Amaryllidaceae Alkaloids
Liliaceae
Lycoris
Alkaloids
Allium
In vitro activities of two antimitotic compounds, pancratistatin and 7-deoxynarciclasine, against Encephalitozoon intestinalis, a microsporidium causing infections in humans. (1/54)
The antiparasitic effect of a collection of compounds with antimitotic activity has been tested on a mammalian cell line infected with Encephalitozoon intestinalis, a microsporidian causing intestinal and systemic infection in immunocompromised patients. The antiparasitic effect was evaluated by counting the number of parasitophorous vacuoles detected by immunofluorescence. Out of 526 compounds tested, 2 (pancratistatin and 7-deoxynarciclasine) inhibited the infection without affecting the host cell. The 50% inhibitory concentrations (IC(50)s) of pancratistatin and 7-deoxynarciclasine for E. intestinalis were 0.18 microM and 0.2 microM, respectively, approximately eightfold lower than the IC(50)s of these same compounds against the host cells. Electron microscopy confirmed the gradual decrease in the number of parasitophorous vacuoles and showed that of the two life cycle phases, sporogony was more sensitive to the inhibitors than merogony. Furthermore, the persistence of meronts in some cells apparently devoid of sporonts and spores indicated that the inhibitors block development rather than entry of the parasite into the host cell. The occurrence of binucleate sporoblasts and spores suggests that these inhibitors blocked a specific phase of cell division. (+info)Lycobetaine acts as a selective topoisomerase II beta poison and inhibits the growth of human tumour cells. (2/54)
The phenanthridine alkaloid lycobetaine is a minor constituent of Amaryllidaceae. Inhibition of cell growth was studied in the clonogenic assay on 21 human tumour xenografts (mean IC(50) = 0.8 microM). The growth of human leukaemia cell lines was also potently inhibited (mean IC(50) = 1.3 microM). Athymic nude mice, carrying s.c. implanted human gastric tumour xenograft GXF251, were treated i.p. with lycobetaine for 4 weeks, resulting in a marked tumour growth delay. Lycobetaine was found to act as a specific topoisomerase II beta poison. In the presence of calf thymus DNA, pure recombinant human topoisomerase II beta protein was selectively depleted from SDS-gels, whereas no depletion of topoisomerase II alpha protein was observed. In A431 cells immunoband-depletion of topoisomerase II beta was induced, suggesting stabilization of the covalent catalytic DNA-intermediate in living cells. It is reasonable to assume that this mechanism will cause or at least contribute significantly to the antitumour activity. (+info)Inhibition of cell cycle progression through specific phase by pancratistatin derivatives. (3/54)
Pancratistatin derivatives, 1-O-(3-hydroxybutyryl)pancratistatin (HBP) and 1-O-(3-O-beta-D-glucopyranosylbutyryl)pancratistatin (GBP), showed strong cytostatic activity against rat embryo fibroblast 3Y1 at concentrations less than 1 microM. When the effect on cell cycle progression was examined in 3Y1 fibroblasts arrested at G0/G1 phase by serum deprivation, HBP, GBP, and pancratistatin inhibited the progression of 3Y1 fibroblasts from G0/G1 to S phase. In addition, when the effect on cell cycle progression was studied in 3Y1 fibroblasts synchronized at late G1/early S phases by treating with hydroxyurea, HBP blocked further progression through S phase, while GBP and pancratistatin did not affect the progression, but retarded it. On the other hand, when the effect of HBP and GBP on the progression was evaluated in promyelocytic leukemia HL-60RG cells synchronized at G0/G1 phase, the cells did not progress into S phase and accumulated in sub G0/G1 phase, which indicated apoptotic cells. These findings suggest that of Amaryllidaceae alkaloids, HBP blocks the progression of cell cycle at least at G0/G1 and S phases and GBP does at least at G0/G1 phase, resulting in apoptosis induction in tumor cells. (+info)Isolation of the acetylcholinesterase inhibitor ungeremine from Nerine bowdenii by preparative HPLC coupled on-line to a flow assay system. (4/54)
In an attempt to isolate the active compound while detecting acetylcholinesterase inhibitory activity, we applied a fluorometric flow assay system to an on-line coupled preparative HPLC. The MeOH extract of Nerine bowdenii showed a strong inhibitory peak in the on-line assay, and the active compound was isolated by CPC and HPLC. It was identified as ungeremine by analysis of its (1)H-NMR, 2D-NMR, and NOESY spectra. The assignment of the active N. bowdenii constituent was also confirmed by co-TLC, co-HPLC, and co-(1)H-NMR experiments using an authentic sample of synthetic ungeremine. The IC(50) value of ungeremine was 0.35 microM, showing stronger activity than galanthamine (2.2 microM). (+info)Localization of ascorbic acid, ascorbic acid oxidase, and glutathione in roots of Cucurbita maxima L. (5/54)
