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Journal ArticleDOI

Saponins, classification and occurrence in the plant kingdom

01 Feb 2007-Phytochemistry (Phytochemistry)-Vol. 68, Iss: 3, pp 275-297
TL;DR: The oleanane skeleton was the most common skeleton and is present in most orders of the plant kingdom, and the relationship between the type of skeleton and the plant origin was investigated.
About: This article is published in Phytochemistry.The article was published on 2007-02-01. It has received 592 citations till now. The article focuses on the topics: Oleanane & Triterpene.
Citations
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Journal ArticleDOI
TL;DR: This review summarizes current knowledge of triterpenoid saponin biosynthesis in plants, molecular activities, evolutionary aspects and perspectives for further gene discovery.

560 citations

Journal ArticleDOI
TL;DR: The correlations between the structure and the cytotoxicity of both steroid and triterpenoid saponins have been described as well as the most common mechanisms of action.
Abstract: Saponins are natural glycosides which possess a wide range of pharmacological properties including cytotoxic activity. In this review, the recent studies (2005–2009) concerning the cytotoxic activity of saponins have been summarized. The correlations between the structure and the cytotoxicity of both steroid and triterpenoid saponins have been described as well as the most common mechanisms of action.

542 citations


Cites background from "Saponins, classification and occurr..."

  • ...2005), distribution (Henry 2005; Vincken et al. 2007), structures (Vincken et al....

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  • ...Pentacyclic triterpenoid saponins belong, in a majority of cases, to oleanane-type, other skeleton types include ursane, lupane, hopane, germanicane, dammarane (Vincken et al. 2007)....

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  • ...The sugar chain can contain from one to several monosaccharide residues, and is usually attached at C-3 (Vincken et al. 2007)....

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  • ...…the more recent tackled biosynthesis (Haralampidis et al. 2002; Kalinowska et al. 2005), distribution (Henry 2005; Vincken et al. 2007), structures (Vincken et al. 2007; Sahu et al. 2008), biological and pharmacological activities of saponins (Sparg et al. 2004; Yang et al. 2006; Wang et al. 2007;…...

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  • ...2007), structures (Vincken et al. 2007; Sahu et al. 2008), biological and pharmacological activities of saponins (Sparg et al....

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Journal ArticleDOI
TL;DR: Recent developments in the field of triterpene biosynthesis are reviewed, an overview of the genes and enzymes that have been identified to date are given, and strategies for discovering new triterpenes pathways are discussed.
Abstract: The triterpenes are one of the most numerous and diverse groups of plant natural products. They are complex molecules that are, for the most part, beyond the reach of chemical synthesis. Simple triterpenes are components of surface waxes and specialized membranes and may potentially act as signaling molecules, whereas complex glycosylated triterpenes (saponins) provide protection against pathogens and pests. Simple and conjugated triterpenes have a wide range of applications in the food, health, and industrial biotechnology sectors. Here, we review recent developments in the field of triterpene biosynthesis, give an overview of the genes and enzymes that have been identified to date, and discuss strategies for discovering new triterpene biosynthetic pathways.

506 citations


Cites background from "Saponins, classification and occurr..."

  • ...They also have a wide range of commercial applications in the food, cosmetics, pharmaceutical, and industrial biotechnology sectors (6, 88, 99, 119, 147)....

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  • ...These sugar chains are usually composed of glucose, galactose, arabinose, rhamnose, xylose, and glucuronic acid (although other sugars may also be incorporated) and are added onto hydroxyl groups or carboxyl groups, forming sugar acetals and sugar esters, respectively (147)....

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Journal ArticleDOI
TL;DR: Although PSM may negatively affect nutrient utilization, there is evidence that methanogenesis could be suppressed without adversely affecting rumen fermentation, which could be exploited to mitigate methane emission in ruminants.

407 citations


Cites background from "Saponins, classification and occurr..."

  • ...The saccharide chains are commonly attached at the C3 position (monodesmosidic), but some sapogenins contain two saccharide chains (bidesmosidic) attached at the C3 and C17 (via C28) position (Vincken et al., 2007)....

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Journal ArticleDOI
TL;DR: Folk medicine supports the studies which have demonstrated that plant-derived terpenoid ingredients can suppress nuclear factor-κB signaling, the major regulator in the pathogenesis of inflammatory diseases and cancer.
Abstract: Traditional medicine has been a fertile source for revealing novel lead molecules for modern drug discovery. In plants, terpenoids represent a chemical defense against environmental stress and provide a repair mechanism for wounds and injuries. Interestingly, effective ingredients in several plant-derived medicinal extracts are also terpenoid compounds of monoterpenoid, sesquiterpenoid, diterpenoid, triterpenoid and carotenoid groups. Inflammatory diseases and cancer are typical therapeutic indications of traditional medicines. Thus folk medicine supports the studies which have demonstrated that plant-derived terpenoid ingredients can suppress nuclear factor-κB (NF-κB) signaling, the major regulator in the pathogenesis of inflammatory diseases and cancer.We review the extensive literature on the different types of terpenoid molecules, totalling 43, which have been verified both inhibiting the NF-κB signaling and suppressing the process of inflammation and cancer. It seems that during evolution, plants have established a terpene-based host defense which also represents a cornucopia of effective therapeutic compounds for common human diseases.

392 citations

References
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Journal ArticleDOI
TL;DR: This commentary aims to review selected effects of ginseng and ginsenosides and describe their possible modes of action, structural and functional relationship to steroids, and potential targets of action.

