ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTAntioxidative and antihemolytic activities of soybean isoflavonesMichael Naim, Benjamin Gestetner, Aron Bondi, and Yehudith BirkCite this: J. Agric. Food Chem. 1976, 24, 6, 1174–1177Publication Date (Print):November 1, 1976Publication History Published online1 May 2002Published inissue 1 November 1976https://doi.org/10.1021/jf60208a029RIGHTS & PERMISSIONSArticle Views415Altmetric-Citations167LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (510 KB) Get e-Alerts Get e-Alerts

AbstractThe influence of alfalfa saponins on growth and on lipid metabolism was studied in mice and quails. The extent of growth inhibition was related to the level of medicagenic acid in the saponin preparation used. Both species differed considerably in their sensitivity to alfalfa saponins, mice being more susceptible than qualis. Female mice overcame the growth impairing effect after a shorter period of adaptation than male mice. After ingestion of saponin both sexes showed an increase of faecal lipids and faecal cholesterol. Consequently concentrations of lipids and cholesterol in the livers of mice were depressed. In response to the lower uptake by the liver a higher rate of incorporation of labelled acetate into lipids and cholesterol of this organ was found. In quails these parameters of lipid metabolism were not influenced by alfalfa saponins, except for an increased rate of cholesterol biosynthesis in the liver.

The prelytic events associated with the interaction of saponins with Physarum polycephalum membrane components were studied. It was found that alfalfa saponins form interaction products with membranal sterols, proteins and phospholipids. The interaction of saponins with proteins affect also certain membranal enzymic activities such as NADH oxidase and Malate dehydrogenase. It is suggested that although the interaction of the saponin with sterols is much more specific than with other membranal components, the lysis of plasmodia of P. polycephalum should be attributed to a concerted attack on the various membrane constituents. In continuation of these interactions, the changes of permeability of plasmodia membrane were expressed by increment of inorganic sodium ions and water influx, traced by lysis, while no efflux of ions was observed.

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTSoybean isoflavones. Characterization, determination, and antifungal activityMichael. Naim, Benjamin. Gestetner, Shmuel. Zilkah, Yehudith. Birk, and Aron. BondiCite this: J. Agric. Food Chem. 1974, 22, 5, 806–810Publication Date (Print):May 1, 1974Publication History Published online1 May 2002Published inissue 1 May 1974https://doi.org/10.1021/jf60195a031RIGHTS & PERMISSIONSArticle Views842Altmetric-Citations160LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (598 KB) Get e-Alerts Get e-Alerts

Chloroplasts isolated from sweetclover leaves contain an enzyme which converts trans-[3-14C]cinnamic acid to 2-hydroxy-trans-[3-14C]cinnamic (o-coumaric) acid. The identity of the product has been verified by recrystallization with unlabeled o-coumaric acid to constant specific activity, and by gas-liquid cochromatography of unlabeled o-coumaric acid and the radioactive product.

A new isoflavone was isolated from soya beans and shown to be 7,4′-dihydroxy, 6-methoxyisoflavone, for which the name glycitein is proposed.

The interactions of saponins with erythrocyte membrane components involved in the hemolytic mechanism were studied. It was found that the alfalfa saponin, medicagenic acid 3-β-O-triglucoside, forms interaction products of different stability with membrane cholesterol, proteins and phospholipids. The resulting structural changes affect only slightly the membranous enzyme activities examined. It is suggested that breakdown of the structure of the membrane stems from a combination of non-specific interactions of saponins with membrane proteins phospholipids and cholesterol leading consequently to hemolysis.

Synthetische Glycoside der Medicagensäure wirken fungistatisch und hämolytisch im gleichen Ausmass wie das natürliche Luzerne-Saponin und unbeeinflusst von der Natur des Zuckers in den Glycosiden. Der hämolytische Index der Medicagensäure ist geringer, die fungistatische Wirkung derselben aber etwas höher als diejenige der Glycoside, was mit der geringeren Wasserlöslichkeit der Medicagensäure erklärt werden kann.

AbstractA sapogenin isolated from the acid hydrolysates of roots or tops of alfalfa (Medicago sativa) has properties and constants identical to those of hederagenin. The corresponding saponin was isolated from a mixture of alfalfa saponins by successive chromatography on Al2 O3 and DEAE‐Sephadex columns. Upon acid hydrolysis it yields glucose, arabinose and hederagenin, similarly to the saponin isolated from Hedera helix.

