Search PubMed⌕ Search

SEARCH · Search PubMed

Results for “ALKALOIDS”

Search indexed PubMed citations on genomics, clinical trials, systematic reviews and public health. Explore titles, authors and supplied subject terms, then open the PubMed record.

Quote a phrase for an exact phrase match. Source license links do not imply unrestricted reuse.

At least 1,063 records · Page 59Linked to original sources
PubMed2005

Protective role of Coptidis Rhizoma alkaloids against peroxynitrite-induced damage to renal tubular epithelial cells.

A study was conducted to elucidate and compare the protective activity of alkaloids from Coptidis Rhizoma (berberine, coptisine, palmatine, epiberberine, jatrorhizine, groenlandicine and magnoflorine) using an LLC-PK(1) cell under peroxynitrite (ONOO(-)) generation model. Treatment with 3-morpholinosydnonimine (SIN-1) led to an increase in cellular ONOO(-) generation in comparison with non-treated cells. However, Coptidis Rhizoma extract and its alkaloids, except for berberine, reduced the cellular ONOO(-) level. In addition, DNA fragmentation induced by SIN-1 was significantly decreased by the extract, and also by coptisine, epiberberine, jatrorhizine, groenlandicine and magnoflorine. Moreover, treatment with berberine, coptisine, palmatine and epiberberine exerted a protective effect against G(0)/G(1)phase arrest of cell cycle induced by SIN-1. The increase in cellular ONOO(-) generation, DNA damage and disturbance of the cell cycle by SIN-1 resulted in a decrease in cell viability. However, Coptidis Rhizoma extract, epiberberine, jatrorhizine, groenlandicine and magnoflorine significantly increased cell viability even at a concentration as low as 10 microg mL(-1). These findings demonstrate that Coptidis Rhizoma extract and its alkaloids can ameliorate the cell damage associated with ONOO(-) generation in renal tubular LLCPK(1) cells, and that the various alkaloids have distinctive mechanisms of action, such as ONOO(-) scavenging, protection from DNA damage and control of the cell cycle. Furthermore, the data suggest that among the Coptidis Rhizoma alkaloids, coptisine is the most effective for protection against SIN-1-induced cellular injury in terms of its potency and content.

Alkaloids↗
PubMed1996

Effects of biscoclaurine alkaloid cepharanthine on newborn rat skin epidermal and dermal cells.

Effects of biscoclaurine alkaloid cepharanthine on proliferation of skin cells were examined in vitro. The alkaloid was found to enhance attachment and cell layer formation of newborn rat skin epidermal cells in culture on type I collagen-coated Millipore filter, and to potentiate production of keratins in these cells. Spreading and growth of skin dermal fibroblasts were inhibited by cepharanthine in a dose-dependent manner, but the alkaloid-treated cells still retained the ability to synthesize type IV collagen. In culture of skin cells containing both epidermal and dermal cells, no growth of epidermal cells or over-growth of dermal fibroblasts was observed in medium without cepharanthine. In contrast, the presence of the alkaloid suppressed the growth of fibroblasts and promoted the formation of epidermal cell layers accompanied by production of keratins. Thus, in comparison with the cells untreated with the alkaloid, cepharanthine-treated skin epidermal and dermal cells in vitro expressed in vivo-like characters.

Alkaloids↗
PubMed2000

Application of liquid chromatography-atmospheric pressure chemical ionization mass spectrometry to the differentiation of stereoisomeric C19-norditerpenoid alkaloids.

