The Relative Content and Distribution of Absorbed Volatile Organic Compounds in Rats Administered Asari Radix et Rhizoma Are Different between Powder- and Decoction-Treated Groups
Abstract
:1. Introduction
2. Results and Discussion
2.1. Identification of ARR VOCs In Vivo in Rats
2.2. Distribution of ARR VOCs In Vivo in Rats
2.2.1. Distribution of VOCs in ARR Powder-Treated Group
2.2.2. Distribution of VOCs in Decoction-Treated Group
2.2.3. Distribution of Main Compounds Identified In Vivo in Rats
2.3. Metabolism of VOCs of ARR
2.3.1. Metabolites of the Oxidation Reaction
2.3.2. Metabolites of the Reduction Reaction
2.4. Review of the Bioactivity and Acute Toxicity of Main Absorbed Constituents
3. Experiment
3.1. Chemicals and Reagents
3.2. Plant Material
3.3. Sample Preparation
3.3.1. Dosage of Administration
3.3.2. Decoction of ARR
3.3.3. Suspension Solution of ARR Powder
3.4. HS-SPME-GC–MS Analysis
3.5. Animals and Drug Administration
3.6. Sample Collection and Preparation
3.7. Identification of Compounds
- Level 1:
- Compounds were identified by comparing their retention time and mass spectra with those of reference compounds.
- Level 2:
- Compounds were identified by comparing their RI and mass spectra with those of the literature.
- Level 3:
- Compounds were identified by searching mass spectra in NIST 11.
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
Abbreviations
ARR | Asari Radix et Rhizoma |
AHM | Asarum heterotropoides Fr. Schmidt var. mandshuricum (Maxim.) Kitag. |
VOCs | Volatile organic compounds |
RI | Retention index |
LD50 | Median lethal dose |
3,5-DMT | 3,5-Dimethoxytoluene |
2,3,5-TMT | 2,3,5-Trimethoxytoluene |
3,4,5-TMT | 3,4,5-Trimethoxytoluene |
GC–MS | Gas chromatography–mass spectrometry |
HPLC | High–performance liquid chromatography |
UPLC | Ultra–performance liquid chromatography |
HS–SPME–GC–MS | Headspace solid–phase microextraction gas–chromatographymass spectrometry |
HPLC–APCI–IT–TOF–MSn | High-performance liquid chromatography–atmospheric pressurechemical ionization–ion trap–time of flight–multistage mass spectrometry |
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Sample Availability: Samples of ARR and the compounds M3, M8, M12, M22, M37, M60, M64, M79, M82, M83, M93, M107, M112, M122 and M138 are available from the authors. Raw GC-MS data in CDF format are available from the MetaboLights repository, https://www.ebi.ac.uk/metabolights/ (Study Identifier: MTBLS2053). |
No. a | Name of Compounds | CAS b | tR (min) | MW c | Formula | RI d | Identification e |
---|---|---|---|---|---|---|---|
M1 | α-Pinene | 80-56-8 | 3.785 | 136 | C10H16 | 1021 | MS, RI |
M2 | Camphene | 79-92-5 | 4.375 | 136 | C10H16 | 1060 | MS, RI |
M3 | β-Pinene | 127-91-3 | 4.955 | 136 | C10H16 | 1099 | MS, RI, REF |
M4 | Sabinene | 3387-41-5 | 5.175 | 136 | C10H16 | 1110 | MS, RI |
M5 | 3-Carene | 13466-78-9 | 5.700 | 136 | C10H16 | 1135 | MS, RI, |
M6 | β-Myrcene | 123-35-3 | 6.080 | 136 | C10H16 | 1154 | MS, RI |
M7 | d-4-Carene | 29050-33-7 | 6.405 | 136 | C10H16 | 1170 | MS, RI |
M8 | Limonene | 138-86-3 | 6.830 | 136 | C10H16 | 1191 | MS, RI, REF |
M9 | Eucalyptol | 470-82-6 | 7.095 | 154 | C10H18O | 1203 | MS, RI |
M10 | o-Cymene | 527-84-4 | 8.630 | 134 | C10H14 | 1267 | MS, RI |
M11 | Terpinolene | 586-62-9 | 8.895 | 136 | C10H16 | 1279 | MS, RI |
M12 | Tridecane | 629-50-5 | 9.217 | 184 | C13H28 | 1293 | MS, RI, REF |
