Article
Chemistry, Organic
Pauline Menelle, Jerome Quintin, Kevin Cottet, Yann Fromentin, Joelle Dupont, Marie-Christine Lallemand, Didier Buisson
Summary: The study successfully identified active microorganisms for the biotransformation of guttiferone A and C from endophytic fungi of Symphonia globulifera. Among the isolates obtained, three were found to be active and were identified as Bipolaris cactivora. The biotransformation products were two regioisomers of oxy-guttiferones, with a ratio similar to that seen in the plant itself.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Medicinal
Si -Si Liu, Rong Huang, Shou-Peng Zhang, Tang-Chang Xu, Kun Hu, Shao-Hua Wu
Summary: Two new nucleoside derivatives, kipukasins O (1) and P (2), one new cyclohexenone derivative, arthropsadiol D (5), and one new natural product, (+)-2,5-dimethyl-3(2H)-benzofuranone (6), were isolated from the culture broth of the endophytic fungus Aspergillus polyporicola R2. The absolute configuration of compound 5 was determined and the antimicrobial activities of these compounds were evaluated.
Article
Plant Sciences
Yan Chen, Huan Wang, Xin Ke, Zihuan Sang, Min Kuang, Weiwei Peng, Jianbing Tan, Yuting Zheng, Zhenxing Zou, Haibo Tan
Summary: Two previously undescribed lactones and three new sesquiterpenoids were isolated from the fungus Phomopsis sp. SZSJ-7B. Their chemical structures were determined by various analytical techniques, and one of the lactones showed significant antibacterial activity against methicillin-resistant Staphylococcus aureus.
FRONTIERS IN PLANT SCIENCE
(2022)
Article
Microbiology
Gaoran Liu, Ruiyun Huo, Yanan Zhai, Ling Liu
Summary: Three new secondary metabolites were isolated from the endophytic fungus of tea tree, with compound 6 showing moderate cytotoxicity against T24 and MCF7 cell lines. The compounds were also evaluated for antibacterial activity.
FRONTIERS IN MICROBIOLOGY
(2021)
Article
Plant Sciences
Chuan Li, Yang Xu, Peinan Fu, Liangdong Guo, Yongsheng Che
Summary: Four new diphenyl ether derivatives were isolated from cultures of the plant endophytic fungus, and their structures were determined by NMR experiments. Two of the compounds exhibited modest cytotoxicity against HepG2 cells.
JOURNAL OF NATURAL PRODUCTS
(2022)
Article
Microbiology
Shikai Zhang, Qing Xu, Changbo Ji, Xiaoyu Han, Yang Zhou, Chao Liang, Linran Ma, Weijian Sun, Yanling Li, Zhengyou Yang, Fengchun Zhao, Yuan Tian
Summary: This study investigates the effects of small molecule-induced secondary metabolites of the endophytic fungus Diaporthe sp. AC1 on antibacterial activity and tumor cytotoxicity. The results show that the compound induced by 1-MT exhibits optimal antibacterial activity and tumor cytotoxicity, while other compounds show varying levels of biological activity.
FRONTIERS IN MICROBIOLOGY
(2023)
Article
Chemistry, Organic
Wenge Zhang, Xiuxiang Lu, Huan Wang, Yan Chen, Jun Zhang, Zhenxing Zou, Haibo Tan
Summary: Ten compounds, including three new ones, were isolated from the endophytic fungus Eutypella scoparia SCBG-8, with eutyscoparol J possessing a rare fused ring system. These compounds show promising antimicrobial activity and low cytotoxicity, indicating their potential as leads for drug development.
TETRAHEDRON LETTERS
(2021)
Article
Biochemistry & Molecular Biology
Di Zhang, Jinyang Zheng, Mingyi Chu, Yao Feng, Huifang Li
Summary: Eight compounds were isolated from the fermentation of an endophytic fungus Cladosporium sp. ZLM-6 derived from Suaeda salsa (Linn.) Pall. Compound 4 showed good inhibitory activity against Pseudomonas aeruginosa, Escherichia coli, and four different vibrios. This study further expanded the chemical diversity of the genus Cladosporium.
