Rapid Mass Spectrometric Study of a Supercritical CO2-extract from Woody Liana Schisandra chinensis by HPLC-SPD-ESI-MS/MS
Abstract
:1. Introduction
2. Results and Discussion
3. Materials and Methods
3.1. Materials
3.2. Chemicals and Reagents
3.3. SC-CO2 Extraction
3.4. Liquid Chromatography
3.5. Mass Spectrometry
4. Conclusions
Author Contributions
Funding
Conflicts of Interest
References
- Hancke, J.L.; Burgos, R.A.; Ahumada, F. Schisandra chinensis (Turcz.) Baill. Fitoterapia 1999, 70, 451–471. [Google Scholar] [CrossRef]
- Wang, Y.-H.; Qiu, C.; Wang, D.-W.; Hu, Z.-F.; Yu, B.-Y.; Zhu, D.-N. Identification of multiple constituents in the traditional Chinese medicine formula Sheng-Mai San and rat plasma after oral administration by HPLC-DAD-MS/MS. J. Pharm. Biomed. Anal. 2011, 54, 1110–1127. [Google Scholar] [CrossRef]
- Chinese Pharmacopoeia Commission. Pharmacopoeia of People’s Republic of China Version; Chinese Medical Science Press: Beijing, China, 2010. [Google Scholar]
- Gutnikova, Z.I. Schizandra chinensis in the Far East. In Materials for the Study of Ginseng and Schizandra Roots; Lazarev, N.V., Ed.; Far East Branch of USSR Academy of Science: Vladivostok, Russia, 1951; pp. 23–43. (In Russian) [Google Scholar]
- Komarov, V.L. Book. Flora of Manshuriae; New York Botanical Garden, LuEsther T. Mertz Library: Bronx, NY, USA, 1901–1907; (In Japanese). [Google Scholar] [CrossRef] [Green Version]
- Komarov, V.L. Species novae florae Asiae orientalis (Manshuriae et Koreae borealis). Works Imp. St. Petersburg Bot. Gard. 1901, 18, 417–449. [Google Scholar]
- Semenov, S.R. On the pharmacology of Schizandra chinensis. Med. Byull. Irkutsk Med. Inst. 1948, 8, 80–81. [Google Scholar]
- Senov, P.I. Schizandra and its use. Aptechnoje Delo. 1953, 2, 70–72. [Google Scholar]
- Brekhman, I.I.; Dardymov, I.V. New substances of plant origin which increase non-specific resistance. Annu. Rev. Pharmacol. Toxicol. 1969, 8, 419–430. [Google Scholar] [CrossRef] [PubMed]
- Brekhman, I.I. Some results of experimental studies of the effects of Ginseng roots and Schizandra preparations. In Materials for the Study of Ginseng and Schizandra Roots; Lazarev, N.V., Ed.; Far East Branch of USSR Academy of Science: Vladivostok, Russia, 1951; pp. 13–16. [Google Scholar]
- Senov, P.I. Materials on pharmacological and chemical analysis of some medicinal formulations produced from different parts of Schizandra chinensis. Aptechnoje Delo. 1952, 3, 5–8. [Google Scholar]
- Golovin, A.N.; Golovina, L.A.; Brekhman, I.I.; Belikov, I.F.; Kuznetsova, G.E. Clinical observations of the effect of Schizandra electrophoresis on the visual function of the eye. In Materials for the Study of Ginseng and Other Medicinal Plants of the Far East; Far East Branch of the USSR Academy of Science, Primorsk Book Publisher: Vladivostok, Russia, 1963; pp. 281–285. [Google Scholar]
