ABSTRACT
In this article, we report on the alkaloid profile and dynamic of alkaloid content and diversity in two Narcissus plants at different stages of development. The alkaloid profile of the two Narcissus species was investigated by GC/MS and HPTLC. Fifty eight Amaryllidaceae alkaloids were detected, and 25 of them were identified in the different organs of N. tazetta and N. papyraceus. The alkaloid 3-O-methyl-9-O-demethylmaritidine is tentatively identified here for the first time from the Amaryllidaceae family, and four alkaloids (tazettamide, sternbergine, 1-O-acetyllycorine, 2,11-didehydro-2-dehydroxylycorine) are tentatively identified for the first time in the genus Narcissus. The different organs of the two species analyzed showed remarkable differences in their alkaloid pattern, type of biosynthesis, main alkaloid and number of alkaloids. Lycorine-type alkaloids dominated the alkaloid, metabolism in N. papyraceus, while alkaloids of narciclasine-, galanthamine- and homolycorine-types were found only in the species N. tazetta L.
Subject(s)
Alkaloids/analysis , Narcissus/chemistry , Plant Extracts/chemistry , Chromatography, Thin Layer , Gas Chromatography-Mass SpectrometryABSTRACT
This study compares the chloroform extracts of bulbs and roots of Narcissus papyraceus Ker Gawl. and Narcissus tazetta L. The cytotoxicity of the plant extracts was evaluated against human hepatocellular carcinoma cell line (HEPG2) and colon carcinoma cell line (HCT116) in comparison to doxorubicin. The extracts from the after-flowering (AF) bulbs of N. tazetta L. and N. papyraceus exhibited strong cytotoxic activity against HEPG2 (IC50: 2.2, 3.5 µg mL(-1)) and HCT116 (IC50: 4.2, 3.9 µg mL(-1)) cell lines, respectively. N. tazetta L. bulbs exhibited the least cell viability percentage in HepG-2 cell line (5.32%), while the AF root extracts of N. papyraceus exhibited the least cell viability percentage in HCT116 cell line (4.93%), when applied at a concentration of 50 µg mL(-1), thereby being more active than doxorubicin at the same concentration.
Subject(s)
Antineoplastic Agents, Phytogenic/chemistry , Narcissus/chemistry , Plant Extracts/chemistry , HCT116 Cells , Hep G2 Cells , Humans , Narcissus/classification , Plant Roots/chemistryABSTRACT
A new, validated, sensitive and cheap method for preliminary quantitative evaluation of acetylcholine esterase inhibitory activity is presented. The proposed method combines HPTLC with data analysis by means of image processing software. An in-situ TLC autobiographic method was employed in which regions of the TLC plate which contain acetylcholinesterase inhibitors show up as white spots against the yellow background. Bleaching of the yellow color, caused by substances with acetylcholinesterase inhibitory activity was observed and recorded using a digital camera. ImageJ, JustTLC and Sorbfil, three image processing programs were evaluated for quantitative measurements. For evaluation of the assay efficiency, acetylcholinesterase inhibitory activity of different Amaryllidaceae plant extracts was expressed as Standard Activity Coefficients (SACs), which are relative measures of the activity to the well known acetylcholinesterase inhibitor eserine. We attempted to validate the method according to the ICH guideline. Different statistical data revealed that all image analysis software are able to detect the acetylcholine esterase inhibitory activity at very low concentration levels with the ImageJ program being the best of all three tested software regarding sensitivity, linearity and precision.
Subject(s)
Cholinesterase Inhibitors/analysis , Chromatography, Thin Layer/methods , Image Processing, Computer-Assisted/methods , Cholinesterase Inhibitors/chemistry , Cholinesterase Inhibitors/metabolism , Linear Models , Narcissus/chemistry , Plant Extracts/chemistry , Reproducibility of Results , Sensitivity and SpecificityABSTRACT
Fifteen Amaryllidaceae alkaloids (1-15) were evaluated for their antiproliferative activities against six distinct cancer cell lines. Several of these natural products were found to have low micromolar antiproliferative potencies. The log P values of these compounds did not influence their observed activity. When active, the compounds displayed cytostatic, not cytotoxic activity, with the exception of pseudolycorine (3), which exhibited cytotoxic profiles. The active compounds showed similar efficacies toward cancer cells irrespective of whether the cell lines were responsive or resistant to proapoptotic stimuli. Altogether, the data from the present study revealed that lycorine (1), amarbellisine (6), haemanthamine (14), and haemanthidine (15) are potentially useful chemical scaffolds to generate further compounds to combat cancers associated with poor prognoses, especially those naturally resistant to apoptosis, such as glioblastoma, melanoma, non-small-cell lung, and metastatic cancers.