High-performance liquid chromatography-atmospheric pressure chemical ionization mass spectrometry (HPLC-APCI-MS) was successfully applied to stereoisomeric C19-norditerpenoid alkaloids at position 1. APCI-MS allowed the easy and precise control of the energy deposition by varying the drift voltage. Comparison of the breakdown curves, observed by changing the potential difference between the first electrode and the second electrode of the APCI ion source, revealed stereochemical dependence of different fragmentations. The APCI spectra of alkaloids were predominantly the [M+H]+ ion and major fragment ion, corresponding to the [M+H-H2O]+ ion or the [M+H-CH3COOH]+ ion, and comparison of the spectra showed that the abundance of fragment ions was significantly higher for C-1 beta-form alkaloids than for C-1 alpha-form alkaloids. The characteristic fragment ions were formed by the loss of a water, acetic acid or methanol molecule at position 8. The fragmentation mechanisms depending on the stereochemistry of the precursor ion could be discerned by recording the spectra in a deuterated solvent system of 0.05 M ammonium acetate in D2O-acetonitrile-tetrahydrofuran. Loss of D2O from the precursor ion gave the fragment ion. This result indicated that the proton of protonation was included in the leaving water molecule. The peak intensity ratio R=[M+H]+/[M+H-H2O]+ manifested the stereochemical differentiation of alkaloids at position 1.

Alkaloids↗
PubMed2003

Norditerpenoid alkaloids from the processed tubers of Aconitum carmichaeli.

Four new and five known norditerpenoid alkaloids were isolated from the processed tubers of Aconitum carmichaeli. The new alkaloids are 14-O-cinnamoylneoline (3), 14-O-anisoylneoline (4) 14-O-veratroylneoline (5), and lipo-14-O-anisoylbikhaconine (8). The known alkaloids are neoline (1), 14-O-acetylneoline (2), foresaconitine (6), crassicauline A (7), and lipohypaconitine (9). Alkaloids 2, 6, and 7 were isolated from this plant for the first time. The structures of the new alkaloids were established by spectroscopic and chemical methods.

Aconitum↗
PubMed2006

Metabolic engineering of cell cultures versus whole plant complexity in production of bioactive monoterpene indole alkaloids: recent progress related to old dilemma.

Monoterpene indole alkaloids (MIAs) are a large class of plant alkaloids with significant pharmacological interest. The sustained production of MIAs at high yields is an important goal in biotechnology. Intensive effort has been expended toward the isolation, cloning, characterization and transgenic modulation of genes involved in MIA biosynthesis and in the control of the expression of these biosynthesis-related genes. At the same time, considerable progress has been made in the detailed description of the subcellular-, cellular-, tissue- and organ-specific expressions of portions of the biosynthetic pathways leading to the production of MIAs, revealing a complex picture of the transport of biosynthetic intermediates among membrane compartments, cells and tissues. The identification of the particular environmental and ontogenetic requirements for maximum alkaloid yield in MIA-producing plants has been useful in improving the supply of bioactive molecules. The search for new bioactive MIAs, particularly in tropical and subtropical regions, is continuously increasing the arsenal for therapeutic, industrially and agriculturally useful molecules. In this review we focus on recent progress in the production of MIAs in transgenic cell cultures and organs (with emphasis on Catharanthus roseus and Rauvolfia serpentina alkaloids), advances in the understanding of in planta spatial-temporal expression of MIA metabolic pathways, and on the identification of factors capable of modulating bioactive alkaloid accumulation in nontransgenic differentiated cultures and plants (with emphasis on new MIAs from Psychotria species). The combined use of metabolic engineering and physiological modulation in transgenic and wild-type plants, although not fully exploited to date, is likely to provide the sustainable and rational supply of bioactive MIAs needed for human well being.

Biotechnology↗
PubMed2006

Analgesic activity of the methanolic extract and total alkaloids of Glaucium paucilobum.

The species of Glaucium have been used in Iranian herbal medicine as laxative, hypnotic, narcotic, and antidiabetic agents and also in the treatment of dermatitis. The analgesic activity of the aerial parts of Glaucium Freyn (Papaveraceae), a native plant of Iran, were studied using formalin, hot plate, and writhing tests in rodents. The methanolic extract and total alkaloids of Glaucium paucilobum caused graded inhibition of both phases of formalin-induced pain. In the hot plate test, i.p. administration of G. paucilobum extract at the doses of 50-90 mg/kg and total alkaloids at the dose of 10-60 mg/kg significantly raised the pain threshold at an observation time of 30 min in comparison with control (p < 0.001). In the writhing test, the extract at the doses of 30-90 mg/kg and total alkaloids at the doses of 10-60 mg/kg produced a significant decrease in the number of writhings in comparison with the control group (p < 0.001). The methanolic extract and total alkaloids of G. paucilobum, at antinociceptive doses, did not affect the motor coordination of animals when assessed in the rotarod model. The results showed that analgesic activity of this plant may be related partly to the alkaloids.