- Sorokhtin, G.N.; Minut-Sorokhtina, O.P. Schizandra chinensis effect on the nervous system functions according to the 10-year experience of the Chair of Physiology of Khabarovsk Medical Institute. In Materials for the Study of Ginseng and Schizandra Roots; Far East Branch of USSR Academy of Science: Leningrad, Russia, 1958; pp. 145–154. [Google Scholar]
- Lebedev, A.A. Schizandrin—A new stimulant from Schizandra chinensis fruits. In Dissertation for a Degree in Medicine; Tashkent University: Tashkent, Uzbekistan, 1967; p. 16. (In Russian) [Google Scholar]
- Panossian, A.; Wikman, G. Pharmacology of Schisandra chinensis Bail.: An overview of Russian research and uses in medicine. J. Ethnopharmacol. 2008, 118, 183–212. [Google Scholar] [CrossRef] [PubMed]
- Perova, I.B.; Malinkin, A.D.; Bessonov, V.V.; Eller, K.I. Investigation of lignans and anthocyanins as the main biologically active polyphenols of Schisandra chinensis fruits. Vopr. Pitan. 2018, 87, 79–87. (In Russian) [Google Scholar] [PubMed]
- Lu, Y.; Chen, D.-F. Analysis of Schisandra chinensis and Schisandra sphenanthera. J. Chromatogr. A 2009, 1216, 1980–1990. [Google Scholar] [CrossRef] [PubMed]
- Kosman, V.M.; Karlina, M.V.; Pozharitskaya, O.N.; Shikov, A.N.; Makarov, V.G.; Vorobieva, V.V.; Lapkina, G.Y. Pharmacokinetics of lignans from Schisandra chinensis. Rev. Clin. Pharmacol. Drug Ther. 2015, 13, 3–21. [Google Scholar]
- Brunner, G. Applications of supercritical fluids. Annu. Rev. Chem. Biomol. Eng. 2010, 1, 321–342. [Google Scholar] [CrossRef] [PubMed]
- Herrero, M.; Mendiola, J.; Cifuentes, A.; Ibanez, E. Review: Supercritical fluid extraction: Recent advances and applications. J. Chromatogr. A 2010, 1217, 2495–2511. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Liang, Y.; Zhou, Y.-Y.; Liu, Y.-N.; Guan, T.-Y.; Zheng, X.; Dai, C.; Xing, L.; Rao, T.; Xie, L.; Wang, G.-J. Study on the plasma protein binding rate of Schisandra lignans based on the LC-IT-TOF/MS technique with relative quantitative analysis. Chin. J. Nat. Med. 2013, 11, 442–448. [Google Scholar] [CrossRef]
- Lou, Z.; Zhang, H.; Gong, C.; Zhu, Z.; Zhao, L.; Xu, Y.; Wang, B.; Zhang, G. Analysis of lignans in Schisandra chinensis and rat plasma by high-performance liquid chromatography diode-array detection, time-of-flight mass spectrometry and quadrupole ion trap mass spectrometry. Rapid Commun. Mass Spectrom. 2009, 23, 831–842. [Google Scholar] [CrossRef] [PubMed]
- Liu, H.; Lai, H.; Jia, X.; Liu, J.; Zhang, Z.; Oi, Y.; Zhang, J.; Song, J.; Wu, C.; Zhang, B.; et al. Comprehensive chemical analysis of Schisandra chinensis by HPLC-DAD-MS combined with chemometrics. Phytomedicine 2013, 20, 1135–1143. [Google Scholar] [CrossRef] [PubMed]
- Yang, J.; Ip, S.P.; Yeung, H.J.; Che, C. HPLC–MS analysis of Schisandra lignans and their metabolites in Caco-2 cell monolayer and rat everted gut sac models and in rat plasma. Acta Pharmaceut. Sinica. B 2011, 1, 46–55. [Google Scholar] [CrossRef] [Green Version]
