Chemical and biological aspects of Narcissus alkaloids.
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Alkaloids↗
Biomedical subjects
Jaume Bastida
Publications and source records attributed to Jaume Bastida.
Antioxidant activity of isoflavones and biflavones isolated from Godoya antioquiensis.
Two biflavones, ochnaflavone (1) and 2",3"-dihydroochnaflavone (2), and two isoflavones, 5,7,4'-trihydroxy-3',5'-dimethoxyisoflavone (piscigenin) (3) and 5,4'-dihydroxy-7,3',5'-trimethoxyisoflavone (4), a new natural compound, were isolated from the leaves of Godoya antioquiensis (Ochnaceae). Their structures were determined on the basis of spectral data and by comparison with data reported in the literature. The isolated compounds were evaluated for their radical scavenging activity using the NBT (nitrobluetetrazolium)/hypoxanthine superoxide and the .OH/luminol chemiluminescence methods. The isolated isoflavones were found to exhibit a strong hydroxyl radical scavenging activity and a moderate inhibition of the superoxide anion, whereas the two biflavones were inactive in the superoxide anion assay and showed a low hydroxyl radical scavenging activity.
Antioxidants↗
Alkaloids from Nerine filifolia.
The novel compounds N-demethylbelladine, 6alpha-methoxybuphanidrine and filifoline, in addition to five known alkaloids, and phenol have been isolated from fresh bulbs of Nerine filifolia (Amaryllidaceae). The structure and stereochemistry of the compounds were determined by physical and spectroscopic methods, including 1D and 2D NMR and mass spectroscopic techniques. An unusual circular dichroism response from filifoline has required a semi-synthetic derivatisation strategy towards key C-11endo analogues of the beta-crinane representative ambelline in which the nature of substituents was observed to have a profound effect on molecular ellipticity. Filifoline was not cytotoxic to myoblast (L6) cells and exhibited no anti-protozoal activity in an in vitro screen against four different parasitic protozoa.
Amaryllidaceae Alkaloids↗
Acylated quercetagetin glycosides with antioxidant activity from Tagetes maxima.
The fractionation of a methanolic extract of Tagetes maxima guided for antioxidant activity resulted in the isolation of three acylated quercetagetin glycosides, quercetagetin-7-O-(6-O-caffeoyl-beta-D-glucopyranoside), quercetagetin-7-O-(6-O-p-coumaroyl-beta-D-glucopyranoside) and quercetagetin-7-O-(6-O-galloyl-beta-D-glucopyranoside), as well as four known flavonoid glycosides. The structural elucidation was accomplished by spectroscopic methods (ESI-MS/MS and NMR). The antioxidant activity of fractions and isolated compounds was determined by checking the scavenging activity against three different radicals: 2,2-diphenyl-1-picrylhydrazyl free radical (DPPH*), hydroxyl (*OH), and superoxide (O2*-). The three isolated compounds exhibited a high radical scavenging activity in comparison with reference compounds.
Acylation↗
Separation and characterization of phenolic compounds in fennel (Foeniculum vulgare) using liquid chromatography-negative electrospray ionization tandem mass spectrometry.
Liquid chromatography (LC) diode array detection (DAD) coupled to negative electrospray ionization (ESI) tandem mass spectrometry (MS/MS) was used for the rapid and sensitive identification of water-soluble phenolic compounds in fennel waste. The plant material was first extracted and then chromatographed on Sephadex LH-20 to afford seven fractions, each of them being subjected to LC-MS analysis. Identification of the compounds was carried out by interpretation of UV, MS, and MS/MS spectra. Forty-two phenolic substances were identified, 27 of which had not previously been reported in fennel, including hydroxycinnamic acid derivatives, flavonoid glycosides, and flavonoid aglycons.
Chemical Fractionation↗
Bioguided isolation and identification of the nonvolatile antioxidant compounds from fennel (Foeniculum vulgare Mill.) waste.