Acetic Acid↗
PubMedDate not supplied

Pyrrolizidine alkaloids from Echium rauwolfii and Echium horridum (Boraginaceae).

Echimidine was isolated from Echium rauwolfii and Echium horridum and identified by MS, 1H- and 13C NMR as a major alkaloid. In addition, structures of 12 minor alkaloids were inferred from GLC and GLC-MS analyses: 7-angeloylretronecine, 7-tigloylretronecine, lycopsamine, 7-acetyllycopsamine, uplandicine, 7-angeloyllycopsamine, 7-tigloyllycopsamine, tigloyl isomer of echimidine, 7-angeloyl-9-(2-methylbutyryl)retronecine, 7-tigloyl-9-(2-methylbutyryl)retronecine, 7-angeloyl-9-(2,3-dihydroxybutyryl)retronecine, and 7-tigloyl-9-(2,3-dihydroxybutyryl)retronecine. Both species had similar alkaloid profiles. Alkaloid extracts exhibited antibacterial effects with a MIC of 1.7 mg/ml in E. coli. Microscopic examination of E. coli treated with different subtoxic alkaloid concentrations (13-52 micrograms/ml) revealed extensive filamentation.

Anti-Bacterial Agents↗
PubMedDate not supplied

Quinolizidine alkaloid profiles of Lupinus varius orientalis, L. albus albus, L. hartwegii, and L. densiflorus.

Alkaloid profiles of two Lupinus species growing naturally in Egypt (L. albus albus [synonym L. termis], L. varius orientalis) in addition to two New World species (L. hartwegii, L. densiflorus) which were cultivated in Egypt were studied by capillary GLC and GLC-mass spectrometry with respect to quinolizidine alkaloids. Altogether 44 quinolizidine, bipiperidyl and proto-indole alkaloids were identified; 29 in L. albus, 13 in L. varius orientalis, 15 in L. hartwegii, 6 in L. densiflorus. Some of these alkaloids were identified for the first time in these plants. The alkaloidal patterns of various plant organs (leaves, flowers, stems, roots, pods and seeds) are documented. Screening for antimicrobial activity of these plant extracts demonstrated substantial activity against Candida albicans, Aspergillus flavus and Bacillus subtilis.

Alkaloids↗
PubMedDate not supplied

Alkaloid profile of leaves and seeds of Lupinus hintonii C. P. Smith.

L. hintonii C. P. Smith grows in the Central Highland forests of Mexico at altitudes between 2800 m to 3200 m above see level. Members of the genus Lupinus produce quinolizidine alkaloids as main chemical defensive compounds against herbivores. Surprisingly alkaloid profiles are rather constant within this species, while substantial variation was found when compared to morphologically closely related other taxa. As part of a phytochemical project on Mexican wild lupins, we report on the alkaloid profiles of seeds and leaves of L. hintonii. 19 alkaloids could be identified by capillary GLC-MS. Six major alkaloids occurred in leaves and seeds: 13-hydroxylupanine (28% and 45% respectively), tetrahydrorhombifoline (31% and 23% respectively), angustifoline (2% and 4% respectively), lupanine (7% and 5% respectively), 13alpha-tigloyloxylupanine (19% and 5% respectively) and 4alpha-angeloyl-3beta-hydroxylupanine (9% and 2%). This chemical pattern resembles that of the North American lupin L. floribundus.

Alkaloids↗
PubMedDate not supplied

Alkaloids in Bulgarian Pancratium maritimum L.

A GC/MS analysis of alkaloids from leaves, bulbs and roots of Pancratium maritimum was performed. From the identified 16 alkaloids, 5 alkaloids were reported for the first time for this plant. Several compounds with pharmacological activity were found. Haemanthamine was main alkaloid in the leaves and bulbs whereas galanthane was found to be main alkaloid in roots.