M13 | Acetoin | 513-86-0 | 9.328 | 88 | C4H8O2 | 1298 | MS, RI |
M14 | p-Cymenene | 1195-32-0 | 12.885 | 132 | C10H12 | 1433 | MS, RI |
M15 | cis-Limonene oxide | 13837-75-7 | 13.135 | 152 | C10H16O | 1441 | MS, RI |
M16 | cis-4-Thujanol | 15537-55-0 | 13.795 | 154 | C10H18O | 1462 | MS, RI |
M17 | 2-Nonen-4-one | 32064-72-5 | 14.270 | 140 | C9H16O | 1477 | MS, RI |
M18 | α-Copaene | 3856-25-5 | 14.485 | 204 | C15H24 | 1485 | MS, RI |
M19 | Pentadecane | 629-62-9 | 14.953 | 212 | C15H32 | 1500 | MS, RI |
M20 | dl-Camphor | 76-22-2 | 15.305 | 152 | C10H16O | 1507 | MS, RI |
M21 | 1-Pentadecene | 13360-61-7 | 16.070 | 210 | C15H30 | 1523 | MS, RI |
M22 | Eucarvone | 503-93-5 | 17.060 | 150 | C10H14O | 1543 | MS, REF |
M23 | l-Aristolene | 6831-16-9 | 17.560 | 204 | C15H24 | 1553 | MS, RI |
M24 | Isopulegol | 89-79-2 | 17.720 | 154 | C10H18O | 1556 | MS, RI |
M25 | β-Copaene | 18252-44-3 | 18.115 | 204 | C15H24 | 1565 | MS, RI |
M26 | Bornyl acetate | 76-49-3 | 18.305 | 196 | C12H20O2 | 1568 | MS, RI |
M27 | 1(10)-Aristolene | 17334-55-3 | 18.760 | 204 | C15H24 | 1577 | MS, RI |
M28 | Fenchol | 1632-73-1 | 18.920 | 154 | C10H18O | 1581 | MS, RI |
M29 | Thymol methyl ether | 1076-56-8 | 19.390 | 164 | C11H16O | 1590 | MS, RI |
M30 | l-Aristolene isomer | 19.650 | 204 | C15H24 | 1596 | MS | |
M31 | β-Cyclocitral | 432-25-7 | 20.510 | 152 | C10H16O | 1610 | MS, RI |
M32 | Methyl benzoate | 93-58-3 | 20.816 | 136 | C8H8O2 | 1615 | MS, RI |
M33 | l-Menthol | 2216-51-5 | 21.220 | 156 | C10H20O | 1621 | MS, RI |
M34 | δ-Guaiene | 3691-11-0 | 21.535 | 204 | C15H24 | 1626 | MS, RI |
M35 | Umbellulone | 24545-81-1 | 21.815 | 150 | C10H14O | 1630 | MS, RI |
M36 | l-Pinocarveol | 547-61-5 | 23.120 | 152 | C10H16O | 1651 | MS, RI |
M37 | Estragole | 140-67-0 | 23.905 | 148 | C10H12O | 1663 | MS, RI, REF |
M38 | Isomenthol | 490-99-3 | 24.295 | 156 | C10H20O | 1670 | MS, RI |
M39 | Verbenol | 473-67-6 | 24.570 | 152 | C10H16O | 1674 | MS, RI |
M40 | Eucarvone isomer | 24.990 | 150 | C10H14O | 1680 | MS | |
M41 | Verbenone | 80-57-9 | 25.240 | 150 | C10H14O | 1684 | MS, RI |
M42 | α-Terpineol acetate | 80-26-2 | 25.300 | 196 | C12H20O2 | 1685 | MS, RI |
M43 | 4-Ethylbenzaldehyde | 4748-78-1 | 25.830 | 134 | C9H10O | 1693 | MS, RI |
M44 | Borneol | 507-70-0 | 25.875 | 154 | C10H18O | 1692 | MS, RI |
M45 | Phellandral | 21391-98-0 | 26.415 | 154 | C10H18O | 1703 | MS, RI |
M46 | Piperitone | 89-81-6 | 26.610 | 152 | C10H16O | 1706 | MS, RI |
M47 | β-Cyclogeraniol | 472-20-8 | 26.960 | 154 | C10H18O | 1711 | MS |
M48 | l-Carvone | 2244-16-8 | 27.270 | 150 | C10H14O | 1716 | MS, RI |
M49 | Berbenone | 80-57-9 | 28.190 | 150 | C10H14O | 1730 | MS, RI |
M50 | trans-Piperitol | 16721-39-4 | 29.165 | 154 | C10H18O | 1745 | MS, RI |
M51 | cis-Piperitol | 16721-38-3 | 29.485 | 154 | C10H18O | 1750 | MS, RI |
M52 | Methyl benzeneacetate | 101-41-7 | 29.955 | 150 | C9H10O2 | 1758 | MS, RI |
M53 | Myrtenol | 515-00-4 | 31.910 | 152 | C10H16O | 1788 | MS, RI |
M54 | 6-Methyl-2-hepten-4-one | 49852-35-9 | 32.060 | 126 | C8H14O | 1790 | MS |
M55 | 3,4-Dimethylbenzaldehyde | 5973-71-7 | 32.061 | 134 | C9H10O | 1790 | MS, RI |
M56 | Cuparene | 16982-00-6 | 32.520 | 202 | C15H22 | 1797 | MS, RI |
M57 | cis-Sabinol | 3310-02-9 | 32.645 | 152 | C10H16O | 1799 | MS, RI |
M58 | Anethol | 104-46-1 | 33.265 | 148 | C10H12O | 1815 | MS, RI |