A bioguided isolation of an aqueous extract of fennel waste led to the isolation of 12 major phenolic compounds. Liquid chromatography coupled to atmospheric pressure chemical ionization mass spectrometry (LC/UV/APCI-MS) combined with spectroscopic methods (NMR) was used for compound identification. Radical scavenging activity was tested using three methods: DPPH*, superoxide nitro-blue tetrazolium hypoxanthine/xanthine oxidase, and *OH/luminol chemiluminescence. In addition to products described in the literature, eight antioxidant compounds were isolated and identified for the first time in fennel: 3-caffeoylquinic acid, 4-caffeoylquinic acid, 1,5-O-dicaffeoylquinic acid, rosmarinic acid, eriodictyol-7-O-rutinoside, quercetin-3-O-galactoside, kaempferol-3-O-rutinoside, and kaempferol-3-O-glucoside. The structures of eriodictyol-7-O-rutinoside and quercetin-3-O-glucuronide were completely elucidated by two-dimensional NMR experiments. The isolated compounds exhibited a strong antiradical scavenging activity, which may contribute to the interpretation of the pharmacological effects of fennel.
Antioxidants↗
Qualitative analysis of phenolic compounds in apple pomace using liquid chromatography coupled to mass spectrometry in tandem mode.
The occurrence of phenolic compounds in apple residues resulting from the juice industry was investigated to provide an alternative use for this raw material. For the identification of these compounds, liquid chromatography coupled to ionspray mass spectrometry in tandem mode (LC/MS/MS) with negative ion detection was used. The residues were first extracted and then chromatographed on Sephadex LH-20 to yield 13 fractions. Positive identification of the compounds was based on their retention times and mass spectra in full scan mode (MS), and in different MS/MS modes (product ion scan, precursor ion scan and neutral loss scan). In this way, 60 compounds, including cinnamic and benzoic acid derivatives and flavonoids, were identified, some of them not previously reported in apple waste.
Chromatography, High Pressure Liquid↗
Characterization of acylated flavonoid-O-glycosides and methoxylated flavonoids from Tagetes maxima by liquid chromatography coupled to electrospray ionization tandem mass spectrometry.
Liquid chromatography coupled to negative electrospray ionization (ESI) tandem mass spectrometry (MS/MS) employing a triple quadrupole mass spectrometer was used in the structural determination of acylated flavonoid-O-glycosides and methoxylated flavonoids occurring in Tagetes maxima. The compounds were identified by experiments in full scan mode (MS), and tandem mass experiments (MS/MS) of precursor ion scan, product ion scan, and neutral loss scan modes. In order to characterize the aglycones of the flavonoid glycosides, in-source fragmentation of the deprotonated molecule [M-H]- followed by product ion scan of the resulting aglycone [A-H]- were performed. This combined approach allowed the identification of 51 phenolic compounds, including flavonoid-O-glycosides acylated with galloyl, protocatechuoyl, coumaroyl or caffeoyl groups, methoxylated flavonoids, and hydroxycinnamic acid and phenolic acid derivatives, none of them previously reported in Tagetes maxima.
Chromatography, High Pressure Liquid↗
Investigation of Lepechinia graveolens for its antioxidant activity and phenolic composition.
A bioguided separation of Lepechinia graveolens (Reg.) Epling. (Lamiaceae) for antioxidant activity was carried out. The ethyl acetate fraction (EAF) from the methanolic extract was chromatographed on Sephadex LH-20 affording five active fractions. The radical scavenging activity of each fraction, as well as that of the isolated compounds, was tested using three different methods. The major isolated antioxidant compounds were identified as luteolin-7-O-glucuronide, rosmarinic acid, and rosmarinic acid methyl ester by means of 1H and 13C NMR and mass spectrometry. Twenty other minor phenolic compounds were determined by liquid chromatography-negative electrospray ionization tandem mass spectrometry. They included hydroxycinnamic acid derivatives, flavonoids and phenolic diterpenes. The major phenolic compound was found to be rosmarinic acid, which was quantitatively determined by high-performance liquid chromatography (HPLC)-diode array detector (DAD). The content of rosmarinic acid was 2.8% (referred to dry weight), this amount being around 30% of the total phenolic content (TPH) of the crude extract. It can be concluded that the antioxidant activity of Lepechinia graveolens was mainly due to rosmarinic acid, which allows this plant species to be considered as a potential new source of this well known natural antioxidant.
