Alkaloids alkaloid noscapine. Medical search. Frequent questions

Noscapine was first characterized from opium poppy ( Papaver somniferum ) by the distinguished French chemist Pierre Jean Robiquet in 1817 ( 1 ) but unlike codeine, which he also discovered, and several other opiates, noscapine is non-painkilling and non-addictive. (ampliconexpress.com)
Noscapine belongs to the phthalideisoquinoline subclass of the structurally diverse isoquinoline alkaloids whereas codeine, morphine, thebaine and oripavine belong to the morphinan subclass ( 10 ). (ampliconexpress.com)
The natural alkaloids are also referred to as opiates and include morphine and codeine. (junadea.com)
Extracts from Papaver somniferum , or the opium poppy, contain opioid alkaloids (e.g. morphine and codeine). (catalogueofopioids.net)
In the Oxford Catalogue of Opioids, there were seven naturally occurring alkaloids (i.e. codeine , morphine , narceine, noscapine , oripavine, paraveretum, and thebaine). (catalogueofopioids.net)

Narceine is an opium alkaloid produced by the Papaver somniferum (opium poppy) plant. (wikipedia.org)
Isoquinoline alkaloids - Isoquinoline alkaloids 1-Benzyl isoquinoline type: Papaverine: An opiate alkaloid isolated from the plant Papaver somniferum and produced synthetically. (powershow.com)
The opium poppy, Papaver somniferum, is the primary source of analgesic opiate alkaloids such as morphine. (dissertation.com)
Many of the estimated 30 or more alkaloids extracted from Papaver somniferum have significant pharmaceutical value. (dissertation.com)
Papaver species are known to produce a large variety of benzylisoquinoline alkaloids, with each species exhibiting a specific alkaloid profile, but only a few genes involved in the biosynthesis or regulation of these complex pathways are known so far. (wustl.edu)
The opioids are a large class of medications related in structure to the natural plant alkaloids found in opium that are derived from the resin of the opium poppy, Papaver somniferum. (junadea.com)

We metabolite profiled capsule extract from three opium poppy varieties developed in Tasmania for alkaloid production that we designate as High Morphine 1 (HM1), High Thebaine 1 (HT1) and High Noscapine 1 (HN1) on the basis of the most abundant alkaloid in each case ( Fig. 1A ). (ampliconexpress.com)
In contrast a number of other functionally characterized genes associated with benzylisoquinoline alkaloid synthesis, including Berberine Bridge Enzyme ( BBE ), Tetrahydroprotoberberine cis-N-MethylTransferase ( TNMT ), Salutaridine Reductase ( SalR ), Salutaridinol 7-O-AcetylTransferase ( SalAT ) and Thebaine 6-O-demethylase ( T6ODM ) were expressed in all three varieties ( Fig. 1B ). (ampliconexpress.com)

Noscapine is an antitumor alkaloid from opium poppy that binds tubulin, arrests metaphase, and induces apoptosis in dividing human cells. (ampliconexpress.com)

ii) Benzyl isoquinoline group alkaloids: These include Papavarine, Noscapine, and Narceine. (biologyease.com)

Noscapine (also known as Narcotine , Nectodon , Nospen , Anarcotine and (archaic) Opiane ) is a benzylisoquinoline alkaloid , of the phthalideisoquinoline structural subgroup, which has been isolated from numerous species of the family Papaveraceae (poppy family). (cloudfront.net)

The biosynthesis of noscapine in P. somniferum begins with chorismic acid , which is synthesized via the shikimate pathway from erythrose 4-phosphate and phosphoenolpyruvate . (cloudfront.net)
Gene expression analysis of these sequences in P. bracteatum, P. somniferum and P. somniferum 'Noscapine' exhibited 39 cDNAs showing differential expression coincident with morphine accumulation. (wustl.edu)

