A new panaxadiol from the acid hydrolysate of Panax ginseng

Li, Tao; Qin, Meng; Yin, Jian; Xing, Rui; Guo, Hao

doi:10.1016/j.cclet.2009.01.015

Cited by 19 publications

(13 citation statements)

References 8 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Its molecular structure was elucidated based on spectroscopic data (IR, MS, 1 H NMR, 13 C NMR and X‐ray; Tao etal. , ). The purity was >99% (determined by HPLC‐ELSD).…”

Section: Methodsmentioning

confidence: 97%

“…Research studies have demonstrated that ginsenosides can stimulate the nervous system (Neale, Camfield, Reay, Stough, & Scholey, 2012). Neopanaxadiol [dammar-(E)-20(22)-ene-3β,12β,25-triol, NPD, structure in Figure 1] is a new panaxadiol component extracted from acid degradation of total ginsenosides and is suggested to have a neuron protection effect (Tao, Meng, Yin, Xing, & Guo, 2009). In order to explore the potential medicinal application of NPD, its pharmacokinetic (PK) profiling needs to be investigated.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Development and validation of an UPLC‐Q/TOF‐MS assay for the quantitation of neopanaxadiol in beagle dog plasma: Application to a pharmacokinetic study

Geng

Wang

et al. 2016

Biomedical Chromatography

View full text Add to dashboard Cite

Neopanaxadiol (NPD), the main panaxadiol constituent of Panax ginseng C. A. Meyer (Araliaceae), has been regarded as the active component for the treatment of Alzheimer's disease. However, few references are available about pharmacokinetic evaluation for NPD. Accordingly, a rapid and sensitive method for quantitative analysis of NPD in beagle dog plasma based on ultra-performance liquid chromatography quadrupole time-of-flight mass spectrometry was developed and validated. Analytes were extracted from plasma by liquid-liquid extraction and chromatographic separation was achieved on an Agilent Zorbax Stable Bond C column. Detection was performed in the positive ion mode using multiple reaction monitoring of the transitions both at m/z 461.4 → 425.4 for NPD and internal standard of panaxadiol. All validation parameters, such as lower limit of quantitation, linearity, specificity, precision, accuracy, extraction recovery, matrix effect and stability, were within acceptable ranges and the method was appropriate for multitude sample determination. After oral intake, NPD was slowly absorbed and eliminated from circulatory blood system and corresponding plasma exposure was low. Application of this quantitative method will yield the first pharmacokinetic profile after oral administration of NPD to beagle dog. The information obtained here will be useful to understand the pharmacological effects of NPD.

show abstract

“…Its molecular structure was elucidated based on spectroscopic data (IR, MS, 1 H NMR, 13 C NMR and X‐ray; Tao etal. , ). The purity was >99% (determined by HPLC‐ELSD).…”

Section: Methodsmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

Development and validation of an UPLC‐Q/TOF‐MS assay for the quantitation of neopanaxadiol in beagle dog plasma: Application to a pharmacokinetic study

Geng

Wang

et al. 2016

Biomedical Chromatography

View full text Add to dashboard Cite

show abstract

“…In order to find more bioactive compounds, acid was used to hydrolyze the ginsenosides to produce the original and artificial triterpene aglycones [12,13]. As part of our ongoing study on the chemical constituents and bioactivities, a lipid-soluble neuroprotective aglycon from the hydrolysate of ginsenosides was extracted and elucidated [14]. We obtained six dammarane ginsenosides (1-6).…”

mentioning

confidence: 99%

“…Compounds 2-6 were determined on the basis of spectral analysis and comparison with reported data [2,[14][15][16][17]. Compound 1 was isolated as a white amorphous powder.…”

mentioning

confidence: 99%

Anti-colon carcinoma cell activity of ginsenosides from the acid hydrolysate of Panax ginseng