To understand the function of ascorbic acid (ASC) in root development, the distribution of ASC, ASC oxidase, and glutathione (GSH) were investigated in cells and tissues of the root apex of Cucubita maxima. ASC was regularly distributed in the cytosol of almost all root cells, with the exception of quiescent centre (QC) cells. ASC also occurred at the surface of the nuclear membrane and correspondingly in the nucleoli. No ASC could be observed in vacuoles. ASC oxidase was detected by immunolocalization mainly in cell walls and vacuoles. This enzyme was particularly abundant in the QC and in differentiating vascular tissues and was absent in lateral root primordia. Administration of the ASC precursor L-galactono-gamma-lactone markedly increased ASC content in all root cells, including the QC. Root treatment with the ASC oxidized product, dehydroascorbic acid (DHA), also increased ASC content, but caused ASC accumulation only in peripheral tissues, where DHA was apparently reduced at the expense of GSH. The different pattern of distribution of ASC in different tissues and cell compartments reflects its possible role in cell metabolism and root morphogenesis. (+info)Effects of lycorine on HL-60 cells via arresting cell cycle and inducing apoptosis. (6/54)
As a natural anti-cancer alkaloid extracted from Amaryllidaceae, lycorine shows various biological effects on tumor cells. The survival rate of HL-60 cells exposed to lycorine was decreased in a dose-dependent manner with 1 microM as the 50% inhibitory concentration (IC50), cell growth was slowed down by arresting cell cycle at G2/M phase, and cell regeneration potential was inhibited. HL-60 cells exhibited typical apoptotic morphological changes, apoptotic DNA "ladder" pattern, and sub-G1 peak in cell phase distribution, showing apoptosis of HL-60 cells. To further understand the apoptotic molecular mechanism of lycorine on HL-60 cells, caspase activity was tested by colorimetric assay, and the expression of Bcl-2 and Bax proteins was examined by Western blotting. The increase of caspase-8, -9, -3 activities demonstrated that caspase was a key mediator of apoptotic pathways induced by lycorine. Under-expression of Bcl-2 and increase of Bax:Bcl-2 ratio showed that Bcl-2 family proteins were involved in apoptosis. Our finding suggests that lycorine can suppress leukemia growth and reduce cell survival via arresting cell cycle and inducing apoptosis of tumor cells. (+info)Antineoplastic agents. 553. The Texas grasshopper Brachystola magna. (7/54)
Bioassay (P388 lymphocytic leukemia cell line and human cancer cell lines) guided separation of an extract prepared from the previously chemically uninvestigated Texas grasshopper Brachystola magna led to isolation of the cancer cell growth inhibitory pancratistatin (1), narciclasine (2), and ungeremine (3). Pancratistatin (1) was first isolated from the bulbs of Hymenocallis littoralis), and the original crystal structure was deduced by X-ray analysis of a monomethyl ether derivative. In the present study pancratistatin (1) was isolated from an extract of B. magna, which led to the X-ray crystal structure of this anticancer drug. Since isoquinoline derivatives 1-3 are previously known only as constituents of amaryllidaceous plants, some of the interesting implications of their rediscovery in the grasshopper B. magna that does not appear to utilize amaryllis family plants were discussed. (+info)An efficient synthesis of (+/-)-Lycoricidine featuring a Stille-IMDAF cycloaddition cascade. (8/54)
[reaction: see text] A highly efficient total synthesis of (+/-)-Lycoricidine is described. The synthesis features the ready preparation of the Lycoricidine skeleton by a Stille-IMDAF cycloaddition cascade. The resulting cycloadduct is then used for the stereocontrolled installation of the other functionality present in the C-ring of the target molecule. (+info)Amaryllidaceae alkaloids are a type of naturally occurring chemical compounds that are found in plants belonging to the Amaryllidaceae family, which includes amaryllis, snowdrop, and daffodil species. These alkaloids have diverse pharmacological activities and have been studied for their potential medicinal properties. Some well-known Amaryllidaceae alkaloids include lycorine, galanthamine, and haemantamine.