M59 | cis-Carveol | 1197-06-4 | 34.050 | 152 | C10H16O | 1835 | MS, RI |
M60 | 3,5-Dimethoxytoluene | 4179-19-5 | 34.260 | 152 | C9H12O2 | 1840 | MS, RI, REF |
M61 | p-Cymen-8-ol | 1197-01-9 | 34.660 | 150 | C10H14O | 1851 | MS, RI |
M62 | 2,3-Dimethyldecahydronaphthalene | 1008-80-6 | 34.995 | 166 | C12H22 | 1859 | MS |
M63 | Guaiacol | 90-05-1 | 35.000 | 124 | C7H8O2 | 1860 | MS, RI |
M64 | Safrole | 94-59-7 | 35.108 | 162 | C10H10O2 | 1862 | MS, RI, REF |
M65 | Benzyl alcohol | 100-51-6 | 35.662 | 108 | C7H8O | 1877 | MS, RI |
M66 | Verbenone isomer | 36.215 | 150 | C10H14O | 1891 | MS | |
M67 | Verbenone isomer | 36.360 | 150 | C10H14O | 1895 | MS | |
M68 | 2-Phenylethanol | 60-12-8 | 36.725 | 122 | C8H10O | 1906 | MS, RI |
M69 | Agarospirol | 1460-73-7 | 37.365 | 222 | C15H26O | 1928 | MS |
M70 | 3,4-Methylenedioxyanisole | 7228-35-5 | 37.450 | 152 | C8H8O3 | 1931 | MS |
M71 | Isosafrole isomer | 37.575 | 162 | C10H10O2 | 1936 | MS | |
M72 | Creosol | 93-51-6 | 38.108 | 138 | C8H10O2 | 1954 | MS, RI |
M73 | 2-Allyl-1,4-dimethoxybenzene | 19754-22-4 | 38.535 | 178 | C11H14O2 | 1968 | MS |
M74 | Thymoquinone | 490-91-5 | 38.880 | 164 | C10H12O2 | 1980 | MS |
M75 | Methyleugenol isomer | 39.055 | 178 | C11H14O2 | 1986 | MS | |
M76 | 6-Allyl-o-cresol | 3354-58-3 | 39.435 | 148 | C10H12O | 2000 | MS |
M77 | 2,4-Dimethylanisole | 6738-23-4 | 39.485 | 136 | C9H12O | 2002 | MS |
M78 | p-Methoxybenzaldehyde | 123-11-5 | 39.630 | 136 | C8H8O2 | 2008 | MS, RI |
M79 | Methyleugenol | 93-15-2 | 39.715 | 178 | C11H14O2 | 2011 | MS, RI, REF |
M80 | o-Methylphenol | 95-48-7 | 39.730 | 108 | C7H8O | 2012 | MS, RI |
M81 | Isosafrole | 120-58-1 | 39.925 | 162 | C10H10O2 | 2020 | MS, RI |
M82 | 2,3,5-Trimethoxytoluene | 38790-14-6 | 40.415 | 182 | C10H14O3 | 2040 | REF |
M83 | 3,4,5-Trimethoxytoluene | 6443-69-2 | 40.610 | 182 | C10H14O3 | 2048 | MS, RI, REF |
M84 | 3,4,5-Trimethoxybenzoic acid | 118-41-2 | 40.780 | 212 | C10H12O5 | 2055 | MS |
M85 | Globulol | 51371-47-2 | 40.910 | 222 | C15H26O | 2061 | MS, RI |
M86 | 1,2,4-Trimethoxybenzene | 135-77-3 | 41.430 | 168 | C9H12O3 | 2083 | MS, RI |
M87 | E-Isocroweacin | 194609-21-7 | 41.755 | 192 | C11H12O3 | 2096 | MS |
M88 | Dihydroeugenol | 2785-87-7 | 41.970 | 166 | C10H14O2 | 2106 | MS, RI |
M89 | Spathulenol | 6750-60-3 | 42.110 | 220 | C15H24O | 2112 | MS, RI |
M90 | Dihydroeugenol isomer | 42.190 | 166 | C10H14O2 | 2116 | MS | |
M91 | Viridiflorol | 552-02-3 | 42.310 | 222 | C15H26O | 2122 | MS, RI |
M92 | Patchoulol | 5986-55-0 | 43.065 | 222 | C15H26O | 2157 | MS, RI |
M93 | Eugenol | 97-53-0 | 43.250 | 164 | C10H12O2 | 2166 | MS, RI, REF |
M94 | 1,2,4-Trimethoxybenzene isomer | 43.565 | 168 | C9H12O3 | 2181 | MS | |
M95 | 4-Methoxysafrole | 18607-93-7 | 43.745 | 192 | C11H12O3 | 2189 | MS, RI |
M96 | m-Eugenol | 501-19-9 | 43.780 | 164 | C10H12O2 | 2191 | MS, RI |
M97 | 2,4,5-Trimethoxybenzoic acid | 490-64-2 | 43.815 | 212 | C10H12O5 | 2192 | MS |
M98 | Thymol | 89-83-8 | 43.850 | 150 | C10H14O | 2194 | MS, RI |
M99 | p-Methoxypropiophenone | 121-97-1 | 43.910 | 164 | C10H12O2 | 2197 | MS |
M100 | Bulnesol | 22451-73-6 | 44.010 | 222 | C15H26O | 2202 | MS, RI |
M101 | α-Bisabolol | 515-69-5 | 44.200 | 222 | C15H26O | 2212 | MS, RI |
M102 | 2-Aminoacetophenone | 551-93-9 | 44.232 | 135 | C8H9NO | 2214 | MS, RI |
M103 | α-Eudesmol | 473-16-5 | 44.325 | 222 | C15H26O | 2219 | MS, RI |
