Abstract
The historical relic of medicinal preparation of senna extract, over 200 years old, was analyzed using RP-HPLC connected with ESI−-MSn. The conditions for extracting the compounds from the sample and separating them by HPLC were optimized. A broad spectrum of glycosides was identified. Both main senna anthraquinone glycosides, sennoside A and sennoside B, were not detected in the sample. Nevertheless, the found presence of other substances typical of senna allows the positive authentication of the sample. Three possible degradation products of sennosides were identified; rhein and two compounds with unresolved structure. Remarkable stability of some glycosides in the historical sample was found. Detailed ESI−-MSn fragmentation mechanisms of sennoside A and B have been proposed.
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References
Sneader W (2005) Drug discovery: a history. Wiley, New York
McGovern PE, Zhang J, Tang J, Zhiqing Zhang Z, Hall GR, Moreau RA, Nunez A, Butrym ED, Richards MP, Wang C, Cheng G, Zhao Z, Wang C (2004) Proc Natl Acad Sci USA 101:17593
McGovern PE, Mirzoian A, Hall GR (2009) Proc Natl Acad Sci USA 106:7361
McGovern PE, Glusker DL, Exner LJ, Voigt MM (1996) Nature 381:480
Nesměrák K, Kunešová J (2015) Ces Slov Farm 64:79
Collegium Pharmaceuticum (1729) Dispensatorium pharmaceuticum Austriaco-Viennense. Kürner, Vienna
Facultas Medica (1739) Dispensatorium medico-pharmaceuticum Pragense. Vetero-Pragae
Nesměrák K, Kudláček K, Babica J (2017) Monatsh Chem 148:1557
Evans WC (2009) Trease and Evans pharmacognosy, 16th edn. Elsevier, Edinburgh
Issekutz B (1971) Die Geschichte der Arzneimittelforschung. Akadémia Kiadó, Budapest
Lemli J (1988) Pharmacology 36(Suppl 1):3
Franz G (1993) Pharmacology 47(Suppl 1):2
Stoll A, Becker B (1950) In: Becker B (ed) Progress in the chemistry of organic natural products, vol 7. Springer, Vienna
Lemli J, Toppet S, Cuveele J, Janssen G (1981) Planta Med 43:11
Schultze W, Jahn K, Richter R (1996) Planta Med 62:540
Merle J, Barthes D, Besson J (1984) Farm Ed Prat 39:233
de Witte P (1993) Pharmacology 47(Suppl 1):86
Lainonen H, Marvola M, Hietala P, Parviainen T (1988) Pharmacol Toxicol 63:37
Goppel M, Franz G (2004) Planta Med 70:432
Demirezer LÖ, Karahan N, Ucakturk E, Kuruuzum A, Guvenalp Z, Kazaz C (2011) Rec Nat Prod 5:261
Bala S, Uniyal GC, Dubey T, Singh SP (2001) Phytochem Anal 12:277
Ohshima Y, Takahashi K (1983) J Chromatogr 258:292
Hayashi S, Yoshida A, Tanaka H, Mitani Y, Yoshizawa K (1980) Chem Pharm Bull 28:406
Komolafe OO (1978) J Chromatogr Sci 16:496
Sun SW, Su HT (2002) J Pharm Biomed Anal 29:881
Rosenthal I, Wolfram E, Meier B (2014) Pharmeur Bio Sci Notes 2014:92
Verma RK, Uniyal GC, Singh SP, Sharma JR, Gupta MM (1996) Phytochem Anal 7:73
Tan J, Zheng M, Duan S, Zeng Y, Zhang Z, Cui Q, Zhang J, Hong T, Bai J, Du S (2018) Molecules 23:1501
Schmidt J (2016) J Mass Spectrom 51:33
Lin LZ, Chen P, Ozcan M, Harnly JM (2008) J Agric Food Chem 56:6671
Barroso WA, Abreu IC, Ribeiro LS, da Rocha CQ, de Souza HP, de Lima TM (2019) Toxicol Vitr 59:179
Afzan A, Abdullah NR, Halim SZ, Rashid BA, Semail RH, Abdullah N, Jantan I, Muhammad H, Ismail Z (2012) Molecules 17:4326
Jin W, Wang YF, Ge RL, Shi HM, Jia CQ, Tu PF (2007) Rapid Commun Mass Spectrom 21:2351
Terreaux C, Wang Q, Ioset JR, Ndjoko K, Grimminger W, Hostettmann K (2002) Planta Med 68:349
Liao W, Chiu K, Mabuni C, Soliman M (1998) Bull Environ Contam Toxicol 61:317
Gao LL, Guo T, Xu XD, Yang JS (2017) Nat Prod Res 31:1529
Wu H, Feng F, Jiang X, Hu B, Qiu J, Wang C, Xiang Z (2020) J Pharm Biomed Anal 179:112938
The European Pharmacopoeia Commission (2013) European pharmacopoeia, vol I, 9th edn. Council of Europe, Strasbourg
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The financial support by the projects SVV 260560 and Progress Q46 of Charles University is gratefully acknowledged.
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Nesměrák, K., Kudláček, K., Čambal, P. et al. Authentication of senna extract from the eighteenth century and study of its composition by HPLC–MS. Monatsh Chem 151, 1241–1248 (2020). https://doi.org/10.1007/s00706-020-02630-5
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DOI: https://doi.org/10.1007/s00706-020-02630-5