BIOCHEMICAL SYSTEMATICS AND ECOLOGY
(2023)
Article
Chemistry, Applied
Ying-Li Li, Ji-Ling Yi, Jin Cai, Xue-Ming Zhou, Li Chen, Xin Zhuo
Summary: A new lactone derivative and a new pyrrolidine derivative, along with six known compounds, were isolated from the fungus Talaromyces assiutensis JTY2. The structures of the new compounds were determined using NMR and HRESIMS, and their inhibitory activities against phytopathogenic fungi and cancer cell lines were evaluated.
NATURAL PRODUCT RESEARCH
(2022)
Article
Chemistry, Applied
Zhiyong Xu, Bingxue Xiong, Jing Xu
Summary: Chemical investigation of the endophytic fungus Phyllosticta capitalensis isolated from the hypocotyls of the Chinese mangrove Bruguiera sexangula led to the isolation of eight known secondary metabolites, whose structures were elucidated and subjected to antimicrobial and cytotoxic activities evaluation. This is the first report of these compounds being isolated from this fungal species.
NATURAL PRODUCT RESEARCH
(2021)
Article
Microbiology
Wenya Weng, Shicui Jiang, Chuchu Sun, Xiaofu Pan, Li Xian, Xuemian Lu, Chi Zhang
Summary: In this study, eight structurally diverse secondary metabolites were isolated and identified from the endophytic fungus Penicillium sp. YT2019-3321 derived from traditional Chinese medicine Lonicera japonica. Among them, a new compound exhibited dose-dependent cytotoxicity against human pancreatic tumor cells and induced apoptosis.
FRONTIERS IN MICROBIOLOGY
(2022)
Article
Biochemistry & Molecular Biology
Shuang Lin, Shan Yan, Yi Liu, Xueke Zhang, Fei Cao, Yan He, Fengli Li, Junjun Liu, Jianping Wang, Zhengxi Hu, Yonghui Zhang
Summary: Several new compounds were isolated from the endophytic fungus Daldinia sp. TJ403-LS1, with compound 1 showing remarkable immunosuppressive and BChE inhibitory activities, indicating their potential for pharmaceutical development.
BIOORGANIC CHEMISTRY
(2021)
Article
Microbiology
Viridiana Morales-Sanchez, Carmen E. Diaz, Elena Trujillo, Sonia A. Olmeda, Felix Valcarcel, Ruben Munoz, Maria Fe Andres, Azucena Gonzalez-Coloma
Summary: The ethyl acetate extract from the endophytic fungus Aspergillus sp. SPH2 showed potential biocontrol properties against various plant pathogens, insect pests, and plant parasites. Compound 1, mellein, demonstrated strong ixodicidal effects, while compound 2, neoaspergillic acid, exhibited potent antifungal effects. The study also suggested that compound 2 may be the biosynthetic precursor of compound 3, neohydroxyaspergillic acid.
Article
Plant Sciences
Liping Huang, Mengsha Wei, Lanqin Li, Qin Li, Weiguang Sun, Xiaotan Yu, Fengqing Wang, Zhengxi Hu, Chunmei Chen, Hucheng Zhu, Yonghui Zhang
Summary: Twelve new fungal polyketides, koningiopisins I-P(1-8) and trichoketides C-F(9-12), together with six known congeners(13-18), were isolated from Trichoderma koningiopsis, a rhizosphere fungus obtained from the medicinal plant Polygonum paleaceum. Their structures and absolute configurations were established by spectroscopic analysis, single-crystal X-ray diffraction, the modified Mosher's method, chemical derivatization, the octant rule, and C-13 NMR and ECD calculations. Compounds 1-5 are tricyclic polyketides possessing an octahydrochromene framework with a 6,8-dioxabicyclo[3.2.1]octane core. Compounds 7 and 8 contain a unique ketone carbonyl group at C-7 and differ from other members of this group of compounds with the ketone carbonyl group at C-1. Compounds 1, 2, and 13 showed inhibitory activity on LPS-induced BV-2 cells on NO production with IC50 values of 14±1, 3.0±0.5, and 8.9±2.7µM, respectively.
