PHYTOCHEMISTRY Phytochemistry 68 (2007) 275–297 www.elsevier.

com/locate/phytochem

Review

Saponins, classification and occurrence in the plant kingdom
Jean-Paul Vincken
a b

a,*

, Lynn Heng a, Aede de Groot b, Harry Gruppen

a

Laboratory of Food Chemistry, Wageningen University, P.O. Box 8129, 6700 EV Wageningen, The Netherlands Laboratory of Organic Chemistry, Wageningen University, P.O. Box 8026, 6700 EG Wageningen, The Netherlands Received 29 November 2005; received in revised form 23 September 2006 Available online 4 December 2006

Abstract Saponins are a structurally diverse class of compounds occurring in many plant species, which are characterized by a skeleton derived of the 30-carbon precursor oxidosqualene to which glycosyl residues are attached. Traditionally, they are subdivided into triterpenoid and steroid glycosides, or into triterpenoid, spirostanol, and furostanol saponins. In this study, the structures of saponins are reviewed and classified based on their carbon skeletons, the formation of which follows the main pathways for the biosynthesis of triterpenes and steroids. In this way, 11 main classes of saponins were distinguished: dammaranes, tirucallanes, lupanes, hopanes, oleananes, taraxasteranes, ursanes, cycloartanes, lanostanes, cucurbitanes, and steroids. The dammaranes, lupanes, hopanes, oleananes, ursanes, and steroids are further divided into 16 subclasses, because their carbon skeletons are subjected to fragmentation, homologation, and degradation reactions. With this systematic classification, the relationship between the type of skeleton and the plant origin was investigated. Up to five main classes of skeletons could exist within one plant order, but the distribution of skeletons in the plant kingdom did not seem to be order- or subclass-specific. The oleanane skeleton was the most common skeleton and is present in most orders of the plant kingdom. For oleanane type saponins, the kind of substituents (e.g. AOH, @O, monosaccharide residues, etc.) and their position of attachment to the skeleton were reviewed. Carbohydrate chains of 1A8 monosaccharide residues can be attached to the oleanane skeleton, most commonly at the C3 and/or C17 atom. The kind and positions of the substituents did not seem to be plant order-specific. Ó 2006 Elsevier Ltd. All rights reserved.
Keywords: Saponin(s); Classification; Biosynthesis; Oxidosqualene; Triterpenoid skeleton(s); Steroids; Substituent(s); Sugar chain(s); Phylogenetic tree

Contents 1. 2. Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Classification of saponins . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2.1. Cyclization of the saponin skeletons from oxidosqualene . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2.2. Eleven skeletons form the basis for classification of saponin structures . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2.3. Distribution of saponin skeletons in the plant kingdom . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Decoration of oleanane type saponins . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3.1. Type of functional groups . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3.2. Bridging . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3.3. Unsaturation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3.4. Saccharide chains . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Concluding remarks . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Acknowledgements . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . References. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Further reading . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 276 276 276 279 279 283 283 285 285 285 286 287 287 291

3.

4.

*

Corresponding author. Tel.: +31 317 482888; fax: +31 317 484893. E-mail address: jean-paul.vincken@wur.nl (J.-P. Vincken).

0031-9422/$ - see front matter Ó 2006 Elsevier Ltd. All rights reserved. doi:10.1016/j.phytochem.2006.10.008

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J.-P. Vincken et al. / Phytochemistry 68 (2007) 275–297

1. Introduction Saponins are generally known as non-volatile, surfaceactive compounds that are widely distributed in nature, occurring primarily in the plant kingdom (Lasztity et al., 1998; Oleszek, 2002; Hostettmann and Marston, 2005). The name ‘saponin’ is derived from the Latin word sapo, which means ‘soap’, because saponin molecules form soap-like foams when shaken with water. They are structurally diverse molecules that are chemically referred to as triterpene and steroid glycosides. They consist of nonpolar aglycones coupled with one or more monosaccharide moieties (Oleszek, 2002). This combination of polar and non-polar structural elements in their molecules explains their soap-like behaviour in aqueous solutions. Saponins have a diverse 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 well as antimicrobial, insecticidal, and molluscicidal activities (Sparg et al., 2004). 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). Although in former times it may have been acceptable to classify compounds based on their physicochemical or biological properties, nowadays it is no longer customary and sensible in natural product chemistry. The structural diversity of compounds showing soap-like properties in aqueous solutions is enormous. Therefore, when the term ‘‘saponin’’ should continue to reflect some value in natural product classification, it should be defined more precisely. This has become possible nowadays because the knowledge on chemical structures of natural products (such as saponins) and their biosynthesic pathways has grown tremendously. 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). Further classification may be based on subsequent biosynthetic transformations of these main carbon skeletons, such as minor rearrangements, typical oxidation, homologation, or degradation patterns, leading to rearranged, seco, homo, or nor compounds. Several reviews have been published 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). These reviews give a dense overview of saponins with all their structural details, yet provide little information about classification based on their chemical structures. 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). The difference between the two classes lies in the fact that the steroid saponins have three methyl groups removed (i.e. they are molecules with 27 C-atoms), whereas in the triterpenoid saponins all 30 C-atoms are retained. From a biosynthetic point of view, this differentiation is of limited use because particularly the triterpenoid saponins represent many different carbon skeletons. Moreover, the biosynthetic transformations within the two groups are neglected and under-estimated. 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. However, such a classification emphasizes incidental structural elements due to secondary biotransformations and does not reflect the main biosynthetic pathways. There are some other classes of compounds that have been considered as saponins, such as the glycosteroidalkaloids (Haralampidis et al., 2002). Although these compounds have the same biosynthetic ancestor as saponins, and contain a steroid type skeleton glycosidically linked to monosaccharide moieties, they will not be considered as saponins in this review. Glycosteroidalkaloids contain a nitrogen atom as an intrinsic and characteristic part of their aglycone structure, which already classifies them as a separate group. The aim of this review is to propose a classification of saponins based on the biosynthesis of the carbon skeletons of the aglycones. Subdivisions of the main classes are based on further modification of the carbon skeletons by minor rearrangement, homologation, cleavage, and degradation. Functionalization of carbon skeletons is predominantly the result of oxidation, resulting in functional groups like hydroxyl groups, carbonyl groups and carboxylic acids, which can be found at many positions in the molecules. These functional groups are often involved in mutual chemical reactions, which may lead to additional characteristic structural elements, such as ether bridges, spiroketals or lactones. Subdivisions based on these structural elements will not be undertaken in this review, as they are the results of secondary type biotransformations. When saponins are classified based on the biosynthesis of the carbon skeletons, it may be expected that similar types of saponins are found in similar plant orders. This expectation is based on the assumption that similar plant orders contain similar types of enzymes, and that these enzymes can probably catalyse similar biotransformations, ultimately leading to similar chemical structures (Vierhuis et al., 2001; Umezawa, 2003). Therefore, attempts were made to link the various carbon skeletons and their substitution patterns to plant orders. 2. Classification of saponins 2.1. Cyclization of the saponin skeletons from oxidosqualene Saponin biosynthesis proceeds via the isoprenoid pathway in which 3 isoprene units (molecules containing 5 C-

