Background: Ginsenosides are the major effective ingredients responsible for the pharmacological effects of ginseng. Malonyl ginsenosides are natural ginsenosides that contain a malonyl group attached to a glucose unit of the corresponding neutral ginsenosides. Methods: Medium-pressure liquid chroma...
Background: Ginsenosides are the major effective ingredients responsible for the pharmacological effects of ginseng. Malonyl ginsenosides are natural ginsenosides that contain a malonyl group attached to a glucose unit of the corresponding neutral ginsenosides. Methods: Medium-pressure liquid chromatography and semipreparative high-performance liquid chromatography were used to isolate purified compounds and their structures determined by extensive one-dimensional- and two-dimensional nuclear magnetic resonance (NMR) experiments. Results: A new saponin, namely malonyl-ginsenoside Re, was isolated from the fresh flower buds of Panax ginseng, along with malonyl-ginsenosides Rb1, Rb2, Rc, Rd. Some assignments for previously published $^1H$- and $^{13}C$-NMR spectra were found to be inaccurate. Conclusion: This study reports the complete NMR assignment of malonyl-ginsenoside Re, $Rb_1$, $Rb_2$, Rc, and Rd for the first time.
Background: Ginsenosides are the major effective ingredients responsible for the pharmacological effects of ginseng. Malonyl ginsenosides are natural ginsenosides that contain a malonyl group attached to a glucose unit of the corresponding neutral ginsenosides. Methods: Medium-pressure liquid chromatography and semipreparative high-performance liquid chromatography were used to isolate purified compounds and their structures determined by extensive one-dimensional- and two-dimensional nuclear magnetic resonance (NMR) experiments. Results: A new saponin, namely malonyl-ginsenoside Re, was isolated from the fresh flower buds of Panax ginseng, along with malonyl-ginsenosides Rb1, Rb2, Rc, Rd. Some assignments for previously published $^1H$- and $^{13}C$-NMR spectra were found to be inaccurate. Conclusion: This study reports the complete NMR assignment of malonyl-ginsenoside Re, $Rb_1$, $Rb_2$, Rc, and Rd for the first time.
* AI 자동 식별 결과로 적합하지 않은 문장이 있을 수 있으니, 이용에 유의하시기 바랍니다.
제안 방법
Identification and characterization of ginsenosides are usually conducted using nuclear magnetic resonance (NMR) analyses, but several imperfections and/or inaccuracies existed in the published NMR data of malonyl ginsenosides given the lack of twodimensional (2D) NMR techniques at the time of characterization. Here, with the help of modern 2D NMR techniques including correlation spectroscopy, rotating frame nuclear Overhauser effect spectroscopy (ROESY), heteronuclear single-quantum coherence (HSQC), and heteronuclear multiple-band coherence (HMBC) experiments, complete NMR assignments of malonyl-ginsenosides Rb1, Rb2, Rc, Rd, and Re were determined for the first time.
Reversed-phase semipreparative high-performance liquid chromatography (HPLC) was performed on an instrument consisting of Prostar/Dynamax system control, a Varian PS-218 pump, and a Prostar 325 UV-Vis detector with a Varian Polaris C18-A semipreparative column(250 mm x 10 mm, 10 μm; Agilent Technologies, Santa Clara, CA, USA).
However, they are reported to be present in significant quantities in ginseng species, so the conventional evaluation index may not comprehensively reflect all ginseng properties or processed products. This study reports a simple and efficient way to prepare malonyl ginsenosides, as well as their physicochemical and NMR data, which provided scientific basis for the preparation of the standard substance.
