Chartspiroton, a Tetracyclic Spiro-naphthoquinone Derivative from a Medicinal Plant Endophytic <i>Streptomyces</i>

Zhao, Huimin; Yang, An‐Gang; Liu, Jian; Bao, Sheng; Ren, Peng; Hu, Yang; Yuan, Tianjie; Hou, Shurong; Xie, Tian; Zhang, Qichun; Chen, Xiabin; Wang, Xiachang; Hu, Lihong

doi:10.1021/acs.orglett.0c00696

Cited by 21 publications

(21 citation statements)

References 31 publications

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“…Although lonicerin has recently found effective to prevent 2,4,6-trinitrobenzenesulfonic acid solution-induced colitis in rats, the mechanism related to the inactivation of NF- κ B signaling pathway remains inexplicit 16 . As part of our effort to characterize active natural products 17 , their unique molecular targets 18 , and corresponding mechanism 19 , we herein have verified the lonicerin's protective effect on DSS-induced colitis. The mechanistic study highlights lonicerin as an anti-inflammatory agent in the prevention of NLRP3–ASC–pro-caspase-1 complex assembly and colitis development.…”

Section: Introductionmentioning

confidence: 70%

Lonicerin targets EZH2 to alleviate ulcerative colitis by autophagy-mediated NLRP3 inflammasome inactivation

Yao

Liu

et al. 2021

Acta Pharmaceutica Sinica B

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112

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Aberrant activation of NLRP3 inflammasome in colonic macrophages strongly associates with the occurrence and progression of ulcerative colitis. Although targeting NLRP3 inflammasome has been considered to be a potential therapy, the underlying mechanism through which pathway the intestinal inflammation is modulated remains controversial. By focusing on the flavonoid lonicerin, one of the most abundant constituents existed in a long historical anti-inflammatory and anti-infectious herb Lonicera japonica Thunb., here we report its therapeutic effect on intestinal inflammation by binding directly to enhancer of zeste homolog 2 (EZH2) histone methyltransferase. EZH2-mediated modification of H3K27me3 promotes the expression of autophagy-related protein 5, which in turn leads to enhanced autophagy and accelerates autolysosome-mediated NLRP3 degradation. Mutations of EZH2 residues (His129 and Arg685) indicated by the dynamic simulation study have found to greatly diminish the protective effect of lonicerin. More importantly, in vivo studies verify that lonicerin dose-dependently disrupts the NLRP3–ASC–pro-caspase-1 complex assembly and alleviates colitis, which is compromised by administration of EZH2 overexpression plasmid. Thus, these findings together put forth the stage for further considering lonicerin as an anti-inflammatory epigenetic agent and suggesting EZH2/ATG5/NLRP3 axis may serve as a novel strategy to prevent ulcerative colitis as well as other inflammatory diseases.

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Section: Introductionmentioning

confidence: 70%

Lonicerin targets EZH2 to alleviate ulcerative colitis by autophagy-mediated NLRP3 inflammasome inactivation

Yao

Liu

et al. 2021

Acta Pharmaceutica Sinica B

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112

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“…Dehydration and oxidation of Vb2 could yield compound 3 . In route 3, decarbonylation of IIIb3 gave IVb3 [ 25 ]. It can transform to Vb3 by tautomerism with loss of one H 2 .…”

Section: Resultsmentioning

confidence: 99%

Structurally Diverse Polycyclic Salicylaldehyde Derivative Enantiomers from a Marine-Derived Fungus Eurotium sp. SCSIO F452

et al. 2021

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To enlarge the chemical diversity of Eurotium sp. SCSIO F452, a talented marine-derived fungus, we further investigated its chemical constituents from a large-scale fermentation with modified culture. Four pairs of new salicylaldehyde derivative enantiomers, euroticins F-I (1–4), as well as a known one eurotirumin (5) were isolated and characterized. Compound 1 features an unprecedented constructed 6/6/6/5 tetracyclic structures, while 2 and 3 represent two new types of 6/6/5 scaffolds. Their structures were established by comprehensive spectroscopic analyses, X-ray diffraction, 13C NMR, and electronic circular dichroism calculations. Selected compounds showed significant inhibitory activity against α-glucosidase and moderate cytotoxic activities against SF-268, MCF-7, HepG2, and A549 cell lines.

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“…[67] A novel tetracyclic polyketide, chartspiroton, was obtained from a therapeutic plant Dendrobium officinale. [68] Seven new Securinega alkaloids, securingines were extracted from Securinega suffruticosa. In addition, their cytotoxic, anti-inflammatory, and neuroprotective activities were also studied.…”

Section: (à )-Rubriflordilactone Bmentioning

confidence: 99%

Natural and Synthetic Spirobutenolides and Spirobutyrolactones

Yadav

Pratap

Ram³

2020

Asian J Org Chem

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Spirobutenolides and spirobutyrolactones structural motifs are widespread in various natural products that exhibit a broad array of biological activities. Additionally, their synthetic analogues also serve as biologically active compounds and building blocks of complex molecules. Owing to the wide range of pharmacological activities and structural diversity of the spirobutenolides and spirobutyrolactones, various efficient synthetic methodologies have been established to construct such interesting scaffolds. In the past decades, numerous total syntheses of spirobutenolides and spirobutyrolactones containing natural products have been reported. Structurally diverse spirobutenolides and spirobutyrolactones have been synthesized by using singlet oxygen, Mannich reaction, aldol condensation, rearrangement reaction , Reformatsky reaction, Michael-addition cyclization, Diels-Alder reaction, photocyclization reaction, and pericyclic reactions. Recently, metal-catalyzed cyclization, photocatalyzed radical cyclization, Baylis-Hillman reaction, asymmetric organocatalysis, NHC catalysis, ring contraction reactions, and hypervalent iodine catalysis have emerged as powerful tools to architect these nuclei. This review gives an overview of advancements in chemically and biologically relevant spirobutenolides and spirobutyrolactones of natural and synthetic origin. It also covers the newer methodologies for the construction of natural as well as synthetic spirobutenolides and spirobutyrolactones along with their potential applications.

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Chartspiroton, a Tetracyclic Spiro-naphthoquinone Derivative from a Medicinal Plant Endophytic Streptomyces

Cited by 21 publications

References 31 publications

Lonicerin targets EZH2 to alleviate ulcerative colitis by autophagy-mediated NLRP3 inflammasome inactivation

Lonicerin targets EZH2 to alleviate ulcerative colitis by autophagy-mediated NLRP3 inflammasome inactivation

Structurally Diverse Polycyclic Salicylaldehyde Derivative Enantiomers from a Marine-Derived Fungus Eurotium sp. SCSIO F452

Natural and Synthetic Spirobutenolides and Spirobutyrolactones

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