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      Chemical diversity of ginseng saponins from Panax ginseng ☆

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      Author(s): , , ∗
      Publication date (Electronic):
      Journal: Journal of Ginseng Research
      Publisher: Elsevier
      Keywords: Araliaceae, dammarane, ginsenoside, Panax ginseng, triterpene

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          Abstract

          Ginseng, a perennial plant belonging to the genus Panax of the Araliaceae family, is well known for its medicinal properties that help alleviate pathological symptoms, promote health, and prevent potential diseases. Among the active ingredients of ginseng are saponins, most of which are glycosides of triterpenoid aglycones. So far, numerous saponins have been reported as components of Panax ginseng, also known as Korean ginseng. Herein, we summarize available information about 112 saponins related to P. ginseng; >80 of them are isolated from raw or processed ginseng, and the others are acid/base hydrolysates, semisynthetic saponins, or metabolites.

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          Brief introduction of Panax ginseng C.A. Meyer.

          T K Yun (2001)
          For many many thousand years, mankind has been using various plants as nutrient, beverage, cosmetics, dye and medicine to maintain health and to improve quality of life. In Aisa, particularly, Panax ginseng C.A. Meyer is considered to be the most precious plant among herbs, and ginseng has been in the spotlight worldwide. Even in the Western world, where there are greatly advanced research facilities and highly qualified man-power available, and are regarded to be capable of conquering any hard-to-cure ailments, many peoples has recently been reported to use herbal medicine, particularly ginseng. In the present compilation of papers, many scientists contributed papers pertaining to "Chemopreventive effects of ginseng". In order to facilitate the readers understand easier and better, I catalogued this collection as follows: The spiritual nature of ginseng in the Far East, the history of ginseng, nomenclature and geographical distribution of ginseng, and type of ginseng products.
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            Proof of the mysterious efficacy of ginseng: basic and clinical trials: metabolic activation of ginsenoside: deglycosylation by intestinal bacteria and esterification with fatty acid.

            Hideo Hasegawa (2004)
            Orally ingested ginsenoside passes through the stomach and small intestine without decomposition by either gastric juice or liver enzymes into the large intestine, where ginsenoside is deglycosylated by colonic bacteria followed by transit to the circulation. Colonic bacteria cleave the oligosaccharide connected to the aglycone stepwise from the terminal sugar to afford the major metabolites, 20S-protopanaxadiol 20-O-beta-D-glucopyranoside (M1) and 20S-protopanaxatriol (M4). These metabolites are further esterified with fatty acids. The resultant fatty-acid conjugates are still active molecules that are sustained longer in the body than parental metabolites. Accumulating evidence strongly suggests that ginsenoside is a prodrug that is activated in the body by intestinal bacterial deglycosylation and fatty acid esterification.
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              In vitro anti-cancer activity and structure-activity relationships of natural products isolated from fruits of Panax ginseng.

              Wei Wang, Yuqing Zhao, Elizabeth R. Rayburn … (2007)
              Panax ginseng and its extracts have long been used for medical purposes; there is increasing interest in developing ginseng products as cancer preventive or therapeutic agents. The present study was designed to determine biological structure-activity relationships (SAR) for saponins present in Panax ginseng fruits. Eleven saponins were extracted from P. ginseng fruits and purified by use of D(101) resin and ordinary and reverse-phase silica gel column chromatography. Their chemical structures were elucidated on the basis of physicochemical constants and NMR spectra. Compounds were then evaluated for SAR with their in vitro cytotoxicity against several human cancer cell lines. The 11 compounds were identified as 20(R)-dammarane-3beta,12beta,20,25-tetrol (25-OH-PPD, 1); 20(R)-dammarane-3beta,6alpha,12beta,20,25-pentol (25-OH-PPT, 2); 20(S)-protopanaxadiol (PPD, 3); daucosterine 4, 20(S)-ginsenoside-Rh(2) (Rh(2), 5); 20(S)-ginsenoside-Rg(3) (Rg(3,) 6); 20(S)-ginsenoside-Rg(2) (Rg(2), 7); 20(S)-ginsenoside-Rg(1) (Rg(1), 8); 20(S)-ginsenoside-Rd (Rd, 9); 20(S)-ginsenoside-Re (Re, 10); and 20(S)-ginsenoside-Rb(1) (Rb(1), 11). Among the eleven compounds, 1, 3 and 5 were the most effective inhibitors of cell growth and proliferation and inducers of apoptosis and cell cycle arrest. For 1, the IC(50) values for most cell lines were in the range of 10-60 microM, at least twofold lower than for any of the other compounds. Compounds 1 and 3 had significant, dose-dependent effects on apoptosis, proliferation, and cell cycle progression. The results suggest that the type of dammarane, the number of sugar moieties, and differences in the substituent groups affect their anti-cancer activity. This information may be useful for evaluating the structure/function relationship of other ginsenosides and their aglycones and for development of novel anticancer agents.
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                Author and article information

                Contributors
                Jeong Hill Park
                Journal
                Journal ID (nlm-ta): J Ginseng Res
                Journal ID (iso-abbrev): J Ginseng Res
                Title: Journal of Ginseng Research
                Publisher: Elsevier
                ISSN (Print): 1226-8453
                ISSN (Electronic): 2093-4947
                Publication date PMC-release: 10 January 2015
                Publication date (Print): October 2015
                Publication date (Electronic): 10 January 2015
                Volume: 39
                Issue: 4
                Pages: 287-298
                Affiliations
                [1]College of Pharmacy, Seoul National University, Seoul, Korea
                Author notes
                [∗ ]Corresponding author. College of Pharmacy, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 151-742, Korea. hillpark@ 123456snu.ac.kr
                Article
                Publisher ID: S1226-8453(15)00003-2
                DOI: 10.1016/j.jgr.2014.12.005
                PMC ID: 4593792
                PubMed ID: 26869820
                SO-VID: 8215fc7b-cd3e-4039-840f-fdd82cd9129d
                Copyright © Copyright © 2015, The Korean Society of Ginseng, Published by Elsevier Ltd.
                License:

                This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).

                History
                Date received : 5 November 2014
                Date revision received : 23 December 2014
                Date accepted : 25 December 2014
                Categories
                Subject: Review Article

                Keywords: araliaceae,dammarane,ginsenoside,panax ginseng,triterpene
                Data availability:
                Keywords: araliaceae, dammarane, ginsenoside, panax ginseng, triterpene

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