Antioxidants↗
Augustamine type alkaloids from Crinum kirkii.
Sixteen more Amaryllidaceae alkaloids have been isolated from bulbs of Crinum kirkii Baker of which noraugustamine and 4a,N-dedihydronoraugustamine are hitherto unknown. Their structures and those of earlier known alkaloids have been established by physical and spectroscopic analysis. Application of 2D NMR techniques was used for complete characterization of the alkaloids as well as of 3-O-acetylsanguinine. 1,2-Diacetyllycorine and 3-O-acetylsanguinine showed activity against Trypanosoma brucci rhodesiense, the parasite associated with sleeping sickness. 3-O-acetylsanguinine also showed some activity against Trypanosoma cruzi.
Alkaloids↗
Improved production of galanthamine and related alkaloids by methyl jasmonate in Narcissus confusus shoot-clumps.
Liquid-shake cultured shoot-clumps of Narcisus confussus were treated with the commonly used biotic elicitors methyl jasmonate, arachidonic acid, chitosan and salicylic acid. The effects of these compounds on the growth of the explants, as well as on the amount of the alkaloids released to the liquid culture medium and accumulated in the tissues at the end of the experiment were studied. The obtained results showed that, in general, high doses of these compounds had a negative effect on the growth of the explants, particularly the salicylic acid. On the contrary, the addition of methyl jasmonate, mainly at 25 microM, promoted the release of galanthamine and other related alkaloids to the liquid medium in proportions of up to 300% in relation to the control explants, and also their accumulation in tissues. The other elicitors studied did not have any interesting effects on the production of these Amaryllidaceae-type alkaloids.
Acetates↗
Investigation of Bolivian plant extracts for their radical scavenging activity and antioxidant activity.
Fifty-four different extracts of nine Bolivian plants belonging to the family Asteraceae were evaluated for their radical scavenging activity by the DPPH*, NBT/hypoxanthine superoxide, and (*)OH/luminol chemiluminescence methods, and for their antioxidant activity by the beta-carotene bleaching test. The total phenolic content was also determined by the Folin-Ciocalteu method, and the oxidative stability by the Rancimat test. Both remarkably high phenolic content and radical scavenging and antioxidant activities were found mainly in the ethyl acetate fractions among the different plant extracts. Some ethyl acetate and even some defatted crude extracts exhibited activities comparable to those of commercial extracts/compounds, thus making it possible to consider some of the studied plants as a potential source of antioxidants of natural origin.
Antioxidants↗
Identification of phenolic compounds in artichoke waste by high-performance liquid chromatography-tandem mass spectrometry.
A new fast and efficient method combining liquid chromatography coupled to ionspray mass spectrometry in tandem mode with negative ion detection is described for the qualitative analysis of artichoke waste. Forty-five phenolic compounds were identified on the basis of their mass spectra in full scan mode, mass spectra in different MS-MS modes, and retention times compared with those of available reference substances. The major compounds were found to be both caffeoylquinic and dicaffeoylquinic acids, luteolin glucuronide, luteolin galactoside, quercetin, and some quercetin glycosides.
Chromatography, High Pressure Liquid↗
Seasonal and spatial variations of alkaloids in Merendera montana in relation to chemical defense and phenology.
Merendera montana (Liliaceae) is an endemic plant broadly, but exclusively, occurring in the Iberian Peninsula where it is one of the most abundant species in rangelands grazed by sheep and on the routes used by migrating sheep herds. In spite of showing a peculiar phenology adapted to Mediterranean regions (leaves remain green from fall to spring and are absent in summer), this species has also successfully colonized high altitude environments (up to 2300 m), and abundant populations can be found in montane and subalpine pasturcs. Chemical analysis has shown a high forage quality as well as the presence of tropolone alkaloids (similar to other species of the genus Merendera), mainly colchicine, 3-demethylcolchicine, and colchicoside. In general terms, the alkaloid content was significantly lower in the subterranean corms than in the leaves. No remarkable seasonal variations in total alkaloids was found, although an increase of colchicoside in the corms and a decrease of colchicine was noted in summer. Both chemical deterrents and phenology could be the cause of the widespread ecological adaptation of Merendera montana. The alkaloid content would prevent intake by wild herbivores during winter, while the absence of aerial organs in summer, coinciding exactly with the highest domestic herbivore pressure, would permit this species to colonize rich soil habitats where there is low plant competition.