- Molino, A.; Larocca, V.; Di Sanzo, G.; Martino, M.; Casella, P.; Marino, T.; Karatza, D.; Musmarra, D. Extraction of bioactive compounds using supercritical carbon dioxide. Molecules 2019, 24, 782. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- De Melo, M.M.R.; Oliveira, E.L.G.; Silvestre, A.J.D.; Silva, C.M. Supercritical fluid extraction of triterpenic acids from Eucalyptus globulus bark. J. Supercrit. Fluids 2012, 70, 137–145. [Google Scholar] [CrossRef]
- Aliev, A.M.; Radjabov, G.K.; Musaev, A.M. Dynamics of supercritical extraction of biological active substances from the Juniperus communis var. saxatillis. J. Supercrit. Fluids 2015, 102, 66–72. [Google Scholar] [CrossRef]
- Baldino, L.; Della Porta, G.; Osseo, L.S.; Reverchon, E.; Adami, R. Concentrated oleuropein powder from olive leaves using alcoholic extraction and supercritical CO2 assisted extraction J. Supercrit. Fluids 2018, 133, 65–69. [Google Scholar] [CrossRef]
- Chai, Y.H.; Yusup, S.; Ruslan, M.S.H.; Chin, B.L.F. Supercritical fluid extraction and solubilization of Carica papaya linn. leaves in ternary system with CO2+ ethanol solvents Chem. Engin. Res. Des. 2020, 156, 31–42. [Google Scholar]
- Morozov, Y.A.; Pupykina, K.A.; Blagorazumnaya, N.V.; Aliev, A.M.; Morozova, E.V. Comparative analysis of carbon dioxide extracts from plant material of Schisandra chinensis: Leaves, woody stems, rhizomes with roots. Med. Bull. Bashkortostan. 2018, 13, 46–51. [Google Scholar]
- Lojkova, L.; Slanina, J.; Mikesova, M.; Taborska, E.; Vejrosta, J. Supercritical fluid extraction of Lignans from Seeds and Leaves of Schisandra chinensis. Phytochem. Anal. 1997, 8, 261–265. [Google Scholar] [CrossRef]
- Choi, Y.H.; Kim, J.; Jeon, S.H.; Yoo, K.-P.; Lee, H.-K. Optimum SFE Conditions for lignans of Schisandra chinensis fruits. Chromatographia 1998, 48, 695–699. [Google Scholar] [CrossRef]
- Sun, H.; Wu, F.; Zhang, A.; Wei, W.; Han, Y.; Wang, X. Profiling and identification of the absorbed constituents and metabolites of Schisandra lignans by ultraperformance liquid chromatography coupled to mass spectrometry. Biomed. Chromatogr. 2013, 27, 1511–1519. [Google Scholar] [CrossRef] [PubMed]
- Lee, D.-K.; Yoon, M.H.; Kang, Y.P.; Yu, J.; Park, J.H.; Lee, J.; Kwon, S.W. Comparison of primary and secondary metabolites for suitability to discriminate the origins of Schisandra chinensis by GC/MS and LC/MS. Food Chem. 2013, 141, 3931–3937. [Google Scholar] [CrossRef] [PubMed]
- Zhang, W.; Wang, Q.; Wang, Y.; Wang, X.-J.; Pu, J.-X.; Gu, Y.; Wang, R. Application of ultrahigh-performance liquid chromatography coupled with mass spectrometry for analysis of lignans and quality control of Fructus Schisandra chinensis. J. Sep. Sci. 2012, 35, 2203–2209. [Google Scholar] [CrossRef] [PubMed]
- Zhestovskaya, Y.S.; Antokhin, A.M.; Taranchenko, V.F.; Vasilevskiy, S.V.; Aksenov, A.V.; Aksenova, Y.B.; Laskina, L.Y.; Rodin, I.A.; Shpigun, O.A. Study of component composition of medicinal plant materials by gas chromatography with mass-spectrometric detection. Khimiya Rastitel’nogo Syr’ya 2018, 3, 149–157. (In Russian) [Google Scholar]
- State Pharmacopeia XII; Scientific Center of Expertise of Medical Products: Moscow, Russia, 2008; pp. 26–121.