참고문헌 (18)
1 Christensen L.P. Ginsenosides: chemistry, biosynthesis, analysis, and potential health effect Adv Food Nutr Res 55 2009 1 99 18772102
2 Sun G.Z. Liu Z. Li X.G. Zheng Y.N. Wang J.Y. Isolation and identification of two malonyl ginsenosides from the fresh root of Panax ginseng Chin J Anal Chem 33 2005 1783 1786
3 Wu W. Sun L. Zhang Z. Guo Y.Y. Liu S.Y. Profiling and multivariate statistical analysis of Panax ginseng based on ultra-high-performance liquid chromatography coupled with quadrupole-time-of-flight mass spectrometry J Pharmaceut Biomed 107 2015 141 150
4 Ren G. Chen F. Degradation of ginsenosides in American ginseng ( Panax quinquefolium ) extracts during microwave and conventional heating J Agric Food Chem 47 1999 1501 1505 10564006
6 Kitagawa I. Taniyama T. Yoshikawa M. Ikenishi Y. Nakagawa Y. Chemical studies on crude drug processing. VI Chemical Structures of Malonyl ginsenosides Rb 1 , Rb 2 , Rc, and Rd Isolated from the root of Panax ginseng C.A. Meyer Chem Pharm Bull 37 1989 2961 2970
7 Sun B.S. Xu M.Y. Li Z. Wang Y.B. Sung C.K. UPLC-Q-TOF-MS/MS analysis for steaming times-dependent profiling of steamed Panax quinquefolius and its ginsenosides transformations induced by repetitious steaming J Ginseng Res 36 2012 277 290 23717129
8 Kitagawa I. Taniyama T. Hayashi T. Yoshikawa M. Malonyl ginsenosides Rb 1 , Rb 2 , Rc and Rd, four new malonylated dammarane-type triterpene oligosaccharides from ginseng radix Chem Pharm Bull 31 1983 3353 3356
9 Yamaguchi H. Kasai R. Matsuura H. Tanaka O. Fuwa T. High-performance liquid chromatographic analysis of acidic saponins of ginseng and related plants Chem Pharm Bull 36 1988 3468 3473 3240541
10 Sun G.Z. Li X.G. Liu Z. Wang J.Y. Yang X.W. Isolation and structure characterization of malonyl-notoginsenoside R 4 from the root of Panax ginseng Chin J Anal Chem 28 2007 1316 1318
11 Ruan C.C. Liu Z. Li X. Liu X. Wang L.J. Pan H.Y. Zheng Y.N. Sun G.Z. Zhang Y.S. Zhang L.X. Isolation and characterization of a new ginsenoside from the fresh root of Panax Ginseng Molecules 15 2010 2319 2325 20428044
12 Wan J.Y. Fan Y. Yu Q.T. Ge Y.Z. Yan C.P. Alolga R.N. Li P. Ma Z.H. Qi L.W. Integrated evaluation of malonyl ginsenosides, amino acids and polysaccharides in fresh and processed ginseng J Pharmaceut Biomed 107 2015 89 97
13 Yan J. Guo X.Q. Li X.G. Wu X.Y. Gou X.J. TLC to fleetly analyze monosaccharide composition of polysaccharide Food Sci 27 2006 603 607
14 Hara S. Okabe H. Mihashi K. Gas-liquid chromatographic separation of aldose enantiomers as trimethylsilyl ethers of methyl 2-(phlyhydroxyalkyl)thiazolidine-4- (R)-carboxylates Chem Pharm Bull 35 1987 501 506
15 Teng R.W. Li H.Z. Chen J.T. Wang D.Z. He Y.N. Yang C.R. Complete assignment of 1 H and 13 C NMR data for nine protopanaxatriol glycosides Mag Reson Chem 40 2002 483 488
16 Cho J.G. In S.J. Jung Y.J. Cha B.J. Lee D.Y. Kim Y.B. Yeom M.H. Baek N.I. Re-evaluation of physicochemical and NMR data of triol ginsenosides Re, Rf, Rg 2 , and 20-gluco-Rf from Panax ginseng roots J Ginseng Res 36 2014 116 122 24748835
17 Yang H. Kim J.Y. Kim S.O. Yoo Y.H. Sung S.H. Complete 1 H-NMR and 13 C-NMR spectral analysis of the pairs of 20(S) and 20(R) ginsenosides J Ginseng Res 38 2014 194 202 25378994
18 Cho J.G. Lee M.K. Lee J.W. Park H.J. Lee D.Y. Lee Y.H. Yang D.C. Baek N.I. Physicochemical characterization and NMR assignments of ginsenosides Rb 1 , Rb 2 , Rc, and Rd isolated from Panax ginseng J Ginseng Res 34 2010 113 121
※ AI-Helper는 부적절한 답변을 할 수 있습니다.