Browse > Article
http://dx.doi.org/10.1016/j.jgr.2016.08.009

Chemical transformation and target preparation of saponins in stems and leaves of Panax notoginseng  

Wang, Ru-Feng (The MOE Key Laboratory for Standardization of Chinese Medicines and the SATCM Key Laboratory for New Resources and Quality Evaluation of Chinese Medicines, Institute of Chinese Materia Medica, Shanghai University of Traditional Chinese Medicine)
Li, Juan (The MOE Key Laboratory for Standardization of Chinese Medicines and the SATCM Key Laboratory for New Resources and Quality Evaluation of Chinese Medicines, Institute of Chinese Materia Medica, Shanghai University of Traditional Chinese Medicine)
Hu, Hai-Jun (The MOE Key Laboratory for Standardization of Chinese Medicines and the SATCM Key Laboratory for New Resources and Quality Evaluation of Chinese Medicines, Institute of Chinese Materia Medica, Shanghai University of Traditional Chinese Medicine)
Li, Jia (The MOE Key Laboratory for Standardization of Chinese Medicines and the SATCM Key Laboratory for New Resources and Quality Evaluation of Chinese Medicines, Institute of Chinese Materia Medica, Shanghai University of Traditional Chinese Medicine)
Yang, Ying-Bo (The MOE Key Laboratory for Standardization of Chinese Medicines and the SATCM Key Laboratory for New Resources and Quality Evaluation of Chinese Medicines, Institute of Chinese Materia Medica, Shanghai University of Traditional Chinese Medicine)
Yang, Li (The MOE Key Laboratory for Standardization of Chinese Medicines and the SATCM Key Laboratory for New Resources and Quality Evaluation of Chinese Medicines, Institute of Chinese Materia Medica, Shanghai University of Traditional Chinese Medicine)
Wang, Zheng-Tao (The MOE Key Laboratory for Standardization of Chinese Medicines and the SATCM Key Laboratory for New Resources and Quality Evaluation of Chinese Medicines, Institute of Chinese Materia Medica, Shanghai University of Traditional Chinese Medicine)
Publication Information
Journal of Ginseng Research / v.42, no.3, 2018 , pp. 270-276 More about this Journal
Abstract
Background: Notoginsenoside Ft1 is a promising potential candidate for cardiovascular and cancer disease therapy owing to its positive pharmacological activities. However, the yield of Ft1 is ultralow utilizing reported methods. Herein, an acid hydrolyzing strategy was implemented in the acquirement of rare notoginsenoside Ft1. Methods: Chemical profiles were identified by ultraperformance liquid chromatography coupled with quadruple-time-of-flight and electrospray ionization mass spectrometry (UPLC-Q/TOF-ESI-MS). The acid hydrolyzing dynamic changes of chemical compositions and the possible transformation pathways of saponins were monitored by ultrahigh-performance LC coupled with tandem MS (UHPLC-MS/ MS). Results and conclusion: Notoginsenoside Ft1 was epimerized from notoginsenoside ST4, which was generated through cleaving the carbohydrate side chains at C-20 of notoginsenosides Fa and Fc, and vinaginsenoside R7, and further converted to other compounds via hydroxylation at C-25 or hydrolysis of the carbohydrate side chains at C-3 under the acid conditions. High temperature contributed to the hydroxylation reaction at C-25 and 25% acetic acid concentration was conducive to the preparation of notoginsenoside Ft1. C-20 epimers of notoginsenoside Ft1 and ST4 were successfully separated utilizing solvent method of acetic acid solution. The theoretical preparation yield rate of notoginsenoside Ft1 was about 1.8%, which would be beneficial to further study on its bioactivities and clinical application.
Keywords
chemical transformation; notoginsenoside Ft1; Panax notoginseng; saponins;
Citations & Related Records
연도 인용수 순위
  • Reference
1 Pei Y, Du Q, Liao PY, Chen ZP, Wang D, Yang CR, Kitazato K, Wang YF, Zhang YJ. Notoginsenoside ST-4 inhibits virus penetration of herpes simplex virus in vitro. J Asian Nat Prod Res 2011;13:498-504.   DOI
2 Cao JQ, Peng F, Zhao YQ. Isolation and identification of a new compound from acid hydrolysate of saponin in stems and leaves of Panax notoginseng. Chin Tradit Herb Drugs 2013;44:137-40.