Sample Availability: Samples fractions are available from the authors. |
№ | Compound | Formula | R1 | R2 | R3 | R4 | R5 | R6 | R7 | R8 | R9 | R10 | R11 |
---|---|---|---|---|---|---|---|---|---|---|---|---|---|
1 | Schisandrin A (Deoxyschisandrin) | C24H32O6 | CH3 | CH3 | CH3 | CH3 | CH3 | CH3 | CH3 | H | CH3 | CH3 | H |
2 | Schisandrol A (Schisandrin) | C24H32O7 | CH3 | CH3 | CH3 | CH3 | CH3 | CH3 | CH3 | H | CH3 | OH | H |
3 | Schisandrin B (Gomisin N, Isokadsuranin) | C23H28O6 | CH3 | CH3 | CH3 | CH3 | CH2 | H | CH3 | H | CH3 | H | |
4 | Schisandrol B (Gomisin A) | C23H28O7 | CH2 | CH3 | CH3 | CH3 | CH3 | CH3 | H | CH3 | OH | H | |
5 | Schisandrin C | C22H24O6 | CH2 | CH3 | CH3 | CH3 | CH3 | H | CH3 | H | CH3 | H | |
6 | Isoschisandrin | C24H32O7 | CH3 | CH3 | CH3 | CH3 | CH3 | CH3 | CH3 | OH | CH3 | H | H |
7 | Gomisin K1 | C23H30O6 | H | CH3 | CH3 | CH3 | CH3 | CH3 | H | CH3 | H | CH3 | H |
8 | Gomisin K2 | C23H30O6 | H | CH3 | CH3 | CH3 | CH3 | CH3 | CH3 | H | CH3 | H | H |
9 | Schisanhenol (Gomisin K3) | C23H30O6 | CH3 | CH3 | H | CH3 | CH3 | CH3 | CH3 | H | CH3 | H | H |
10 | Gomisin H | C23H30O7 | CH3 | CH3 | H | CH3 | CH3 | CH3 | CH3 | H | CH3 | OH | H |
11 | Tigloylgomisin H | C28H36O8 | CH3 | CH3 | Tigloyl | CH3 | CH3 | CH3 | CH3 | H | CH3 | OH | H |
12 | Angeloygomisin H | C28H36O8 | CH3 | CH3 | Angeloyl | CH3 | CH3 | CH3 | CH3 | H | CH3 | OH | H |
13 | Benzoylgomisin H | C30H34O8 | CH3 | CH3 | Benzoyl | CH3 | CH3 | CH3 | CH3 | H | CH3 | OH | H |
4 | Gomisin J | C22H28O6 | H | CH3 | CH3 | CH3 | CH3 | H | H | CH3 | H | CH3 | H |
15 | Schisanhenol B | C22H26O6 | CH3 | CH3 | H | CH3 | CH2 | H | CH3 | H | CH3 | H | |
16 | Gomisin N | C23H28O6 | CH3 | CH3 | CH3 | CH3 | CH2 | CH3 | H | CH3 | H | H | |
17 | Gomisin L1 | C22H26O6 | CH3 | CH3 | H | CH3 | CH2 | H | CH3 | H | CH3 | H | |
18 | Gomisin L2 | C22H26O6 | H | CH3 | CH3 | CH3 | CH2 | H | CH3 | H | CH3 | H | |
19 | Gomisin M1 | C22H26O6 | CH3 | CH3 | H | CH3 | CH2 | CH3 | H | CH3 | H | H | |
20 | Gomisin M2 | C22H26O6 | CH3 | CH3 | CH3 | H | CH2 | CH3 | H | CH3 | H | H | |
21 | Gomisin O | C23H28O7 | CH2 | CH3 | CH3 | CH3 | CH3 | CH3 | CH3 | H | H | OH | |
22 | Isogomisin O | C23H28O7 | CH3 | CH3 | CH3 | CH3 | CH2 | H | CH3 | H | CH3 | OH | |
23 | Angeloylsogomisin O | C28H34O8 | CH2 | CH3 | CH3 | CH3 | CH3 | CH3 | CH3 | H | H | O-angeloyl | |
24 | Gomisin P | C23H28O8 | CH2 | CH3 | CH3 | CH3 | CH3 | H | CH3 | OH | CH3 | OH | |
25 | Tigloylgomisin P | C28H34O9 | CH2 | CH3 | CH3 | CH3 | CH3 | H | CH3 | OH | CH3 | O-tigloyl | |
26 | Angeloylgomisin P (Schisantherin C) | C28H34O9 | CH2 | CH3 | CH3 | CH3 | CH3 | H | CH3 | OH | CH3 | O-angeloyl | |
27 | Schisantherin A (Gomisin C) | C30H32O9 | CH2 | CH3 | CH3 | CH3 | CH3 | CH3 | CH3 | OH | H | O-bensoyl | |