1,816 citations


"Saponins, classification and occurr..." refers background in this paper

  • ...…1991; Kitagawa, 2002; Heng et al., 2006b), foaming and emulsifying properties (Price et al., 1987), pharmacological and medicinal properties (Attele et al., 1999), haemolytic properties (Oda et al., 2000; Sparg et al., 2004), as well as antimicrobial, insecticidal, and molluscicidal…...

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Journal ArticleDOI
TL;DR: Isolation studies of saponins were examined to determine which are the more commonly studied plant families and in which families saponin have been identified.

1,245 citations


"Saponins, classification and occurr..." refers background in this paper

  • ...…over the last two decades, focussing on biosynthesis, isolation, structural elucidation, and biological activities of saponins (Kulshreshtha et al., 1972; Mahato et al., 1988, 1992a; Mahato and Nandy, 1991a; Mahato and Sen, 1997; Tan et al., 1999; Connolly and Hill, 2000; Sparg et al., 2004)....

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  • ...All saponins derived from this oleanyl carbocation are classified as oleanane type saponins (Sparg et al., 2004)....

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  • ...…Heng et al., 2006b), foaming and emulsifying properties (Price et al., 1987), pharmacological and medicinal properties (Attele et al., 1999), haemolytic properties (Oda et al., 2000; Sparg et al., 2004), as well as antimicrobial, insecticidal, and molluscicidal activities (Sparg et al., 2004)....

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  • ...Saponins have found wide applications in beverages and confectionery, as well as in cosmetics (Price et al., 1987; Petit et al., 1995; Uematsu et al., 2000) and pharmaceutical products (Sparg et al., 2004)....

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  • ...In a recent review (Sparg et al., 2004), saponins were classified into three classes, namely, the triterpenoid saponins, the spirostanol saponins and the furostanol saponins....

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Journal ArticleDOI
TL;DR: Methods currently used for the quantitative analysis of saponins, sapogenols, and glycoalkaloids are critically considered; advances in the use of newer methods being emphasized.
Abstract: Saponins occur widely in plant species and exhibit a range of biological properties, both beneficial and deleterious. This review, which covers the literature to mid 1986, is concerned with their occurrence in plants and their effects when consumed by animals and man. After a short discussion on the nature, occurrence, and biosynthesis of saponins, during which the distinction between steroidal and triterpenoid saponins is made, the structures of saponins which have been identified in a variety of plants used as human foods, animal feedingstuffs, herbs, and flavorings are described. Many of these compounds have been characterized only during the last 2 decades, and modern techniques of isolation, purification, and structural elucidation are discussed. Particular consideration is given to mild chemical and enzymatic methods of hydrolysis and to recent developments in the application of NMR and soft ionization MS techniques to structural elucidation. Methods currently used for the quantitative analysis of saponins, sapogenols, and glycoalkaloids are critically considered; advances in the use of newer methods being emphasized. The levels of saponins in a variety of foods and food plants are discussed in the context of the methods used and factors affecting these levels, including genetic origin, agronomic, and processing variables, are indicated. Critical consideration is given to the biological effects of saponins in food which are very varied and dependent upon both the amount and chemical structure of the individual compounds. The properties considered include membranolytic effects, toxic and fungitoxic effects, adverse effects on animal growth and performance, and the important hypocholesterolemic effect. A final section deals briefly with the pharmacological effects of saponins from ginseng, since use of this plant is increasing in certain sections of western society as well as being traditional in the Orient.

635 citations


"Saponins, classification and occurr..." refers background in this paper

  • ...Saponins have found wide applications in beverages and confectionery, as well as in cosmetics (Price et al., 1987; Petit et al., 1995; Uematsu et al., 2000) and pharmaceutical products (Sparg et al., 2004)....

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  • ...…range of properties, which include sweetness and bitterness (Grenby, 1991; Kitagawa, 2002; Heng et al., 2006b), foaming and emulsifying properties (Price et al., 1987), pharmacological and medicinal properties (Attele et al., 1999), haemolytic properties (Oda et al., 2000; Sparg et al., 2004), as…...

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Journal ArticleDOI

592 citations


"Saponins, classification and occurr..." refers background in this paper

  • ...Saponins are often subdivided into two main classes, the triterpenoid and the steroid saponins (Abe et al., 1993), which are both derived from the 30 carbon atoms containing precursor oxidosqualene (Haralampidis et al., 2002)....

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  • ...1) (Abe et al., 1993; Haralampidis et al., 2002)....

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  • ...Many different kinds of cyclases (e.g. cycloartenol synthase, lanosterol synthase, b-amyrin synthase) have been described, and their mechanisms of action are well documented (Abe et al., 1993; Wendt et al., 2000; Wendt, 2005; Haralampidis et al., 2002; Thoma et al., 2004)....

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  • ...Saponins are often subdivided into two main classes, the triterpenoid and the steroid saponins (Abe et al., 1993), which are both derived from the 30 carbon atoms containing precursor oxidosqualene (Haralampidis et al....

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  • ...cycloartenol synthase, lanosterol synthase, b-amyrin synthase) have been described, and their mechanisms of action are well documented (Abe et al., 1993; Wendt et al., 2000; Wendt, 2005; Haralampidis et al., 2002; Thoma et al., 2004)....

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Journal ArticleDOI
TL;DR: The triterpenoids are a large group of natural products derived from C(30) precursors and each of these structures is classified and mechanisms for their formation are provided.

500 citations


"Saponins, classification and occurr..." refers background in this paper

  • ...These advancements have stimulated the classification of natural products based on the biosynthesis of their carbon skeletons (Devon and Scott, 1972; Connolly and Hill, 1991; Xu et al., 2004)....

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