M104 | Piperonal | 120-57-0 | 44.340 | 150 | C8H6O3 | 2219 | MS, RI |
M105 | Isothymol | 499-75-2 | 44.390 | 150 | C10H14O | 2222 | MS, RI |
M106 | α-Cadinol | 481-34-5 | 44.435 | 222 | C15H26O | 2225 | MS, RI |
M107 | Elemicin | 487-11-6 | 44.505 | 208 | C12H16O3 | 2228 | MS, RI, REF |
M108 | 3,4,5-Trimethoxytoluene isomer | 44.765 | 182 | C10H14O3 | 2242 | MS | |
M109 | Methoxyeugenol isomer | 44.870 | 194 | C11H14O3 | 2248 | MS | |
M110 | Isospathulenol | 88395-46-4 | 44.935 | 220 | C15H24O | 2251 | MS, RI |
M111 | cis-Isoeugenol | 5912-86-7 | 45.080 | 164 | C10H12O2 | 2258 | MS, RI |
M112 | β-Asarone | 5273-86-9 | 45.180 | 208 | C12H16O3 | 2264 | MS, RI, REF |
M113 | 1,2,4-Trimethoxybenzene isomer | 45.360 | 168 | C9H12O3 | 2273 | MS | |
M114 | 1,2,3,4-Tetramethoxybenzene | 21450-56-6 | 45.590 | 198 | C10H14O4 | 2286 | MS, RI |
M115 | 1,2,4-Trimethoxybenzene isomer | 46.360 | 168 | C9H12O3 | 2334 | MS | |
M116 | 3,4-Methylenedioxyacetophenone | 3162-29-6 | 46.400 | 164 | C9H8O3 | 2337 | MS |
M117 | Chavicol | 501-92-8 | 46.605 | 134 | C9H10O | 2350 | MS, RI |
M118 | 1,2,4-Trimethoxybenzene isomer | 46.670 | 168 | C9H12O3 | 2355 | MS | |
M119 | Kaurene | 34424-57-2 | 46.785 | 272 | C20H32 | 2362 | MS, RI |
M120 | Methylvanillin | 120-14-9 | 47.240 | 166 | C9H10O3 | 2394 | MS, RI |
M121 | Methoxyeugenol isomer | 47.304 | 194 | C11H14O3 | 2398 | MS | |
M122 | 3,4-Methylenedioxypropiophenone | 28281-49-4 | 47.395 | 178 | C10H10O3 | 2405 | MS, REF |
M123 | Apiol | 523-80-8 | 47.510 | 222 | C12H14O4 | 2415 | MS, RI |
M124 | Amilfenol | 80-46-6 | 47.560 | 164 | C11H16O | 2418 | MS |
M125 | 6-Allyl-2-methylphenol | 3354-58-3 | 47.755 | 148 | C10H12O | 2435 | MS |
M126 | Methoxyeugenol isomer | 47.835 | 194 | C11H14O3 | 2441 | MS | |
M127 | Kakuol isomer | 47.895 | 194 | C10H10O4 | 2446 | MS | |
M128 | Mellein | 1200-93-7 | 48.255 | 178 | C10H10O3 | 2475 | MS, RI |
M129 | 2,4-Dimethoxyacetophenone | 829-20-9 | 48.345 | 180 | C10H12O3 | 2483 | MS |
M130 | 2,6-Dimethoxyacetophenone | 2040-04-2 | 48.585 | 180 | C10H12O3 | 2503 | MS |
M131 | 1-(3,4-Methylenedioxyphenyl)-propane-1-ol | 6890-30-8 | 48.777 | 180 | C10H12O3 | 2521 | MS |
M132 | Piperonol | 495-76-1 | 48.928 | 152 | C8H8O3 | 2534 | MS |
M133 | Methoxyeugenol isomer | 48.935 | 194 | C11H14O3 | 2534 | MS | |
M134 | 3-Methoxy-5-methylphenol | 3209-13-0 | 48.985 | 138 | C8H10O2 | 2538 | MS, RI |
M135 | 2′,4′-Dimethoxypropiophenone | 831-00-5 | 49.045 | 194 | C11H14O3 | 2544 | MS |
M136 | 4,6-Dimethoxy-phthalide | 58545-97-4 | 49.065 | 194 | C10H10O4 | 2546 | MS |
M137 | Methoxyeugenol | 6627-88-9 | 49.069 | 194 | C11H14O3 | 2547 | MS, RI |
M138 | Kakuol | 18607-90-4 | 49.295 | 194 | C10H10O4 | 2567 | MS, REF |
M139 | 2′,4′-Dimethoxy-3′-methylpropiophenone isomer | 49.690 | 208 | C12H16O3 | 2602 | MS | |
M140 | Xanthoxylin | 90-24-4 | 49.760 | 196 | C10H10O4 | 2608 | MS |
M141 | 3,4-Methylenedioxyphenyl-1-propanal | 30830-55-8 | 49.915 | 178 | C10H10O3 | 2620 | MS |
M142 | 2′,4′-Dimethoxy-3′-methylpropiophenone isomer | 50.226 | 208 | C12H16O3 | 2645 | MS | |
M143 | 3,4,5-Trimethoxyphenyl-2-propanone | 16603-18-2 | 50.270 | 224 | C12H16O4 | 2648 | MS |
M144 | 4-(Dimethoxymethyl)-1,2-dimethoxybenzene | 59276-33-4 | 50.615 | 212 | C11H16O4 | 2676 | MS |
M145 | Propioveratrone | 1835-04-7 | 50.740 | 194 | C11H14O3 | 2686 | MS |