28 | Schisantherin B (Gomisin B, Schisandrer B) | C28H34O9 | CH2 | CH3 | CH3 | CH3 | CH3 | CH3 | CH3 | OH | H | O-angeloyl | |
29 | Gomisin S | C23H30O7 | CH3 | CH3 | CH3 | CH3 | CH3 | CH3 | H | CH3 | H | CH3 | OH |
30 | Gomisin R (6-Epi-gomisin) | C22H24O7 | CH2 | CH3 | CH3 | CH2 | CH3 | H | CH3 | H | H | ||
31 | Deangeloylgomisin B | C23H28O8 | CH2 | CH3 | CH3 | CH3 | CH3 | CH3 | CH3 | OH | H | OH | |
32 | Gomisin F | C28H34O9 | CH3 | CH3 | CH3 | CH3 | CH2 | CH3 | CH3 | OH | H | O-angeloyl | |
33 | Gomisin G | C30H32O9 | CH3 | CH3 | CH3 | CH3 | CH2 | CH3 | CH3 | OH | H | O-bensoyl | |
34 | Epigomisin O | C23H28O7 | CH2 | CH3 | CH3 | CH3 | CH3 | CH3 | CH3 | CH3 | H | H | |
35 | Angeloylgomisin Q | C29H38O9 | CH3 | CH3 | CH3 | CH3 | CH3 | CH3 | H | CH3 | CH3 | OH | O-angeloyl |
№ | Identification | Formula | Calcula-ted Mass | Observed Mass [M + H]+ | Observed Mass [M + Na]+ | MS/MS Stage 1 Fragmentation | MS/MS Stage 2 Fragmentati-on | MS/MS Stage 3 Fragmentation |
---|---|---|---|---|---|---|---|---|
1 | Schisandrin C [(12S,13R)-3,22-dimethoxy-12,13-dimethyl-5,7,18,20-tetraoxapentacyclo [13.7.0.02,10.04,8.017,21]docosa-1(22),2,4(8),9,15,17(21)-hexaene] | C22H24O6 | 384.4224 | 385.02 | 355.01; 323.02 | 323.01; 299.02; 269.03; 234.98 | 307.98; 235.05 | |
2 | Gomisin M1 (Gomisin L1) [(9S,10R)-4,5,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo [10.7.0.02,7.014,18]nonadeca-1(19),2,4,6,12,14(18)-hexaen-3-ol] | C22H26O6 | 386.4382 | 408.95 | 290.99; 394.03; 326.08; 274.96 | 260.97; 242.89; 172.97 | ||
3 | Gomisin L2 [(9S,10R)-3,4,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.02,7.014,18]nonadeca-1(19),2,4,6,12,14(18)-hexaen-5-ol] | C22H26O6 | 386.4382 | 386.98 | 356.98; 325.00; 284.93; 259.03; 226.99; 167.02; 137.17 | 297.04; 226.98; 182.97 | ||
4 | Gomisin M2 [(9S,10R)-3,4,5-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.02,7.014,18]nonadeca-1(19),2,4,6,12,14(18)-hexaen-19-ol] | C22H26O6 | 386.4382 | 387.01 | 355.01; 324.01; 284.97 | 339.98; 324.02; 284.97; 226.96 | 324.94; 296.90 | |
5 | Gomisin J [(9S,10R)-3,4,15,16-tetramethoxy-9,10-dimethyltricyclo[10.4.0.02,7]hexadeca-1(16),2,4,6,12,14-hexaene-5,14-diol] | C22H28O6 | 388.4541 | 389.04 | 325.03; 357.01; 226.96; 286.97 | 227.01; 241.00; 269.03; 297.01 | 226.98; 198.98 | |
6 | Pregomisin [5-[(2S,3R)-4-(3-hydroxy-4,5-dimethoxyphenyl)-2,3-dimethylbutyl]-2,3-dimethoxyphenol] | C22H30O6 | 390.47 | 391.00 | 237.07; 205.03; 288.91; 326.96; 359.00 | 205.00; 173.00 | ||
7 | Schisandrin B (Gomisin N, Isokadsuranin) [3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.02,7.014,18]nonadeca-1(19),2,4,6,12,14(18)-hexaene] | C23H28O6 | 400.3648 | 401.07 | 369.04 | 354.04; 338.00 | 322.97; 295.03; 264.03 | |