1997.. Vincken et al. 1997. Amimoto et al. It has been shown that. All hopane type saponins described in plants (see above) contain a hydroxyl group at the C3 atom. 1). A shift of the C16AC17 bond leads to the tetracyclic C17 baccharenyl carbocation and can be followed by a reaction with the C24AC25 double bond to produce the pentaAglycone structures of saponins were obtained from year 1987 up to and including 2005 from www.. A proton-initiated cyclization of the ‘chair–chair–chair’ conformation results in the tetracyclic dammarenyl C20 carbocation... Hamed and El-Emary. Many different kinds of cyclases (e. Zhao et al. / Phytochemistry 68 (2007) 275–297 277 atoms) are first linked in a head-to-tail manner to each other. A series of hydride and methyl shifts in the dammarenyl carbocation leads to the tirucallenyl C8 carbocation. respectively. Haralampidis et al. 2002). respectively (Haralampidis et al. Sahpaz et al. All saponins derived from this carbocation are classified as hopane type saponins (Hamed et al. An important difference between the two resulting skeletons lies in the stereochemistry. Biswas et al. Woldemichael and Wink. We have found no information in the literature. The 5-membered ring next to the C20 dammarenyl carbocation can expand either by a shift of the C16AC17 bond. Sun and Chen. 1992. Two farnesyl pyrophosphates are subsequently linked in a tail-to-tail manner to give a compound of 30 carbon atoms. and then via a series of hydride shifts to the C13 oleanyl carbocation.. 2003). All saponins derived from this carbocation are classified as lupane type saponins (Pambou Tchivounda et al.. which is the common starting point for cyclization reactions in triterpenoid biosynthesis (Fig. or by a shift of the C13AC17 bond. 2002). 1997. 2005).. 2000. . the carbocations are neutralized by proton elimination to give a double bond or a cyclopropanyl ring.-P. cycloartenol synthase. Sanoko et al.. which can be deprotonated to yield taraxasterane type saponins (Yahara et al. 2004). Thoma et al. This carbocation can undergo further shifts of a methyl group and a hydride to the C5 cucurbitanyl carbocation. Ma et al. 1996. 1993.g. In Fig. which undergoes a series of hydride and methyl shifts ultimately leading to the intermediate C9 lanosteryl carbocation. 1 cyclic C25 lupenyl carbocation. Kennelly et al. All saponins derived from this carbocation are classified as cucurbitane type saponins (Oobayashi et al. Sahu et al. 1990. 1998. 2000. 2003). Haralampidis et al. Finally. Squalene is oxidized to oxidosqualene. 2001. whether hopanes in plants are formed from oxidosqualene (as is indicated in Fig. Voutquenne et al. Meselhy and Aboutabl. and all saponins derived from this carbocation are classified as dammarane type saponins (Ryu et al. using ‘‘saponin’’ and ‘‘structure’’ as key words. lanosterol synthase.. either via the ‘chair–chair–chair’ or via the ‘chair– boat–chair’ conformation. Zhao et al... Oxidosqualene is converted to cyclic derivatives via protonation and epoxide ring opening.. and all saponins derived from this carbocation are classified as tirucallane type saponins (Teng et al. Meselhy. 1). After cyclization of the ‘chair–chair–chair’ conformation. Wendt et al. which lead to the formation of new carbocations. The ursane skeleton is also called the a-amyrin skeleton. 2005. 1996. and their mechanisms of action are well documented (Abe et al. 1993. 2002.. 1999. 1998. the methyl group at the C8 atom is pointing upwards and the one at the C14 atom is pointing downwards... Wandji et al. Elgamal et al. first to the C18 germanicenyl carbocation. 2002). Treyvaud et al.. which creates a carbocation that can undergo several types of cyclization reactions.. 2003. 1992). Yook et al. 1993. 2004). 1.. From the proton-initiated cyclization of the ‘chair– boat–chair’ conformation of oxidosqualene. 1997. 1998. 1997.. ultimately produces the C13 carbocation. hopanes are cyclized from squalene by squalene-hopene cyclase (reviewed by Wendt (2005)). 2002). 1991. 1996. All saponins derived from this oleanyl carbocation are classified as oleanane type saponins (Sparg et al. the main cyclization and rearrangement reactions are shown that lead to the triterpenoid and steroid skeletons that have been found to occur in the saponins in our literature search. which can be cyclized by a reaction with the double bond in the side chain to form the C25 pentacyclic hopenyl carbocation. in bacteria. or by reaction with water to give a hydroxyl group. All saponins derived from cycloartenol are classified as cycloartane type saponins (Choi et al. and this skeleton is also referred to as the b-amyrin skeleton (Haralampidis et al. Cyclization of oxidosqualene to saponins can proceed in two ways. 1) or from squalene. 1) (Abe et al. 2001. After these cyclizations. 2000. b-amyrin synthase) have been described. A methyl shift in the germanicenyl carbocation... 1999.. The lanosteryl carbocation may also undergo deprotonation of the C19 methyl group leading to formation of a cyclopropane ring as is found in cycloartenol.1 The type of cyclase that is involved in the cyclization reaction primarily determines the skeleton that is formed (Fig. A shift of the a methyl group in the germanicenyl carbocation produces the C20 taraxasterenyl carbocation.com.... Wendt. Chakravarty et al.. a-amyrin synthase and b-amyrin synthase. 1997.. 1989.sciencedirect. 2003.. Oleanane type saponins have been isolated from a wide array of plants (Osbourn. called squalene (Holstein and Hohl. The lupenyl carbocation can be rearranged further. A shift of the C13AC17 bond in the C20 dammarenyl carbocation leads to a C17 carbocation. which can be deprotonated to ursane type saponins (Babady-Bila et al. 2000).. whereas the opposite is the case after cyclization of the ‘chair–boat–chair’ conformation (see the dammarenyl and protosteryl carbocations.. 2001)... 2004).. 2002). 1999. Cheng et al. Xiang et al. Xu et al. Verotta et al. which is most clearly shown by the configurations of the C8 and the C14 atoms. followed by several hydride shifts. a tetracyclic protosteryl C20 carbocation is obtained. resulting in the 15 C-atom molecule farnesyl pyrophosphate. 2004).. 1992. Radwan et al. 2002. subsequent rearrangements can proceed in different ways by a series of hydride shifts and/or methyl migrations.J. The a-amyrin and b-amyrin skeletons are the cyclization products of distinct cyclases... in Fig.. Xu and Xu.

