L (OP + docetaxel in rat plasma) Tmax: 163.80 ± 11.82 min (docetaxel) Tmax: 104.60 ± 11.68 min (OP + docetaxel) | [106] |
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Mottaghipisheh, J. Oxypeucedanin: Chemotaxonomy, Isolation, and Bioactivities. Plants 2021, 10, 1577. https://doi.org/10.3390/plants10081577
Mottaghipisheh J. Oxypeucedanin: Chemotaxonomy, Isolation, and Bioactivities. Plants. 2021; 10(8):1577. https://doi.org/10.3390/plants10081577
Chicago/Turabian StyleMottaghipisheh, Javad. 2021. "Oxypeucedanin: Chemotaxonomy, Isolation, and Bioactivities" Plants 10, no. 8: 1577. https://doi.org/10.3390/plants10081577