Yin

Cong

et al. 2013

Chem Nat Compd

Self Cite

View full text Add to dashboard Cite

isolated from the acid hydrolysate of Panax ginseng. Compound 1 was only mentioned in a patent literature, and there is no spectroscopic data elsewhere. This paper is the first to elucidate the structure of compound 1 on the basis of spectroscopic evidence. The biological activities of compounds 1-6, crude ginsenosides, and the ginsenoside-hydrolysate were determined in human colon carcinoma cell. Compounds 1-3 and the ginsenoside-hydrolysate exhibited anti-human colon carcinoma cell activity, with IC 50 of 66.1, 72.4, 50.1, and 25.7 Pg/mL, respectively.Keywords: Panax ginseng, 20(R)-dammar-25-ethoxy-3E,12E,20-triol, acid hydrolysate, ginsenoside.Panax ginseng C. A. Mey. (Araliaceae) has been used in traditional medicine in Asia since ancient times [1] to improve health and vitality as a dietary supplement and to treat various diseases such as psychopathy, neuropathy, and diabetes mellitus [2]. The pharmacological activities of ginseng or its crude extracts are based on the presence of a mixture of ginsenosides [3]. It was reported that more than 40 ginsenosides have been isolated and identified from ginseng species [4], and ginsenosides have been reported to have anticancer, antiarrhythmia, and anti-HIV activities [5][6][7][8][9] and are also viral protease inhibitors [10,11]. In order to find more bioactive compounds, acid was used to hydrolyze the ginsenosides to produce the original and artificial triterpene aglycones [12,13]. As part of our ongoing study on the chemical constituents and bioactivities, a lipid-soluble neuroprotective aglycon from the hydrolysate of ginsenosides was extracted and elucidated [14]. We obtained six dammarane ginsenosides (1-6). Compound 1 was only mentioned in a patent literature, and there is no spectroscopic data elsewhere. Because complete and confident assignment of spectroscopic data is crucial for confirming chemical structures and evaluating the purity of natural products, we undertook a thorough spectroscopic analysis of compound 1. In this paper we report the isolation and structural elucidation of compound 1 and five other known ginsenosides, as well as the inhibitory activities of isolated ginsenosides against human colon carcinoma cell.

show abstract

“…The IC 50 of the three hydrolysates were 47.8, 29.6, and 39.5 Pg/mL, respectively, and that of the crude ginsenosides was 127.2 Pg/mL against SW1116 cell lines. The 10% hydrolysate was the most active with respect to the value of IC 50 (the lower the value, the stronger the activity), so this hydrolysate was subject to normal-phase and reversed-phase silica gel column chromatography and repeated HPLC to afford compound 1 and five known ginsenosides that were confirmed as 20R,24R-dammar-20(24)-epoxy-3E,12E,25-triol (2) [9], 20R-panaxdiol (3) [10], dammar-(E)-20(22)-ene-3E,12E,25-triol (4, NPD) [11], 20R-protopanaxadiol (5) [12], and 20R-dammar-25-ethoxy-3E,12E,20-triol (6) [13,14] by comparing their NMR spectroscopic data with the literature values. (Table 1), which was confirmed by its 13 C and 1 H NMR data.…”

mentioning

confidence: 99%

Structure of Acid Hydrolysate of Total Ginsenosides and Their Cytotoxic Activity

et al. 2014

Self Cite

View full text Add to dashboard Cite

Keywords: (20S,22S)-dammar-22,25-epoxy-3E,12E,20-triol, acid hydrolysate, ginsenoside.Ginsenosides are considered to be the main bioactive constituents of Panax ginseng, which has a range of biological activities including anticancer [1-3], angiogenesis [4][5][6], and neuroprotective effects [7]. As a part of our continuing studies, a bioassay-guided isolation of the degradation products of ginsenosides was performed, and six ginsenosides (1-6) were obtained from the fraction. Compound 1, a new aglycone with an oxacyclopentane ring at the C-17 side chain, was isolated, which differed from the ocotillol type ginsengenin and has never been reported before in approximately over 200 saponins that have been isolated from ginseng plants [8]. Herein, we describe the isolation and structural elucidation of compound 1 and the other five known ginsenosides, as well as the inhibitory activities of isolated ginsenosides against human cancer cell lines.The crude ginsenosides were refluxed in 50% EtOH with 5, 10, and 15% hydrochloric acid and extracted with an equal volume of CHCl 3 three times, and the organic layer was evaporated to yield the ginsenoside hydrolysate. The IC 50 of the three hydrolysates were 47.8, 29.6, and 39.5 Pg/mL, respectively, and that of the crude ginsenosides was 127.2 Pg/mL against SW1116 cell lines. The 10% hydrolysate was the most active with respect to the value of IC 50 (the lower the value, the stronger the activity), so this hydrolysate was subject to normal-phase and reversed-phase silica gel column chromatography and repeated HPLC to afford compound 1 and five known ginsenosides that were confirmed as 20R,24R-dammar-20(24)-epoxy-3E,12E,25-triol (2) [9], 20R-panaxdiol (3) [10], dammar-(E)-20(22)-ene-3E,12E,25-triol (4, NPD) [11], 20R-protopanaxadiol (5) [12], and 20R-dammar-25-ethoxy-3E,12E,20-triol (6) [13, 14] by comparing their NMR spectroscopic data with the literature values.

show abstract

A new panaxadiol from the acid hydrolysate of Panax ginseng

Cited by 19 publications

References 8 publications

Development and validation of an UPLC‐Q/TOF‐MS assay for the quantitation of neopanaxadiol in beagle dog plasma: Application to a pharmacokinetic study

Development and validation of an UPLC‐Q/TOF‐MS assay for the quantitation of neopanaxadiol in beagle dog plasma: Application to a pharmacokinetic study

Anti-colon carcinoma cell activity of ginsenosides from the acid hydrolysate of Panax ginseng

Structure of Acid Hydrolysate of Total Ginsenosides and Their Cytotoxic Activity

Contact Info

Product

Resources

About