Vincken et al. .278 J. / Phytochemistry 68 (2007) 275–297 Fig. The cyclization of oxidosqualene to the various saponin skeletons.-P. 1.

the MagnoliInternational union of pure and applied chemistry home page.. as soon as sufficient examples of such new skeletons have been found in nature. leading to cholesterol. 1983..2.uk/iupac/. Mimaki et al. 1974. the 27-nor (5d) (He et al. Besides the carbon skeleton. following the biosynthesis of their carbon skeleton.. the phylogenetic tree presented in Fig. leading to different types of triterpenoid skeletons. These modifications include mostly oxidation and glycosylation reactions. cycloartanes. 1998.. Lanosterol can also undergo demethylation and isomerisation of the double bond. 3 covers only from the kingdom to the subclass. oleananes. 1996. ACHO. Of the 11 main saponin skeletons mentioned in this review. but have not been characterized as saponins. Zheng et al. Pollmann et al. 1998). which are indicated as separate subclasses as shown in Fig. which cover the main saponin skeletons that have been found in our literature search. 1998. 1997a. indicates that the cyclization is catalysed by different cyclases (cycloartenol and lanosterol synthase... and steroids. rearrangement and degradation reactions... Miyase et al.. the 28-nor (5e) (Ueckert et al. 1997b. 2005).. New skeletons can be introduced easily in this system.. cucurbitanes. 2002. 2005). 2001. The side chain at the five membered ring in the hopane skeleton can be rearranged to the rearranged hopanes (4a) (Sahu et al.. ACH2OH.qmul. 2 . and the 15. 2001) or be degraded to the bis-nor hopanes (4b) (Sahu et al. 2003. Moreover. The steroid skeleton (11) can be homologated to the 24-bis-homo skeleton (11a) (Pires et al. or minor rearrangement to related skeletons. subclass. this does not interfere with the main principle of classification of saponins based on the biosynthesis of the carbon skeleton of their aglycones. Zheng et al. After cyclization.itis. 1998. ACOOH. 1991a). There are. 2. the number and position of double bonds. 1995.16-seco-skeleton (1b) (Seaforth et al. / Phytochemistry 68 (2007) 275–297 279 Deprotonation of the lanosteryl carbocation gives lanosterol and all saponins derived from lanosterol are classified as lanostane type saponins (Pires et al. 2005a). 2003)... 1997).. 2002). http:// www.. tirucallanes. 3 The website http://www. several other biosynthetic pathways known for triterpenoids.. Konishi et al.. division. Vincken et al. All these secondary modifications lead to skeletons. AOH. 2. taraxasteranes. 1998. rearrangement and degradation. and or glycosyl residues). it can be seen that saponins are present in two major classes within the plant kingdom. The skeletons in Fig. The oleanane skeleton (5) can be fragmented to the 17.. 2004).usda. Furthermore. lanostanes. 2001). however. The dammarane skeleton (1) can undergo further processing to give the 3. 2. which has been indicated as a 22-homo pregnane skeleton. 2004). The diversity of saponin aglycones can be seen from several reviews (Agarwal and Rastogi. 1. 1992. 1996a.4-seco-skeleton (1a) (Kennelly et al. 2000).22-seco skeleton (5a) (Lavaud et al. Mahato et al. Taketa et al.4-seco-skeleton (3a) (Shirasuna et al. and to the skeleton (11c) (Mimaki et al. Ikuta et al. hopanes. the aglycones differ in their number and/or type of substituents attached (e. 1994).3 From Fig. or cleaved to the 18. sub-kingdom.. Achenbach et al. lupanes. degradation to nor or bis-nor compounds. order. family. class.19-seco skeleton (7b) (Li et al... 1998. Eleven skeletons form the basis for classification of saponin structures The 11 carbon skeletons shown in Fig... @O. several have been found to undergo ring cleavage (leading to seco-skeletons).. 1988. which have not been included in our overview as the glycosylated form of this compound has not been described in the literature to our knowledge. Park et al. Degradation of the oleanane skeleton leads to the 23-nor (5c) (Jia et al. homo.. An example is the friedelanes (Corsino et al.. Although we may have overlooked some of these glycosylated triterpenoids and steroids. Oulad-Ali et al. several other triterpene skeletons may occur in nature as glycosides. which belongs to the pregnane type steroids. 1996.chem. Plants can be classified based on their physical characteristics and are hierarchically divided into kingdom.. As the numbers of plant species that have been identified so far are numerous. represent the end products of cyclization. Junkuszew et al.. Fig. and spirocompounds..J. the steroid skeleton can be degraded in the sidechain to the nor-skeleton (11b) (Saijo et al. Dong et al. ¨ 2002)... ursanes. ACH3. 2. dammaranes. Ahmad et al. Very little is known about the enzymes and the biological pathways mediating these modifications (Haralampidis et al.ac. in Tables 1–4 only class to order is indicated. The saponins derived from this skeleton are classified as steroid type saponins (Yahara et al. 1991. homologation (leading to homo or bis-homo skeletons). ultimately yielding the saponins that are found in nature. additional modifications of the different carbon skeletons follow. 1989. lactones.g. 1992). 1997. to a cyclopropane ring or a double bond.-P. 3. it is of interest to investigate the possible relationship between the plant origin (taxonomy) and the type of saponin. genus and species.. The ursane skeleton can be rearranged to the 20epi skeleton (7a) (Ouyang et al. and nor compounds the numbering of the main skeleton is maintained. or rearranged to a ring A nor-ring B homo skeleton (5b) (Kanchanapoom et al. The difference in deprotonation.. Corea et al. 3 shows the phylogenetic tree of the various plants from which saponins have been isolated. 2002). 2 are numbered according to the IUPAC2 rules. in the seco.. Mamedova et al. 1995). or the 30-nor skeletons (5f) (Ikuta and Itokawa. Zheng and Yang. Mahato and Nandy. The lupane skeleton (3) can be cleaved to give the 3. Cheng et al. respectively). 1998). 2002)..3. 2000). Distribution of saponin skeletons in the plant kingdom With the isolated aglycones summarised into basic skeletons in Fig.gov/ for taxonomy was used to assign the various plant species described in the literature to the different plant orders..