Subject(s)
Amaryllidaceae Alkaloids/isolation & purification , Amaryllidaceae Alkaloids/pharmacology , Antineoplastic Agents, Phytogenic/isolation & purification , Antineoplastic Agents, Phytogenic/pharmacology , Drug Resistance, Neoplasm/drug effects , Phenanthridines/isolation & purification , Phenanthridines/pharmacology , Amaryllidaceae Alkaloids/chemistry , Antineoplastic Agents, Phytogenic/chemistry , Apoptosis/drug effects , Drug Screening Assays, Antitumor , Humans , Molecular Structure , Phenanthridines/chemistryABSTRACT
The work reported in this paper aims at developing an accurate, specific, repeatable and robust HPTLC method for the determination of galanthamine in different Amaryllidaceae plant extracts.
Subject(s)
Chromatography, Thin Layer/methods , Galantamine/analysis , Liliaceae/chemistry , Plant Extracts/chemistry , CalibrationABSTRACT
A phytochemical investigation of the bulbs and flowers of Hymenocallis littoralis SALISB., cultivated in Egypt, was carried out, which resulted in the isolation of four alkaloids, lycorine (1), hippeastrine (2), 11-hydroxyvittatine (3), and (+)-8-O-demethylmaritidine (4), and of two flavonoids, quercetin 3'-O-glucoside (5), and rutin (6). The volatile constituents of the plant flowers were analyzed for the first time by GC/MS, which led to the identification of 26 known compounds (Table 1). Finally, the antimicrobial activity of the petroleum ether extract of the flowers of H. littoralis was investigated.
Subject(s)
Amaryllidaceae Alkaloids/pharmacology , Flavonoids/pharmacology , Magnoliopsida/chemistry , Phenanthridines/pharmacology , Rutin/pharmacology , Amaryllidaceae Alkaloids/chemistry , Amaryllidaceae Alkaloids/isolation & purification , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/isolation & purification , Anti-Bacterial Agents/pharmacology , Dose-Response Relationship, Drug , Flavonoids/chemistry , Flavonoids/isolation & purification , Flowers/chemistry , Glucosides , Microbial Sensitivity Tests , Molecular Conformation , Phenanthridines/chemistry , Phenanthridines/isolation & purification , Plant Roots/chemistry , Pseudomonas aeruginosa/drug effects , Quercetin/analogs & derivatives , Rutin/chemistry , Rutin/isolation & purification , Staphylococcus aureus/drug effects , Stereoisomerism , Structure-Activity RelationshipABSTRACT
A new lycorine-type alkaloid, named (-)-amarbellisine, was isolated from the bulbs of Egyptian Amaryllis belladonna L. together with the well known alkaloids (-)-lycorine, (-)-pancracine, (+)-vittatine, (+)-11-hydroxyvittatine, and (+)-hippeastrine. The new alkaloid, containing the pyrrolo[de]phenanthridine ring system, was essentially characterised by spectroscopic and optical methods, and proved to be the 2-methoxy-3a,4,5,7,11b,11c-hexahydro-1H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridinol. By using HPTLC technique we also carried out a comparative study of the relative and total alkaloidal content at two different stages of plant growth. Finally, the antimicrobial activity of the isolated alkaloids was assayed.
Subject(s)
Amaryllidaceae Alkaloids/isolation & purification , Liliaceae/chemistry , Amaryllidaceae Alkaloids/chemistry , Chromatography, High Pressure Liquid/methods , Egypt , Liliaceae/growth & development , Magnetic Resonance Spectroscopy , Molecular StructureABSTRACT
Two new alkaloids; ent-6alpha/6beta-hydroxybuphanisine, (-)-8-demethylmaritidine and seven known alkaloids were isolated from Pancratium sickenbergeri grown in Egypt. Three of the known alkaloids were tested in the NCI cytotoxicity screen, but were found to be inactive.