M146 | 2′,4′-Dimethoxypropiophenone | 831-00-5 | 50.760 | 194 | C11H14O3 | 2687 | MS |
M147 | Dihydromethyleugenol | 5888-52-8 | 51.135 | 180 | C11H16O2 | 2714 | MS |
M148 | 2′,4′-Dimethoxy-3′-methylpropiophenone | 77942-13-3 | 51.435 | 208 | C12H16O3 | 2734 | MS |
M149 | 1-Hydroxy-2-(prop-2-enyl)-4,5- methylenedioxybenzene | 19202-23-4 | 51.670 | 178 | C10H10O3 | 2750 | MS |
M150 | 3-(2,4,6-Trimethoxyphenyl)-2-butanone | 26537-69-9 | 51.850 | 238 | C13H18O4 | 2761 | MS |
M151 | 1,2-Dimethoxy-4-(1,2-dimethox yethyl)-benzene | 477884-01-8 | 52.195 | 226 | C12H18O4 | 2785 | MS |
M152 | 1-Hydroxy-2-(prop-2-enyl)-4,5- methylenedioxybenzene isomer | 52.665 | 178 | C10H10O3 | 2814 | MS | |
M153 | Syringic acid | 530-57-4 | 55.055 | 198 | C9H10O5 | 2934 | MS |
No. | Constituents | RI | Powder-Treated Group | Decoction-Treated Group | ||||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
FE | UR | BL | BR | HE | LU | SP | LI | KI | ST | IN | FE | UR | BL | BR | HE | LU | SP | LI | KI | ST | IN | |||
M1 | α-Pinene | 1021 | ● | |||||||||||||||||||||
M2 | Camphene | 1060 | ● | |||||||||||||||||||||
M3 | β-Pinene | 1099 | ● | ● | ||||||||||||||||||||
M4 | Sabinene | 1110 | ● | |||||||||||||||||||||
M5 | 3-Carene | 1135 | ● | ● | ● | |||||||||||||||||||
M6 | β-Myrcene | 1154 | ● | ● | ||||||||||||||||||||
M7 | d-4-Carene | 1170 | ● | |||||||||||||||||||||
M8 | Limonene | 1191 | ● | ● | ||||||||||||||||||||
M9 | Eucalyptol | 1203 | ● | ● | ● | ● | ● | |||||||||||||||||
M10 | o-Cymene | 1267 | ● | ● | ● | |||||||||||||||||||
M11 | Terpinolene | 1279 | ● | ● | ||||||||||||||||||||
M12 | Tridecane | 1293 | ● | |||||||||||||||||||||
M13 | Acetoin | 1298 | ● | |||||||||||||||||||||
M14 | p-Cymenene | 1433 | ● | |||||||||||||||||||||
M16 | cis-4-Thujanol | 1462 | ● | |||||||||||||||||||||
M18 | α-Copaene | 1485 | ● | |||||||||||||||||||||
M19 | Pentadecane | 1500 | ● | |||||||||||||||||||||
M20 | dl-Camphor | 1507 | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | |||||||
M21 | 1-Pentadecene | 1523 | ● | |||||||||||||||||||||
M22 | Eucarvone | 1543 | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ||||||||||
M23 | l-Aristolene | 1553 | ● | ● | ||||||||||||||||||||
M25 | β-Copaene | 1565 | ● | |||||||||||||||||||||
M26 | Bornyl acetate | 1568 | ● | ● | ● | |||||||||||||||||||
M27 | 1(10)-Aristolene | 1577 | ● | ● | ||||||||||||||||||||
M28 | Fenchol | 1581 | ● | ● | ||||||||||||||||||||
M29 | Thymol methyl ether | 1590 | ● | ● | ||||||||||||||||||||
M30 | l-Aristolene isomer | 1596 | ● | |||||||||||||||||||||
M31 | β-Cyclocitral | 1610 | ● | ● | ||||||||||||||||||||
M33 | l-Menthol | 1621 | ● | |||||||||||||||||||||
M34 | δ-Guaiene | 1626 | ● | ● | ||||||||||||||||||||
M35 | Umbellulone | 1630 | ● | ● | ||||||||||||||||||||
M37 | Estragole | 1663 | ● | ● | ● | ● | ● | ● | ● | ● | ● | |||||||||||||
M38 | Isomenthol | 1670 | ● | |||||||||||||||||||||
M40 | Eucarvone isomer | 1680 | ● | ● | ● | ● | ||||||||||||||||||
M41 | Verbenone | 1684 | ● | |||||||||||||||||||||
M44 | Borneol | 1692 | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | |||||||||||
M45 | Phellandral | 1703 | ● | ● | ||||||||||||||||||||
M46 | Piperitone | 1706 | ● | ● | ● | ● | ||||||||||||||||||
M48 | l-Carvone | 1716 | ● | |||||||||||||||||||||
M49 | Berbenone | 1730 | ● | ● | ● | ● | ||||||||||||||||||
M50 | trans-Piperitol | 1745 | ● | |||||||||||||||||||||
