Narciclasine-4-O-β-d-glucopyranoside, a glucosyloxy amidic phenanthridone derivative from Pancratium maritimum

Abou‐Donia, Amina H.; Giulio, A. De; Evidente, Antonio; Gaber, Mohsen; Habib, Ahsan; Lanzetta, Rosa; Din, Ahmed A. Seif El

doi:10.1016/0031-9422(91)83226-b

Cited by 37 publications

(35 citation statements)

References 9 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Successively, from bulbs of the abovecited Egyptian P. maritimum a new glucosyloxy alkaloid was isolated and characterized as narciclasine-4-O-b-D-glucopyranoside. When tested in Artemia salina the new glucoside showed cytotoxic activity very similar to narciclasine(Abou-Donia et al 1991).…”

mentioning

confidence: 95%

Anticancer evaluation of structurally diverse Amaryllidaceae alkaloids and their synthetic derivatives

Evidente

Kornienko

2009

Phytochem Rev

Self Cite

View full text Add to dashboard Cite

Plants of the Amaryllidaceae family have been under intense scrutiny for the presence of the specific metabolites responsible for the medicinal properties associated with them. The study began in 1877 with the isolation of alkaloid lycorine from Narcissus pseudonarcissus and since then more than 100 alkaloids, exhibiting diverse biological activities, have been isolated from the Amaryllidaceae plants. Based on the present scientific evidence, it is likely that isocarbostyril constituents of the Amaryllidaceae, such as narciclasine, pancratistatin and their congeners, are the most important metabolites responsible for the therapeutic benefits of these plant species in the folk medical treatment of cancer. Notably, Narcissus poeticus L., used by the ancient Greek physicians, is now known to contain about 0.12 g of narciclasine per kg of fresh bulbs. The focus of the present research work is the chemistry and biology of these compounds as specifically relevant to their potential use in medicine. In particular, the anticancer evaluation of lycorine, narciclasine as well as of other Amaryllidaceae alkaloids and their synthetic derivatives are presented in this paper. The structure-activity relationships among some groups of Amaryllidaceae alkaloids will be discusse

show abstract

mentioning

confidence: 95%

Anticancer evaluation of structurally diverse Amaryllidaceae alkaloids and their synthetic derivatives

Evidente

Kornienko

2009

Phytochem Rev

Self Cite

View full text Add to dashboard Cite

show abstract

“…Glucosylated derivatives of narciclasine such as kalbreclasine found in Haemanthus kalbreyeri [43] or the 4-O-β-Dglucopyranoside found in Pancratium maritimum have been isolated. This glucoside showed cytotoxic and antitumor activity very similar to narciclasine in Artemia salina and potato disk assays [44]. Seed germination inhibition was found for narciclasine.…”

Section: Ii) Isolation and Biological Activitymentioning

confidence: 95%

Chemistry and Synthesis of Highly Oxygenated Alkaloids from Amaryllidaceae: Lycoricidine, Narciclasine, Pancratistatin and Analogs

Chapleur¹,

Chrétien²,

Ahmed³

et al. 2006

COS

View full text Add to dashboard Cite

Plants of the genus Amaryllidaceae produce a number of alkaloids and other non-basic related molecules, some of them showing antitumor activities. The low availability of these often-complex structures, coupled with their interesting biological properties, has stimulated a long-standing interest in the chemistry community. Total syntheses of challenging structures such as lycoricidine, narciclasine and pancratistatin, which are highly oxygenated tetracyclic systems comprising up to six contiguous chiral centers on ring C, have been accomplished. These well-known structures, more than thirty years for lycoricidine, continue to stimulate interest in synthetic work to provide enough synthetic material or analogs, and also are a model target to test or develop new synthetic methodologies. The synthetic studies around these complex phenanthridinones made use of the latest up-to-date synthetic methodologies and led to the development of novel methods of functionalization and carbon-carbon bond formation. The purpose of this review is to summarize recent total syntheses and synthetic approaches towards these three highly oxygenated members of this particular class of alkaloids over the last twenty years. The review is arranged according to the different strategies used for the construction of the benzophenanthridinone ring system.

show abstract

“…In continuation of a previous phytochemical investigation carried out on the Egyptian P. maritimum L. in the flowering stage, [43,47,48] we carried out a preliminary chromatographic screening on the bulbs and roots of the plant collected at the pre-flowering stage compared to the previous phytochemical investigation of the same plant at the flowering stage for the alkaloidal content.…”

Section: Chromatographic Screening Of the Bulbs And Roots Of Pancratimentioning

confidence: 99%

Screening of Pancratium maritimum L. for acetylcholinesterase inhibitory alkaloids using thin layer chromatography in combination with bioactivity staining

Shawky¹,

Abou-Donia²,

El-Din³

et al. 2013

J Nat Pharm

View full text Add to dashboard Cite

Background: Inhibition of acetylcholinesterase (AChE), the key enzyme in the breakdown of acetylcholine, is considered as a promising strategy for the treatment of neurological disorders such as Alzheimer's disease, senile dementia, ataxia, and myasthenia gravis. A potential source of AChE inhibitors is certainly provided by the abundance of plants in nature. Several methods for screening of AChE inhibitory activity from natural sources has been reported based on Ellman's reactions. Methods: This study was undertaken for the fi rst time to evaluate the anticholinesterase activity of Pancratium maritimum L., aiming to discover new candidates for anticholinesterase compounds. The second part of the study deals with a comparison of chromatographic screening of the bulbs and roots of the plant at pre-fl owering stage of growth for the alkaloidal content and a previous phytochemical investigation of the same plant at fl owering stage of growth using high performance thin layer chromatography technique. Results and Conclusion: The results of the preliminary chromatographic screening showed that the stage of growth has a remarkable effect on the type of alkaloids present.

show abstract

Narciclasine-4-O-β-d-glucopyranoside, a glucosyloxy amidic phenanthridone derivative from Pancratium maritimum

Cited by 37 publications

References 9 publications

Anticancer evaluation of structurally diverse Amaryllidaceae alkaloids and their synthetic derivatives

Anticancer evaluation of structurally diverse Amaryllidaceae alkaloids and their synthetic derivatives

Chemistry and Synthesis of Highly Oxygenated Alkaloids from Amaryllidaceae: Lycoricidine, Narciclasine, Pancratistatin and Analogs

Screening of Pancratium maritimum L. for acetylcholinesterase inhibitory alkaloids using thin layer chromatography in combination with bioactivity staining

Contact Info

Product

Resources

About