Sesquiterpene lactones from Elephantopus scaber exhibit cytotoxic effects on glioma cells by targeting GSTP1

Yan, Qiulin; Bai, Ming; Zhang, Xin; Song, Shao‐Jiang; Yao, Guo‐Dong

doi:10.1016/j.bioorg.2022.106183

Cited by 7 publications

(2 citation statements)

References 46 publications

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“…Among the numerous NPs, sesquiterpene lactones (STLs) are a large class of plant secondary metabolites comprising more than 5000 compounds found in the plant kingdom, which are widely distributed in Asteraceae, Solanaceae, Euphorbiaceae, or other plants . Previous studies have reported that many STLs exhibit excellent antitumor, anti-inflammatory, or other pharmacological activities, − and they are innate chemical defense substances in plants that prevent the invasions from fungi, bacteria, insects, herbivores, or other pests. − Particularly, STLs containing the α-methylene-γ-butyrolactone structural fragment possess the prominent biological activities. A majority of these compounds show excellent inhibitory effects on pathogenic microorganisms, and they are usually used as ideal lead compounds for developing of novel antibacterial/antifungal agents. , …”

Section: Introductionmentioning

confidence: 99%

Discovery of Natural Sesquiterpene Lactone 1-O-Acetylbritannilactone Analogues Bearing Oxadiazole, Triazole, or Imidazole Scaffolds for the Development of New Fungicidal Candidates

Zhi

Yuan

et al. 2023

J. Agric. Food Chem.

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In recent decades, natural products have been considered important resources for developing of new agrochemicals because of their novel architectures and multibioactivities. Consequently, herein, 1-O-acetylbritannilactone (ABL), a natural sesquiterpene lactone from Inula britannica L., was used as a lead for further modification to discover fungicidal candidates. Six series of ABL-based derivatives containing an oxadiazole, triazole, or imidazole moiety were designed and synthesized, and their antifungal activities were also evaluated in vitro and in vivo. Bioassay results revealed that compounds 8d, 8h, and 8j (EC50 = 61.4, 30.9, and 12.4 μg/mL, respectively) exhibited more pronounced inhibitory activity against Fusarium oxysporum than their precursor ABL (EC50 > 500 μg/mL) and positive control hymexazol (EC50 = 77.2 μg/mL). Derivatives 8d and 11j (EC50 = 19.6 and 41.5 μg/mL, respectively) exhibited more potent antifungal activity toward Cytospora mandshurica than ABL (EC50 = 68.3 μg/mL). Compound 10 exhibited excellent and broad-spectrum antifungal activity against seven phytopathogenic fungal mycelia. Particularly, the inhibitory activity of compound 10 against the mycelium of Botrytis cinerea was more than 10.8- and 2.3-fold those of ABL and hymexazol, respectively. Meanwhile, derivative 10 (IC50 = 47.7 μg/mL) displayed more pronounced inhibitory activity against the spore of B. cinerea than ABL (IC50 > 500 μg/mL) and difenoconazole (IC50 = 80.8 μg/mL). Additionally, the in vivo control efficacy of compound 10 against B. cinerea was further studied using infected tomatoes (protective effect = 58.4%; therapeutic effect = 48.7%). The preliminary structure–activity relationship analysis suggested that the introduction of the 1,3,4-oxadiazole moiety (especially the 1,3,4-oxadiazole heterocycle containing the 4-chlorophenyl, 2-furyl, or 2-pyridinyl group) on the skeleton of ABL was more likely to produce potential antifungal compounds. These findings pave the way for further design and development of ABL-based derivatives as potential antifungal agents.

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Section: Introductionmentioning

confidence: 99%

Discovery of Natural Sesquiterpene Lactone 1-O-Acetylbritannilactone Analogues Bearing Oxadiazole, Triazole, or Imidazole Scaffolds for the Development of New Fungicidal Candidates

Zhi

Yuan

et al. 2023

J. Agric. Food Chem.

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“…Among them, germacranolide SLs featuring a distinctive 10-membered carbocycle fused with an α-methylene-γ-butyrolactone moiety often exhibit a broad range of pharmacological effects, such as cytotoxic, anti-inflammatory, antiviral, and neuroprotective bioactivities. Notably, parthenolide, a representative SL of the germacranolide class, has aroused broad interest from the chemical and pharmaceutical community by virtue of its multiple pharmacological activities, particularly the superior anticancer effects, and its derivative, ACT001, was designated as an orphan drug for the treatment of glioblastoma by the Food and Drug Administration and is currently undergoing phase II clinical trials …”

Section: Introductionmentioning

confidence: 99%

Highly Modified Sesquiterpene Lactones with Cytotoxic Activities from Strobocalyx chunii

Gao

Zhang

et al. 2023

J. Org. Chem.

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Three new germacranolide sesquiterpene lactones (SLs), strochunolides A−C (1−3, respectively), and a new guaianolide SL, strochunolide D (4), were isolated from Strobocalyx chunii and structurally characterized. Compound 1 is the first example of a dihomo-germacranolide SL, characterized by an unprecedented 6/10/5 tricyclic scaffold incorporating an additional fused δ-lactone C-ring. The structure of a known germacranolide SL, spicatolide C (5), was revised as its 8-epimer. Compound 3 exhibited potent in vitro cytotoxic activity against the HL-60 cell line, with an IC 50 value of 0.18 ± 0.01 μM.

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A highly oxidized germacranolide from elephantopus tomentosus inhibits the growth of hepatocellular carcinoma cells by targeting EGFR in vitro and in vivo

Li,

Niu,

Jia

et al. 2024

Bioorganic Chemistry

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Sesquiterpene lactones from Elephantopus scaber exhibit cytotoxic effects on glioma cells by targeting GSTP1

Cited by 7 publications

References 46 publications

Discovery of Natural Sesquiterpene Lactone 1-O-Acetylbritannilactone Analogues Bearing Oxadiazole, Triazole, or Imidazole Scaffolds for the Development of New Fungicidal Candidates

Discovery of Natural Sesquiterpene Lactone 1-O-Acetylbritannilactone Analogues Bearing Oxadiazole, Triazole, or Imidazole Scaffolds for the Development of New Fungicidal Candidates

Highly Modified Sesquiterpene Lactones with Cytotoxic Activities from Strobocalyx chunii

A highly oxidized germacranolide from elephantopus tomentosus inhibits the growth of hepatocellular carcinoma cells by targeting EGFR in vitro and in vivo

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