Lycorine has been shown to have antiviral, antimalarial, and anti-cancer properties. Galanthamine is a reversible acetylcholinesterase inhibitor that has been used in the treatment of Alzheimer's disease. Haemantamine has been studied for its potential as an anti-arrhythmic agent.
It is important to note that while Amaryllidaceae alkaloids have shown promise in preclinical studies, further research is needed to determine their safety and efficacy in humans before they can be approved for medical use. Additionally, some of these alkaloids can be toxic in high concentrations, so it is important to exercise caution when handling or consuming plants that contain them.
I'm sorry for any confusion, but "Liliaceae" is not a medical term. It is a taxonomic category in botany, specifically it is the family name for plants that include lilies, tulips, and related species. In a medical context, you might be referring to the specific plant species themselves, or possibly the allergic reactions some people can have to the pollen of these plants. If you have any more specific questions about botanical terms in a medical context, I'd be happy to try and help further.
"Lycoris" is a term that pertains to a genus of herbaceous, flowering plants in the amaryllis family (Amaryllidaceae). These plants are native to eastern and southern Asia, and they are known for their attractive, funnel-shaped flowers that bloom in late summer or early fall.
However, it seems that you may be looking for a medical definition of "Lycoris." In this context, there is no widely recognized medical term called "Lycoris." It's possible that you might be referring to "lycorine," which is a toxic alkaloid found in several plants of the Amaryllidaceae family, including those of the genus Lycoris.
Lycorine has shown potential as an anticancer agent in laboratory studies, but its clinical use is not established due to its high toxicity and limited research on its safety and efficacy in humans. It's important to note that lycorine should only be used under the supervision of medical professionals for experimental or therapeutic purposes.
In the context of medicine, particularly in psychiatry and psychology, "Narcissus" or "Narcissistic" is not typically used as a standalone medical definition. However, it is associated with Narcissism and Narcissistic Personality Disorder (NPD).
Narcissism is a personality trait characterized by a grandiose sense of self-importance, a lack of empathy for others, a need for excessive admiration, and feelings of entitlement. It's named after the Greek mythological figure Narcissus, who fell in love with his own reflection.
Narcissistic Personality Disorder (NPD) is a mental disorder characterized by these narcissistic traits, but to such an extent that they cause significant impairment in personal relationships and professional life.
Please note that only a qualified healthcare professional can diagnose such conditions.
Alkaloids are a type of naturally occurring organic compounds that contain mostly basic nitrogen atoms. They are often found in plants, and are known for their complex ring structures and diverse pharmacological activities. Many alkaloids have been used in medicine for their analgesic, anti-inflammatory, and therapeutic properties. Examples of alkaloids include morphine, quinine, nicotine, and caffeine.