.280 J. and their various derivatives.-P. 2. Structures of the 11 main classes of carbon skeletons of saponins after cyclization. Vincken et al. / Phytochemistry 68 (2007) 275–297 Fig.

/ Phytochemistry 68 (2007) 275–297 281 Fig. It can be seen that oleanane (5) is the most common skeleton occurring in almost all orders. Rhamnales and Zingiberales. Behind the citations. except Solanales. whereas Liliopsida is the class of monocotyledons. namely. The absence of oleanane skeletons in these four orders Table 1 Distribution of the various carbon skeletons of saponins in the plant kingdom Plant Subclass Ordera 18 1 5 1 6 11 6 4 23 9 1 8 1 4 1 1 11 26 7 42 3 2 3 5 1 23 2 46 2 No. plant order. The number of plant species from which saponins have been isolated is indicated for each order.11b.4a.e.11c 11 2 a All references used for each plant order can be found in the reference list. Magnoliophyta. and the division. i. opsida and the Liliopsida.5b. [Apiales – Cussonia racemosa]. is indicated between brackets behind the citation.4b 5.11b 1 3 1 1 1a 11 7 7. Within the class of Liliopsida.1b 7 7 9 8 11. Both classes belong to the sub-kingdom.3a 3 1. there are six sub-classes. or in the section further reading.5f 4. Magnoliopsida is the class of dicotyledons. Each sub-class contains 1 or more orders. Hamamelidae. comprising 46 different species for which the presence of saponins has been documented.5e 5 5 5 5 5.5d. the Commelinidae.5f 5 5 5 5 5 5 5.5a. which are the flowering plants or the angiosperms. Liliales has the most.5f 5. there are three sub-classes. . Vincken et al. of species Skeletons Dam Tir Lup Hop Ole 5. Dilleniidae. followed by the Fabales.J. to which the plant species described in that publication belongs. Asteridae. Within the class of Magnoliopsida.5c. Liliidae and Zingiberidae. 7a 8 9 11 1 3. the plant order. In the reference list and the section Further reading.5f 5 5 Tar 6 Urs 7 7 7b 7 7 7 7 11 7 10 Ccl Lan Cuc Ste Class of Magnoliopsida Asteridae Asterales Campanulales Dipsacales Gentianales Lamiales Rubiales Scrophulariales Solanales Caryophyllidae Caryophyllales Dilleniidae Ebenales Lecythidales Primulales Theales Violales Hamamelidae Juglandales Magnoliidae Nymphaeales Ranunculales Rosidae Apiales Celastrales Fabales Myrtales Polygalales Rhamnales Rosales Santalales Sapindales Class of Liliopsida Commelinidae Cyperales Liliidae Liliales Zingiberidae Zingiberales 3 6 8 11. Asteridae and Rosidae consist of 8 and 9 orders.11b 11. Phylogenetic tree showing the plant subclasses from which saponins have been isolated and characterised. namely. which are all vascular plants. Caryophyllidae.5f 5. 3. The distribution of the various saponin skeletons in the different plant orders is presented in Table 1.11a 11. Trache- obionta.5f 5 5 5 5 5 5 5. For instance. having 42 species that contain saponins.-P. genus and species are indicated. Magnoliidae and Rosidae. Juglandales. respectively.

