The structure elucidation of Rhazinilam, a new class of Alkaloids from the apocynaceae, by X-ray analysis

Abraham, Donald J.; Rosenstein, R. D.; Lyon, Robert L.; Fong, Harry H. S.

doi:10.1016/s0040-4039(01)84471-3

Cited by 88 publications

(33 citation statements)

References 1 publication

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“…Crude rhazinilam (1.45 g) was obtained by chromatography (Silica gel Merk 7734, in hexane/ethyl acetate lil). Pure rhazinilam (0.8 g) obtained after recrystallisation in ethyl ether was identified [Abraham and Rosenstein, 1972;Ratcliffe et al, 1973;Thoison et a]. , 19871 by UV, IR spectra, optical rotation, X-ray structure, NMR (proton NMR, I3C NMR and twodimensional NMR ['H/'H and 'H/"C] with a Brucker WB-400) and mass spectrometric analyses (molecular ion peak at 294 mass units and a peak corresponding to M-CH,CH, at 265 mass units; electron impact AEI MS-50).…”

Section: Materials and Methods Chemicalsmentioning

confidence: 99%

Rhazinilam mimics the cellular effects of taxol by different mechanisms of action

David

Sévenet

Morgat

et al. 1994

Cell Motil. Cytoskeleton

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We have investigated the effects of the microtubule poison rhazinilam on microtubule assembly in vivo and in vitro. In mammalian cells, rhazinilam mimics the effects of taxol and leads to microtubule bundles, multiple asters, and microtubule cold stability. In vitro, rhazinilam protected preassembled microtubules from cold-induced disassembly, but not from calcium ion-induced disassembly. Moreover, both at 0 degrees C and at 37 degrees C, rhazinilam induced the formation of anomalous tubulin assemblies (spirals). This process was prevented by maytansine and vinblastine, but not by colchicine. Preferential saturable and stoichiometric binding of radioactive rhazinilam to tubulin in spirals was observed with a dissociation constant of 5 microM. This binding was abolished in the presence of vinblastine and maytansine. In contrast, specific binding of radioactive rhazinilam to tubulin assembled in microtubules was undetectable. These results demonstrate that rhazinilam alters microtubule stability differently than taxol, and that the overall similar effects of rhazinilam and taxol on the cellular cytoskeleton are the consequence of two distinct mechanisms of action at the molecular level.

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Section: Materials and Methods Chemicalsmentioning

confidence: 99%

Rhazinilam mimics the cellular effects of taxol by different mechanisms of action

David

Sévenet

Morgat

et al. 1994

Cell Motil. Cytoskeleton

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“…Shortly after the first isolation, its structure was elucidated by single crystal X-ray diffraction analysis [71]. It features a tetracyclic scaffold with a nine-membered ring and an all-carbon quaternary stereocenter.…”

Section: Resultsmentioning

confidence: 99%

Formal total syntheses of classic natural product target molecules via palladium-catalyzed enantioselective alkylation

Liu¹,

Liniger²,

McFadden³

et al. 2014

Beilstein J. Org. Chem.

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SummaryPd-catalyzed enantioselective alkylation in conjunction with further synthetic elaboration enables the formal total syntheses of a number of “classic” natural product target molecules. This publication highlights recent methods for setting quaternary and tetrasubstituted tertiary carbon stereocenters to address the synthetic hurdles encountered over many decades across multiple compound classes spanning carbohydrate derivatives, terpenes, and alkaloids. These enantioselective methods will impact both academic and industrial settings, where the synthesis of stereogenic quaternary carbons is a continuing challenge.

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“…Eburnamine derivative dimeric alkaloids ( Figure 14 (224) with an eburnamine-quebrachamine derivatives, were isolated from eight Melodinus species by column chromatography (CC),TLC, RP-18 gel, Sephadex LH-20 [6,14,21,27,42,43,45,65,[68][69][70][71].The absolute configuration of 220 and 221 was determined using ECD exciton chirality method. M. insulaepinorum furnished an eburnamine-kopsinine bisalkaloid, insulopinine (225) [24].…”

Section: Bisindole Alkaloidsmentioning

confidence: 99%

“…Other monomeric alkaloids, 204-210 ( Figure 13) (-)-Rhazinilam (204) was a natural compound isolated from M. australis and M. henryi, whose tetracyclic structure possesses an axially chiral phenyl-pyrrole subunit bridged by a ninemembered lactam ring [18,35,48,68]. Melohenine B (205), 14, 15-dehydromelohenine B (206) and…”

mentioning

confidence: 99%

Phytochemical and Pharmacological Properties of the Genus Melodinus – A Review

Jiang¹,

Zhang²,

Chen³

2016

Trop. J. Pharm Res

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Melodinus is an important genus comprising of approximately 53 species of medicinal plants (Apocynaceae). Some species have been used in Chinese folk medicine for the treatment of meningitis in children, rheumatic heart diseases, and diuresis, as well as a decongestive against migraine and sinusitis. This paper is a review of the literature up to May 2015 and describes 263 compounds from 69 articles, and includes chemical constituents isolated from Melodinus, mainly indole alkaloids, quinoline alkaloids, dimeric alkaloids, terpenoids and other compounds. It is also hoped that an overview of their cytotoxic characteristics will further the development of new anti-cancer agents.

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The structure elucidation of Rhazinilam, a new class of Alkaloids from the apocynaceae, by X-ray analysis

Cited by 88 publications

References 1 publication

Rhazinilam mimics the cellular effects of taxol by different mechanisms of action

Rhazinilam mimics the cellular effects of taxol by different mechanisms of action

Formal total syntheses of classic natural product target molecules via palladium-catalyzed enantioselective alkylation

Phytochemical and Pharmacological Properties of the Genus Melodinus – A Review

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