Effect of ester groups on the haemolytic action of sapogenins—II

Segal, Ruth; Milo-Goldzweig, Ilana; Schupper, H.; Zaitschek, D.V.

doi:10.1016/0006-2952(70)90276-5

Cited by 18 publications

(11 citation statements)

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Section: )mentioning

confidence: 99%

“…Unfortunately, no comparative structure-activity relationship have been performed on both the free acid and the methyl ester saponins to establish if the same factors systematically influence hemolytic activity. 8,16) We thus wished to synthesize the natural saponin 3hederagenin (isomaltosyl-hederagenin) 6 (Chart 1), and their corresponding methyl esters (1a, 2a, 3a, 4a, 5a, 6a). Compound 1 has been isolated from Fatsia japonica 17) and from the leaves of Barbarea vulgaris and possesses feeding deterrent activity against the larvae of the insect Plutella xylostella.…”

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confidence: 99%

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Synthesis and Hemolytic Activity of Some Hederagenin Diglycosides

Chwalek

Plé

Voutquenne-Nazabadioko

2004

Chem. Pharm. Bull.

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Saponins are steroid or triterpenoid glycosides which are widespread in terrestrial and marine plants and possess various biological and pharmacological activities. 1) One of the first known activities of saponins is their ability to lyse erythrocytes.1) This hemolytic activity has long been studied and the origin of the phenomenon is generally ascribed to their amphiphilic properties, but the exact mechanism is not yet known especially when considering the structural diversity of saponins. It has been shown that saponins are capable of interacting with membrane cholesterol 2-4) forming pits and holes which produce a destabilisation of the membrane by a micellar type-arrangement. 5) Some authors have postulated that the last step consists of an enzymatic deglycosylation that releases the aglycon and produces cell lysis.6,7) Aglycons can show weak hemolytic activity but are not solely responsible for cell destruction. While the aglycon is very important in considering structure-activity relationships, the contribution of the sugar moiety is also significant. 8) Hemolytic activity depends on the nature, number and sequence of the sugars in the saponin.Our laboratory has long been interested in saponin isolation and identification, and, more recently, in their hemolytic structure-activity relationships. The study of hemolytic activity is a way of gaining insight into how saponins react at the membrane surface. We have compared many saponins with various triterpenoid aglycons and, as Schlösser and Wulff,8) have established that a polar substitution in ring A and weak polar substitution in rings D and E increases hemolytic activity and that monodesmosidic triterpenoid saponins are generally more active than bidesmosidic ones. 9)Structure-activity relationships of some synthetic saponins of oleanolic acid, 10-12) methyl oleanolate 13) and of other triterpenoid or steroid aglycons 14,15) have been previously established. It is thus known that the effect of the sugar residue on hemolytic activity is not transferable from one aglycon to one another. We wished to complete our study by analyzing the influence of the sugar units on hemolytic activity using hederagenin as the exclusive aglycon. Hederagenin saponins are largely represented in nature and possess many biological activities such as hemolytic, antiviral, antimicrobial, fongicidal, molluscicidal, or cytotoxic.1) With aglycons such as hederagenin, possessing a carboxylic group in position 28, it is known that hemolytic activity is greater when the free acid is esterified as a methyl ester. Unfortunately, no comparative structure-activity relationship have been performed on both the free acid and the methyl ester saponins to establish if the same factors systematically influence hemolytic activity. 8,16) We thus wished to synthesize the natural saponin 3hederagenin (isomaltosyl-hederagenin) 6 (Chart 1), and their corresponding methyl esters (1a, 2a, 3a, 4a, 5a, 6a). Compound 1 has been isolated from Fatsia japonica 17) and from the leaves of Barbarea vulgaris and ...

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Section: )mentioning

confidence: 99%

mentioning

confidence: 99%

Synthesis and Hemolytic Activity of Some Hederagenin Diglycosides

Chwalek

Plé

Voutquenne-Nazabadioko

2004

Chem. Pharm. Bull.

