Depsidones and diaryl ethers from potato endophytic fungus Boeremia exigua

Chen, Yao; Sun, Li-Tang; Yang, Huixiang; Li, Zhenghui; Liu, Ji‐Kai; Ai, Hong‐Lian; Wang, Guo-Kai; Feng, Tao

doi:10.1016/j.fitote.2020.104483

Cited by 12 publications

(9 citation statements)

References 11 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Compounds 82 and 83 were obtained as a racemic mixture having 10 R ([ α ] D + 199.2) and 10 S ([ α ] D − 206.5) configurations, respectively that were further separated into enantiomers on chiral HPLC column. In the MTT assay, 83 (IC 50 33.1 μM) possessed cytotoxic capacity against MCF–7 compared to taxol (IC 50 0.008 μM) ( Chen et al, 2020 ).…”

Section: Bioactivities Of Depsidonesmentioning

confidence: 99%

“…The molecular docking implied that 31 suppressed IL-1β production via binding to the TLR2/1 protein active site ( Ding et al, 2019 ). Compounds 7 , 34 , and 82 – 84 revealed anti-inflammation potential (IC 50 s 19.4–34.4 μM) on NO formation induced by LPS in RAW264.7 macrophages, where 7 and 83 had potent potential (IC 50 s 22.6 and 19.9 μM, respectively) relative to PDTC (IC 50 23.1 μM, ammonium pyrrolidine dithiocarbamate) ( Chen et al, 2020 ) ( Table S5 ).…”

Section: Bioactivities Of Depsidonesmentioning

confidence: 99%

See 1 more Smart Citation

Recent advances on natural depsidones: sources, biosynthesis, structure-activity relationship, and bioactivities

Khayat

Ghazawi

Samman

et al. 2023

PeerJ

View full text Add to dashboard Cite

Depsidones are a class of polyphenolic polyketides that have been proposed to be biosynthesized from oxidative coupling of esters of two polyketidic benzoic acid derivatives. They are principally encountered in fungi and lichens. In addition to their diversified structural features, they revealed varied bioactivities such as antimicrobial, antimalarial, cytotoxic, anti-inflammatory, anti-Helicobacter pylori, antimycobacterial, antihypertensive, anti-diarrheal, antidiabetic, phytotoxic, anti-HIV, anti-osteoclastogenic, and butyrylcholinesterase, tyrosinase, hyaluronidase, and acetylcholinesterase inhibition. The current work was targeted to provide an overview on the naturally reported depsidones from various sources in the period from 2018 to the end of 2022 including their structures, biosynthesis, sources, and bioactivities, as well as the reported structure-activity relationship and semisynthetic derivatives. A total of 172 metabolites with 87 references were reviewed. The reported findings unambiguously demonstrated that these derivatives could be promising leads for therapeutic agents. However, further in-vivo evaluation of their potential biological properties and mechanistic investigations are needed.

show abstract

Section: Bioactivities Of Depsidonesmentioning

confidence: 99%

Section: Bioactivities Of Depsidonesmentioning

confidence: 99%

Recent advances on natural depsidones: sources, biosynthesis, structure-activity relationship, and bioactivities

Khayat

Ghazawi

Samman

et al. 2023

PeerJ

View full text Add to dashboard Cite

show abstract

“…Their variable linked patterns and different substituents lead to rich structural diversity. Naturally occurring depsides and depsidones were recently found with a wide array of remarkable bioactivities, including antimicrobial [ 8 , 9 ], α-glucosidase inhibitory [ 10 , 11 ], anti-inflammatory [ 12 , 13 ], cytotoxic [ 12 ], antioxidant [ 14 ], and anti-viral activities [ 15 ], arousing considerable interest from the communities of chemistry and pharmacology [ 6 , 16 ]. Curiously, a depsidone natural product, norstictic acid, was very recently reported as a key selective allosteric transcriptional regulator in a patient-derived model of triple-negative breast cancer [ 17 ].…”