'Allium' is a genus of plants that includes several species which are commonly used as vegetables or spices, such as onions, garlic, leeks, shallots, and chives. These plants are characterized by their distinctive strong smell and taste, which are caused by sulfur-containing compounds. They have been widely used in traditional medicine for their potential health benefits, including antibacterial, antiviral, and anti-inflammatory properties.
Phenanthridines are a class of heterocyclic aromatic organic compounds that consist of a phenanthrene core (a polycyclic aromatic hydrocarbon made up of three benzene rings) fused with a pyridine ring (a six-membered ring containing five carbon atoms and one nitrogen atom). They have the chemical formula C12H9N.
Phenanthridines are important in medicinal chemistry because some of their derivatives exhibit various biological activities, such as antitumor, antibacterial, antifungal, anti-inflammatory, and antiviral properties. Some well-known phenanthridine derivatives include the chemotherapeutic agents amsacrine and doxorubicin, which are used to treat various types of cancer.
It's worth noting that while phenanthridines have important medical applications, they can also be toxic or harmful if not handled properly. Therefore, it's essential to follow proper safety protocols when working with these compounds in a laboratory setting.
4-Methylcatechol
Scadoxus puniceus
Homolycorine
Pancratistatin
Hamayne
Aza-Cope rearrangement
Galantamine total synthesis
Lycorine
Narciclasine
Haemanthamine
Zephyranthes rosea
Zephyranthes robusta
Zephyranthes carinata
Polychlorinated carbazoles
Hippeastrum
Narcissus asturiensis
Galantheae
Amaryllidaceae
Narcissus (plant)
Brunsvigia bosmaniae
Nina Rønsted
Galanthus
Alkaloid
Lycoris radiata
Boophone
Babesiosis
Hymenocallis pimana
Lapiedra
Families of Asparagales
Taxonomy of Narcissus
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Narcissus3
- The Amaryllidaceae alkaloids are produced by species of Amaryllidaceae including Narcissus spp. (frontiersin.org)
- The cytochrome P45O activities of the naturally occurring Amaryllidaceae alkaloid narciclasine (3), isolated from Narcissus pseudonarcissus, and synthetic derivative trans-dihydronarciclasine (5) are reported. (mcmaster.ca)
- Simultaneous quantitative analysis of biologically important Amaryllidaceae alkaloids in Narcissus tazetta L. subsp. (jrespharm.com)
Phenanthridine Amaryllidaceae alkaloid2
- Lycorine, a medicinal plant-derived phenanthridine Amaryllidaceae alkaloid [ 4 ], seems to possess such properties for PCa drug research and development. (oncotarget.com)
- Lycorine, the main phenanthridine Amaryllidaceae alkaloid, exhibits significant antitumor activity in cancer cells that display resistance to proapoptotic stimuli: an investigation of structure-activity relationship and mechanistic insight. (ac.be)
Lycorine5
- Lycorine, a natural alkaloid extracted from the Amaryllidaceae plant family, has been reported to exhibit a wide range of physiological effects, including the potential effect against cancer. (oncotarget.com)
- DI-fusion Holdings: Lycorine, the main phenanthridine Amaryllidaceae. (ac.be)
- 6. Li A # , Du Z # , Liao M, Feng Y, Ruan H*, Jiang H.* Discovery and characterisation of lycorine-type alkaloids in Lycoris spp. (tjmu.edu.cn)
- The bulb contains alkaloids, notably lycorine and crinamine[283]. (pfaf.org)
- Ridderstjerne is said to contain lycorine and other alkaloids that can be toxic to your dog. (wagwalking.com)
Galanthus2
- Alkaloid Profiling of Galanthus woronowii Losinsk. (jrespharm.com)
- The alkaloid galanthamine, first isolated from Galanthus woronowii (Amaryllidaceae), is approved by the FDA for the palliative treatment of mild to moderate Alzheimer's disease due to its acetylcholinesterase (AChE) inhibitory activity. (inra.fr)
Genera1
- It is important to note that brunsvigias, like all the other genera of Amaryllidaceae, have a very high alkaloid content, and therefore can be extremely toxic. (sanbi.org)
