New Alkaloids from Cryptolepis sanguinolenta

Paulo, Alexandra; Gomes, Eduardo; Houghton, Peter J.

doi:10.1021/np50124a002

Cited by 89 publications

(81 citation statements)

References 5 publications

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“…6. A correlation was observed from the N-methyl resonance to the aromatic proton resonating at 8 ROE correlation observed from the N-methyl substituent is important in that it excludes cryptolepine from consideration as a possible substructural component of the TC-6 structure.…”

Section: Resultsmentioning

confidence: 97%

“…The proton resonating at 7.86 ppm was originally paired to the carbon resonating at 133.85 ppm. Again using correlations observed in the HMBC spectrum, spin system A is revised to pair the proton at 8 One of the significant advantages of Structure Elucidator is the ability of the spectroscopist to work with the program family to resolve ambiguities of this type successfully. In contrast, a spectroscopist working alone when faced with these sorts of entangled, closely spaced proton and carbon chemical shifts could spend a vast amount of time without success, particularly once correlations from the various protons to their respective long-range coupled carbons are added when the HMBC data are considered in attempting to solve the structure.…”

Section: Resultsmentioning

confidence: 99%

“…3,4 The isolation and structural characterization of numerous new members of the indoloquinoline family of alkaloids has been reported in the intervening years. Variations in the ring fusion of the indoloquinoline nucleus have been found; 5,6 several indolobenzazepines have been reported: 7,8 some dimeric structures including cryptomisrine (1), 9 biscryptolepine (2) 6 and cryptoquindoline (3) 8 have been isolated and characterized along with more complex systems that include cryptospirolepine 10 and cryptolepicarboline (4), 11 the latter being a mixed dimer all of the available data was not assembled in 1991-92 when these data were first examined.…”

Section: Introductionmentioning

confidence: 99%

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Quindolinocryptotackieine: the elucidation of a novel indoloquinoline alkaloid structure through the use of computer‐assisted structure elucidation and 2D NMR

Blinov¹,

Elyashberg²,

Martirosian³

et al. 2003

Magnetic Reson in Chemistry

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Numerous indoloquinoline alkaloid structures have been identified from extracts of the West African plant Cryptolepis sanguinolenta. Recently, through the use of 2D NMR methods and cryogenic NMR probe technology in conjunction with computer-assisted structure elucidation (CASE) methods, the structures of some chemical degradation products of this family of alkaloids have also been reported. We now report the characterization of a novel indoloquinoline dimeric alkaloid, quindolinocryptotackieine, through the extensive utilization of CASE methods. The NMR data presented here were collected over a decade earlier before the elucidation of the structure was possible, since manual analysis did not present a conclusive structure, whereas CASE produced a series of structures from which the structure could be verified. The original mass spectrometric (MS) data collected for the sample were problematic. Contemporary MS data were instead recollected from remaining small quantities of this alkaloid using modern instrumentation. The re-collected data gave a usable molecular ion and several key fragment ions that were diagnostically useful.

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Section: Resultsmentioning

confidence: 97%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Quindolinocryptotackieine: the elucidation of a novel indoloquinoline alkaloid structure through the use of computer‐assisted structure elucidation and 2D NMR

Blinov¹,

Elyashberg²,

Martirosian³

et al. 2003

Magnetic Reson in Chemistry

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“…The roots of the plant are known to contain alkaloids, notably quindoline, cryptolepine, and other related compounds [2][3][4]. The aqueous root extract of the plant is biologically active and has medicinal properties.…”

mentioning

confidence: 99%

“…A decoction of the roots has been used in clinical therapy, both of malaria and of urinary and upper respiratory tract infection at the Centre for Scientific Research into Plant Medicine (CSRPM) in Ghana since 1974 [2]. The roots of the plant are known to contain alkaloids, notably quindoline, cryptolepine, and other related compounds [2][3][4]. The aqueous root extract of the plant is biologically active and has medicinal properties.…”

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confidence: 99%

Characterisation of fatty acids in the roots of Cryptolepis sanguinolenta

2011

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UDC 547.915The roots of Cryptolepis saguinolenta were extracted with petroleum ether (40-60qC) to afford the oil in 0.7% yield to the wet mass of raw material. The fatty acid methyl esters (FAME) were separated and analyzed by GC-MS. The following fatty acids as their methyl esters in various proportions were obtained: linoleic acid (52%), palmitic acid (17%), stearic acid (5.8%), margaric acid (2.8%), oleic acid (1.8%), and arachidic acid (1.8%). The most abundant fatty acid identified was the essential dietary fatty acid linoleic acid in the proportion of 52%, which underscores the health and nutritional benefits of the plant besides its medicinal properties, which was the aim of this work.Keywords: Cryptolepis sanguinolenta, fatty acid methyl ester, gas chromatography-mass spectrometry. Cryptolepis sanguinolenta (Lindl.) Schlechter (Asclepiadaceae) is a plant native to West Africa and used in the treatment of malaria [1]. A decoction of the roots has been used in clinical therapy, both of malaria and of urinary and upper respiratory tract infection at the Centre for Scientific Research into Plant Medicine (CSRPM) in Ghana since 1974 [2]. The roots of the plant are known to contain alkaloids, notably quindoline, cryptolepine, and other related compounds [2][3][4]. The aqueous root extract of the plant is biologically active and has medicinal properties. In the in vitro toxicity analysis of the aqueous extract of C. sanguinolenta using V79 cells, a Chinese hamster lung fibroblast frequently used to assess genetic toxicity and a number of organ-specific human cell lines, the aqueous extract caused a dose-and time-dependent reduction in viability of the V79 cell line. Cryptolepine, the major alkaloid of the plant and in the antimalarial decoction, is a cytotoxic DNA intercalator and a potential anticancer agent [5].The traditional antimalarial decoction is prepared either by boiling the powder of the root in water for about two hours and strained or by maceration with ethanol in a preparation popularly called 'Bitters' in Ghana. The preparation methods of the antimalarial decoction are such that fatty acids esters are also extracted into the decoction. The antimalarial preparation is therefore a mixture of alkaloids, fatty acids, and other phytoconstituents. Besides the alkaloids therefore, fatty acid esters are also consumed in the use of the roots of the plant for malaria treatment.The aim of this work was to determine the fatty acids in the roots of the plant Cryptolepis sanguinolenta and to assess the health implications from the perspective of the fatty acids intake in the use of the plant in the management of malaria fever in Ghana.Several recent reports have focused on the structures and NMR spectroscopy of the alkaloidal constituents of the West African medicinal plant Cryptolepis sanguinolenta (Lindl.) Schlechter (Asclepiadaceae) [4,6,7]. Unlike the alkaloids, not much attention has been given to the study of fatty acids of C. sanguinolenta inspite of the high patronage of the plant as an antimalarial in...

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Encounters with Elephants: A Personal Perspective on Ethnopharmacology

Houghton

2015

Ethnopharmacology

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New Alkaloids from Cryptolepis sanguinolenta

Cited by 89 publications

References 5 publications

Quindolinocryptotackieine: the elucidation of a novel indoloquinoline alkaloid structure through the use of computer‐assisted structure elucidation and 2D NMR

Quindolinocryptotackieine: the elucidation of a novel indoloquinoline alkaloid structure through the use of computer‐assisted structure elucidation and 2D NMR

Characterisation of fatty acids in the roots of Cryptolepis sanguinolenta

Encounters with Elephants: A Personal Perspective on Ethnopharmacology

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