Muscarine, Imidazole, Oxazole, and Thiazole Alkaloids

Jin, Zhong

doi:10.1002/chin.200411270

Cited by 3 publications

(4 citation statements)

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“…As a delineation, only MNPs with intact pyrrole functionality are described, whereas indole alkaloids [ 20 ], the saturated heterocycles pyrroline and pyrrolidine [ 21 ], as well as other fused systems (e.g., carbazoles) and pyrrole derivatives lacking a genuine pyrrole core [ 22 , 23 , 24 , 25 ], will not be covered. Several other specific overviews focusing on subclasses such as bromopyrroles [ 26 , 27 ] and pyrrole-imidazole alkaloids (PIA) [ 13 , 14 , 28 ] or with the focus on the isolation source [ 14 , 25 , 27 ], have been published. In contrast, we intend to provide the reader with an impression of the multiple facets of pyrrole alkaloids in the marine environment.…”

Section: Introductionmentioning

confidence: 99%

Marine Pyrrole Alkaloids

2021

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Nitrogen heterocycles are essential parts of the chemical machinery of life and often reveal intriguing structures. They are not only widespread in terrestrial habitats but can also frequently be found as natural products in the marine environment. This review highlights the important class of marine pyrrole alkaloids, well-known for their diverse biological activities. A broad overview of the marine pyrrole alkaloids with a focus on their isolation, biological activities, chemical synthesis, and derivatization covering the decade from 2010 to 2020 is provided. With relevant structural subclasses categorized, this review shall provide a clear and timely synopsis of this area.

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Section: Introductionmentioning

confidence: 99%

Marine Pyrrole Alkaloids

2021

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“…One of the earliest advances in understanding of the mechanisms underlying chemical neurotransmission was the identification of two classes of receptors for acetylcholine [13]. As stated earlier, the two classes of receptors were first separated based on the binding profiles of two agents, muscarine and nicotine, both of which were derived from plants [55,56]. This highlights the preservation of the ligand-binding domains of the cholinergic receptors in the face of significant changes in the gene sequences that have occurred since the divergence of plants and animals.…”

Section: Acetylcholine Receptors: Evolutionary Adaptations To Diverse Rolesmentioning

confidence: 99%

Evolution of the human CNS cholineric system: has this resulted in the emergence of psychiatric disease?

Dean

2009

Aust NZ J Psychiatry

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The aim of the present study was to review the available literature on the evolutionary processes that have led to the development of the human central nervous system (CNS) cholinergic system and to test the hypothesis that such processes may have contributed to the emergence of psychiatric diseases. First, it is clear that the molecular components that have come together to form the cholinergic system in the human CNS initially had functions that were not involved in neurotransmission. Indeed, components of the cholinergic system of the human CNS may be present in nearly all forms of life and may have existed since life began. Significantly, components of the human CNS cholinergic system had begun to interact with each other millions of years ago, long before the appearance of any nervous system. Moreover, there are data to suggest that changes in the mammalian CNS cholinergic system can involve involved gene and environment interactions. Evidence is available to support the notion that the changes in functioning of the human CNS cholinergic system in individuals with psychiatric disorders may have resulted from both Darwinian and Lamarckian concepts of evolution.

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“…In nature, heterorings are obtained in post-translational modifications from standard amino acid residues such as threonine, serine, and cysteine (Metelev and Ghilarov 2014). They occur in highly modified macrocyclic peptides; thiopeptides or cyanobactins (Bagley et al 2005;Jin 2011). In many cases, these compounds have promising anti-tumour, anti-bacterial, or anti-malaria activities (Davyt and Serra 2010).…”

Section: Introductionmentioning

confidence: 99%

“…Residues with thiazole ring have the most diverse side chains among other rings (thiazoline, oxazole, and oxazoline). Literature survey reveals that in natural compounds they can be found as thiazole-glycine (Kai et al 2012;Debono et al 1992;Engelhardt et al 2010;Jüttner et al 2001), alanine (Kai et al 2012;Bagley et al 2000;Castro Rodríguez et al 2002;Engelhardt et al 2010), valine (Bagley et al 2005;Hughes and Moody 2007;Bertram and Pattenden 2007;Jüttner et al 2001), serine (Zhang et al 2009), methionine (Jüttner et al 2001), threonine (Davyt and Serra 2010), leucine (Davyt and Serra 2010), isoleucine (Jüttner et al 2001), asparagine (Zhang and Liu 2013;Young and Walsh 2011), phenylalanine (Davyt and Serra 2010), dehydroalanine (Aoki et al 1991), dehydrobutyrine (Kai et al 2012;Walsh et al 2010) and other (Bagley et al 2005;Jin 2011). The important feature of the thiazole ring is the presence of the sp 2 sulfur atom which has a larger size than carbon, nitrogen, or oxygen, and its ability to engage in donating n o → σ* interaction (σ-holes) with the lone pairs of neighbouring heteroatoms.…”

Section: Introductionmentioning

confidence: 99%

Thiazole–amino acids: influence of thiazole ring on conformational properties of amino acid residues

2021

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Post-translational modified thiazole–amino acid (Xaa–Tzl) residues have been found in macrocyclic peptides (e.g., thiopeptides and cyanobactins), which mostly inhibit protein synthesis in Gram + bacteria. Conformational study of the series of model compounds containing this structural motif with alanine, dehydroalanine, dehydrobutyrine and dehydrophenylalanine were performed using DFT method in various environments. The solid-state crystal structure conformations of thiazole–amino acid residues retrieved from the Cambridge Structural Database were also analysed. The studied structural units tend to adopt the unique semi-extended β2 conformation; which is stabilised mainly by N–H⋯NTzl hydrogen bond, and for dehydroamino acids also by π-electron conjugation. The conformational preferences of amino acids with a thiazole ring were compared with oxazole analogues and the role of the sulfur atom in stabilising the conformations of studied peptides was discussed.

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Muscarine, Imidazole, Oxazole, and Thiazole Alkaloids

Abstract: For Abstract see ChemInform Abstract in Full Text.

Cited by 3 publications

References 1 publication

Marine Pyrrole Alkaloids

Marine Pyrrole Alkaloids

Evolution of the human CNS cholineric system: has this resulted in the emergence of psychiatric disease?

Thiazole–amino acids: influence of thiazole ring on conformational properties of amino acid residues

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