Section: Introductionmentioning

confidence: 99%

Anti-Osteoclastogenic and Antibacterial Effects of Chlorinated Polyketides from the Beibu Gulf Coral-Derived Fungus Aspergillus unguis GXIMD 02505

Zhang

Huang

et al. 2022

Marine Drugs

View full text Add to dashboard Cite

One new depsidone derivative, aspergillusidone H (3), along with seven known biosynthetically related chlorinated polyketides, were obtained from the Beibu Gulf coral-derived fungus Aspergillus unguis GXIMD 02505. Their structures were determined by comprehensive physicochemical and spectroscopic data interpretation. Notably, the X-ray crystal structure of 2 and the previously unknown absolute configuration of 8, assigned by ECD calculations, are described here for the first time. Compounds 1–5, 7 and 8 exhibited inhibition of lipopolysaccharide (LPS)-induced NF-κB in RAW 264.7 macrophages at 20 μM. In addition, the two potent inhibitors (2 and 7) dose-dependently suppressed RANKL-induced osteoclast differentiation without any evidence of cytotoxicity in bone marrow macrophages cells (BMMs). This is the first report of osteoclastogenesis inhibitory activity for the metabolites of these kinds. Besides, compounds 1, 2, 4, and 6–8 showed inhibitory activity against marine biofilm-forming bacteria, methicillin-resistant Staphylococcus aureus, Microbulbifer variabilis, Marinobacterium jannaschii, and Vibrio pelagius, with their MIC values ranging from 2 to 64 μg/mL. These findings provide a basis for further development of chlorinated polyketides as potential inhibitors of osteoclast differentiation and/or for use as anti-fouling agents.

show abstract

“…Due to their special structural features and various functional groups, eremophilane-type sesquiterpenes possess a lot of biological activities such as anti-inflammatory [ 21 ], antitumor [ 10 ], and antibacterial [ 22 , 23 ] activities, which have received increasing interest in the recent years. As part of our ongoing efforts to discover bioactive terpenoids derived from endophytic fungi [ 24 , 25 , 26 , 27 ], a chemical investigation on the cultural broth of B. exigua in rice medium was carried out. As a result, four new highly oxygenated eremophilane-type sesquiterpenes, boeremialanes A–D ( 1 – 4 ), were isolated from cultures of the fungus B. exigua .…”

Section: Introductionmentioning

confidence: 99%

Four New Highly Oxygenated Eremophilane Sesquiterpenes from an Endophytic Fungus Boeremia exigua Isolated from Fritillaria hupehensis

Yao

et al. 2022

JoF

Self Cite

View full text Add to dashboard Cite

Four new eremophilane-type sesquiterpenes, boeremialanes A–D (1–4) were obtained from solid substrate cultures of Boeremia exigua (Didymellaceae), an endophytic fungus isolated from Fritillaria hupehensis (Liliaceae). Boeremialanes A–C (1–3) are highly oxygenated eremophilanes with a benzoate unit attached at the C-13 position and are rarely found in nature. Their structures and absolute configurations were determined by extensive spectroscopic methods, electronic circular dichroism (ECD), and nuclear magnetic resonance (NMR) calculations with DP4+ analysis. Boeremialane D (4) potently inhibited nitric oxide production in lipopolysaccharide-treated RAW264.7 macrophages with an IC50 of 8.62 μM and was more potent than the positive control, pyrrolidinedithiocarbamate (IC50 = 23.1 μM).

show abstract

Depsidones and diaryl ethers from potato endophytic fungus Boeremia exigua

Cited by 12 publications

References 11 publications

Recent advances on natural depsidones: sources, biosynthesis, structure-activity relationship, and bioactivities

Recent advances on natural depsidones: sources, biosynthesis, structure-activity relationship, and bioactivities

Anti-Osteoclastogenic and Antibacterial Effects of Chlorinated Polyketides from the Beibu Gulf Coral-Derived Fungus Aspergillus unguis GXIMD 02505

Four New Highly Oxygenated Eremophilane Sesquiterpenes from an Endophytic Fungus Boeremia exigua Isolated from Fritillaria hupehensis

Contact Info

Product

Resources

About