Profiling2
- Alkaloid Profiling and Cholinesterase Inhibitory Potential of Crinum x amabile Donn. (ub.edu)
- In conclusion, the results of this first alkaloid profiling of the Rauhia species indicate that R. multiflora is an important natural source of galanthamine-type structures and could be used as a model for the development of biotechnological tools necessary to advance the sustainable production of galanthamine. (inra.fr)
Norbelladine2
- Members of the monocot subfamily Amaryllidoideae present a unique type of alkaloids, the norbelladine alkaloids, which are 4-methylcatechol derivatives combined with tyrosine. (wikipedia.org)
- Main conclusion: Transcriptome analysis of Leucojum aestivum led to the identification of 50 key genes associated with Amaryllidaceae alkaloid biosynthesis including norbelladine synthase which localized in the cytosol and catalyzed norbelladine formation. (tau.ac.il)
Species6
- A toxic alkaloid found in Amanita muscaria (fly fungus) and other fungi of the Inocybe species. (harvard.edu)
- Obtaining this active pharmaceutical ingredient, still sourced on an industrial scale from the Amaryllidaceae species, is a challenge for pharmaceutical companies due to its low natural yield and the high cost of its synthesis. (inra.fr)
- The aim of this work was to determine the alkaloid profile of three different Rauhia (Amaryllidaceae) species collected in Peru, and to assess the potential application of their extracts for the treatment of Alzheimer's disease. (inra.fr)
- Alkaloids extracted from various species of Cinchona. (nih.gov)
- In the same species, the amount of alkaloids is different in different organs of the plant and, moreover, varies depending on the phase of vegetation and environmental conditions. (medprep.info)
- Usually, the sum of alkaloids in all Solanaceae species includes both main alkaloids, but in all possible proportions, one of them prevails. (medprep.info)
Biosynthesis4
- Central to the biosynthesis of the majority of these alkaloids is a C-C phenol-coupling reaction that can have para-para', para-ortho' , or ortho-para' regiospecificity. (frontiersin.org)
- The discovery of CYP96T1 is of special interest because it catalyzes the first major branch in Amaryllidaceae alkaloid biosynthesis. (frontiersin.org)
- The limited supply of some Amaryllidaceae alkaloids and diversity of biological activities make the biosynthesis of Amaryllidaceae alkaloids a topic of interest for biotechnology. (frontiersin.org)
- The diversity of these alkaloids depends on which amino alcohol was formed in the process of biosynthesis from tropane (tropine, scopine or ecgonine) and with what organic acids these amino alcohols subsequently formed esters. (medprep.info)
Abstract1
- Abstract: The Amaryllidaceae alkaloids (AAs) are a large group of plant specialized metabolites, which are known for their biological activities. (tau.ac.il)
Galanthamine1
- Computational experiments were carried out on the activity of the galanthamine-type alkaloids identified in R. multiflora toward five different human AChE structures. (inra.fr)
Cholinesterase1
- Amaryllidaceae alkaloids are of main interest because of their cholinesterase inhibition potential, which is the main palliative treatment available for this disease. (inra.fr)
Isolation2
- Thus, this study describes the isolation of the alkaloids of this plant, and their inhibition of the enzymes acetylcholinesterase (eeAChE) and butyrylcholinesterase (eqBuChE), being galanthine the main component. (inra.fr)
- in the factory isolation of the alkaloid from plants, it is traditionally obtained its inactive racemate - atropine in the form of a salt - Atropini sulfas. (medprep.info)
Plant1
- The plant contains alkaloids with fused pyrrolidine and piperidine rings (derivatives of tropine, scopine and ecgonine). (medprep.info)
Family1
- Ridderstjerne belongs to the Amaryllidaceae family and to the genus Hippeastrum spp. (wagwalking.com)