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTAlfalfa saponins. VIII. Titrimetric method for determination of medicagenic acid in alfalfa (Medicago sativa)Yehuda Tencer, Shraga Shany, Benjamin Gestetner, Yehudith Birk, and Aron BondiCite this: J. Agric. Food Chem. 1972, 20, 6, 1149–1151Publication Date (Print):November 1, 1972Publication History Published online1 May 2002Published inissue 1 November 1972https://doi.org/10.1021/jf60184a005RIGHTS & PERMISSIONSArticle Views50Altmetric-Citations7LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (367 KB) Get e-Alertsclose Get e-Alerts

The structural features of sterols, which enable them to interact with lucerne saponins, were studied. It was found that an intact steroid ring structure having the conformation of cholestanol, to which a side chain characteristic to cholesterol or phytosterols is attached, is essential for the formation of a sterol-saponin addition product. Unlike the complex formed between digitonin and cholesterol, these addition products are extremely unstable and their formation is not dependent on the presence of a 3-β-hydroxyl group. In addition products formed with cholesterol or 7-dehydrocholesterol an approximately 1:5 molar ratio exists between saponin and sterol, whereas in the case of other sterols this ratio is approximately 1:8. Although lucerne saponins readily form addition products with a variety of sterols, a preferential affinity to cholesterol and 7-dehydrocholesterol was found when the addition product was formed while cholesterol and one of the other sterols were present simultaneously in the reaction mixture. These preferential affinities were demonstrated also by bioassays conducted with the fungus Sclerotium rolfsii Sacc.

The carbohydrate moiety of a highly toxic lucerne saponin was found to be a trisaccharide, which has been characterized as O -β- d -glucopyranosyl (1 → 6)-β- d -glucopyranosyl (1 → 3) β- d -glucopyranose by enzymatic hydrolysis, full and partial acid hydrolysis and gas chromatographic analysis of the methanolysis products of the methylated saponin. The results of enzymatic degradation of the saponin indicate a glycosidic bond between the carbohydrate moiety and the aglycone; analogy to other saponins and theoretical considerations point toward an attachment at C 3 of the aglycone.

AbstractBy precipitation with animal or plant sterols (cholesterol or β‐sitosterol), saponins extracts from lucerne tops (SEt) or roots (SEr) were separated into two main groups of saponins. The aglycone moiety of the group precipitated by sterol is composed of medicagenic acid and an unidentified lucerne sapogenin, whereas the non‐precipitable saponins contain a variety of soyasapogenols as their aglycones. No qualitative difference could be observed in the composition of the sugar moiety of the two groups of saponins. It was found that only the sterol‐precipitable saponins are able to lyse red blood cells and arrest the growth of the fungus Sclerotium rolfsii Sacc. Though the origin of the sterol has no influence on the composition and biological properties of the saponins precipitated by them, the antifungal activity of lucerne saponins could be counteracted only by the addition of cholesterol, but not of β‐sitosterol to the culture medium.Lucerne saponins precipitated by sterol were separated by thin‐layer chromatography into three fractions. Antifungal and haemolytic activities are concentrated mainly in the fractions having high Rf values. The absence of these fractions from SEt accounts for the lower degree of biological activity exhibited by SEt as compared with that of SEr. The antifungal activity of the various sapogenins is found to be concentrated mainly in medicagenic acid and to a lesser extent in the unidentified sapogenin. Blocking the functional groups of medicagenic acid greatly diminished its antifungal activity.

Die aus Wurzeln von Luzerne isolierten Saponine wirken stärker hämolytisch als diejenigen in den grünen Teilen dieser Pflanze. Die hämolytisch wirksameren Saponine sind reicher an Medicagensäure und es wird angenommen, dass diese für die hämolytische Wirkung der Saponine verantwortlich ist. Die Anwesenheit von 2 Carboxylgruppen in der Medicagensäure scheint für ihre hämolytische Wirkung von ausschlaggebender Bedeutung zu sein, da der Dimethylester dieser Säure nicht mehr hämolytisch wirkt.

AbstractThe role of sapogenins in the antibiological effects exerted by lucerne saponins has been studied. Data are presented, showing that lucerne sapogenins are more toxic towards Tribolium castaneum larvae than their respective saponins, from which they are isolated. Medicagenic acid and to a lesser extent a new, hitherto unidentified sapogenin are the main growth‐depressing factors, the soyasapogenols being almost harmless in this respect. When cholesterol is also included in the diet, the negative influence of the sapogenins is completely abolished. The counteraction found with cholesterol, as well as with various plant sterols, of the growth inhibition of the larvae caused by dietary saponin extracts (SE) was studied quantitatively with different SE: sterol ratios. It is shown that the amount of cholesterol needed to counteract fully the growth impairment depends on the toxicity of the SE preparation and its concentration in the diet. The counteracting property of plant sterols on larval growth depression leads to the conclusion that a built‐in defence mechanism exists in lucerne against the antibiological effects of saponins.

AbstractLucerne saponin extracts have been prepared from lucerne tops and roots by two different methods. The root extracts possess stronger haemolytic activity and to a certain extent are stronger foaming agents than those from the tops. Thin‐layer chromatographic (t.l.c.) analyses showed that acid hydrolysates of the different preparations contain soyasapogenols A, B, C, D, E, medicagenic acid and an unidentified sapogenin‐like spot. When submitted to t.l.c. and paper electrophoresis the first pair of extracts have been separated into six fractions each, and the other extracts into seven fractions each. The root extract and to a lesser extent that from the tops, depress growth of Tribolium castaneum larvae but the inhibitory effect can be reversed when cholesterol is incorporated in the diet. Germination of cotton seeds is inhibited in soils on which lucerne has been grown or on soils supplemented with lucerne meal from tops and roots.