Alkaloids↗
PubMedDate not supplied

In vitro organogenesis and alkaloid accumulation in Datura innoxia.

The kinetics of tropane alkaloids accumulation in different organs such as roots, leaves, stems, flowers and seeds of Datura innoxia was investigated by GC-MS. Twenty-six tropane alkaloids were detected. The ester derivatives of tropine (3alpha-tigloyloxytropine and 3-tigloyloxy-6-hydroxytropine) are the major compounds. Undifferentiated callus were established from the stem explants of Datura innoxia using Murashige and Skoog (MS) medium supplied with 6-benzylaminopurine (BA, 1 mg l(-10) and indole-3-acetic acid (IAA, 0.5 mg l(-1)) in combination for 6 weeks. Callus differentiation was initiated by subculture onto solid MS medium, free from hormones, for more than 10 months. Initially, shoots were formed after four weeks from subculture. Further subculturing in basal MS medium without growth regulators initiated the rooting of a shooty callus after 6 weeks. Investigation of the alkaloid content of the unorganized and organized callus revealed that callus (either green or brown) yielded only trace amounts of alkaloids. On the other hand, re-differentiated shoots contained mainly scopolamine while re-differentiated roots biosynthesized hyoscyamine as the main alkaloid.

Alkaloids↗
PubMed2002

Piperidine alkaloids in sitka spruce with varying levels of resistance to white pine weevil (Coleoptera: Curculionidae).

Our objective was to evaluate piperidine alkaloids as potential resistance factors in Sitka spruce, Picea sitchensis (Bong.) Carr, at risk to attack by white pine weevils, Pissodes strobi (Peck). We sampled 72 seedlings in each of two replicated field trials in the Oregon Coast Range. The seedlings were grown from open-pollinated seeds of putatively "resistant" or "susceptible" off-site parental sources. Alkaloid concentrations in bark and foliage were measured in previously unattacked trees at the time of weevil host selection. Leader mortality was evaluated in the fall to gauge actual resistance in the sample trees. Five families had < or = 25% topkill and seven sustained >50% topkill. Alkaloid concentrations differed significantly among families, but the major alkaloids did not appear to be functionally linked with topkill or useful indicators of resistance. However, our study design did not address all potential resistance mechanisms. Therefore, before concluding that Sitka spruce alkaloids have no influence on white pine weevils, complementary laboratory and field experiments are needed.

Alkaloids↗
PubMed2005

If you've got it, flaunt it: ingested alkaloids affect corematal display behavior in the salt marsh moth, Estigmene acrea.

Plant-derived pyrrolizidine alkaloids play an important role in the biology of the salt marsh moth, Estigmene acrea (Lepidoptera: Arctiidae). They are phagostimulants for larvae and they stimulate the growth and development of adult male androconial organs called coremata. In this study, we have shown that the pyrrolizidine alkaloid monocrotaline N-oxide (MNO) fed to larvae also affects the courtship behavior of adult males. Males fed a diet containing MNO display their coremata while males fed on the same diet without alkaloid rarely display. This explains why it has been difficult to replicate field observations of the "lekking" behavior of this species in the laboratory where animals are frequently raised on commercially available diets devoid of alkaloids. Corematal inflation was observed in isolated males and in laboratory leks. The effect of larvae feeding on pyrrolizidine alkaloid on the reproductive behavior of adults suggests that this substance may modify the development of the moth's nervous system and contribute to their unusual dual mating strategies. MNO was also shown to be an adequate precursor for the production of the courtship pheromone hydroxydanaidal.

Animals↗
PubMed2003

Current progress in the chemistry and pharmacology of akuammiline alkaloids.

