Die Glykoside der Rhizome von <i>Apocynum cannabinum</i> L. 3. Mitteilung. Glykoside und Aglykone, 208. Mitteilung

Gołab, T; Trabert, C. H.; Jäger, Herb.; Reichstein, T.

doi:10.1002/hlca.19590420713

Cited by 27 publications

(4 citation statements)

References 29 publications

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“…Cryptic instars (I–II) appeared to lack effective secondary defences beyond attempting to escape, while the first response of brightly coloured instars (III–V) was regurgitation – a known secondary defence and mechanism of attaining unprofitability among caterpillars (Bowers 1993). Hemp and spreading dogbanes produce several bitter, emetic and toxic cardenolides (Golab et al . 1959; Lee, Rosazza & Carew 1972; Malcolm 1992; Abe & Yamauchi 1994), which may bequeath mature Saucrobotys caterpillars their objectionable status as prey items.…”

Section: Discussionmentioning

confidence: 99%

Ontogenetic colour change and the evolution of aposematism: a case study in panic moth caterpillars

Grant

2007

Journal of Animal Ecology

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Summary 1.Aposematism is a widely used antipredator strategy in which an organism possesses both warning coloration and unprofitable characters. Theoretical evidence suggests that aposematic colour should develop when high opportunity costs imposed by crypsis force an organism to engage in conspicuous behaviours. Hence, it is expected that ontogenetic colour change (OCC) in larval insects should include aposematism when foraging needs compel behavioural modifications that preclude a continued state of crypsis. 2. To test this idea, I first investigated whether OCC in caterpillars of the panic moth Saucrobotys futilalis was indicative of a switch from cryptic to aposematic coloration. I then examined the context of panic moth OCC as it related to foraging patterns and behavioural conspicuousness. 3. Early Saucrobotys instars are a cryptic green, but later instars become progressively more orange and develop black spots. Early instar larvae forage cryptically on the inner parenchyma of silked-together host plant leaves to avoid predation, but are rapidly forced to engage in conspicuous foraging behaviours as they outgrow the resources afforded by their shelters. Both coloration and behaviour reach maximal conspicuousness in final instar larvae. 4. As predicted, OCC encompassed a change from crypsis to aposematism in Saucrobotys . Aposematic function was demonstrated by changes in both antipredator behaviour patterns and effectiveness of predator deterrence in early and late instars. Moreover, increased opportunity costs of crypsis and behavioural conspicuousness coincided with the onset of aposematic coloration. 5. This pattern of OCC suggests that aposematic coloration in Saucrobotys develops as a response to constraints imposed by crypsis. Moreover, my study illustrates the importance of the study of ontogenetic patterns in determining how behaviour, morphology, and predator responses interact to influence the initial evolution of phenomena such as aposematism.

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Section: Discussionmentioning

confidence: 99%

Ontogenetic colour change and the evolution of aposematism: a case study in panic moth caterpillars

Grant

2007

Journal of Animal Ecology

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“…5 Some of biologically important cardiotonic steroids, such as antiaroside B (which showed a strongly positive inotropic effect with a large safety index) 6 and cannogenol-3-O-α-L-rhamnoside (which exhibited potent anticancer activity) 7b share as a common aglycone (+)-cannogenol (1). 8 Additionally, (+)-1 itself exhibited potent cytotoxicity against human cancer cell lines. 9 Hence, a wide variety of synthetic approaches have been developed in pursuit of cardiotonic steroids.…”

Section: ■ Introductionmentioning

confidence: 99%

“… For instance, uscharin strongly inhibited the Notch signaling pathway, which could be important for the treatment of neurodegenerative diseases, and a triazole-bearing derivative of ouabain was found to be a highly selective inhibitor of the α4-isoform of Na + /K + -ATPase and therefore may be suitable as a novel male contraceptive . Some of biologically important cardiotonic steroids, such as antiaroside B (which showed a strongly positive inotropic effect with a large safety index) and cannogenol-3- O -α- l -rhamnoside (which exhibited potent anticancer activity) share as a common aglycone (+)-cannogenol ( 1 ) . Additionally, (+)- 1 itself exhibited potent cytotoxicity against human cancer cell lines .…”

Section: Introductionmentioning

confidence: 99%

Total Synthesis of the Cardiotonic Steroid (+)-Cannogenol

2021

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The total synthesis of (+)-cannogenol, an aglycon common to various biologically important cardiotonic glycosides, has been achieved. Synthesis of the versatile intermediate involves Mizoroki−Heck and intramolecular Diels−Alder reactions from the enantiomerically pure CDring segment, newly prepared in a multidecagram scale this time. Total synthesis by the site-selective transformations of the versatile intermediate demonstrated the applicability of our synthetic approach.