JOURNAL OF NATURAL PRODUCTS
(2023)
Article
Biochemistry & Molecular Biology
Mahsa Khoshbakht, Jason Srey, Donovon A. Adpressa, Annika Jagels, Sandra Loesgen
Summary: The plant endophyte Chalara sp. can transform the epigenetic modifier vorinostat into unique polyketides called chalanilines, with the potential to diversify the chemical diversity of these compounds. By synthesizing nineteen different vorinostat analogs and isolating five novel compounds, including two fluorinated chalanilines, this study has demonstrated a precursor-directed process to expand the class of aminofulvene-containing natural products. Although the tested compounds did not show bioactivity in antimicrobial or cell viability assays, this research provides a new approach for studying these compounds.
Correction
Multidisciplinary Sciences
Marine Vallet, Tim U. H. Baumeister, Filip Kaftan, Veit Grabe, Anthony Buaya, Marco Thines, Ales Svatos, Georg Pohnert
NATURE COMMUNICATIONS
(2020)
Article
Chemistry, Organic
Marine Vallet, Filip Kaftan, Veit Grabe, Fatemeh Ghaderiardakani, Simona Fenizia, Ales Svatos, Georg Pohnert, Thomas Wichard
Summary: Symbiosis is a dominant form of life in marine ecosystems, such as interactions between macroalgae and bacteria. Mass spectrometry profiling and imaging techniques can reveal symbiotic interactions between bacteria and macroalgae. This study provides a basis for understanding bacterial symbioses in aquatic ecosystems and offers a new tool for microbiome research.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Quentin Ronzon, Wei Zhang, Nicolas Casaretto, Elisabeth Mouray, Isabelle Florent, Bastien Nay
Summary: Our study reports the multiple, site-selective, metal-catalyzed C-H functionalization of a programmed 4-hydroxyquinoline, demonstrating its ability to introduce diversity into a biologically relevant chemical library.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Biochemistry & Molecular Biology
Ombeline Sculfort, Melanie McClure, Bastien Nay, Marianne Elias, Violaine Llaurens
Summary: Chemical defences in animals vary significantly between individuals, with factors such as larval host plants and brood lines influencing the type and amount of defensive compounds. The study highlights the continuous increase in chemical defences throughout the life of H. numata, with a significant effect of brood lines on CG concentrations. The overlooked effect of synthesis capabilities, which may be genetically determined, is also emphasized.
JOURNAL OF CHEMICAL ECOLOGY
(2021)
Article
Chemistry, Organic
Oscar Gayraud, Benjamin Laroche, Nicolas Casaretto, Bastien Nay
Summary: Aspochalasins are leucine-derived cytochalasins with a high level of biosynthetic oxidation, inspiring a two-phase strategy in total synthesis. A putative biomimetic tetracyclic intermediate was synthesized through an intramolecular Diels-Alder reaction to install the isoindolone core of cytochalasins, with the branched precursor obtained from a stereoselective Ireland-Claisen rearrangement. This also represents a formal synthesis of trichoderone A.
Article
Chemistry, Organic
Zi-Rong Zeng, Wang-Sheng Li, Bastien Nay, Pei Hu, Hai-Yan Zhang, Hong Wang, Xu-Wen Li, Yue-Wei Guo
Summary: A novel diterpenoid, sinunanolobatone A (1), with an unprecedented carbon framework, along with new casbane diterpenoids (2 and 3) and known related compounds (4-8) were isolated from the Sanya soft coral Sinularia nanolobata. The structure of the new compounds was determined using various analytical methods and a biosynthetic pathway for compound 1 was proposed. Compound 1 exhibited significant inhibitory activity against LPS-induced inflammation in BV-2 microglial cells.