8 | Schisanhenol (Gomisin K3) [(9S,10R)-4,5,14,15,16-pentamethoxy-9,10-dimethyltricyclo[10.4.0.02,7]hexadeca-1(16),2,4,6,12,14-hexaen-3-ol] | C23H30O6 | 402.4807 | 403.05 | 371.01; 340.03; 301.01; 259.00 | 340.03; 315.01; 300.98; 286.01; 233.07 | 324.99; 270.99; 227.02 | |
9 | Gomisin O [(8R,9S,10S)-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.02,7.014,18]nonadeca-1(19),2,4,6,12,14(18)-hexaen-8-ol] | C23H28O7 | 416.3642 | 417.01 | 356.97; 373.01 | 329.00 | 313.97; 270.00 | |
10 | Erigomisin O [(8S,9S,10S)-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.02,7.014,18]nonadeca-1(19),2,4,6,12,14(18)-hexaen-8-ol] | C23H28O7 | 416.3642 | 416.96 | 356.98; 340.98; 308.97 | 328.95; 313.98 | ||
11 | Schisandrin A (Deoxyschisandrin) [(9R,10S)-3,4,5,14,15,16-hexamethoxy-9,10-dimethyltricyclo[10.4.0.02,7]hexadeca-1(16),2,4,6,12,14-hexaene] | C24H32O6 | 416.5073 | 417.01 | 316.00; 346.99; 402.01 | 300.96; 284.95; 242.02 | ||
12 | Demethylated metabolites of Schisandrol A | 440.95 | 279.00; 322.89; 306.86; 258.89; 202.99 | 259.94;220.86; 137.02 | ||||
13 | Schisandrol A (Schisandrin) [(9R,10S)-3,4,5,14,15,16-hexamethoxy-9,10-dimethyltricyclo[10.4.0.02,7]hexadeca-1(16),2,4,6,12,14-hexaen-9-ol] | C24H32O7 | 432.5067 | 433.50 | 415.03 | 384.04; 359.03 | 368.99; 353.05 | |
14 | 7, 8-Dihydroxy-schisandrin | C24H32O8 | 448.5061 | 470.95 | 332.90; 348.90; 200.84; 230.30; 274.74 | 332.89; 274.94; 244.93; 202.98; 155.17 | ||
15 | Tigloylgomisin O [[(8R,9S,10S)-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.02,7.014,18]nonadeca-1(19),2,4,6,12,14(18)-hexaen-8-yl] (E)-2-methylbut-2-enoate] | C28H34O8 | 498.5648 | 521.92 | 208.01; 250.08; 304.99; 359.99; 402.85; 436.83 | 191.00; 375.89 | ||
16 | Angeloylsogomisin O [[(9S,10S,11R)-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.02,7.014,18]nonadeca-1(19),2,4,6,12,14(18)-hexaen-11-yl] (Z)-2-methylbut-2-enoate] | C28H34O8 | 498.5648 | 387.16 | 355.12 | 323.00; 341.00; 295.02; 262.94; 210.100 | 308.98; 262.97; 220.24 | |
17 | Angeloygomisin H [[(9S,10S)-10-hydroxy-4,5,14,15,16-pentamethoxy-9,10-dimethyl-3-tricyclo[10.4.0.02,7]hexadeca-1(16),2,4,6,12,14-hexaenyl] (Z)-2-methylbut-2-enoate] | C28H36O8 | 500.3806 | 500.95 | 368.93; 433.87; 472.83; 334.94; 288.84; 244.92; 207.21; 169.02 | 368.92; 352.97; 299.90; 244.80; 208.95; 156.99; 125.89 | ||
18 | Micrantherin A | C28H36O8 | 500.5806 | 522.93 | 422.91; 328.94; 386.00; 476.94 | 407.87; 392.92; 364.93; 350.88; 320.91; 295.02 | ||
19 | Gomisin E [(11R,12R,15R,24S,25S)-12-hydroxy-18,19,20-trimethoxy-11,12,24,25-tetramethyl-4,6,9,14-tetraoxapentacyclo[13.7.3.03,7.08,22.016,21]pentacosa-1,3(7),8(22),16,18,20-hexaen-13-one] | C28H34O9 | 514.3642 | 514.99 | 384.98; 355.03; 322.99 | 354.99; 322.97 | ||
20 | Schisantherin D [[(11S,12S,13S)-12-hydroxy-3,22-dimethoxy-12,13-dimethyl-5,7,18,20-tetraoxapentacyclo[13.7.0.02,10.04,8.017,21]docosa-1(22),2,4(8),9,15,17(21)-hexaen-11-yl] | C29H28O9 | 520.5272 | 542.89 | 380.89; 408.36; 451.55; 334.99; 200.93 | |||