/ Phytochemistry 68 (2007) 275–297 H.OH. CH2OH.OH* OH* H. CH2OH CH3.OH CH3 CH3 CH3 C10 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 H.OH CH3 CH3 CH3 CH3 CH3 OH* OH* H.OH OH H.OH Celastrales Fabales H. @O OH OH C4a CH3.–O–  H. CHO. CH2OH. CHO –O– CH3 CH3 H. CHO CH3 OH* Shaded columns indicate the carbon positions containing the methyl groups that were originally present in oxidosqualene.OH CH3 CH3 CH3.OH H. COOH COOH CH2OH*.OH H. CH2OH. CH2OH*.OH CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 Rosidae H. COOH CH2OH. e.OH CH3 CH3 CH3. COOH CH3. but they are included because they can be oxidised. CH2OH H. COOH H.OH H. CH2OH.OH OH OH OH OH OH CH3 CH3 CH3 CH3 CH3 CH3 CH2OH CH3 CH3 CH3.OH* H.OH OH C3 OH OH OH OH OH OH OH OH OH. COOH CH3. COOH CH3 CH3 CH3 CH3: COOH* CH3.OH H. CH2OH CH3 CH3 CH3 CH3 OH OH CH3 COOH CH3. COOH CH3. COOH CH3 CH3.OH* H. CH2OH.OHà C22 Class of Magnoliopsida Asteridae Asterales Campanulales Dipsacales Gentianales Lamiales Rubiales Scrophulariales Caryophyllidae Dilleniidae Caryophyllales Ebenales Lecythidales Primulales H. CHO.OH OH H.COOH* CH2OH.-P.OH* H. CH2OH*.OH C17 COOHà COOH COOH CH2OH. Indicates that other substituents might be attached. CH2OH. COOH COOH CH2OH.OH* H.OH H. COOH* H. @O H.OH* COOH COOH CH2OH*. CHO CH3.OH H. CH2OH CH3. by an ester linkage. OCH3 H.OH H. CHO. CH2OH. CH2OH CH3.OH H. CH2OH H.OH H. COOH* CH3. @O. OH H. COOH CH3. COOH* CH3 CH3 CH3. COOH* CH3 CH3 CH3.OH* H.OH OH OH CH3 CH3 CH3 CH3: CH2OH.OH H. CH2OH CH3. COOH CH3. Indicates an epoxide at the respective carbon atoms. In principle.OH H.OH H. . COOH* CH2OH CH3.–O– H.COOH * C19 C20 CH3 CH3 CH3 CH3 CH3 C21 H. CH2OH CH3. CH2OH.OH* H.OH* OH H. CH2OH CH3 CH3.OH H.OH H.OH* Class of Liliopsida Commelinidae Cyperales Liliidae Liliales a *   OH OH OH CH3. CH2OH*.OH C11 C12 C13 C14 CH3 CH3 CH3 CH3 CH3 CH3. COOH CH3 CH3 CH3 CH3 CH3 C15 C16 H. CH2OH.OH.OH* H. COOH CH2OH.OH CH3. CHO CH2OH COOH* COOH* CH3. CHO.OH C6 C8 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 H. these are not substituents.OH H. CHO.OH J.g.OH H.OH Magnoliidae Theales Violales Nymphaeales Ranunculales Apiales OH OH OH OH OH CH3. COOH CH3. @O OH OH* H.OH* H. CH2OH CH3. COOH* COOH H.CH2OH. CHO CH3 CH3 CH3 CH3 CH3 CH3 CH3 OH CH3 CH3. CH2OH.OH OH OH*. COOH CH3.OH H. COOH* H. Vincken et al. @O Myrtales Polygalales Rosales Santalales Sapindales H.OH* H. COOH* CH3 CH3. COOH H. CH2OH.OH H.OH* H. COOH CH3.OH*.OH H.CH2OH.282 Table 2 Substituents attached to carbon atoms of the oleanane skeleton (5) in different plants Plant Subclass Order Substituents attached to C2 H.

all belonging to Caryophyllales.1. (3). Occasionally. / Phytochemistry 68 (2007) 275–297 Table 3 Saccharide chains attached to oleanane (skeleton (5)) saponins in different plant orders Plant Subclass Class of Magnoliopsida Asteridae Order Asterales Campanulales Dipsacales Gentianales Lamiales Rubiales Scrophulariales Caryophyllales Ebenales Lecythidales Primulales Theales Violales Nymphaeales Ranunculales Apiales Celastrales Fabales Myrtales Polygalales Rosales Santalales Sapindales Cyperales Liliales is is is is is is is is attached attached attached attached attached attached attached attached Number of glycosyl residues per chain attached to C3a 1–3 2–3 1–8 1–3 1–5 1–3 1–4 1–4 1–4 3 3–5 2 1–3 1 1–4 1–4 1–3 1–6 1 1 2–4 1–3 1–4 3 1–2 C4b C16c C17d 1–6 2–4 1–2 1–2 3–5 1–4 2 1–4 1–6 1 C20e C21f 283 C22g 1 1 1 1 Caryophyllidae Dilleniidae 1 Magnoliidae Rosidae 1 2 1 1 1–7 1–4 1–2 1–8 1 3–5 1–6 1 1–5 1–2 1–2* 1–2 1 Class of Liliopsida Commelinidae Liliidae a b c d e f g * 4–6 Saccharide Saccharide Saccharide Saccharide Saccharide Saccharide Saccharide Saccharide chain chain chain chain chain chain chain chain by an acetal linkage to the hydroxyl at C3 of the skeleton. by an acetal linkage to the hydroxyl at C16 of the skeleton. a summary of the various substituents and their positions is presented in Table 2 for the different plant orders. leaves.J. Mollugo spergula.e. Decoration of oleanane type saponins 3. and (7). i. (5c). seco or nor) usually occur together with their precursor in one order. the oleananes seem to be unique in Campanulales. We have not observed that specific saponin skeletons are associated with particular parts of a plant. by an acetal linkage to the hydroxyl at C21 of the skeleton.e. Vincken et al. Lecythidales. stems. eight in total. The order of Fabales shows the largest diversity in saponin main skeletons (Table 1). . It can be noticed that processed skeletons (e.-P. (5). (8). which are apparently not processed further. seeds and fruits. saponins of the same skeleton can be obtained from various plant parts. which include the roots. Within the class of Magnoliopsida. Gentianales. Theales. by an acetal linkage to the hydroxyl at C22 of the skeleton. five in total. and (11). The tirucallanes and cucurbitanes seem orderspecific. (4a). to the oleanane skeleton via monoterpenoid unit. by an ester linkage to a carboxyl group (C28) linked to the C17 of the skeleton. (5). Polygalales and Santalales. the occurrence of which has been reported by different research groups in four different species (Glinus lotoides. it can be concluded that the distribution of saponin skeletons does not seem to be plant subclass-specific. Saponins have been isolated from different parts of the plants. may indicate that these orders have not been analysed for it. (3). bark. 3. but with on only one report each such a conclusion would be premature. (4b). One exception might be the hopanes. (5f). although it should be noted that many of these orders contain only one plant species that was analyzed. (4). as it is the most common skeleton found in the plant kingdom.g. by an ester linkage to a carboxyl group (C23 or C24) linked to the C4 of the skeleton. Type of functional groups As the biosynthesis of saponins involves the introduction of various functional groups at different positions of the skeletons. (9). Polycarpon succulentum). i. Nymphaeales. and does not necessarily mean that they are not present. Myrtales. the whole plant was used. by an acetal linkage to the CH2OH group (C29 or C30) at C20 of the skeleton. The order of Caryophyllales has most different skeletons when processed skeletons are included. From the data in Table 1. This table shows only the substituents present in saponins having the oleanane skeleton (5).