Adaptation, Physiological↗
Anti-human immunodeficiency virus type 1 (HIV-1) activity of lectins from Narcissus species.
Mannose-specific lectins (MSLs) were isolated from bulbs of fifteen wild Narcissus species growing in Spain and assayed for their HIV-1 infection inhibitory activity in MT-4 cells and compared to the Narcissus pseudonarcissus agglutinin (NPA), the commercially available MSL obtained from daffodils. Almost all the tested MSLs were found to be active, showing EC50 values (microg/mL) similar to that of NPA, with some being comparable to those obtained with dextran sulfate without significant cytotoxicity. However, on a molar basis almost all of the MSLs tested exhibited lower EC50 values than dextran sulfate whilst six MSLs had values lower than AZT. The most efficacious anti-HIV-1 activity was exhibited by the Narcissus tortifolious MSL, which was 10- (microg/mL) and 100- (molarity) fold more potent than dextran sulfate. Significantly, although this MSL was 15-fold less potent than AZT in terms of quantity (microg/mL), it was 68-fold more potent on a molar basis. The antiviral indices, a ratio of the concentrations that produce cytotoxicity and HIV-1 replication, were calculated and three of the MSLs, N. confusus, N. leonensis and N. tortifolius reported 1.5-, 2- and 8.5-fold greater AI values than dextran sulfate or AZT. Comparison of MSL haemagglutination activities (HAA) to their anti-HIV-1 activities showed that there was no significant correlation. It was suggested that this may be due to a dissociation between both activities as a consequence of multiple isolectin composition.
Anti-HIV Agents↗
Galanthamine pattern in Narcissus confusus plants.
Galanthamine is an Amaryllidaceae-type alkaloid with acetylcholinesterase inhibitory activity which is used in the treatment of Alzheimer's disease. The distribution of galanthamine and four other alkaloids in different organs of Narcissus confusus plants, as well as the variations occurring during the ontogenic cycle of this plant species, was studied. The five alkaloids were found to be present in all the organs at every stage, with the exception of haemanthamine in senescent flowers. The highest amount of alkaloids occurred in the bulb at the emerging stage, galanthamine being the most abundant, reaching a concentration of up to 2.5 % referred to dry weight.
Alkaloids↗
Alkaloids from Eucharis amazonica (Amaryllidaceae).
Thirteen alkaloids have been isolated from dried bulbs and leaves of flowering Eucharis amazonica (Amaryllidaceae). The alkaloids, 7-methoxyoxoassoanine, 6-O-methylpretazettine and apohaemanthamine, are reported for the first time from a natural source.
Alkaloids↗
Comparison between the radical scavenging activity and antioxidant activity of six distilled and nondistilled mediterranean herbs and aromatic plants.
Thirty-six different extracts of six herbs and aromatic plants (fennel, common melilot, milfoil, lavandin cv. Super, spike lavender, and tarragon) were evaluated for their radical scavenging activity by the DPPH*, NBT/hypoxanthine superoxide, and *OH/luminol chemiluminescence methods, and for their antioxidant activity by the beta-carotene blenching test. The total phenolic content was also determined by the Folin-Ciocalteu method. The plant material included cultivated plants and their wastes after being distilled for essential oils. Both remarkably high phenolic content and radical scavenging activities were found for the ethyl acetate and dichloromethane fractions among the different plant extracts. In general, the distilled plant material was found to exhibit a higher phenolic content as well as antioxidant and radical scavenging activities than the nondistilled material. Ethyl acetate and dichloromethane extracts, and even some crude extract, of both distilled and nondistilled plants exhibited activities comparable to those of commercial extracts/compounds, thus making it possible to consider some of them as a potential source of antioxidants of natural origin.
Acetates↗