M53 | Myrtenol | 1788 | ● | ● | ||||||||||||||||||||
M56 | Cuparene | 1797 | ● | |||||||||||||||||||||
M57 | cis-Sabinol | 1799 | ● | |||||||||||||||||||||
M59 | cis-Carveol | 1835 | ● | ● | ● | |||||||||||||||||||
M60 | 3,5-Dimethoxytoluene | 1840 | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | |||||||
M61 | p-Cymen-8-ol | 1851 | ● | ● | ||||||||||||||||||||
M62 | 2,3-Dimethyldecahydronaphthalene | 1859 | ● | |||||||||||||||||||||
M64 | Safrole | 1862 | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | |||||
M67 | Verbenone isomer | 1895 | ● | |||||||||||||||||||||
M69 | Agarospirol | 1928 | ● | |||||||||||||||||||||
M70 | 3,4-Methylenedioxyanisole | 1931 | ● | ● | ||||||||||||||||||||
M71 | Isosafrole isomer | 1936 | ● | |||||||||||||||||||||
M73 | 2-Allyl-1,4-dimethoxybenzene | 1968 | ● | |||||||||||||||||||||
M74 | Thymoquinone | 1980 | ● | ● | ● | ● | ● | ● | ● | |||||||||||||||
M75 | Methyleugenol isomer | 1986 | ● | ● | ||||||||||||||||||||
M77 | 2,4-Dimethylanisole | 2002 | ● | |||||||||||||||||||||
M79 | Methyleugenol | 2011 | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ||||
M81 | Isosafrole | 2020 | ● | ● | ● | ● | ● | ● | ● | |||||||||||||||
M82 | 2,3,5-Trimethoxytoluene | 2040 | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● |
M83 | 3,4,5-Trimethoxytoluene | 2048 | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● |
M84 | 3,4,5-Trimethoxybenzoic acid | 2055 | ● | ● | ● | ● | ● | ● | ● | ● | ● | |||||||||||||
M85 | Globulol | 2061 | ● | ● | ● | |||||||||||||||||||
M86 | 1,2,4-Trimethoxybenzene | 2083 | ● | ● | ||||||||||||||||||||
M87 | E-Isocroweacin | 2096 | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ||||||||||||
M89 | Spathulenol | 2112 | ● | ● | ● | |||||||||||||||||||
M91 | Viridiflorol | 2122 | ● | ● | ||||||||||||||||||||
M92 | Patchoulol | 2157 | ● | ● | ||||||||||||||||||||
M93 | Eugenol | 2166 | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | |||||
M95 | 4-Methoxysafrole | 2189 | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | |||||||||||
M97 | 2,4,5-Trimethoxybenzoic acid | 2192 | ● | ● | ● | ● | ● | |||||||||||||||||
M98 | Thymol | 2194 | ● | ● | ● | ● | ● | |||||||||||||||||
M99 | p-Methoxypropiophenone | 2197 | ● | ● | ● | ● | ● | ● | ||||||||||||||||
M100 | Bulnesol | 2202 | ● | |||||||||||||||||||||
M101 | α-Bisabolol | 2212 | ● | |||||||||||||||||||||
M103 | α-Eudesmol | 2219 | ● | |||||||||||||||||||||
M104 | Piperonal | 2219 | ● | ● | ● | ● | ||||||||||||||||||
M105 | Isothymol | 2222 | ● | ● | ||||||||||||||||||||
M106 | α-Cadinol | 2225 | ● | |||||||||||||||||||||
M107 | Elemicin | 2228 | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ||||||||
M108 | 3,4,5-Trimethoxytoluene isomer | 2242 | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | |||||||||||
M109 | Methoxyeugenol isomer | 2248 | ● | ● | ||||||||||||||||||||
M110 | Isospathulenol | 2251 | ● | |||||||||||||||||||||
M112 | β-Asarone | 2264 | ● | ● | ● | ● | ● | |||||||||||||||||
M113 | 1,2,4-Trimethoxybenzene isomer | 2273 | ● | ● | ||||||||||||||||||||
M114 | 1,2,3,4-Tetramethoxybenzene | 2286 | ● | ● | ● | |||||||||||||||||||
M116 | 3,4-Methylenedioxyacetophenone | 2337 | ● | ● | ● | ● | ● | |||||||||||||||||
M117 | Chavicol | 2350 | ● | ● | ● | ● | ● | ● | ● | |||||||||||||||
M119 | Kaurene | 2362 | ● | ● | ||||||||||||||||||||