Akuammiline alkaloids are a family of monoterpene indole alkaloids of renewed medicinal interest. These bases act as ligands for a heterogeneous group of molecular targets and, consequently, display a wide variety of pharmacological activities. For example, pseudoakuammigine (2) exhibits opioid activity in vivo, echitamine (4) has been reported to have promising cytotoxic activity, and corymine (121) behaves as an antagonist of the glycine receptor. Oddly enough, these alkaloids have not raised enough interest in the organic synthesis community, remaining inaccessible; even the entry to their pentacyclic framework continues elusive. Recently, several akuammiline bases have been isolated and identified including bisindole alkaloids, such as vingramine (103) or rausutrine (110), which incorporate akuammiline-type subunits. This review covers the advances in the chemistry and pharmacology of akuammiline alkaloids reported within the last ten years.

Animals↗
PubMed1992

Comparison of larkspur alkaloid extract and lithium chloride in maintaining cattle aversion to larkspur in the field.

Lithium chloride (LiCl) and larkspur (Delphinium barbeyi) alkaloid extract were compared in their effect as an emetic to create taste aversions to fresh larkspur. They were further compared in the field to determine whether the indigenous larkspur alkaloids were more effective in maintaining the aversion when conditioned cattle were subjected to the social pressure (social facilitation) of control cattle eating larkspur. Taste aversions were produced in two groups of 1-yr-old cattle by offering fresh larkspur and then gavaging with either LiCl at 200 mg/kg of BW or larkspur alkaloid extract at 1.1 to 1.6 mL/kg of BW. The third group (control) was gavaged with water. The alkaloid group was slower to form an aversion than the lithium group, requiring four doses compared with two doses. All groups were then taken to larkspur-infested rangeland to test the aversion in the field. In the first field trial in which groups grazed separately, both aversion-induced groups generally abstained from eating larkspur. In the second trial in which all groups grazed together, both aversion-induced groups consumed less than half as much larkspur as the controls, but neither group abstained completely. Larkspur alkaloids did not maintain the aversion to larkspur to a greater degree than did LiCl when aversion-induced cattle were subjected to social facilitation.

Alkaloids↗
PubMed1996

Assessment of the mitogenic potential of the alkaloids produced by endophyte (Acremonium coenophialum)-infected tall fescue (Festuca arundinacea) on bovine vascular smooth muscle in vitro.

The objective of these experiments was to test the hypothesis that the major alkaloid classes found in endophyte-infected tall fescue could act as growth promoters for vascular smooth muscle. Bovine vascular smooth muscle cells (VSMC) from the dorsal metatarsal artery were grown in vitro and exposed to five concentrations (10(-6), 10(-8), 10(-9), 10(-11) and 0 M) of ergonovine, alpha-ergocryptine, ergovaline, and N-acetyl loline for 48 h. The mitogenic potential of the alkaloids was tested on both actively growing cells (serum fed, 10% fetal bovine serum) and quiescent cells (serum starved, 0.1% serum) to assess the need for serum constituents for alkaloid induced growth or toxicity. Ergonovine stimulated (P < .07) VSMC growth at 10(-6) M concentration in growing and quiescent culturs and at 10(-8) M concentration in quiescent cultures. alpha-Ergocryptine stimulated (P < .01) growth at 10(-6) M concentration in growing cultures and at 10(-8) and 10(-9) M concentrations in quiescent cultures. Ergovaline exhibited a dual activity on the growth of VSMC in culture, stimulating (P = .06) growth of quiescent cells at 10(-9) M concentration but inhibiting (P < .05) growth of growing cultures at concentrations of 10(-6) and 10(-9) M. This duality of activity was also noted for N-acetyl loline: N-acetyl loline stimulated (P < .05) growth of quiescent cultures at concentrations of 10(-8), 10(-9), and 10(-11) M but inhibited (P < .05) growth of growing cultures at concentrations of 10(-8) and 10(-9) M. The growth effects of the alkaloids in vitro on VSMC support in part the hypothesis that the alkaloids may contribute to the vascular complications noted in cattle grazing endophyte-infected tall fescue through hyperplasia of the intima. This would result in a decreased luminal diameter of the blood vessels and a resultant decrease in blood flow to the afflicted tissues. The diminished blood flow to tissues would result in tissue death and reduced ability to dissipate heat.