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“…Sapogenins containing 16α-OH or 16-keto in connection with 3β-OH exhibit very high hemolytic activity. They asserted that the presence of 3β-OH is essential for hemolytic activity, which is in contradiction to statements of Segal et al [104]. The type of saponins and number (monodesmosidic, bidesmosidic) of sugar chains also affect the hemolytic activity.…”

Section: Hemolytic Activity Of Saponinsmentioning

confidence: 78%

“…High hemolytic activity was observed in the case of ester groups in the aglycone part because saponifaction leads to the abolishing of the hemolytic activity, while esterification of carboxyl groups seems to enhance the hemolytic activity. In further studies, Segal et al [104] modified different steroid sapogenins (hecogenin-a, kryptogenin-a) and a triterpene sapogenin (glycyrrhetinic acid) to investigate the influence of ester groups on hemolytic activity. A comparison was made between esterified sapogenins containing additional polar groups and sapogenins containing ester groups.…”

Section: Quil A: a Promising Adjuvant In Vaccinesmentioning

confidence: 99%

Saponin Interactions with Model Membrane Systems – Langmuir Monolayer Studies, Hemolysis and Formation of ISCOMs

Groot

Müller‐Goymann

2016

Planta Med

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Saponins are surface-active glycosides from different plants and marine organisms [1] and are subdivided into triterpenoid and steroid glycosides based on the nature of their aglycone (or sapogenin) [2,3]. The aglycone of triterpene saponins consists of a C 30 skeleton, whereas the steroid aglycone consists of a C 27 skeleton subdivided into spirostane and furostane types. The difference between both types of steroid agly- Abstract !Saponins are used in medicine due to their pharmacological and immunological effects. To better understand interactions of saponins with model membranes and natural membranes of, for example, erythrocytes, Langmuir film balance experiments are well established. For most saponins, a strong interaction with cholesterol was demonstrated in dependence of both the aglycone part and the sugar moieties and is suggested to be correlated with a strong hemolytic activity, high toxicity, and high surface activity, as was demonstrated for the steroid saponin digitonin. In general, changes in the sugar chain or in substituents of the aglycone result in a modification of the saponin properties. A promising saponin with regard to fairly low hemolytic activity and high adjuvant effect is α-tomatine, which still shows a high affinity for cholesterol. An interaction with cholesterol and lipids has also been proven for the Quillaja saponin from the bark of Quillaja saponaria Molina. This triterpene saponin was approved in marketed vaccines as an adjuvant due to the formation of immunostimulating complexes. Immunostimulating complexes consist of a Quillaja saponin, cholesterol, phospholipids, and a corresponding antigen. Recently, another saponin from Quillaja brasiliensis was successfully tested in immunostimulating complexes, too. Based on the results of interaction studies, the formation of drug delivery systems such as immunostimulating complexes or similar self-assembled colloids is postulated for a variety of saponins.

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“…Saponins interact with biomembrane, disturb the fluidity of membranes leading to holes. Saponins reduce proteins digestibility by forming saponins-proteins complexes (Segal et al 2003). Hence, it is suggested that genotypes (LL-1122, LL-1203, LL-1209, LL-1231, LL-1255, LL-1312) having lower saponin content should be commercialized from nutritional point of view.…”

Section: Distribution Of Saponins In Lentil Genotypesmentioning

confidence: 99%

Biochemical mapping of lentil (Lens culinaris Medik) genotypes for quality traits

et al. 2015

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Six genotypes and thirty-eight advance breeding lines of lentil (Lens culinaris Medik.) were evaluated for carbohydrate composition, soluble proteins, mineral content and antinutritional traits such as phenolic compounds, tannins, trypsin inhibitors, saponins and phytic acid. The average content of total sugars, starch and proteins was found to be 47.18, 421.2, 236.24 mg/g, respectively. Lentil genotypes contained higher content of iron, followed by zinc and the least content of copper.

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Effect of ester groups on the haemolytic action of sapogenins—II

Cited by 18 publications

References 4 publications

Synthesis and Hemolytic Activity of Some Hederagenin Diglycosides

Synthesis and Hemolytic Activity of Some Hederagenin Diglycosides

Saponin Interactions with Model Membrane Systems – Langmuir Monolayer Studies, Hemolysis and Formation of ISCOMs

Biochemical mapping of lentil (Lens culinaris Medik) genotypes for quality traits

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