21 | Benzoylgomisin O [[(8R,9S,10S)-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.02,7.014,18]nonadeca-1(19),2,4,6,12,14(18)-hexaen-8-yl] benzoate] | C30H32O9 | 520.5703 | 542.91 | 380.89 | 364.66; 308.93; 193.02 | ||
22 | Benzoylgomisin H [[(9S,10S)-10-hydroxy-4,5,14,15,16-pentamethoxy-9,10-dimethyl-3-tricyclo[10.4.0.02,7]hexadeca-1(16),2,4,6,12,14-hexaenyl] benzoate] | C30H34O8 | 522.5862 | 522.99 | 491.30; 448.09; 421.07; 399.03; 377.05; 335.11; 302.95; 269.78 | 271.39; 213.02 | ||
23 | Gomisin D [12,25-dihydroxy-18,19,20-trimethoxy-11,12,24,25-tetramethyl-4,6,9,14-tetraoxapentacyclo[13.7.3.03,7.08,22.016,21]pentacosa-1,3(7),8(22),16,18,20-hexaen-13-one] | C28H34O10 | 530.5636 | 553.97 | 510.97; 478.98; 400.97; 372.91; 334.94; 248.99; 202.87 | 382.92; 354.95; 339.03; 312.11; 277.00; 248.99; 189.03 | ||
24 | Gomisin G [[(9S,10S,11S)-10-hydroxy-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.02,7.014,18]nonadeca-1(19),2,4,6,12,14(18)-hexaen-11-yl] benzoate] | C30H32O9 | 536.3697 | 536.93 | 436.92; 414.99; 371.03; 341.04 | 422.80; 390.84; 360.99 | ||
25 | Schisantherin A (Gomisin C) [[(8S,9S,10S)-9-hydroxy-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.02,7.014,18]nonadeca-1(19),2,4,6,12,14(18)-hexaen-8-yl] benzoate] | C30H32O9 | 536.5697 | 537.95 | 414.99; 371.05; 340.98 | 370.99; 341.02 | 341.01; 310.01; 282.06 | |
26 | Benzoylgomisin Q [[(8S,9S,10S)-9-hydroxy-3,4,5,14,15,16-hexamethoxy-9,10-dimethyl-8-tricyclo[10.4.0.02,7]hexadeca-1(16),2,4,6,12,14-hexaenyl] benzoate] | C31H36O9 | 552.3121 | 552.99 | 415.05; 436.98; 384.03 | 384.03; 400.01; 359.00 | 369.02; 352.99; 338.00 |
© 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
Share and Cite
Razgonova, M.; Zakharenko, A.; Pikula, K.; Kim, E.; Chernyshev, V.; Ercisli, S.; Cravotto, G.; Golokhvast, K. Rapid Mass Spectrometric Study of a Supercritical CO2-extract from Woody Liana Schisandra chinensis by HPLC-SPD-ESI-MS/MS. Molecules 2020, 25, 2689. https://doi.org/10.3390/molecules25112689
Razgonova M, Zakharenko A, Pikula K, Kim E, Chernyshev V, Ercisli S, Cravotto G, Golokhvast K. Rapid Mass Spectrometric Study of a Supercritical CO2-extract from Woody Liana Schisandra chinensis by HPLC-SPD-ESI-MS/MS. Molecules. 2020; 25(11):2689. https://doi.org/10.3390/molecules25112689
Chicago/Turabian StyleRazgonova, Mayya, Alexander Zakharenko, Konstantin Pikula, Ekaterina Kim, Valery Chernyshev, Sezai Ercisli, Giancarlo Cravotto, and Kirill Golokhvast. 2020. "Rapid Mass Spectrometric Study of a Supercritical CO2-extract from Woody Liana Schisandra chinensis by HPLC-SPD-ESI-MS/MS" Molecules 25, no. 11: 2689. https://doi.org/10.3390/molecules25112689