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Natural Product Reports Oct 2016Covering: July 2012 to June 2015. Previous review: Nat. Prod. Rep., 2013, 30, 869-915The structurally diverse imidazole-, oxazole-, and thiazole-containing secondary... (Review)
Review
Covering: July 2012 to June 2015. Previous review: Nat. Prod. Rep., 2013, 30, 869-915The structurally diverse imidazole-, oxazole-, and thiazole-containing secondary metabolites are widely distributed in terrestrial and marine environments, and exhibit extensive pharmacological activities. In this review the latest progress involving the isolation, biological activities, and chemical and biogenetic synthesis studies on these natural products has been summarized.
Topics: Alkaloids; Animals; Bacteria; Biological Products; Imidazoles; Marine Biology; Molecular Structure; Muscarine; Oxazoles; Peptides, Cyclic; Porifera
PubMed: 27714029
DOI: 10.1039/c6np00067c -
PloS One 2013Mushroom-forming fungi produce a wide array of toxic alkaloids. However, evolutionary analyses aimed at exploring the evolution of muscarine, a toxin that stimulates the... (Review)
Review
Mushroom-forming fungi produce a wide array of toxic alkaloids. However, evolutionary analyses aimed at exploring the evolution of muscarine, a toxin that stimulates the parasympathetic nervous system, and psilocybin, a hallucinogen, have never been performed. The known taxonomic distribution of muscarine within the Inocybaceae is limited, based only on assays of species from temperate regions of the northern hemisphere. Here, we present a review of muscarine and psilocybin assays performed on species of Inocybaceae during the last fifty years. To supplement these results, we used liquid chromatography-tandem mass spectrometry (LC-MS/MS) to determine whether muscarine was present in 30 new samples of Inocybaceae, the majority of which have not been previously assayed or that originated from either the tropics or temperate regions of the southern hemisphere. Our main objective is to test the hypothesis that the presence of muscarine is a shared ancestral feature of the Inocybaceae. In addition, we also test whether species of Inocyabceae that produce psilocybin are monophyletic. Our findings suggest otherwise. Muscarine has evolved independently on several occasions, together with several losses. We also detect at least two independent transitions of muscarine-free lineages to psilocybin-producing states. Although not ancestral for the family as a whole, muscarine is a shared derived trait for an inclusive clade containing three of the seven major lineages of Inocybaceae (the Inocybe, Nothocybe, and Pseudosperma clades), the common ancestor of which may have evolved ca. 60 million years ago. Thus, muscarine represents a conserved trait followed by several recent losses. Transitions to psilocybin from muscarine-producing ancestors occurred more recently between 10-20 million years ago after muscarine loss in two separate lineages. Statistical analyses firmly reject a single origin of muscarine-producing taxa.
Topics: Agaricales; Animals; Evolution, Molecular; Fruiting Bodies, Fungal; Genetic Speciation; Humans; Muscarine; Phylogeny; Psilocybin; Sequence Analysis, DNA
PubMed: 23717644
DOI: 10.1371/journal.pone.0064646 -
Natural Product Reports Jun 2011A great number of structurally diverse natural products containing five-membered heterocyclic subunits, such as imidazole, oxazole, thiazole, and their saturated... (Review)
Review
A great number of structurally diverse natural products containing five-membered heterocyclic subunits, such as imidazole, oxazole, thiazole, and their saturated congeners, are abundant in nature. These naturally occurring metabolites often exhibit extensive and pharmacologically important biological activities. The latest progress in the isolation, biological activities, chemical synthetic studies, and biosynthetic pathways on these natural products is summarized in this review.
Topics: Alkaloids; Biological Factors; Imidazoles; Molecular Structure; Muscarine; Oxazoles; Structure-Activity Relationship; Thiazoles
PubMed: 21472175
DOI: 10.1039/c0np00074d -
Natural Product Reports Mar 2009Nature abounds with a great number of natural products containing five-membered heterocyclic subunits, such as imidazoles, oxazoles and thiazoles, and their... (Review)
Review
Nature abounds with a great number of natural products containing five-membered heterocyclic subunits, such as imidazoles, oxazoles and thiazoles, and their corresponding saturated imidazolines, oxazolines and thiazolines. These naturally occurring metabolites often exhibit pharmacologically important biological activities. In this review, the isolation, biological activities, chemical synthetic studies, and biosynthetic pathways of these natural products are summarized.
Topics: Alkaloids; Biological Factors; Imidazoles; Molecular Structure; Muscarine; Oxazoles; Structure-Activity Relationship; Thiazoles
PubMed: 19240947
DOI: 10.1039/b718045b -
Natural Product Reports Apr 2005Novel and structurally diverse natural products containing imidazol-, oxazole-, or thiazole-unit(s) display a wide variety of biological activities. The isolation,... (Review)
Review
Novel and structurally diverse natural products containing imidazol-, oxazole-, or thiazole-unit(s) display a wide variety of biological activities. The isolation, biological activity and total synthesis of naturally occurring muscarine, imidazole, oxazole and thiazole alkaloids have been reviewed. The literature covers from January 2003 to June 2004.
Topics: Alkaloids; Biological Factors; Imidazoles; Molecular Structure; Muscarine; Oxazoles; Structure-Activity Relationship; Thiazoles
PubMed: 15806197
DOI: 10.1039/b316104h -
Natural Product Reports Dec 2003The occurrence, structure determination, biological activities, as well as total syntheses of muscarine, imidazole, oxazole and thiazole alkaloids have been reviewed.... (Review)
Review
The occurrence, structure determination, biological activities, as well as total syntheses of muscarine, imidazole, oxazole and thiazole alkaloids have been reviewed. The literature covers from the middle of 2001 to the end of 2002, and 149 references are cited.
Topics: Alkaloids; Biological Factors; Imidazoles; Molecular Structure; Muscarine; Oxazoles; Structure-Activity Relationship; Thiazoles
PubMed: 14700201
DOI: 10.1039/b304142p -
Natural Product Reports Oct 1989
Review
Topics: Alkaloids; Bacteria; Muscarine; Oxazoles; Peptides; Plants; Streptomyces
PubMed: 2694028
DOI: 10.1039/np9890600503 -
Natural Product Reports Apr 1995
Review
Topics: Animals; Humans; Imidazoles; Muscarine; Oxazoles; Peptides; Thiazoles
PubMed: 7739813
DOI: 10.1039/np9951200135 -
Natural Product Reports Aug 1994
Review
Topics: Alkaloids; Imidazoles; Molecular Structure; Muscarine; Oxazoles; Peptides; Plants; Streptomyces; Thiazoles
PubMed: 15200020
DOI: 10.1039/np9941100395 -
Natural Product Reports Feb 1992
Review
Topics: Alkaloids; Animals; Fungi; Imidazoles; Muscarine; Oxazoles; Peptides; Plants; Thiazoles
PubMed: 1579262
DOI: 10.1039/np9920900081