. 2006a). 2006a).. Hu et al. 1995). Linkage type and anomeric configuration are not taken into account. Possibly. ribose. 1983.. / Phytochemistry 68 (2007) 275–297 Table 4 Sugars present in the saccharide chains of oleanane (skeleton (5)) saponins in different plant orders Plant Subclass Order Constituent monosaccharidesa. Ara. The hydroxyl group at carbon atoms C21 and C22 can contain various uncommon groups. Rha. N-acetyl glucosamine.. Heng et al. This type of saponin was found to be unstable at various conditions (Okubo and Yoshiki. C12AOAC13 (Osbourn. 2005. C11AOAC12 (Gromova et al. DDMP substituted oleananes have been the focus of several studies. Heng et al.5-dihydroxy-6-methyl-4H-pyran-4-one) (Massiot et al. respectively. Gal.g. rhamnose. 4. Okubo and Yoshiki. Qui. glucuronic acid. C17. The OH group is distributed throughout many carbon atoms and plant orders. 1996. The methyl group at the C10 atom is only functionalized in the Fabales (Periandra dulcis (Hashimoto et al. Decroos et al.. Hu et al. The methyl groups are often functionalized... 2002. 2003). except that saponins from the class of Liliopsida have less substituents. quinovose (deoxyglucose). Occasionally. DDMP is most commonly found in saponins isolated from legumes such as peas (Daveby et al. such as those from Ranunculales. glucose... Berhow et al. Being the native saponin in soy and peas (Daveby et al. and C20 show the largest diversity in substituents attached to the oleanane skeleton. CHO and COOH groups. 1980. Rib.. and to prolonged exposure to aqueous conditions (Heng et al. e. and xylose. GlcA. Hu et al.3-dihydro2. Heng et al. 1993)). Fuc. 1998.. whereas those at C4. which is illustrated in Fig. 2002. 1996. The methyl group attached at the C14 atom is moderately processed. This is reflected by the presence of CH2OH. From this table. 2006a.b Api X X Ara X X X X X X X X X X X X X X X X X X X X X X Fuc X Gal X Glc X X X X X X X X X X X X X X X X X X X X X X X GlcA X GlcNAc Qui Rha X X X X X X X X X X Rib Xyl X X X X X X X X* X X X X X X X X X X X X X X X X X X X Class of Magnoliopsida Asteridae Asterales Campanulales Dipsacales Gentianales Lamiales Rubiales Scrophulariales Caryophyllidae Caryophyllales Dilleniidae Ebenales Lecythidales Primulales Theales Violales Magnoliidae Nymphaeales Ranunculales Rosidae Apiales Celastrales Fabales Myrtales Polygalales Rosales Santalales Sapindales Class of Liliopsida Commelinidae Liliidae a X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X   X X X X X X X X Cyperales Liliales X X X X b *   Api. 2006a. It might be expected that substituents attached by the same or similar bonds . 1998..284 J. 2005. No particular trend between the type of substituents at different carbon positions and the type of plants can be seen. 2002.b). it can be seen that carbon atoms C4.. epoxides are encountered as substituents in oleanane type saponins. In rare cases Xyl can be oxidized. the substituent DDMP (2. 2006a). In rare cases unsaturated. GlcNAc. 1996.. 2002) and lupin seeds (Ruiz et al. as the acetal bond that links the DDMP group to the saponin aglycone at the C22 position is sensitive to both acidic and basic conditions. which indicates a lower degree of oxidation compared to the saponins from the Magnoliopsida. and Xyl represent apiose. fucose.. 1998) and Cyperales. but the one attached at the C8 atom is not processed in any of the plant orders. 1982. C17. Suttisri et al..b). epoxidases mediate the addition of oxygen to the double bond in the skel- eton.. Heng et al. soybeans (Decroos et al. Substituents at the C22 atom can be liable to chemical reactions. and C20 are heavily processed and oxidized to different degrees. in a similar way as squalene epoxidase converts squalene to oxidosqualene. galactose. Glc. arabinose.-P. Vincken et al..

