Biological Activities and Chemistry of Saponins from Panax ginseng C. A. Meyer

Abstract

The roots of Panax ginseng C. A. Meyer, known as Korean ginseng have been a valuable and important folk medicine in the East Asian countries, such as China, Korea and Japan for about 2000 years. Panax is derived from a word ''panacea'', which means cure-all diseases and longevity as well as physical strength and resistance. As the use of traditional Chinese herbs as a food supply becomes more and more popular in the western countries, sales of Panax ginseng are increasing in North America and Europe as well as other parts of the world. Active constituents found in most ginseng species include ginsenosides, polysaccharides, peptides, polyacetylenic alcohols and fatty acids. Major active components in Panax ginseng are the ginsenosides, a group of saponins with triterpenoid dammarane structure. More than 30 ginsenosides have been isolated, and known compounds are identified but new compounds were elucidated. Pharmacological effects of ginseng have been demonstrated in cancer, diabetes mellitus, cardiovascular system, immune system and central nervous system including anti-stress and anti-oxidant activity. We have focused this review on the effect of ginseng on diabetes, anticancer activity and cardiovascular system and chemical structures of ginsenosides. In addition, our recent biological study on 20(S)-ginsenoside Rg 3 is also touched upon as follows. Multidrug resistance (MDR) has been a major problem in cancer chemotherapy. In this study in vitro and in vivo modulations of MDR by 20(S)-ginsenoside Rg 3 (Rg 3 ), a saponin characteristic of red ginseng, was investigated. In flow cytometric analysis using rhodamine 123 as an artificial substrate, Rg 3 promoted accumulation of rhodamine 123 in drug-resistant human fibrocarcinoma KBV 20C cells in a dose-dependent manner, but it had no effect on parental KB cells. Additionally Rg 3 inhibited [ 3 H]-vinblastine efflux and reversed MDR to DOX (doxorubicin), COL, VCR (vincristine) and VP-16 in KBV20C cells. Reverse transcriptase-polymerase chain reaction and immuno-blot analysis after exposure of KBV20C cells to Rg 3 showed that inhibition of drug efflux by Rg 3 was due to neither repression of MDR1 gene expression nor P-glycoprotein (Pgp) level. Photo-affinity labeling study with [ 3 H]-azidopine, however, revealed that Rg 3 competed with [ 3 H]-azidopine for binding to the Pgp demonstrating that G-Rg 3 competed with anticancer drug for binding to Pgp thereby blocking drug efflux. Furthermore, Rg 3 increased life span in mice implanted with DOXresistant murine leukemia P388 cells in vivo and inhibited body weight increase significantly. Further clinical trial of Rg 3 in reversal of Pgp-associated MDR is highly feasible.

Molecular docking studies of anti-apoptotic BCL-2, BCL-XL, and MCL-1 proteins with ginsenosides from Panax ginseng

“…There are 38 known ginsenosides and the structures of these ginsenosides include a four-ring rigid steroid skeleton with a modified side chain 17 . These ginsenosides are reported to have various pharmacological effects, including immunomodulatory, anti-stress, anti-hyperglycemic, anti-inflammatory, antiallergic, anti-atherosclerotic, anti-hypertensive, antioxidant, anti-diabetic, and anti-cancer effects, as well as effects on the cardiovascular system and central nervous system [18][19][20] . The pharmacological effects of ginseng have been demonstrated in many experimental studies.…”

Medicinal plants used in the management of diabetes by traditional healers of Narok County, Kenya

“…Flavonoids increases glucose uptake (Granados et al, 2015), insulin secretion (Mohan and Nandhakumar, 2014), prevent Beta-cell apoptosis (Pinent et al, 2008) possess antioxidant activity and modulate renal glucose reabsorption (Lukačínová et al, 2008). Saponin hypoglycemic activity associated with increased insulin secretion by rejuvenating β-cells, modulating calcium channels (Koneri et al, 2014), antiglycation, antioxidant , antiobesity activity (Park et al, 2005) and amelioration of diabetes complications related to liver and kidney function, and glucose metabolism (Patel et al, 2012). Tannins has antihyperlipidemic and hepatoprotective activity (Babby, 2014).…”

Dammarane-type Saponins from the Black Ginseng

“…2). Ginsenoside SG 1 (1), an amorphous powder, has the molecular formula C36H62O10 deduced by a high-resolusion electrospray- C-NMR data of 1 were similar to those of 20R-ginsenoside Rh 1 9 except for the signals belonging to the side-chain part (C-22 -C-27) of the aglycone. The structure of 1, especially the side-chain, was assigned by was proposed as E form based on the 13 C-NMR agreements of C-24, 26, and 27 with those in the literature 15 and, furthermore, the NOE correlation H-26/H-24 in the ROESY spectrum of 1 (Fig.…”

“…[1][2][3][4] Traditionally, ginseng has been processed to make white ginseng (WG, roots air-dried after peeling) and red ginseng (RG, roots steamed at 98 -100 o C without peeling) to enhance its preservation and efficacy, which is associated with the changes in the chemical constituents, especially newly formed ginsenosides as results of steaming process, considerably.…”

“…[5][6][7] Meanwhile, its constituents have been analyzed, but not extensively in respect to that of other conventional ginsengs. 7 Subsequently, in our ongoing systematic ginseng-research, the current study on chemical components of the black ginseng led to the isolation of two new saponins, named ginsenosides SG 1 (1) and SG 2 (2) (Fig. 1), along with twenty compounds, including ginsenoside Rh2 (3), 8 20R-ginsenoside Rh1 (4), 9 ginsenoside Rk 3 (5), 10 ginsenoside Rh 4 (6), 10 6'-acetyl ginsenoside Rg 1 (7), 11 ginsenoside Rg 6 (8), 12 20E-ginsenoside F 4 (9), 13 ginsenoside Rg 2 (10), 14 ginsenoside Rg1 (11), 15 ginsenoside Rf (12), 16 ginsenoside Rg 3 (13), 17 ginsenoside Rk 1 (14), 10 6'''-acetyl ginsenoside Re (15), 11 ginsenoside Re (16), 15 ginsenoside Rs 2 (17), 18 ginsenoside Rd (18), 15 ginsenoside F3 (19), 15 ginsenoside Rb1 (20), 15 ginsenoside Rc (21), 15 and ginsenoside Rb 2 (22) 15 ( Fig.…”