3 Yi JH, Kim MY, Kim YC, Jeong WS, Bae DW, Hur JM, Jun M. Change of ginsenoside composition in red ginseng processed with citric acid. Food Sci Biotechnol 2010;19:647-53.   DOI
4 Wu W, Qin QJ, Guo YY, Sun JH, Liu SY. Studies on the chemical transformation of 20(S)-protopanaxatriol (PPT)-type ginsenosides Re, Rg2, and Rf using rapid resolution liquid chromatography coupled with quadruple-time-of-flight mass spectrometry (RRLC-Q-TOF-MS). J Agr Food Chem 2012;60:10007-14.   DOI
5 Shen KK, Ji LL, Gong CY, Ma YB, Yang L, Fan Y, Hou MQ, Wang ZT. Notoginsenoside $Ft_{1}$ promotes angiogenesis via HIF-$1{\alpha}$ mediated VEGF secretion and the regulation of PI3K/AKT and Raf/MEK/ERK signaling pathways. Biochem Pharmacol 2012;84:784-92.   DOI
6 Shen KK, Leung SWS, Ji LL, Huang Y, Hou MQ, Xu AM, Wang ZT, Vanhoutte PM. Notoginsenoside Ft1 activates both glucocorticoid and estrogen receptors to induce endothelium-dependent, nitric oxide-mediated relaxations in rat mesenteric arteries. Biochem Pharmacol 2014;88:66-74.
7 Gao B, Huang L, Liu H, Wu H, Zhang E, Yang L, Wu X, Wang Z. Platelet $P2Y_{12}$ receptors are involved in the haemostatic effect of notoginsenoside Ft1, a saponin isolated from Panax notoginseng. Br J Pharmacol 2014;171:214-23.   DOI
8 Gao B, Shi HL, Li X, Qiu SP, Wu H, Zhang BB, Wu XJ, Wang ZT. p38 MAPK and ERK1/2 pathways are involved in the proapoptotic effect of notoginsenoside Ft1 on human neuroblastoma SH-SY5Y cells. Life Sci 2014;108:63-70.   DOI
9 Chen JT, Li HZ, Wang D, Zhang YJ, Yang CR. New dammarane monodesmosides from the acidic deglycosylation of notoginseng-leaf saponins. Helv Chim Acta 2006;89:1442-8.   DOI
10 Cicero AFG, Vitale G, Savino G, Arletti R. Panax notoginseng (Burk.) effects on fibrinogen and lipid plasma level in rats fed on a high-fat diet. Phytother Res 2003;17:174-8.   DOI
11 Wan JB, Yang FQ, Li SP, Wang YT, Cui XM. Chemical characteristics for different parts of Panax notoginseng using pressurized liquid extraction and HPLC-ELSD. J Pharmaceut Biomed Anal 2006;41:1596-601.   DOI
12 Ng TB. Pharmacological activity of sanchi ginseng (Panax notoginseng). J Pharm Pharmacol 2006;58:1007-19.   DOI
13 Qi LW, Wang CZ, Yuan CS. Isolation and analysis of ginseng: advances and challenges. Nat Prod Rep 2011;28:467-95.   DOI
14 Yang WZ, Hu Y, Wu WY, Ye M, Guo DA. Saponins in the genus Panax L. (Araliaceae): a systematic review of their chemical diversity. Phytochemistry 2014;106:7-24.   DOI
15 Liu C, Han JY, Duan YQ, Huang X, Wang H. Purification and quantification of ginsenoside $Rb_{3}$ and Rc from crude extracts of caudexes and leaves of Panax notoginseng. Sep Purif Technol 2007;54:198-203.   DOI
16 Zhang X, Song FR, Cui M, Liu ZQ, Liu SY. Investigation of the hydrolysis of ginsenosides by high performance liquid chromatography-electrospray ionization mass spectrometry. Planta Med 2007;73:1225-9.   DOI
17 Dan M, Xie GX, Gao XF, Long XB, Su MM, Zhao AH, Zhao T, Zhou MM, Qiu YP, Jia W. A rapid ultra-performance liquid chromatography-eelectrospray ionisation mass spectrometric method for the analysis of saponins in the adventitious roots of Panax notoginseng. Phytochem Analysis 2009;20:68-76.   DOI
