scholarly journals Gold-catalyzed formation of pyrrolo- and indolo-oxazin-1-one derivatives: The key structure of some marine natural products

2015 ◽  
Vol 11 ◽  
pp. 897-905 ◽  
Author(s):  
Sultan Taskaya ◽  
Nurettin Menges ◽  
Metin Balci
Keyword(s):  
Natural Products ◽  
Double Bond ◽  
Marine Natural Products ◽  
Cascade Reactions ◽  
Cyclization Reaction ◽  
Cyclization Reactions ◽  
Double Bond Isomerization

Various N-propargylpyrrole and indolecarboxylic acids were efficiently converted into 3,4-dihydropyrrolo- and indolo-oxazin-1-one derivatives by a gold(III)-catalyzed cyclization reaction. Some of the products underwent TFA-catalyzed double bond isomerization and some did not. Cyclization reactions in the presence of alcohol catalyzed by Au(I) resulted in the formation of hemiacetals after cascade reactions.

scholarly journals Berberine bridge enzyme-like oxidase-catalysed double bond isomerization acts as the pathway switch in cytochalasin synthesis

2022 ◽  
Vol 13 (1) ◽  
Author(s):  
Jin-Mei Zhang ◽  
Xuan Liu ◽  
Qian Wei ◽  
Chuanteng Ma ◽  
Dehai Li ◽  
...  
Keyword(s):  
Natural Products ◽  
Double Bond ◽  
Chemical Conversion ◽  
Isomerization Reaction ◽  
Heterologous Host ◽  
Nonribosomal Peptide ◽  
Double Bond Isomerization ◽  
General Acid ◽  
Berberine Bridge Enzyme

AbstractCytochalasans (CYTs), as well as their polycyclic (pcCYTs) and polymerized (meCYTs) derivatives, constitute one of the largest families of fungal polyketide-nonribosomal peptide (PK-NRP) hybrid natural products. However, the mechanism of chemical conversion from mono-CYTs (moCYTs) to both pcCYTs and meCYTs remains unknown. Here, we show the first successful example of the reconstitution of the CYT core backbone as well as the whole pathway in a heterologous host. Importantly, we also describe the berberine bridge enzyme (BBE)-like oxidase AspoA, which uses Glu538 as a general acid biocatalyst to catalyse an unusual protonation-driven double bond isomerization reaction and acts as a switch to alter the native (for moCYTs) and nonenzymatic (for pcCYTs and meCYTs) pathways to synthesize aspochalasin family compounds. Our results present an unprecedented function of BBE-like enzymes and highly suggest that the isolated pcCYTs and meCYTs are most likely artificially derived products.

The discoipyrroles: A multifaceted approach to understand a novel family of marine natural products

Planta Medica ◽  
2015 ◽  
Vol 81 (11) ◽  
Author(s):  
DA Colosimo ◽  
F Cai ◽  
Y Hu ◽  
MB Potts ◽  
MA White ◽  
...  
Keyword(s):  
Natural Products ◽  
Marine Natural Products ◽  
Multifaceted Approach

Synthesis of Marine Natural Products 1

1992 ◽  
Author(s):  
K. F. Albizati ◽  
V. A. Martin ◽  
M. R. Agharahimi ◽  
D. A. Stolze
Keyword(s):  
Natural Products ◽  
Marine Natural Products

Synthesis and Biological Evaluation of the Antimicrobial Natural Product Lipoxazolidinone A

2018 ◽  
Author(s):  
Jonathan J. Mills ◽  
Kaylib R. Robinson ◽  
Troy E. Zehnder ◽  
Joshua G. Pierce
Keyword(s):  
Natural Products ◽  
Natural Product ◽  
Mechanism Of Action ◽  
Marine Natural Products ◽  
Biological Evaluation ◽  
Lead Compounds ◽  
Follow Up Studies ◽  
Initial Resistance ◽  
Synthesis And Biological Evaluation

The lipoxazolidinone family of marine natural products, with an unusual 4-oxazolidinone heterocycle at their core, represents a new scaffold for antimicrobial discovery; however, questions regarding their mechanism of action and high lipophilicity have likely slowed follow-up studies. Herein, we report the first synthesis of lipoxazolidinone A, 15 structural analogs to explore its active pharmacophore, and initial resistance and mechanism of action studies. These results suggest that 4-oxazolidinones are valuable scaffolds for antimicrobial development and reveal simplified lead compounds for further optimization.

Neuroprotective Activities of Marine Natural Products from Marine Sponges

2016 ◽  
Vol 23 (4) ◽  
pp. 360-382 ◽  
Author(s):  
Mousa Alghazwi ◽  
Yen Qi Kan ◽  
Wei Zhang ◽  
Wei Ping Gai ◽  
Xiao-Xin Yan
Keyword(s):  
Natural Products ◽  
Marine Natural Products ◽  
Marine Sponges

Antitubercular Marine Natural Products

2018 ◽  
Vol 25 (20) ◽  
pp. 2304-2328 ◽  
Author(s):  
Lishu Wang ◽  
Jungfeng Wang ◽  
Juan Liu ◽  
Yonghong Liu
Keyword(s):  
Natural Products ◽  
Marine Natural Products ◽  
Antitubercular Activity ◽  
Marine Resources ◽  
Drug Candidates ◽  
New Drug ◽  
Chemical Constitution

Due to the importance of nature as a source of new drug candidates, the purpose of this article is to emphasize the marine natural products, which exhibit antitubercular activity, published between January 2000 and May 2016, with 138 quotations to 250 compounds obtained from marine resources. These metabolites are organized by chemical constitution and named as simple alkyl lipids derivatives, aromatics derivatives, peptides, alkaloids, terpenoids, steroids, macrolides, and polycyclic polyketides.

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