M122 | 3,4-Methylenedioxypropiophenone | 2405 | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● |
M123 | Apiol | 2415 | ● | |||||||||||||||||||||
M126 | Methoxyeugenol isomer | 2441 | ● | ● | ● | ● | ||||||||||||||||||
M127 | Kakuol isomer | 2446 | ● | ● | ● | ● | ● | ● | ● | ● | ● | |||||||||||||
M128 | Mellein | 2475 | ● | ● | ● | ● | ● | |||||||||||||||||
M131 | 1-(3,4-Methylenedioxyphenyl)-propane-1-ol | 2520 | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ||||||||||
M135 | 2′,4′-Dimethoxypropiophenone | 2544 | ● | ● | ||||||||||||||||||||
M138 | Kakuol | 2567 | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● |
M139 | 2′,4′-Dimethoxy-3′-methylpropiophenone isomer | 2602 | ● | ● | ● | ● | ● | ● | ● | |||||||||||||||
M140 | Xanthoxylin | 2608 | ● | ● | ● | ● | ● | ● | ● | ● | ||||||||||||||
M148 | 2′,4′-Dimethoxy-3′-methylpropiophenone | 2734 | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | ● | |||
M153 | Syringic acid | 2934 | ● | |||||||||||||||||||||
Total: | 49 | 40 | 24 | 15 | 14 | 14 | 17 | 27 | 36 | 59 | 33 | 19 | 26 | 11 | 5 | 5 | 6 | 9 | 15 | 22 | 28 | 17 | ||
Total 98 original constituents were identified in the powder group. | Total 43 original constituents were identified in the decoction group. |
No. | Metabolites | RI | Powder-Treated Group | Decoction-Treated Group | ||||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
FE | UR | BL | BR | HE | LU | SP | LI | KI | ST | IN | FE | UR | BL | BR | HE | LU | SP | LI | KI | ST | IN | |||
M15 | cis-Limonene oxide | 1441 | ● | ● | ● | |||||||||||||||||||
M24 | Isopulegol | 1556 | ● | ● | ||||||||||||||||||||
M36 | l-Pinocarveol | 1651 | ● | ● | ||||||||||||||||||||
M39 | Verbenol | 1674 | ● | |||||||||||||||||||||
M42 | α-Terpineol acetate | 1685 | ● | |||||||||||||||||||||
M47 | β-Cyclogeraniol | 1711 | ● | |||||||||||||||||||||
M51 | cis-Piperitol | 1750 | ● | |||||||||||||||||||||
M88 | Dihydroeugenol | 2106 | ● | ● | ● | ● | ● | ● | ||||||||||||||||
M96 | m-Eugenol | 2191 | ● | |||||||||||||||||||||
M111 | cis-Isoeugenol | 2258 | ● | |||||||||||||||||||||
M132 | Piperonol | 2534 | ● | |||||||||||||||||||||
M137 | Methoxyeugenol | 2547 | ● | |||||||||||||||||||||
M141 | 3,4-Methylenedioxyphenyl-1-propanal | 2620 | ● | |||||||||||||||||||||
M147 | Dihydromethyleugenol | 2714 | ● | |||||||||||||||||||||
M149 | 1-Hydroxy-2-(prop-2-enyl)-4,5-methylenedioxybenzene | 2750 | ● | |||||||||||||||||||||
Total: | 1 | 9 | 0 | 0 | 0 | 0 | 0 | 1 | 4 | 1 | 1 | 0 | 5 | 0 | 0 | 0 | 0 | 0 | 1 | 1 | 0 | 0 | ||
Total 12 metabolites were identified in the powder group. | Total 6 metabolites were identified in the decoction group. |
3,5-Dimethoxytoluene (M60) | Safrole (M64) | Methyleugenol (M79) | 2,3,5-Trimethoxytoluene (M82) | 3,4,5-Trimethoxytoluene (M83) | Eugenol (M93) | Kakuol (M138) | |||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
P | D | Ratio | P | D | Ratio | P | D | Ratio | P | D | Ratio | P | D | Ratio | P | D | Ratio | P | D | Ratio | |
FE | 7.19 | n.d. | / | 3.25 | 0.0058 | 560.3 | 2.04 | 0.0052 | 392.3 | 3.45 | 0.005 | 690.0 | 4.07 | 0.01 | 407.0 | 0.10 | 0.02 | 5.4 | 1.36 | 0.70 | 1.9 |
UR | 0.54 | n.d. | / | 0.04 | 0.0038 | 10.5 | 0.12 | 0.0064 | 18.8 | 0.65 | 0.030 | 21.7 | 1.10 | 0.32 | 3.4 | 5.66 | 6.58 | 0.9 | 16.79 | 10.51 | 1.6 |
BL | 2.68 | n.d. | / | 2.54 | n.d. | / | 0.5 | n.d. | / | 1.91 | 0.032 | 59.7 | 2.11 | 0.31 | 6.8 | n.d. | n.d. | / | 0.10 | 0.02 | 6.4 |
