Die Strukturen von C‐Fluorocurin, C‐Mavacurin und Pleiocarpamin. 57. Mitteilung über Curare‐Alkaloide

Hesse, Manfred; Philipsborn, W. Von; Schumann, D.; Spiteller, Gerhard; Spiteller‐Friedmann, M.; Taylor, W. I.; Schmid, Hans; Karrer, P.

doi:10.1002/hlca.19640470325

Cited by 114 publications

(53 citation statements)

References 26 publications

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“…The maximum production of alkaloids occurs at low levels of phosphate, nitrate and ammonia in the medium (Schlatmann et (Hesse et al, 1964;Akhgari et al, 2015).…”

Section: Resultsmentioning

confidence: 99%

Gas Chromatography-Mass Spectrometry (GC-MS) Analysis of Indole Alkaloids Isolated from <i>Catharanthus roseus </i> (L.) G. Don Cultivated Conventionally and Derived from In vitro Cultures

Wesołowska

Grzeszczuk

Wilas

et al. 2016

Not Bot Horti Agrobo

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Catharanthus roseus (periwinkle) is a medicinal plant commonly known for its wide biological activity. In many countries different parts of this plant are used for the treatment of diabetes, hypertension and for menstrual regulation. Due to the ability of production of alkaloids, which can be applied in cancer therapy, is still extensively investigated. Two, the most valuable alkaloids (vincristine and vinblastine) are present in C. roseus in very low concentrations. Micropropagation is promising technique used to enhance the level of important secondary metabolites. The main objective of present study was alkaloids extraction from plants cultivated conventionally and derived from in vitro cultures. In this order the aerial parts of periwinkle were extracted with 96% ethanol at room temperature (method I) and heated with 96% ethanol at 55 °C for 90 minutes (method II). The obtained mixtures of different indole alkaloids were analyzed by gas chromatography -mass spectrometry (GC-MS). Analysis revealed the presence of 15 alkaloids, among which vindoline, vindorosine, isovindolinine and ajmalicine were the most abundant. The obtained results indicated that the propagation method had a significant effect on the percentage content of alkaloids in C. roseus herb. Plants derived from in vitro cultures were richer in vindorosine and vindoline, while conventionally cultivated -in tetrahydroalstonine and ajmalicine. Moreover, in case of isovindolinine, vindolinine and ajmalicine, extraction at 55 °C was more effective, while for pericyclivine -maceration at room temperature. Interestingly, the pericyclivine was not detected in the mixture of alkaloids obtained from periwinkle herb by the extraction at 55 °C.

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“…The maximum production of alkaloids occurs at low levels of phosphate, nitrate and ammonia in the medium (Schlatmann et (Hesse et al, 1964;Akhgari et al, 2015).…”

Section: Resultsmentioning

confidence: 99%

Gas Chromatography-Mass Spectrometry (GC-MS) Analysis of Indole Alkaloids Isolated from <i>Catharanthus roseus </i> (L.) G. Don Cultivated Conventionally and Derived from In vitro Cultures

Wesołowska

Grzeszczuk

Wilas

et al. 2016

Not Bot Horti Agrobo

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“…sich aus Villalstonin das kiirzlich aufgekliirte [4] Indolalkaloid Pieiocarpaniin (1) [5]. Diese Resultate weisen darauf hin, dass Villalstonin zur Gruppe der Indolalkaloide gehort.…”

unclassified

“…Villalstonin (2) lasst sich rnit Pyridin/Acetanhydrid nicht acetylieren und zeigt im IR. (CC1,) keine OH-Absorption, (4,.517)~) und 286 (3,96), Minima bei 216 (4,40) und 261 (3,57), Schultern bei 250 (4,OO) und 294 nm (3,93). Dieses Spektrum wurde als Additionsspektrum zweier voneinander unabhiingiger Indolchromophore aufgefasst [2] .…”

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Die Struktur des Alstonia‐Alkaloides Villalstonin Vorläufige Mitteilung

Hesse

Hürzeler

Gemenden

et al. 1965

Helvetica Chimica Acta

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Vorlaufige Mitteilung Das Alkaloid Villalstonin wurde im Jahre 1934 von SHARP aus verschiedenen AIstonia-Arten isoliert [l] , Die bisher am Villalstoiiin crhobenen cheniischeri Befunde [l] [Z] [3] lassen sich wie folgt zusammenfassen : Es handelt sich um ein zweibasisches ((dimeres)) Alkaloid der Summenformel C,,H4,04N4. Die zwei basischen Sticltstoffatome sind tertiar, Als funktionelle Gruppen treten weiter 2 N-Methyl-, einz Carbomethoxy-Gruppe sowie mindestens eine Athyliden-Gruppe auf. Bei der Kaliumhydroxidschmelze resultieren a-Methylindol, Indol-2-carbonsaure und eine Base mit dem UV.-Spektrum des Harmans. Auch bei der Selendehydrierung entsteht eine harmanahnliche Base [ 2 ] . Unter dex Einwirkung von 70-proz. Perchlorsaure bildet Die wichtigstcn Befunde und Experimente, die zur Ableitung der Struktur 2 von VilIalstonin fiihrten, wurden am 16. November 1964 in einem Kolloquium der HOFFMANN-LA ROCHE AG, Basel, am 12. Januar 1965 an der Technischen Universitat Berlin und am 16. Februar 1965 an der Harvard Univcrsity, Cambridgc, Mass., bekanntgcgcbcn. 44 __ 4, In konz. Salzsaure allcin ist 2 weitgehend stabil. 5, Die approximative Zusammensetzung des Gemisches wurde diinnschichtchromatographisch direkt nach dcr Rcaktion geschatzt.

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“…[2] Recently, Kam and coworkers isolated pleiomaltinine [3] 1 (Figure 1), an unusual alkaloid-pyrone natural product that is able to reverse multidrug-resistance in vincristine-resistant KB (VJ300) cells (IC 50 =12 μg/mL in the presence of 0.1 μg/mL of vincristine). They proposed that pleiomaltinine may be derived biosynthetically from the indole-alkaloid pleiocarpamine [4] 2 , co-isolated from the same plant species ( Alstonia angustofolia ), and the 2-methylene-3,4-diketone [5] 3 derived from dehydrogenation of naturally occurring maltol 4 . We were intrigued by intermediate 3 and its potential reactivity in cycloaddition chemistry analogous to the known properties of o- quinone methides.…”

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confidence: 99%