Biological activities and distribution of plant saponins.

Ginsenosides are a special group of triterpenoid saponins that can be classified into two groups by the skeleton of their aglycones, namely dammarane‐ and oleanane‐type. Ginsenosides are found nearly exclusively in Panax species (ginseng) and up to now more than 150 naturally occurring ginsenosides have been isolated from roots, leaves/stems, fruits, and/or flower heads of ginseng. Ginsenosides have been the target of a lot of research as they are believed to be the main active principles behind the claims of ginsengs efficacy. The potential health effects of ginsenosides that are discussed in this chapter include anticarcinogenic, immunomodulatory, anti‐inflammatory, antiallergic, antiatherosclerotic, antihypertensive, and antidiabetic effects as well as antistress activity and effects on the central nervous system. Ginsensoides can be metabolized in the stomach (acid hydrolysis) and in the gastrointestinal tract (bacterial hydrolysis) or transformed to other ginsenosides by drying and steaming of ginseng to more bioavailable and bioactive ginsenosides. The metabolization and transformation of intact ginsenosides, which seems to play an important role for their potential health effects, are discussed. Qualitative and quantitative analytical techniques for the analysis of ginsenosides are important in relation to quality control of ginseng products and plant material and for the determination of the effects of processing of plant material as well as for the determination of the metabolism and bioavailability of ginsenosides. Analytical techniques for the analysis of ginsenosides that are described in this chapter are thin‐layer chromatography (TLC), high‐performance liquid chromatography (HPLC) combined with various detectors, gas chromatography (GC), colorimetry, enzyme immunoassays (EIA), capillary electrophoresis (CE), nuclear magnetic resonance (NMR) spectroscopy, and spectrophotometric methods.

Ginsenosides: Chemistry, biosynthesis, analysis and potential health effects

The class of steroid-like compounds designated cardiac glycosides includes well-known drugs such as digoxin, digitoxin, and ouabain. Their continued efficacy in treatment of congestive heart failure and as anti-arrhythmic agents is well appreciated. Less well known, however, is the emerging role of this category of compounds in the prevention and/or treatment of proliferative diseases such as cancer. New findings within the past five years have revealed these compounds to be involved in complex cell-signal transduction mechanisms, resulting in selective control of human tumor but not normal cellular proliferation. As such, they represent a promising form of targeted cancer chemotherapy. New clinical studies of their anticancer potential as single or adjuvant treatments may provide insight into these potentially valuable therapeutic options. This review focuses on recent findings on cellular pharmacology of cardiac glycosides as they relate to treatment of human cancer and attempts to explain why these agents have been overlooked in the past.

Cardiac glycosides as novel cancer therapeutic agents

The therapeutic potential of ginseng has been studied extensively, and ginsenosides, the active components of ginseng, are shown to be involved in modulating multiple physiological activities. This article will review the structure, systemic transformation and bioavailability of ginsenosides before illustration on how these molecules exert their functions via interactions with steroidal receptors. The multiple biological actions make ginsenosides as important resources for developing new modalities. Yet, low bioavailability of ginsenoside is one of the major hurdles needs to be overcome to advance its use in clinical settings.

https://link.springer.com/content/pdf/10.1186%2F1749-8546-5-20.pdf

Pharmacology of ginsenosides: a literature review.

Antioxidant and anti-tumor promoting activities of the methanol extract of heat-processed ginseng.

A genuine glycoside, named ginsenoside Rh4, was isolated from Korean red ginseng (Panax ginseng C. A. Meyer) through repeated column chromatography, and its chemical structure was established to be 6-O-beta-D-glucopyranosyldammar-20(22),24-diene-3 beta,6 alpha,12 beta-triol by spectral and chemical methods. The stereochemistry of a double bond at C-20(22) of ginsenoside Rh4 was characterized as (E) from a NOESY experiment in the 1H-NMR of the aglycone. Cytotoxic activities of ginsenoside Rh4 and its aglycone against cancer cell lines were evaluated by use of the SRB method.

Ginsenoside Rh4, a genuine dammarane glycoside from Korean red ginseng

Two phenanthrenes were isolated from the aerial part of Dendrobium nobile Lindl. and their structures were identified to be 4,7-dihydroxy-2-methoxy-9,10-dihydrophenanthrene (1) and denbinobin (2), among which the former has been first isolated from this plant. These two compounds were found to be cytotoxic against A549 (human lung carcinoma), SK-OV-3 (human ovary adenocarcinoma), and HL-60 (human promyelocytic leukemia) cell lines. Compound 1 also showed antitumor activity on the life span of ICR mice intraperitoneally implanted with 1 x 10(6) cells of sarcoma 180.

In Vitro and In Vivo Antitumoral Phenanthrenes from the Aerial Parts of Dendrobium nobile

A genuine dammarane glycoside, named ginsenoside Rg5, has been isolated by repeated column chromatography and preparative HPLC from the MeOH extract of Korean red ginseng (Panax ginseng C.A. Meyer). The chemical structure of ginsenoside Rg5 was determined as 3-O-[β-D-glucopyranosyl (1→2)-β-D-glucopyranosyl] dammar-20(22),24-diene-3β,12β-diol by spectral and chemical methods. The stereostructure of a double bond at C-20(22) of ginsenoside Rg5 was characterized as (E) from the chemical shift of C-21 in the13C-NMR and a NOESY experiment in the1H-NMR.

Ginsenoside Rg5, a genuine dammarane glycoside from Korean red ginseng

In order to elucidate the cytotoxicity-structure correlation of ginseng-derived components, several prosapogenins and sapogenins were prepared from Korean red ginseng (Panax ginseng) saponins by acid hydrolysis or alkaline cleveage, and their chemical structures were identified by a combination of spectral and physical methods. Some of these degradation products showed the cytotoxic activities against various cancer cell lines, A549, SK-OV-3, SK-Mel-2, P388, L 1210 and K562. The significant difference in cytotoxicity between stereoisomers was not found and the activity was inversely proportional to the number of sugars linked to sapogenins. Diol-type prosapogenins and sapogenins showed higher cytotoxicity than triol-type ones.

Cytotoxicities of ginseng saponins and their degradation products against some cancer cell lines

A new dammarane glycoside named ginsenoside Rf2 has been isolated from Korean red ginseng (Panax ginseng) and its chemical structure has been elucidated as 6-O-[alpha-L-rhamnopyranosyl (1-->2) beta-D-glucopyranosyl]dammarane-3 beta, 6 alpha, 12 beta, 20(R), 25-pentol by chemical and spectral methods.

You Hui Lee

Papers

Ginsenoside Rh4, a genuine dammarane glycoside from Korean red ginseng

In Vitro and In Vivo Antitumoral Phenanthrenes from the Aerial Parts of Dendrobium nobile

Ginsenoside Rg5, a genuine dammarane glycoside from Korean red ginseng

Cytotoxicities of ginseng saponins and their degradation products against some cancer cell lines

Ginsenoside Rf2, a new dammarane glycoside from Korean red ginseng (Panax ginseng)