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“…[17] beim Adonitoxigenin durchgefuhrt worden. Sie hat spater, besonders in derAusfuhrungsform nach KATZ [18] (Methanol als Losungsmittel), auch bei anderen 5/?-Cardenoliden teilweise sehr gute Ausbeuten geliefert, SO beim Cannogenin [19], Sarmentosid [ZO], Antiosigenin [21] und Convallosid [22]. Urn jedoch bei Alloglaucotoxigenin eine Verseifung oder die Bildung eines cyclischen Halbacetals zu vermeiden, haben wir hier von der Verwendung von HC1 in Methanol abgesehen.…”

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Alloglaucotoxigenin, Strukturbestimmung Glykoside und Aglykone, 280. Mitteilung

Brandt

Stöcklin

Reichstein

1966

Helvetica Chimica Acta

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Glykoside und Aglykone, 280. MitteiIungZ) von R. Brandt, W. Stocklin und T. Reichstein (16. V. 66) Friihere Befunde. Aus den Samen von Coronilla glauca L. (Fabaceae = Leguminosae-Papilionatae) isolierten STOLL et al. [2] nach Fermentierung ein Furocumarin (= Psoralen) [3] und vier krist. Cardenolide : Alloglaucotoxigenin, Corotoxigenin (11), Coroglaucigenin (111) und Glaucorigenin . Corotoxigenin und Coroglaucigenin wurden seither, teilweise in Form von Glykosiden, auch in verschiedenen anderen Pflanzen aufgefunden [4 bis 121 3), und ihre Struktur ist entsprechend den Formeln I1 und I11 aufgeklart [5] [S]. Glaucorigenin kommt nur in geringen Mengen in den Samen vor, und unseres Wissens ist uber seine Struktur nichts weiteres bekannt. Alloglaucotoxigenin stellt ein Hauptgenin dieser Samen dar und wurde bisher nur in C o r o d l a glauca nachgewiesen [a]. Wir berichten hier uber die Isolierung4) und Struktur dieses Stoffes, die im Einverstandnis mit Herrn Dr. J. RENZ, einem seiner Entdecker, durchgefuhrt wurde. Alloglaucotoxigenin besitzt danach die Formel I V eines 15P-Hydroxycorotoxigenins, was sich aus folgenden Resultaten ergibt. STOLL et al. [Z] haben fur Alloglaucotoxigenin die hypothetische Formel I vorgeschlagen, wobei die Konfiguration am Ring A offen gelassen wurde. Sie berichteten uber folgende Befunde : Die Bruttoformel C23H3206 war durch Analysen gut gesichert. Der Stoff lieferte ein krist. Di-0-acetyl-Derivat C2,HS6O8, aus dem sich mit Hydroxylamin ein krist. Oxim C2,H3,0,N und mit CrO, eine krist. Saure C27H3609 bereiten liessen, wodurch die Anwesenheit einer Aldehydgruppe bewiesen war. Bei der Eehandlung mit HCI-Methanol entstand ein krist. Methyl-cyclohalbacetal C,4H3,06. Ganz gleich verhielt sich Corotoxigenin (11). Diese Reaktion ist, wie wir heute wissen, besonders fur 19-Aldehyde von 3/l-Hydroxy-5ct-steroiden charakteristisch. Die Anwesenheit eines Butenolidringes war auf Grund der positiven LEGL-Reaktion

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Die Glykoside der Rhizome von Apocynum cannabinum L. 3. Mitteilung. Glykoside und Aglykone, 208. Mitteilung

Cited by 27 publications

References 29 publications

Ontogenetic colour change and the evolution of aposematism: a case study in panic moth caterpillars

Ontogenetic colour change and the evolution of aposematism: a case study in panic moth caterpillars

Total Synthesis of the Cardiotonic Steroid (+)-Cannogenol

Alloglaucotoxigenin, Strukturbestimmung Glykoside und Aglykone, 280. Mitteilung

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