BR | 2.48 | n.d. | / | 1.94 | n.d. | / | 0.4 | n.d. | / | 0.75 | 0.007 | 107.1 | 0.64 | 0.06 | 10.7 | n.d. | n.d. | / | 0.07 | 0.01 | 13.0 |
HE | 1.45 | n.d. | / | 0.98 | n.d. | / | 0.26 | n.d. | / | 0.54 | 0.007 | 77.1 | 0.46 | 0.05 | 9.2 | n.d. | 0.004 | / | 0.06 | 0.005 | 12.5 |
LU | 1.27 | n.d. | / | 0.98 | n.d. | / | 0.24 | n.d. | / | 0.39 | 0.008 | 48.8 | 0.33 | 0.05 | 6.6 | 0.05 | 0.01 | 5.2 | 0.09 | 0.01 | 10.9 |
SP | 1.86 | n.d. | / | 1.43 | 0.0004 | 3575.0 | 0.9 | 0.0016 | 562.5 | 0.97 | 0.009 | 107.8 | 0.59 | 0.06 | 9.8 | 0.02 | 0.01 | 3.0 | 0.16 | 0.01 | 21.7 |
LI | 7.09 | 0.0017 | 4170.6 | 5.03 | 0.0012 | 4191.7 | 1.29 | 0.0032 | 403.1 | 2.26 | 0.031 | 72.9 | 1.89 | 0.24 | 7.9 | 0.05 | 0.02 | 2.6 | 0.05 | 0.04 | 1.2 |
KI | 4.63 | 0.0019 | 2436.8 | 2.48 | 0.0018 | 1377.8 | 0.88 | 0.0051 | 172.5 | 2.58 | 0.056 | 46.1 | 2.78 | 0.56 | 5.0 | 0.22 | 0.23 | 0.9 | 1.13 | 0.31 | 3.6 |
ST | 35.16 | 0.0025 | 14,064.0 | 46.54 | n.d. | / | 34.99 | 0.0801 | 436.8 | 18.84 | 0.293 | 64.3 | 17.07 | 1.90 | 9.0 | 0.20 | 0.05 | 4.1 | 8.58 | 2.36 | 3.6 |
IN | 13.06 | 0.0021 | 6219.0 | 16.02 | 0.0025 | 6408.0 | 12.38 | 0.0069 | 1794.2 | 6.56 | 0.026 | 252.3 | 5.83 | 0.13 | 44.8 | 0.06 | 0.12 | 0.5 | 2.01 | 0.22 | 9.2 |
No. | Compounds | LD50 (Oral) a | Distribution b | Content c |
---|---|---|---|---|
M20 | dl-Camphor | mouse, 1310 mg/kg [35] | P (FE, UR, BL, HE, LU, LI, KI, ST, IN) D (FE, UR, LI, KI, ST, IN) | 0.11% |
M37 | Estragole | mouse, 1250 mg/kg [36] | P (BL, BR, HE, LU, SP, LI, KI, ST, IN) D (n.d.) | 0.28% |
M44 | Borneol | mouse, 1059 mg/kg [35] | P (FE, UR, BL, SP, KI, ST, IN) D (FE, UR, KI, ST) | 0.12% |
M64 | safrole | mouse, 2350 mg/kg [33,36] | P (FE, UR, BL, BR, HE, LU, SP, LI, KI, ST, IN) D (FE, UR, SP, LI, KI, IN) | 23.74% |
M79 | Methyleugenol | rat, 1179 mg/kg [33] | P (FE, UR, BL, BR, HE, LU, SP, LI, KI, ST, IN) D (FE, UR, SP, LI, KI, ST, IN) | 4.69% |
M104 | Piperonal | rat, 2700 mg/kg [37] | P (UR, BL) D (UR, BL) | 0.07% |
M112 | β-Asarone | mouse, 418 mg/kg [38] | P (BL, LI, KI, ST) D (ST) | 0.04% |
M122 | 3,4-Methylenedioxypropiophenone | mouse, 2150 mg/kg [39] | P (FE, UR, BL, BR, HE, LU, SP, LI, KI, ST, IN) D (FE, UR, BL, BR, HE, LU, SP, LI, KI, ST, IN) | 1.58% |
M131 | 1-(3,4-Methylenedioxyphenyl)-propane-1-ol | mouse, 720 mg/kg [40] | P (FE, BL, SP, LI, KI, IN) D (FE, UR, LI, KI, ST, IN) | 0.15% |
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Liu, G.-X.; Xu, F.; Shang, M.-Y.; Wang, X.; Cai, S.-Q. The Relative Content and Distribution of Absorbed Volatile Organic Compounds in Rats Administered Asari Radix et Rhizoma Are Different between Powder- and Decoction-Treated Groups. Molecules 2020, 25, 4441. https://doi.org/10.3390/molecules25194441
Liu G-X, Xu F, Shang M-Y, Wang X, Cai S-Q. The Relative Content and Distribution of Absorbed Volatile Organic Compounds in Rats Administered Asari Radix et Rhizoma Are Different between Powder- and Decoction-Treated Groups. Molecules. 2020; 25(19):4441. https://doi.org/10.3390/molecules25194441
Chicago/Turabian StyleLiu, Guang-Xue, Feng Xu, Ming-Ying Shang, Xuan Wang, and Shao-Qing Cai. 2020. "The Relative Content and Distribution of Absorbed Volatile Organic Compounds in Rats Administered Asari Radix et Rhizoma Are Different between Powder- and Decoction-Treated Groups" Molecules 25, no. 19: 4441. https://doi.org/10.3390/molecules25194441