J. 1996. Interestingly. 2-methyl butanoyl (Lu et al. single unsaturation should be present at position C12AC13 (Larhsini et al. 3. Single or double unsaturation can exist at different positions of a skeleton. It was also noticed that some oleanane type saponins did not have any double bonds (Germonprez et al.... 2000). but it is always engaged in an oxygen bridge with C17 (indicated by underlining in Table 2).. / Phytochemistry 68 (2007) 275–297 285 Fig. Melek et al. Gromova et al. 2005) substituents.. The hydroxyl group at the C13 atom never occurs in a free form. and that a reaction with water under formation of a hydroxyl group may also occur.... such as C17AC(@O)AOAC21 (Garai and Mahato. 2004. Sakai et al. 1996..4. Liang et al.. 1997. 2004. which is formed by C13AOH and C17ACOOH (Ikuta and Morikawa. The oxidized methyl group at the C17 atom can also form bridges with other oxidized carbon atoms of the oleanane skeleton.. (acetal or ester linkages) are vulnerable during extraction and/or analytical procedures. or C18AC19 (Matsuda ´ et al. The various positions of unsaturation probably reflect that the cyclases can differ in their ability of facilitating hydride shifts. 2005. Bridging Certain substituents (Table 2) attached to the oleanane skeleton (5) may react with each other. 2004). DDMP (Kudou et al..... cinnamoyl (Germonprez et al. Saccharide chains Saponins belonging to the same skeletal group can have a huge variation in the number and type of monosaccharide . Huang et al. Trojanowska et al. which is formed from a C13AOH and a C17ACH2OH or a C17ACHO.. C20 and C21. Wandji et al. 2000). 2000). The most common bridging is a C13AOACH2AC17 ether linkage (Pistelli et al.. Ester bridges also occur. 1997. 2003. 2004. In the oleanane skeleton (5). X represents both positions 21 and 22 of the oleanane skeleton. Unsaturation Unsaturation (double bonds) usually results from deprotonation of the carbocation that is formed after cyclization of the skeleton (Fig.. 2000.. tigloyl (Yoshikawa et al.3. 1998). N-methyl anthranilic acid (Germonprez et al. 2004).... The fact that two double bonds can occur in oleanane type saponins indicates that additional desaturation reactions occur downstream of the cyclization process. Sanchez-Contreras et al. Huang et al. 2005). Sanchez-Contreras et al. Lu et al..2. hexenoyl (Yoshikawa et al. 1999).. 2000).. More complex groups that contain glycosyl units linked to the C21 position of the oleanane skeleton (5) via a monoterpenoid moiety have also been reported (Zou et al. Waffo-Teguo et al. 1992. Pistelli et al. Voutquenne et al. leading to the formation of oxygen bridges..-P. 2000). Double unsaturations were found at position C9AC11 and C12AC13 (Marx Young et al.. bridging seems to occur mainly in saponins from the class of Magnoliopsida. 2000). Ebata et al.. 2003). the double bond can also be found at position C11AC12 (always in conjunction with bridging between C13 and C17.. 2002). 1992. and C17ACH2AOAC(@O)AC20 (Yayli et al. Structures of substituents at the hydroxyl group of the C21 and C22 atoms of the oleanane skeleton (5). The groups include benzoyl (Trojanowska et al. 21 and 22 indicate the position of the oleanane skeleton at which the substituent is attached. 1993). Klimek et al. which may lead to underestimation of their abundance in plant extracts. 1996. 2003.. 4... Yamamoto ´ et al. 2000). and less frequently in those from the class of Liliopsida. 2000). Vincken et al. 1993.. such as C13AOAC(@O)AC17.. ´ Ebata et al. or an acetal-linked bridge C13AOACH(OH)AC17 (Germonprez et al. 2000).. 1993.. This suggests that the carbocation can also be neutralised in a way other than proton elimination. 1997. Huang et al. 3. The substituents that can be involved in bridge formation are usually those between the hydroxymethylene group at the C17 atom and hydroxyl groups at C13. 2000.. Marx Young et al. which is consistent with the observation that the saponins from the latter have a lower degree of oxidation.. Melek et al.. 1998). 3. 2000). resulting from deprotonation of the oleananyl carbocation. 2002. as well as ´ C11AC12 and C13AC18 (Yamamoto et al.. angeloyl (Germonprez et al. 1996. although proton initiated isomerisation of a double bond may also take place. 2004. However. 2003. respectively. Woldemichael et al. 1).. Sanchez-Contreras et al. 1997). and monoterpenoid (Zou et al.

2005) or C22 atom ß (Mohamed et al... Nigam et al... 4. Alves de Carvalho et al. an alfalfa (Oleszek et al.. 1997. little evidence to support this hypothesis was found. Matsuda et al. Sapindales (Lavaud et al.. 2005). 2000).. 1994b. 1993. The plant orders of Dipsacales and Fabales show the largest diversity in chain length. C20. at C3. Mori et al.. 1995. Woldemichael and Wink.. the point of attachment to the skeleton and the number of glycosyl residues per chain of the various saccharide chains attached to oleanane skeleton (5). there is little variation in the type of monosaccharide residues.. It was observed that saponin biosynthesis does not seem to be plant order specific. 2002)... ¨ 1993. 1992).. 2003. Kuroda et al. Mussaenda pubescens (Zhao et al. Sapindales (Jayasinghe et al..g. 1994). The number and type of saccharide chains can vary enormously. 1995b. Caryophyllales (Li et al. ¨ 1997. saponins from Zygophyllum species (Sapindales. Mbafor et al.. at different positions. 1998.. Ribose is only present in the Ranunculales (Wang et al. 2002) do not have a sugar chain attached at C3. Saponins that contain a monosaccharide chain at one carbon position of the skeleton. Quinovose. Apiales (Ebata et al. 1995). 1992).. such as apiose. 1997) has only one monosaccharide residue at the C22 atom. 1994). Fabales (Oleszek et al. 1997a). It has previously been reported (Haralampidis et al. fucose. Erythrina sigmoidea (Mbafor et al. 2000a.. Zou et al.. Kuroda et al. quinovose and ribose.... 1996b). Lamiales (Burger et al. This may be true for most saponins. 2001.. 2005)... Apiose is present in the Asterales (Su et al. 1992) and an Acacia auriculiformis saponin (Mahato et al. but not for all. Rosales (Guo and Kenne. Rosales (Guo et al. Ebenales (Li et al.. Ebenales (Wandji et al... Table 3 summarises. 1996. Voutquenne et al. Solubility might be enhanced by the presence of charged groups in the saccharide chains... Exceptions to this are... whereas fucose is present in Asterales (Shao et al. 2005. Zou et al. 1996b). C16.286 J. such as the Rubiales (Zhao et al.. 2003). rhamnose. 2000. Charrouf et al. occurring in all plant orders except the Theales. 1998). from 1 to 8 monosaccharide residues. 1992) and Sapindales (Voutquenne et al. and glucuronic acid residues.. 2000). Fabales (Oleszek et al.. 1993a). Sanchez-Contreras et al.. 1998. for each plant order. 1992. for instance. 1990). because e. 1994)... 2000). However. Nicolas et al. Moreover.... seems more order specific than apiose and fucose.. The sugar chains consisting of three monosaccharide residues are the most diverse. Most of the saponins are monodesmosides or bidesmosides. xylose and glucuronic acid (Table 4). 2002) that all saponins have a sugar chain attached to the C3 atom of their aglycones as a common feature.. 1997)... 2000. The Fabales contain the largest number of possible glycosylation sites. The saccharide chains in the oleanane type saponins (5) commonly contain glucose. and Myrtales (Table 3). 2001). Schopke et al. can have a longer saccharide chain at another position (Schopke et al. 2005). and these are short chains of 1 or 2 residues only. Woldemichael and Wink. Apiose and fucose are distributed in many plant orders. which means that they contain either 1 or 2 saccharide chains. 1997). C21 and C22. Woldemichael et al. Scrophulariales (Klimek et al.g. 2002). 2001).. ¨ 1996. 1999) occurs only in the Fabales. the saponins from Acanthopanax spinosus (Miyakoshi et al. 1992b). 1998) and Acanthopanax japonicus (Park et al. and is present only in the Fabales and Sapindales (Beutler et al. M’Bark et al. Polygalales (Zhang et al. / Phytochemistry 68 (2007) 275–297 residues attached. not only with respect to the biosynthe- .. 2005). 1993). Vaccaria segetalis (Yun et al... e. Caryophyllales (Schroder et al. Sang et al. there are 16 different disaccharide chains and 22 different trisaccharide chains present in the Fabales alone (without accounting for different linkage types and branching).. There are a few cases in which sacharide chains are attached at the C4... 1992b. Nyberg et al. 2001.. C4. such as sulphated glycosyl units (as in the three-residue chain of ´ Bupleurum rigidum saponins. Zou et al. Mbafor et al. as e. 1995.. 1995a). Fabales (Beutler et al. which are tridesmoside saponins. Yui et al. saponins from Erythrina sigmoidea (Fabales. Elgamal et al. Lamiales (Yamamoto et al. Glycosylation at the C16 atom is only observed in the Lamiales (Yamamoto et al. Oligosaccharyl chains are usually attached at the C3 and/or the C17 (via C28) atom(s) and they have a length of 1–8 residues. C20. 1996). Rubiales (Gariboldi et al. The class of Liliopsida seems to be less diverse than that of Magnoliopsida with respect to glycosylation patterns. Pollmann et al. 1997).. Burger et al. Concluding remarks By considering the biosynthetic origin of the various saponins and simplifying the structures of their aglycones through the consideration of only their carbon skeletons. However. Glycosylation at the C21 atom occurs in the Fabales (Mahato et al. Rubiales (He et al. we have been able to classify the various saponins that have been described in the literature into 11 main classes. 2003) and Liliales (Asada et al.. Glycosylation at the C4 atom can be present in several plant orders.g... 1998) and Liliales (Asada et al. 1992) and Sapindales (Sakurai et al.. 2002.. Pereira da Silva et al.... but also in the Lecythidales (Massiot et al. 1997. Nymphaeales. 1997. 1999) have only one monosaccharide residue at C3 and/or C17. C17. Simonet et al. Campanulales (He et al. Guo et al. Glycosylation at the C20 (Yes ilada et al. Vincken et al. A few less common monosaccharide residues are also found. on the other hand. 1996.. 2000). It might be hypothesized that a short saccharide chain (one or two glycosyl residues) requires the presence of an additional longer one to make the saponin water-soluble.. respectively. 1995b.. ¨ 1997) and Lafoensia glyptocarpa (Myrtales.. our review of structures does not substantiate a relationship between short saccharide chains and the presence of charged groups.. 2002).-P. C21 and C22 atoms.. 1994a. Nyberg et al. arabinose. 1992...