The benzylisoquinoline alkaloid (BIA) is a diverse category of alkaloids including berberine, morphine, sanguinarine, hydrastine and many more. (biomedcentral.com)
Tetrandrine (TET) is a bis-benzylisoquinoline alkaloid, which is identified as an active ingredient in Radix Stephanae tetrandrae (a Chinese medicinal herb). (biomedcentral.com)

Morphine is the most important opium alkaloid used as a narcotic analgesic. (biologyease.com)

Virus-induced gene silencing resulted in accumulation of pathway intermediates allowing gene function to be linked to noscapine synthesis and a novel biosynthetic pathway to be proposed. (ampliconexpress.com)
This thesis focuses on the design and synthesis of novel compounds to probe the emerging SAR of Noscapine related compounds. (dissertation.com)
Recent literature reported the synthesis of N-carbamoyl/N-thiocarbamoyl analogues of noscapine but the biological activity for this series of compounds was not published. (dissertation.com)
This chapter focused on the synthesis of noscapine analogues, which comprised multiple modifications on the same noscapine core to determine whether activity could be further improved. (dissertation.com)
Chapter 4 examines the synthesis of a noscapine mimetic, and the installation of an isoindolin-1-one moiety entailing of the exact substitution pattern of the noscapine phthalide. (dissertation.com)

The findings from our work demonstrated that the activity of noscapine derivatives could be improved through the introduction of multiple modifications on the same core. (dissertation.com)
b) Semisynthetic derivatives of opium alkaloids, e.g. (biologyease.com)
Modifications of morphine-like alkaloid derivatives led to the production of semi-synthetic opioids (e.g. heroin and oxycodone). (catalogueofopioids.net)

Elucidation of the biosynthetic pathway will enable improvement in commercial production of noscapine and related bioactive molecules. (ampliconexpress.com)
We found noscapine to be unique to HN1 relative to HM1 and HT1 as were 53 other low abundance compounds, some of which are candidate intermediates in the noscapine biosynthetic pathway (table S1). (ampliconexpress.com)
The remainder of the noscapine biosynthetic pathway is largely governed by a single biosynthetic 10-gene cluster. (cloudfront.net)
Alkaloids can be classified on the basis of biological activities, chemical structure and biosynthetic pathways. (biomedcentral.com)

While the biosynthesis of morphinans has been elucidated at the molecular level ( 11 - 16 ) our knowledge of noscapine biosynthesis has not advanced significantly since the demonstration using isotope labeling in the 1960s, that it is derived from scoulerine ( 17 ). (ampliconexpress.com)
Understanding the biochemical genetics underpinning noscapine biosynthesis should enable improved production of this important pharmaceutical and related molecules both in poppy and other systems. (ampliconexpress.com)
These reactions produce ( S )- reticuline , a key branchpoint intermediate in the biosynthesis of benzylisoquinoline alkaloids. (cloudfront.net)

Heroin is derived from the morphine alkaloid found in opium. (junadea.com)

Transcriptomic analysis revealed the exclusive expression of 10 genes encoding five distinct enzyme classes in a high noscapine-producing poppy variety, HN1. (ampliconexpress.com)
Identification of genes exclusively present in the genome of a noscapine producing poppy variety, HN1 (High Noscapine 1). (ampliconexpress.com)

Noscapine has been used as a human cough suppressant for decades with its effect on the cough reflex and bronchial muscles being reported as early as 1954 ( 2 ), and the bioavailability and pharmacokinetics of the orally administered form being more recently established ( 3 ). (ampliconexpress.com)
Noscapine constitutes a low percentage of the alkaloid content of opium and has been used as a cough suppressant in humans. (dissertation.com)

A naturally occurring opium alkaloid that is a centrally acting antitussive agent. (harvard.edu)
Alkaloids are naturally occurring secondary metabolites, low molecular weight, and nitrogen containing compounds that are found in more than 20% of plant species [ 1 ]. (biomedcentral.com)

Chorismic acid is a precursor to the amino acid tyrosine , the source of nitrogen in benzylisoquinoline alkaloids. (cloudfront.net)

Noscapine is often used as an antitussive medication. (cloudfront.net)