Editorial Material
Chemistry, Multidisciplinary
Bastien Nay
ACS CENTRAL SCIENCE
(2021)
Review
Geochemistry & Geophysics
Yun Deng, Marine Vallet, Georg Pohnert
Summary: The annual patterns of plankton succession in the ocean determine ecological and biogeochemical cycles, and the interplay between photosynthetic eukaryotes and microbiota balances the composition of aquatic planktonic ecosystems. Chemical signaling plays a key role in these interactions, influencing species succession and community composition.
ANNUAL REVIEW OF MARINE SCIENCE
(2022)
Article
Chemistry, Organic
Bruce Lockett-Walters, Simon Thuillier, Emmanuel Baudouin, Bastien Nay
Summary: This study presents the shortest synthesis method for radulanin A to date, utilizing a less explored photochemical ring expansion reaction. The method has been adapted for larger-scale preparation, enabling biological investigations into the herbicidal properties of this natural product.
Article
Chemistry, Multidisciplinary
Quentin Ronzon, Wei Zhang, Thomas Charote, Nicolas Casaretto, Gilles Frison, Bastien Nay
Summary: This study describes the total synthesis of two fungal cyclotripeptides, (+)-cinereain and (-)-janoxepin, which possess a complex heterocyclic core and exhibit interesting phytotoxic and antimalarial activities. The key step in the synthesis is a one-pot cascade reaction that releases a reactive spiro[2-vinylcyclopropane-1,5'-pyrimidine-4',6'-dione] intermediate through the cyclocondensation of two fragments. This intermediate undergoes a spontaneous retro-Claisen rearrangement, leading to the formation of a 2,5-dihydrooxepin-fused heterocyclic product. The challenging oxepin ring is finally forged through a palladium-catalyzed beta-hydride elimination of an allylic fluoride intermediate.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Benjamin Joyeux, Antoine Gamet, Nicolas Casaretto, Bastien Nay
Summary: Latrunculins, marine toxins used in cell biology, can be effectively blocked from actin polymerization by developing new synthetic strategies and methods. This study proposes an alternative disconnection and subsequent stereoselective transformations to construct a stereopentade that allows for the synthesis of Latrunculin and analogues, starting from (+)-beta-citronellene. Key stereoselective transformations involve asymmetric Krische allylation, aldol reaction, and Tishchenko-Evans reduction with ester transposition.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Editorial Material
Chemistry, Organic
Bastien Nay
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Agathe Fayet, Sophie Bourcier, Nicolas Casaretto, Bastien Nay, Gilles Frison
Summary: The Hock rearrangement is an acid catalyzed reaction involving organic hydroperoxides and resulting in an oxidative cleavage of adjacent C-C bonds. Its mechanism has not been studied in detail. In this work, we conducted a theoretical study on the Hock rearrangement using InCl3 as a Lewis acid catalyst. We aimed to understand the mechanism of this reaction and rationalize the influence of substrate electronic properties. Our investigation revealed the co-existence of several energetically close reaction pathways and suggested that In2Cl6 species coordinated to the substrate play a central role in the catalytic cycle.
Article
Chemistry, Organic
Alexandra E. E. Bosnidou, Agathe Fayet, Cristina Cheibas, Oscar Gayraud, Sophie Bourcier, Gilles Frison, Bastien Nay
Summary: This article describes a tandem reaction between a Hock or Criegee oxidative cleavage and a nucleophilic addition onto the oxocarbenium species (specifically a Hosomi-Sakurai-type allylation), catalyzed by InCl3. It was successfully applied to the synthesis of 2-substituted benzoxacycles (chromanes and benzoxepanes), including the synthesis of the 2-(aminomethyl)chromane part of sarizotan and the total synthesis of erythrococcamide B.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Agronomy
Simon Thuillier, Stefania Viola, Bruce Lockett-Walters, Bastien Nay, Benjamin Bailleul, Emmanuel Baudouin
Summary: Radulanin A, synthesized by liverworts, exhibits phytotoxic activity by inhibiting photosynthesis and targeting the Q(B) site of Photosystem II (PSII). The findings provide insights for the development of potential herbicides.
PEST MANAGEMENT SCIENCE
(2023)
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
