Studies Concerned with the Structure and Synthesis of the Anti‐viral Tropolone Glycoside Liriosmaside A DOI Creative Commons
Qi Chen,

Yaping Zhan,

Michael G. Gardiner

et al.

ChemistryOpen, Journal Year: 2025, Volume and Issue: unknown

Published: April 8, 2025

Abstract A bromotropone corresponding to the agylcone of glycosylated sesquiterpenoid natural product liriosmaside has been prepared over ten steps and in a fully regio‐controlled manner through gem ‐dibromocyclopropane‐mediated ring‐expansion readily accessible decalenone. Pd[0]‐mediated glucosylation reaction applied this afforded mixture from which an enantiomerically pure cross‐coupling could be obtained its structure confirmed single‐crystal X‐ray analysis derivative. Various (unsuccessful) attempts are described selectively acylate last compound thereby install 3‐hydroxy‐3‐methylglutaric acid or HMGA‐containing side chain title product. literature survey other products embodying HMGA motif suggest that co‐metabolite B S ‐configured at C3”. The evaluation glucosylated tropone series anti‐bacterial, anti‐fungal cytotoxicity assays reveals it is inactive all these so emphasizing prospect related troponoids, including B, can serve as useful models for new anti‐viral agents.

Language: Английский

Terpene synthases in disguise: enzymology, structure, and opportunities of non-canonical terpene synthases DOI
Jeffrey D. Rudolf, Chin‐Yuan Chang

Natural Product Reports, Journal Year: 2019, Volume and Issue: 37(3), P. 425 - 463

Published: Oct. 25, 2019

Twelve families of enzymes that perform terpene synthase-like reactions but do not resemble canonical synthases in sequence or structure are reviewed.

Language: Английский

Citations

136
Genetic factors involved in rhizosphere colonization by phytobeneficial Pseudomonas spp. DOI Creative Commons
Antoine Zboralski, Martin Filion

Computational and Structural Biotechnology Journal, Journal Year: 2020, Volume and Issue: 18, P. 3539 - 3554

Published: Jan. 1, 2020

Graphical abstractAbstractPlant growth-promoting rhizobacteria (PGPR) actively colonize the soil portion under influence of plant roots, called rhizosphere. Many plant-beneficial Pseudomonas spp. have been characterized as PGPR. They are ubiquitous rod-shaped motile Gram-negative bacteria displaying a high metabolic versatility. Their capacity to protect plants from pathogens and improve growth closely depends on their rhizosphere colonization abilities. Various molecular cellular mechanisms involved in this complex process, such chemotaxis, biofilm formation, secondary metabolites biosynthesis, versatility, evasion immunity. The burst genome sequencing recent years has crucial better understand how they In review, we discuss advances regarding these underlying bacterial genetic factors required for successful colonization.

Language: Английский

Citations

102
Enzymatic Intermolecular Hetero-Diels–Alder Reaction in the Biosynthesis of Tropolonic Sesquiterpenes DOI
Qibin Chen, Jie Gao, Cooper S. Jamieson

et al.

Journal of the American Chemical Society, Journal Year: 2019, Volume and Issue: 141(36), P. 14052 - 14056

Published: Aug. 28, 2019

Diels–Alder reactions are among the most powerful synthetic transformations to construct complex natural products. Despite that increasing of enzymatic intramolecular have been discovered, intermolecular Diels–Alderases rarely described. Here, we report an hetero-Diels–Alder reaction in biosynthesis tropolonic sesquiterpenes and functionally characterize EupfF as first fungal hetero-Diels–Alderase. We demonstrate catalyzed dehydration a hydroxymethyl-containing tropolone (5) generate reactive o-quinone methide (6) might further stereoselectively control subsequent with (1E,4E,8Z)-humulenol (8) produce enantiomerically pure neosetophomone B (1). Our results reveal biosynthetic pathway 1 expand repertoire activities cyclases.

Language: Английский

Citations

93
Cephalotane diterpenoids: structural diversity, biological activity, biosynthetic proposal, and chemical synthesis DOI
Jin‐Xin Zhao,

Zhan‐Peng Ge,

Jian‐Min Yue

et al.

Natural Product Reports, Journal Year: 2024, Volume and Issue: 41(7), P. 1152 - 1179

Published: Jan. 1, 2024

Covering: up to the end of 2023Cephalotane diterpenoids are a unique class natural products exclusive genus Cephalotaxus, featuring rigid 7,6,5,6-fused tetracyclic architecture. The study cephalotanes dates back 1970s, when harringtonolide (1), Cephalotaxus troponoid with peculiar norditerpenoid carbon skeleton, was first discovered. In recent years, prototype C20 proposed as cephalotane were disclosed, which triggered intense studies on this diterpenoid family. To date, cumulative total 105 great structural diversity and biological importance have been isolated. addition, significant advances made in field synthesis biosynthesis years. This review provides complete overview chemical structures, bioactivities, biosynthetic aspects, completed all isolated diterpenoids, will help guide future research compounds.

Language: Английский

Citations

16
The fungal natural product class of the sorbicillinoids: structures, bioactivities, biosynthesis, and synthesis DOI Creative Commons
Tobias M. Milzarek, Tobias A. M. Gulder

Natural Product Reports, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Sorbicillinoids are a growing class of fungal natural products combining complex molecular architectures with pharmaceutically relevant bioactivities. This review covers their structural diversity, biosynthesis, and synthetic studies.