Noscapine can increase the effects of centrally sedating substances such as alcohol and hypnotics . (cloudfront.net)

This graph shows the total number of publications written about "Noscapine" by people in Harvard Catalyst Profiles by year, and whether "Noscapine" was a major or minor topic of these publication. (harvard.edu)
Below are the most recent publications written about "Noscapine" by people in Profiles. (harvard.edu)

Current published literature examined modifications at the 7- and 9′-position separately on the noscapine scaffold. (dissertation.com)
These two independent modifications of the noscapine core demonstrated improvements in activity could be achieved through the chemical manipulation of different sites on the noscapine core. (dissertation.com)

Analysis of an F2 mapping population indicated the genes are tightly linked in HN1, and bacterial artificial chromosome sequencing confirmed they exist as a complex gene cluster for plant alkaloids. (ampliconexpress.com)
Here we used a genomic approach to discover genes responsible for the determination of a specific alkaloid profile. (wustl.edu)

From the compounds synthesized in this initial series of N-substituted analogues the N-ethyl cyclic ether noscapine analogue showed activity against both PC3 and MCF-7 cancer cell lines with an EC50 of 6.7 and 3.58 μM. (dissertation.com)
A database of benzylisoquinoline compounds has been created, which provides comprehensive information about benzylisoquinoline alkaloids. (biomedcentral.com)

The history of safe use as an anti-tussive, rapid absorption after oral administration and apoptosis-inducing effect on a number of cancer cell lines, may place noscapine at an advantage over other tubulin binding anticancer natural products such as the well established taxanes ( 9 ). (ampliconexpress.com)
a) Natural opium alkaloids, e.g. (biologyease.com)
Nowadays, non-natural alkaloids are growing rapidly as a result of bioorganic and stereochemistry research. (biomedcentral.com)

Alkaloids belonging to this class are found to be pharmacologically active and show potential therapeutic properties. (biomedcentral.com)

The demonstration in 1998 that noscapine acts as a potent antitumor agent that binds to tubulin, affecting its polymerisation, arresting cell division and inducing apoptosis ( 4 ) was followed by its antitumor activity being demonstrated in various forms of cancer ( 5 - 8 ). (ampliconexpress.com)
We were unable to demonstrate the activity of noscapine in either cellular line (Chapter 2). (dissertation.com)

i) Phenanthrin group of alkaloids, e.g. (biologyease.com)

Antifibrotic effects of noscapine through activation of prostaglandin E2 receptors and protein kinase A. J Biol Chem. (harvard.edu)
Noscapine should not be taken in conjunction with warfarin as the anticoagulant effects of warfarin may be increased. (cloudfront.net)

Thus it is important to collect and compile benzylisoquinoline alkaloids in order to explore their usage in medicine. (biomedcentral.com)
This database will also serve researchers working in the field of synthetic biology, as developing medicinally important alkaloids using synthetic process are one of important challenges. (biomedcentral.com)

The current version of BIAdb contains information about 846 unique benzylisoquinoline alkaloids, with multiple entries in term of source, function leads to total number of 2504 records. (biomedcentral.com)

Current research has implicated noscapine in the ability to suppress the proliferation of various metastatic cellular lines within in vitro models. (dissertation.com)

In Chapter 3 we explore the SAR of the noscapine scaffold further. (dissertation.com)

This information was processed and compiled in order to create a comprehensive database of benzylisoquinoline alkaloids, called BIAdb. (biomedcentral.com)

Codeine5

Papaver6

Thebaine2

Opium poppy1

Narceine1

Narcotine1

Somniferum2

Benzylisoquinoline alkaloid2

Analgesic1

Synthesis5

Derivatives3

Biosynthetic4

Biosynthesis3

Heroin1

Poppy2

Cough suppressant2

Naturally2

Nitrogen1

Antitussive1

Centrally1

Profiles2

Modifications2

Genes2

Compounds2

Natural3

Found1

Activity2

Group1

Effects2

Important2

Unique1

Current1

Explore1

Database1