18 Qi LW, Wang HY, Zhang H, Wang CZ, Li P, Yuan CS. Diagnostic ion filtering to characterize ginseng saponins by rapid liquid chromatography with time-of-flight mass spectrometry. J Chromatogr A 2012;1230:93-9.   DOI
19 Chu C, Xu SJ, Li XN, Yan JZ, Liu L. Profiling the ginsenosides of three ginseng products by LC-Q-TOF/MS. J Food Sci 2013;78:C653-9.   DOI
20 Lee SM, Kim SC, Oh J, Kim JH, Na M. 20(R)-Ginsenoside Rf: a new ginsenoside from red ginseng extract. Phytochem Lett 2013;6:620-4.   DOI
21 Sun CP, Gao WP, Zhao BZ, Cheng LQ. Optimization of the selective preparation of 20(R)-ginsenoside Rg3 catalyzed by d, l-tartaric acid using response surface methodology. Fitoterapia 2013;84:213-21.   DOI
22 Chen GT, Yang M, Song Y, Lu ZQ, Zhang JQ, Huang HL, Wu LJ, Guo DA. Microbial transformation of ginsenoside $Rb_{1}$ by Acremonium strictum. Appl Microbiol Biotechnol 2008;77:1345-50.   DOI
23 Du XW, Wills RBH, Stuart DL. Changes in neutral and malonyl ginsenosides in American ginseng (Panax quinquefolium) during drying, storage and ethanolic extraction. Food Chem 2004;86:155-9.   DOI
24 Xiang H, Liu YX, Zhang BB, Huang JH, Li Y, Yang B, Huang ZX, Xiang FJ, Zhang HL. The antidepressant effects and mechanism of action of total saponins from the caudexes and leaves of Panax notoginseng in animal models of depression. Phytomedicine 2011;18:731-8.   DOI
25 Dong A, Ye M, Guo HZ, Zheng JH, Guo DA. Microbial transformation of ginsenoside $Rb_{1}$ by Rhizopus stolonifer and Curvularia lunata. Biotechnol Lett 2003;25:339-44.   DOI
26 Zhao YQ, Yuan CL, Lu HR. Isolation and identification of 20(R)-ginsenoside-Rh2: (an Anti-cancer constituent) from the fruits of Panax ginseng C. A. Meyer. Chin J Chin Mat Med 1991;16:678-9.
27 Mao Q, Yang J, Cui XM, Li JJ, Qi YT, Zhang PH, Wang Q. Target separation of a new anti-tumor saponin and metabolic profiling of leaves of Panax notoginseng by liquid chromatography with eletrospray ionization quadrupole time-of-flight mass spectrometry. J Pharmaceut Biomed 2012;59:67-77.   DOI
28 Park CS, Yoo MH, Noh KH, Oh DK. Biotransformation of ginsenosides by hydrolyzing the sugar moieties of ginsenosides using microbial glycosidases. Appl Microbiol Biot 2010;87:9-19.   DOI
29 Wang D, Liao PY, Zhu HT, Chen KK, Xu M, Zhang YJ, Yang CR. The processing of Panax notoginseng and the transformation of its saponin components. Food Chem 2012;132:1808-13.   DOI
30 Kwon SW, Han SB, Park IH, Kim JM, Park MK, Park JH. Liquid chromatographic determination of less polar ginsenosides in processed ginseng. J Chromatogr A 2001;921:335-9.   DOI
31 Sun S, Wang CZ, Tong R, Li XL, Fishbein A, Wang Q, He TC, Du W, Yuan CS. Effects of steaming the root of Panax notoginseng on chemical composition and anticancer activities. Food Chem 2010;118:307-14.   DOI
32 Teng RW, Li HZ, Wang DZ, Yang CR. Hydrolytic reaction of plant extracts to generate molecular diversity: new dammarane glycosides from the mild acid hydrolysate of root saponins of Panax notoginseng. Helv Chim Acta 2004;87:1270-8.   DOI