Acremonium↗
PubMedDate not supplied

Binding of bisbenzylisoquinoline alkaloids to phosphatidylcholine vesicles and alveolar macrophages: relationship between binding affinity and antifibrogenic potential of these drugs.

A group of bisbenzylisoquinoline alkaloids has been shown to exhibit various degrees of effectiveness in preventing silica-induced fibrosis in animal models. The objective of the present study was to characterize the binding of several of these alkaloids to phosphatidylcholine vesicles and rat alveolar macrophages using fluorometric and equilibrium dialysis methods, respectively. The lipid binding affinity of these alkaloids was found to depend upon several structural factors including hydrophobic substitutions, chiral configurations, and double oxygen bridge-restricted confirmation of the benzylisoquinoline moieties. Tetrandrine, which is a highly effective agent in preventing fibrosis, showed strong binding to both lipid vesicles and alveolar macrophages. In contrast, certain analogues of tetrandrine such as curine and tubocurine, which have little or no effect on silicosis, exhibited only weak binding to lipid vesicles and almost no binding to cells. The moderate binding affinity of fangchinoline to vesicles and cells corresponded to a moderate effectiveness of the compound as an antifibrogenic agent. Methoxyadiantifoline, an alkaloid of unknown antifibrogenic potential, also exhibited high binding affinities for lipid and cells. In conclusion, the results of these studies indicate that alveolar macrophages exhibit large binding capacities for certain members of this class of bisbenzylisoquinoline alkaloids. A positive correlation was observed between binding affinity to alveolar macrophages and the reported antifibrotic potency of these compounds. These data also suggest that the ability of these drugs to interact with alveolar macrophages may be a key step in inhibition of the progression of silica-induced pulmonary disease.

1,2-Dipalmitoylphosphatidylcholine↗
PubMed2026

Integrated Metabolomic and Transcriptomic Analysis Reveals Tissue-Specific Secondary Metabolic Differentiation and Indole Alkaloid Accumulation in Evodia rutaecarpa.

Evodia rutaecarpa is a valuable medicinal plant, yet its non-medicinal tissues remain largely underexplored. Here, we integrated ultra-performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS)-based widely targeted metabolomics and RNA sequencing (RNA-seq) transcriptomics to systematically profile the metabolic and transcriptional landscapes of roots, stems, leaves, and flowers of Evodia rutaecarpa (Juss.) Benth. Our aim was to characterize tissue-specific metabolic differentiation and its underlying transcriptional regulatory mechanisms. Metabolomic analysis, employing principal component analysis (PCA) and orthogonal partial least squares-discriminant analysis (OPLS-DA) with robust model parameters (R2Y > 0.9, Q2 > 0.5), identified 3090 differential metabolite features (variable importance in projection, VIP > 1.0; p < 0.05) across the four tissues, which exhibited distinct tissue-specific clustering patterns. Integrated Kyoto Encyclopedia of Genes and Genomes (KEGG) enrichment analysis and weighted gene co-expression network analysis (WGCNA) revealed that roots specifically accumulated quinolone alkaloids and flavonoid glycosides, accompanied by the coordinated upregulation of genes involved in flavonoid and phenylpropanoid biosynthetic pathways. In contrast, stems, leaves, and flowers were enriched in indole alkaloids (evodiamine and rutaecarpine) and volatile oil precursors, with concurrent upregulation of genes involved in tryptophan metabolism and indole alkaloid biosynthesis (e.g., tryptophan decarboxylase, TDC; s N-methyltransferase, NMT). Notably, leaves and flowers displayed particularly high accumulation levels of these bioactive alkaloids, suggesting their potential as alternative sources for industrial and pharmaceutical applications. WGCNA further identified multiple transcription factors and structural gene modules tightly correlated with evodiamine accumulation, offering promising candidate regulators for future biosynthetic pathway engineering. Collectively, this multi-omics integration study systematically elucidates the tissue-partitioned secondary metabolism of Evodia rutaecarpa (Juss.) Benth. and provides a solid scientific foundation for full-plant resource utilization, targeted development of non-medicinal tissues, and future metabolic engineering of indole alkaloid production.

Evodia rutaecarpa↗