Cardenolid- und Pregnanglykoside

Reichstein, T.

doi:10.1007/bf00592754

Cited by 79 publications

(19 citation statements)

References 231 publications

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“…The stereochemistry of the steroid portion of cardiac glycosides is unusual in that the C/D and usually the A/B ring junctions have the cis-configuration (11). The general chemistry of the cardiac glycosides and the genins has been well documented (24,251, and the chemistry of the sugar residues of natural and semisynthetic glycosides has been reviewed (26,27). For many years, studies on structure-activity relationships of cardiac glycosides have been limited to the determination of relative potency ratios of naturally occurring glycosides or to relatively minor semisynthetic modifications of functional groups common to this class.…”

Section: Properties Of Naturally Occurring Cardiotonic Steroidsmentioning

confidence: 99%

Synthesis and Biological Activity of Semisynthetic Digitalis Analogs

Thomas

Boutagy

Gelbart

1974

Journal of Pharmaceutical Sciences

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Section: Properties Of Naturally Occurring Cardiotonic Steroidsmentioning

confidence: 99%

Synthesis and Biological Activity of Semisynthetic Digitalis Analogs

Thomas

Boutagy

Gelbart

1974

Journal of Pharmaceutical Sciences

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“…None of the compounds included in Fig. 2 is from crucifers, but Reichstein (1967) 2): supplied by Prof. R. Gmelin; the other compounds by Prof. T. Reichstein.…”

Section: Resultsmentioning

confidence: 99%

Host Plant Selection of Monophagous and Oligophagous Flea Beetles Feeding on Crucifers

Nielsen

1978

Entomologia Exp Applicata

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Feeding responses of two oligophagous species, Phyllotreta nemorum and P. undulata, and two monophagous species, P. armoraciae and P. tetrastigma, feeding on horseradish, Armoracia rusticana, and large bittercress, Cardamine amara, respectively, have been evaluated by means of leaf disc tests.All species feed only on plants containing glucosinolates. Extracts made from a number of such species were tested for feeding inhibitory activity. There is good negative correlation between plant acceptability and feeding inhibitory activity of extracts in P. nemorum, but the monophagous species reject some plants which do not contain feeding inhibitors. Cucurbitacins from Iberis species have been identified as feeding inhibitors to P. nemorum and cardiac glycosides from Cheiranthus and Erysimum to P. undulata and P. tetrastigma.Both acceptable and unacceptable plants contain highly stimulatory glucosinolates to P. ar'moraciae and P. nemorum, and the beetles are not able to recognize their host plants solely by their content of glucosinolates. Preliminary results suggest that certain flavonoids from radish and horseradish are feeding stimulants to the two flea beetle species.A number of insect species feed solely on plants containing glucosinolates (mustard oil glucosides) and the compounds are known to stimulate feeding in a number of these insects (Hicks, 1974; Nielsen, 1978; Schoonhoven, 1972). Usually, these insects are able to discriminate between different glucosinolate containing plant species. The present study was undertaken in order to investigate the role played by plant chemicals in this discrimination in four flea beetle species and to identify some of the active compounds. Insects with wide and narrow host plant ranges were included in order to investigate whether they relied on different mechanisms when selecting appropriate host plants.Phyllotreta nemorurn L. and P. undulata Kutsch are common pest species all over Europe, feeding on a number of plants containing glucosinolates (Dobson, 1956; Heikertinger, 1925;Mohr, 1966;Nielsen, 1977). P. tetrastigma (Com.) is described as feeding on crucifers growing in moist places by Mohr (1966) but no plant species are mentioned. Only large bittercress, Cardamine amara, is mentioned as host plant by Hansen (1927) and Heikertinger (1925), and at least in Denmark there is a decided preferencefor this plant even though, occasionally, the beetle may be found on other species (Nielsen, unpubl.). P. armoraciae (Koch) is

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“…Eine Aufklarung gelang bisher nur bei einigen Vertretern der erstgenannten Gruppe. Ferner konnte gezeigt werden, dass es sich bei den Kedde-negativen Glykosiden vorwiegend urn Esterglykoside handelt, wie sie auch in zahlreichen anderen Asclepiadaceen gefunden wurden [8]. -Im folgenden wird die Untersuchung der vier Extrakte einzeln besprochen.…”

unclassified

Inhaltstoffe der Wurzeln von Margaretta rosea Oliv. Glykoside und Aglykone, 323. Mitteilung

Sierp

Stöcklin

Reichstein

1970

Helvetica Chimica Acta

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The roots of Margaretta rosea Oliv., subsp. rosea Bullock contain cardenolides mixed with Kedde negative ester glycosides. 6 Cardenolides were identified by paper chromatography (PC) and thin layer chromatography (TLC). Three of them were free aglycones (uzarigenin (l), corotoxigenin (3) and coroglaucigenin (5)' the other three their corresponding 6-deoxy-p-~-allopyranosides (ascleposide (2), gofruside (4) and frugoside (6). Only two cardenolides (1 and 5) were isolated in crystalline form. The behaviour of the more polar portion of the glycoside mixture shows that D-gluco derivatives of a t least 5 of the 6 cardenolides mentioned were also present.The Kedde negative glycosides were a complicated mixture containing mainly 2,6-dideoxysugars linked to esterified polyhydroxy-pregnanes. After mild acid hydrolysis cymarose, oleandrose

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Cardenolid- und Pregnanglykoside

Cited by 79 publications

References 231 publications

Synthesis and Biological Activity of Semisynthetic Digitalis Analogs

Synthesis and Biological Activity of Semisynthetic Digitalis Analogs

Host Plant Selection of Monophagous and Oligophagous Flea Beetles Feeding on Crucifers

Inhaltstoffe der Wurzeln von Margaretta rosea Oliv. Glykoside und Aglykone, 323. Mitteilung

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