Language: Английский

Citations

1
Electrochemical Nickel-Catalyzed C(sp2)-H Functionalization of Tropones with Aldehydes DOI Creative Commons
Andrea Brunetti, Sofia Kiriakidi,

Mauro Garbini

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 3184 - 3190

Published: Feb. 6, 2025

A direct electroreductive functionalization of tropones employing aldehydes as alkylating agents is reported. This C(sp2)-H process leverages the mediation electroactive nickel complexes, enabling a wide range both native and substituted (44 examples) to be alkylated selectively at α-position in high yields (up 90%). Combined electrochemical, spectroelectrochemical, computational analyses disclosed whole mechanistic pathway revealed key role played by reduced Ni complexes activating tropone core toward condensation with aldehydes.

Language: Английский

Citations

1
Hinokitiol Prevents Diabetic Acute Kidney Injury by Mitigating ER Stress DOI
Tahib Habshi, Hrushikesh Kulkarni, Neha Dagar

et al.

Cell Biology International, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 27, 2025

ABSTRACT Acute kidney injury (AKI) in diabetic conditions often advances to chronic disease (CKD), exacerbated by ischemia–reperfusion (IRI) through pathomechanisms such as endoplasmic reticulum (ER) stress and inflammation. Currently, available treatment options for AKI are not uniformly effective, highlighting the need novel interventions. This study aimed examine renoprotective effects of hinokitiol, a natural tropolone compound, against with its capability decrease ER inflammation, along apoptosis. involved NRK‐52E cells grown in‐vitro under high‐glucose subjected 10 mM sodium azide elicit hypoxia/reperfusion (HRI). The expression key markers like binding immunoglobulin protein (BiP), R/PKR‐like kinase (PERK), eukaryotic initiation factor‐2 (eIF2α) well inflammatory proteins was markedly diminished hinokitiol pretreatment (50 μM). Hinokitiol further reduced apoptosis cells. Similarly, in‐vivo study, male Wistar rats STZ‐induced Type 1 diabetes (55 mg/kg, i.p .) were treated 50 100 mg/kg/day . 5 days, followed induction via bilateral IRI. significantly elevated plasma blood urea nitrogen (BUN), creatinine, urinary molecule‐1 (KIM‐1) levels tubular damage rats. also respective expressions rats, demonstrated immunohistochemical analysis immunoblotting. These findings suggest that alleviates modulating PERK/CHOP/NF‐κB axis, likeliness viable therapeutic technique alleviating AKI.

Language: Английский

Citations

1
Untapped Potential of Marine-Associated Cladosporium Species: An Overview on Secondary Metabolites, Biotechnological Relevance, and Biological Activities DOI Creative Commons
Gamal A. Mohamed, Sabrin R. M. Ibrahim

Marine Drugs, Journal Year: 2021, Volume and Issue: 19(11), P. 645 - 645

Published: Nov. 18, 2021

The marine environment is an underexplored treasure that hosts huge biodiversity of microorganisms. Marine-derived fungi are a rich source novel metabolites with unique structural features, bioactivities, and biotechnological applications. Marine-associated

Language: Английский

Citations

42
Secondary metabolite biosynthetic diversity in the fungal family Hypoxylaceae and Xylaria hypoxylon DOI Creative Commons
Eric Kuhnert, Jorge C. Navarro-Muñoz, Kevin Becker

et al.

Studies in Mycology, Journal Year: 2021, Volume and Issue: 99(1), P. 100118 - 100118

Published: June 1, 2021

To date little is known about the genetic background that drives production and diversification of secondary metabolites in Hypoxylaceae . With recent availability high-quality genome sequences for 13 representative species one relative ( Xylaria hypoxylon ) we attempted to survey diversity biosynthetic pathways these organisms investigate their true potential as metabolite producers. Manual search strategies based on accumulated knowledge biosynthesis fungi enabled us identify 783 across 14 studied species, majority which were arranged gene clusters (BGC). The similarity BGCs was analysed with BiG-SCAPE engine organised into 375 cluster families (GCF). Only ten GCFs conserved all indicating speciation accompanied by changes metabolism. From compounds produced family members some can be directly correlated identified highlighted herein azaphilone, dihydroxynaphthalene, tropolone, cytochalasan, terrequinone, terphenyl brasilane giving insights evolution those compound classes. Vice versa , products various predicted through homology analysis from other shown ergot alkaloid, trigazaphilone, curvupallide, viridicatumtoxin swainsonine BGCs. However, had no obvious links or well-studied fungi. These findings highlight number strongly underrepresents a tremendous unidentified still hidden. Moreover, increasing numbers genomes further becoming available, likelihood revealing new encode new, potentially useful will significantly improve. Reaching better understanding biology producers, development methods manipulation, crucial access treasures.

Language: Английский

Citations

35
Photosensitizer-free visible-light-promoted glycosylation enabled by 2-glycosyloxy tropone donors DOI Creative Commons
Jing Zhang,

Zhao-Xiang Luo,

Xia Wu

et al.

Nature Communications, Journal Year: 2023, Volume and Issue: 14(1)

Published: Dec. 4, 2023

Photochemical glycosylation has attracted considerable attention in carbohydrate chemistry. However, to the best of our knowledge, visible-light-promoted via photoactive glycosyl donor not been reported. In study, we report a photosensitizer-free visible-light-mediated approach using 2-glycosyloxy tropone as donor. This reaction proceeds at ambient temperature give wide range O-glycosides or oligosaccharides with yields up 99%. method is further applied stereoselective preparation various functional phosphates/phosphosaccharides, construction N-glycosides/nucleosides, and late-stage natural products pharmaceuticals on gram scales, iterative synthesis hexasaccharide. The protocol features uncomplicated conditions, operational simplicity, substrate scope (58 examples), excellent compatibility groups, scalability (7 high yields. It provides an efficient for accessing O/N-glycosides glycans.

Language: Английский

Citations

15