Naturally1
- Alijevic O, McHugh D, Rufener L, Mazurov A, Hoeng J, Peitsch M ( 2020 ) An electrophysiological characterization of naturally occurring tobacco alkaloids and their action on human alpha4beta2 and alpha7 nicotinic acetylcholine receptors. (multichannelsystems.com)
Extracts2
- The alkaloids were identified by gas chromatography coupled to mass spectrometry (GC-MS), and the AChE inhibitory activity of the extracts was analyzed. (inra.fr)
- Tests on pure mesembrine hydrochloride substantiated that sunlight and aqueous conditions are required to facilitate this transformation and obtain the active alkaloids.Patnala 2009 This traditional fermentation removes harmful oxalates while retaining the active alkaloids.Smith 1998 In extracts, the alkaloids are more bioavailable across the intestinal, buccal, and mucosal tissues. (proessencekanna.com)
Derivatives1
- Other tropane derivatives, found in the same plants in small quantities, as well as liquid and volatile pyridine derivatives, often associated with tropane alkaloids, are of no practical importance. (medprep.info)
Biological1
- Alkaloids from all major structural classes of Amaryllidaceae alkaloids have biological activities. (frontiersin.org)
Pharmaceutical1
- Some of these alkaloids have potential pharmaceutical applications or are already established medicines. (frontiersin.org)
Main2
- Alkaloids are called natural nitrogen-containing compounds of the main character, formed in plants. (medprep.info)
- Of natural pharmacologically active substances, alkaloids are the main group from which modern medicine draws the largest number of highly effective drugs. (medprep.info)
Plants2
- According to world literature, by the end of the past decade, the number of alkaloids isolated from the higher plants of the Earth's flora exceeded 5000. (medprep.info)
- According to modern concepts, alkaloid-bearing plants make up 10% of the entire world flora. (medprep.info)
Found1
- Mesembrine, a phenylethylamine alkaloid, was first extracted from S. tortuosum in 1898.Smith 1998 It is the major alkaloid found in S. tortuosum, occurring at levels of 0.3% in the leaves and 0.86% in the stems. (proessencekanna.com)
Activity1
- Gas chromatography-mass spectroscopy confirms that the unfermented preparation of S. tortuosum contains more alkaloids than the fermented one.Lubbe 2010 Although data are conflicting, reports suggest that activity is only observed when S. tortuosum is fermented, not when it is dried or fresh.Smith 1996 Fermentation causes transformation of mesembrine to delta-7 mesembrenone. (proessencekanna.com)
Type3
- As a further synthetic application, a stereoselective synthesis of 5,11-methanomorphanthridin-3-one, which shares a key skeleton with montanine-type Amaryllidaceae alkaloids has been achieved by using this chemistry. (researcher-app.com)
- Furthermore, the diastereoselective synthesis of the framework of montanine-type Amaryllidaceae alkaloids has also been explored by using this chemistry. (researcher-app.com)
- Within this study, we have generated a pilot series of compounds (1-20) structurally inspired from belladine-type Amaryllidaceae alkaloids, namely carltonine A and B, and evaluated their acetylcholinesterase (AChE) and BuChE inhibition properties. (inrae.fr)
Active1
- The mesembrine alkaloids are the most active of these subgroups.Jeffs 1981 Other alkaloids include mesembrone, mesembrenol, and turtuosamine. (proessencekanna.com)
Include1
- Specific examples of alkaloids derived from (10b R ,4a S )-noroxomaritidine include haemanthamine, maritidine, vittatine, and pretazettine. (frontiersin.org)
Study1
- This study provides an Amaryllidaceae transcriptome that will be very helpful to identify genes for characterization studies in AA metabolism in planta or using heterologous systems. (tau.ac.il)
Form1
- Tropine in nightshades is esterified with tropic acid to form the alkaloid hyoscyamine. (medprep.info)