Effects of stress on alkaloid metabolism in Crinum asiaticum☆

Ghosal, Shibnath; Singh, Suman Kumar; Unnikrishnan, Sankara G.

doi:10.1016/0031-9422(90)80023-a

Cited by 20 publications

(6 citation statements)

References 10 publications

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“…Lycorine-type alkaloids are common in nature; however, lycorine N -oxides are rare. Heretofore, only five lycorine N -oxides, 3- O -acetylnarcissidine N -oxide, ungiminorine N -oxide, lycorine N -oxide, pancratinine D, and incartine N -oxide, were reported. In this study, two new lycorine N -oxide alkaloids ( 9 and 10 ) were isolated from Z. carinata , and the absolute configurations of the N -oxide moieties in 9 and 10 were determined to be R and S , respectively, by single-crystal X-ray diffraction analysis.…”

Section: Resultsmentioning

confidence: 99%

Acetylcholinesterase Inhibitory Alkaloids from the Whole Plants of Zephyranthes carinata

et al. 2017

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Eleven new alkaloids (1-11), classified as the 12-acetylplicamine (1), N-deformyl-seco-plicamine (2), plicamine (3-6), 4a-epi-plicamine (7), seco-plicamine (8), and lycorine (9-11) framework types, along with 15 known alkaloids (12-26) were isolated from the whole plants of Zephyranthes carinata. The structures of the new alkaloids 1-11 were established by extensive spectroscopic data interpretation. The absolute configurations of 9 and 10 were defined by single-crystal X-ray diffraction analysis. Zephycarinatines A (1), B (2), and G (7) represent the first examples of 12-acetylplicamine, N-deformyl-seco-plicamine, and 4a-epi-plicamine alkaloids, respectively. Alkaloids 6, 11, 17, and 20-23 exhibited AChE inhibitory activities with IC values ranging from 1.21 to 184.05 μM, and a preliminary structure-activity relationship is discussed.

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Section: Resultsmentioning

confidence: 99%

Acetylcholinesterase Inhibitory Alkaloids from the Whole Plants of Zephyranthes carinata

et al. 2017

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“…Only one other significant peak was found at m/e 240.8. We did not observe any higher molecular weight species that might be indicative of glycosylated or phosphatidylated derivatives of lycorine reportedly present in the fruit, flowers, and sap of various Crinum species (1,30,36).…”

Section: Electrospray Mass Spectrometrymentioning

confidence: 45%

“…However, the most satisfactory separations were obtained using the basic mobile phase reported in (35). This volatile buffer system provided better peak profiles than other mobile phases, such as the methanol-water systems used by (30), and when used in a gradient system produced higher selectivity. Under semipreparative conditions, the lycorine eluted as a single peak with a retention time of 17 min, free of other contaminating peaks.…”

Section: Hplc Analysis Of Lycorinementioning

confidence: 86%

“…Despite this, there are few protocols specifically available for the isolation of lycorine. Methods for the identification of the ''total alkaloids'' fraction of a tissue typically require extraction with alcohol fol-lowed by a series of partitionings with solvents of differing polarities and then recrystallization (12,29,30) and/or the use of low-pressure column techniques (31,32). In all cases, while the procedures are simple to execute, they are labor-intensive and are not suited to the routine isolation of milligram quantities of lycorine, because of the large number of handling steps.…”

confidence: 99%

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Purification of the Alkaloid Lycorine and Simultaneous Analysis of Ascorbic Acid and Lycorine by Micellar Electrokinetic Capillary Chromatography

Davey

Persiau

Bruyn

et al. 1998

Analytical Biochemistry

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The pyrrolophenanthridine alkaloid lycorine has frequently been used as a specific inhibitor to help elucidate the function of ascorbic acid (vitamin C) in a wide range of biological processes. It was recently reported that this function can be exercised by inhibiting the activity of L-galactono-1,4-lactone dehydrogenase, the terminal enzyme of ascorbic acid biosynthesis, although working with the purified enzyme, we have been unable to repeat this result. Here, we present a procedure for the purification and analysis of lycorine by high-performance liquid chromatography from two Crinum species and describe for the first time a method that allows the simultaneous analysis of ascorbic acid and lycorine in tissue extracts of Crinum asiaticum by micellar electrokinetic chromatography.

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“…Mechanical injury caused almost complete hydrolysis of the alkaloidal conjugates and could be accompanied by oxidative modification, e.g. l-O-palmitoyl-2-0-(1 '-0-palmitoyl-2'-0-stearoyl)-glycerophosphoryllycorine (1) gave lycorine (2) and the N-oxide (3). Epilycorine (4) was found in the ' normal ' extraction but not in the 'protected ' extracted procedure.…”

Section: Occurrence and Structural Studiesmentioning

confidence: 99%