Nakajima. M. T.. 1999.. 219–228 [Primulales – Maesa balansae]. A.S.D.H. four novel sweet-tasting triterpene glycosides from the leaves of Abrus precatorius.. Gruppen.. L. Two triterpene saponins from Arenaria filicaulis. J. Charrouf. Ahmad. Connolly. 1992.. B. Lanzotti. Phytochemistry 55.. C..M. The 11 main skeletons of saponins identified in this review may serve as a stepping-stone for further classification of new saponins that will be isolated in the future. Steroidal saponins from Asparagus dumosus.. Burger.. Prod. Oliveira.C. Corea. 189–193 [Caryophyllales – Arenaria filicaulis]. Gromova. S.. H. Terpenes.S. Academic Press.. Multiple constituents and multiple actions.. 2000. 1509–1517 [Fabales – Archidendron ellipticum]. B. R. Mahato. Wu. Food Agric. Vincken. Triterpenoids.A. Phytochemistry 66..B.. Li. Sarkar. M.. H. A. A. Tetrahedron 60. Phytochemistry 41.. P. K. Grenby...da S..V.. Effect of storage and extraction on ratio of soyasaponin I to 2. 1998.R. Sec. References Abe.A. 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He did his Ph. His research interests concentrated on total syntheses of natural products. pheromones).J. especially sesqui. In 1972. Vincken et al. he joined food industry as product development manager starch derivatives. and he was a post-doctoral fellow with Prof.D. Next. In 2000. After his retirement he focused his attention on anabolic steroids. in organic chemistry in 1967 under the supervision of Prof. / Phytochemistry 68 (2007) 275–297 Professor Aede de Groot received his MSc in organic chemistry and technical chemistry in 1964 from the University of Groningen in The Netherlands. which are abundantly available from Nature. repellants. In his present position he is in charge of protein research within the chair of food chemistry. he was appointed as full professor in bio-organic chemistry at Wageningen University. and after that he was an assistant professor at the Technical University of Eindhoven. . E. He has retired from this position in 2004.D.-P. van Tamelen where he got his first training in synthesis of natural products. he did his Ph. flavour and fragrance and pharmaceuticals (steroids).D. he was appointed as assistant professor at the Laboratory of Food Chemistry of Wageningen University. and on syntheses starting from terpenes. 297 Professor Harry Gruppen (1960) received his MSc in food technology in 1985 from Wageningen University in The Netherlands. Hans Wijnberg. Dr. From 1969 to 1971 he gained industrial experience at the Dutch State Mines (DSM) on electro-organic synthesis. Dr.and diterpenes with physiologically active properties in the field of crop protection (anti-feedants.E. protein-interactions with other non-volatile food constituents and controlled enzymatic hydrolysis of proteins in relation to techno-functionality and bio-functionality of food proteins and peptides. Subsequently. After his Ph. in Food Chemistry (cereal cell wall carbohydrates. His key area of research and teaching is in plant proteins (especially legumes and tuber proteins). 1992) at Wageningen University. he was appointed as associate professor and since 2005 he holds a personal chair in food chemistry. also in Groningen.