6a/6b-Hydroxy-3-O-methylepimaritidine, Two New Alkaloids from Narcissus tazetta L. var. chinensis Roem

Ma, Guoyi; Li, Hui-Yin; Lu, Chun-E; Yang, Xueming; Hong, Shan-Hai

doi:10.3987/r-1986-08-2089

Cited by 12 publications

(7 citation statements)

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“…11-hydoxyvittatine and tazettine reduced viability at concentrations higher than 50 µM (73.8% and 85.2% viable cells, respectively) and obliquine was toxic from 100 µM (82.6%) (Figure 5B). The AAs CC 50 were not reached at the concentrations used in our assays.…”

Section: Resultsmentioning

confidence: 78%

“…Alkaloids 5 and 6 were identified comparing our data with those reported by Frahm et al (1985) [46], Bastida et al (1995) [47], Pabuççuoglu et al (1989) [48] and Ghosal et al (1985) [49] when isolated from Crinum asiaticum, Narcissus cantabricus and Sternbergia sicula, respectively. Likewise, alkaloids 7 and 8 were identified by comparing their data with those described by Ma et al (1986) [50], Antoun et al (1993) [41], Forgo and Hoffmann (2005) [51], Bastida et al (1987) [52] and Evidente et al (1994) [53] when isolated from Hymenocallis expansa, Narcissus tazetta L. var chinensis roem, Leucojum vernum and Narcissus confusus, respectively. Finally, alkaloids 9 and 10 were identified by comparison with those reported by Evidente (1986) [54] and Ali et al (1984) [55] when isolated from Hippeastrum vittatum and Stenbergia lutea, respectively.…”

Section: Resultsmentioning

confidence: 99%

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Cytotoxicity and Antiviral Properties of Alkaloids Isolated from Pancratium maritimum

Masi¹,

Lecce²,

Mérindol

et al. 2022

Toxins

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Ten Amaryllidaceae alkaloids (AAs) were isolated for the first time from Pancratium maritimum collected in Calabria region, Italy. They belong to different subgroups of this family and were identified as lycorine, which is the main alkaloid, 9-O-demethyllycorine, haemanthidine, haemanthamine, 11-hydroxyvittatine, homolycorine, pancracine, obliquine, tazettine and vittatine. Haemanthidine was isolated as a scalar mixture of two 6-epimers, as already known also for other 6-hydroxycrinine alkaloids, but for the first time they were separated as 6,11-O,O′-di-p-bromobenzoyl esters. The evaluation of the cytotoxic and antiviral potentials of all isolated compounds was undertaken. Lycorine and haemanthidine showed cytotoxic activity on Hacat cells and A431 and AGS cancer cells while, pancracine exhibited selective cytotoxicity against A431 cells. We uncovered that in addition to lycorine and haemanthidine, haemanthamine and pancracine also possess antiretroviral abilities, inhibiting pseudotyped human immunodeficiency virus (HIV)−1 with EC50 of 25.3 µM and 18.5 µM respectively. Strikingly, all the AAs isolated from P. maritimum were able to impede dengue virus (DENV) replication (EC50 ranged from 0.34–73.59 µM) at low to non-cytotoxic concentrations (CC50 ranged from 6.25 µM to >100 µM). Haemanthamine (EC50 = 337 nM), pancracine (EC50 = 357 nM) and haemanthidine (EC50 = 476 nM) were the most potent anti-DENV inhibitors. Thus, this study uncovered new antiviral properties of P. maritimum isolated alkaloids, a significant finding that could lead to the development of new therapeutic strategies to fight viral infectious diseases.

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Section: Resultsmentioning

confidence: 78%

Section: Resultsmentioning

confidence: 99%

Cytotoxicity and Antiviral Properties of Alkaloids Isolated from Pancratium maritimum

Masi¹,

Lecce²,

Mérindol

et al. 2022

Toxins

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“…[16][17][18][19][20][21][22][23] A number of synthetic efforts have been employed to solve the challenging problem of incorporating these steri-cally congested stereocenters into the 5,10b-ethanophenanthridine structural framework. In this context, intramolecular oxidative para-para phenolic coupling [24][25][26][27][28] and Pictet-Spengler cyclization [19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38] of 3-aryl hydroindole derivatives have emerged as the two main strategies. In the former approach, spiro-fused dienone precursor 7 is obtained by the para-para coupling of substituted norbelladine derivatives employing various oxidizing agents, [24,25,27] photochemical cyclization, [26] intramolecular Heck reaction, [39] and cyclization of an intermediate iron carbonyl complex.…”

Section: Introductionmentioning

confidence: 99%

Construction of the 5,10b‐Phenanthridine Skeleton Using [3+2]‐Cycloaddition of a Non‐Stabilized Azomethine Ylide: Total Synthesis of (±)‐Maritidine and (±)‐Crinine Alkaloids

2010

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Vicinal quaternary and tertiary stereocenters of the 5,10b‐phenanthridine skeleton 1 are constructed simultaneously in one step by the [3+2]‐cycloaddition of non‐stabilized azomethine ylide 9, generated by sequential double desilylation of 10 utilizing silver(I) fluoride as a one‐electron oxidant. The regio‐ as well as stereochemical origin of this cycloaddition reaction is explained through a favorable transition state 9″. The strategy is successfully applied for the total synthesis of the biologically active alkaloids (±)‐maritidine (1a), (±)‐crinine (1b), and their analogues (1d, 1e, and 1f).

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“…Standard Compounds. Standard compounds ( 1−11 ) were obtained from a variety of common Narcissus cultivars using standard extraction and separation methods and were identified by comparison of the physical (mp, [α] D ) and spectroscopic data (UV, 1 H and 13 C NMR) with literature values. − The purity of the compounds was determined by gas chromatography using FID and NPD.…”

Section: Methodsmentioning

confidence: 99%

A Rapid Quantitative Method for the Analysis of Galanthamine and Other Amaryllidaceae Alkaloids by Capillary Column Gas Chromatography

Bastos

Nanayakkara

et al. 1996

J. Nat. Prod.

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A rapid and sensitive capillary column gas chromatographic method for the identification and quantification of Amaryllidaceae alkaloids is reported. Well-resolved, sharp and symmetrical peaks were obtained for compounds of four different chemical skeleton types of these alkaloids. A 15 m DB-1 capillary column was used for this purpose, and the time of analysis of all compounds was 15 min. This procedure required only small amounts of dried plant material and was developed with the addition of an internal standard.

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6a/6b-Hydroxy-3-O-methylepimaritidine, Two New Alkaloids from Narcissus tazetta L. var. chinensis Roem

Cited by 12 publications

References 0 publications

Cytotoxicity and Antiviral Properties of Alkaloids Isolated from Pancratium maritimum

Cytotoxicity and Antiviral Properties of Alkaloids Isolated from Pancratium maritimum

Construction of the 5,10b‐Phenanthridine Skeleton Using [3+2]‐Cycloaddition of a Non‐Stabilized Azomethine Ylide: Total Synthesis of (±)‐Maritidine and (±)‐Crinine Alkaloids

A Rapid Quantitative Method for the Analysis of Galanthamine and Other Amaryllidaceae Alkaloids by Capillary Column Gas Chromatography

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