Structure–activity relationship studies of the phytotoxic properties of the diterpenic moiety of breviones

Carrera, Ceferino; Chinchilla, Nuria; Fronczek, Frank R.; Galindo, Juan C. G.; Macías, Francisco A.

doi:10.1002/ps.3831

Cited by 5 publications

(4 citation statements)

References 32 publications

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“…Several studies suggested that CHFR gene expression is frequently silenced by promoter hypermethylation in gastric cancer 8-12. Additionally, CHFR promoter methylation improved the gastric cancer sensitivity to microtubule inhibitors such as docetaxel and paclitaxel 13, 14. However, the samples of these studies were too small to confirm solid results.…”

Section: Introductionmentioning

confidence: 88%

CHFR Promoter Hypermethylation Is Associated with Gastric Cancer and Plays a Protective Role in Gastric Cancer Process

Dai

Zhou

et al. 2019

J. Cancer

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Background : Chromosomally unstable tumors account for 50% of gastric cancer. CHFR plays a role in controlling chromosomal instability and its inactivation will eventually lead to tumorigenesis. In addition to genetic deletion, DNA methylation could silence the expression of many cancer-related genes including CHFR. Its methylation was found to be associated with the initiation and progression of gastric cancer. Methods : We performed a meta-analysis involving methylation analyses of CHFR promoter in gastric cancer. Nineteen studies with 1,249 tumor tissues and 745 normal tissues had been included in current study. Results : We found that CHFR methylation was significantly higher in gastric cancer (studies numbers = 15, cases/controls = 862/745, odds ratio (OR) = 7.46, 95% confidence index (95% CI) = 4.99-11.14). Methylation array data was also obtained from Gene Expression Omnibus (GEO) and The Cancer Genome Atlas network (TCGA). There were 7 out of 13 CHFR methylation probes target to the same CpG island region (hg19, 131973620-131975130) showed the CHFR methylation was higher in gastric cancers than normal controls. Eight probes showed CHFR promoter hypermethylation was associated with longer overall survival of gastric cancer patients (Hazard Ratio < 1). Conclusions : The CHFR promoter hypermethylation was associated with gastric cancer and played a protective role in gastric cancer process. Its methylation could be a potential biomarker for the diagnosis and prognosis of gastric cancer.

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Section: Introductionmentioning

confidence: 88%

CHFR Promoter Hypermethylation Is Associated with Gastric Cancer and Plays a Protective Role in Gastric Cancer Process

Dai

Zhou

et al. 2019

J. Cancer

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“…Diterpenes and sesquiterpene lactones are two large families of widely studied natural products that show a broad range of biological activities. For example, diterpenes are known as anticancer, anti-diabetic (Nagarajan and Brindha, 2012), anti-inflammatory (Kapewangolo et al, 2015), anti-oxidant (Kolak et al, 2009) or phytotoxic compounds (Carrera et al, 2015). In contrast, sesquiterpene lactones have been reported to show a variety of activities, such as antimicrobial, antitumour, anti-inflammatory, cytotoxic, antiviral, antimalarial, antibacterial and antifungal.…”

Section: Introductionmentioning

confidence: 99%

Phytotoxicity evaluation of sesquiterpene lactones and diterpenes from species of the Decachaeta , Salvia and Podachaenium genera

Rial

Varela

Molinillo

et al. 2016

Phytochemistry Letters

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Decachaeta, Salvia and Podachaenium genera are known for their wide variety of biological activities. Synthetic herbicides have caused a variety of environmental and resistance problems. Natural products represent an important alternative to combat such issues. Sesquiterpene lactones and diterpenes are families of bioactive natural products for which a range of activities have been described. The bioactivities of nine sesquiterpene lactones, eight heliangolides, one guaianolide and twenty two diterpenes isolated from species of the Decachaeta, Salvia and Podachaenium genera were tested by applying a methodical procedure that involves assays of compounds on etiolated wheat coleoptiles (Triticum aestivum), Standard Target Species (STS) and two important weeds (barnyardgrass and brachiaria). The results clearly show that all of the sesquiterpene lactones studied were active on coleoptiles. In addition, six lactones were phytotoxic on both STS and weeds, meaning that these compounds could be used in the development of natural herbicide models.

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“…Polyketides, a series of metabolites derived from polyketide synthases (PKS), always show abundant structure diversities and also various pharmaceutical potentials . However, there are only a few herbicidal assessments of natural polyketides − and no herbicidal reports of the heptaketide series bearing the trans -fused decalin skeleton. Therefore, the isolation and significant herbicidal potentials of new polyketides 1 – 3 and known 4 could not only enrich the structure diversities of herbicide metabolites from microbes but also exhibit a herbicide heptaketide skeleton, which might also show the potential of new target sites.…”

Section: Resultsmentioning

confidence: 99%

Herbicidal Polyketides and Diketopiperazine Derivatives fromPenicillium viridicatum

Wang

Sun

Xiao

et al. 2019

J. Agric. Food Chem.

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Herbicidal activity-guided isolation from the fermentation extract of Penicillium viridicatum had obtained two herbicidal series of polyketides (1−7) and diketopiperazine derivatives (8−11), especially including three novel polyketides (1−3). The structures and absolute configurations of new polyketides 1−3 were elucidated by extensive spectroscopic analyses, as well as comparisons between measured and calculated ECD spectra. Novel polyketides 1−3 and known 4, all bearing the heptaketide skeleton with a trans-fused decalin ring of 8-CH 3 substitution, could significantly inhibit the radicle growth of Echinochloa crusgalli seedlings with a dose-dependent relationship. Especially at the concentration of 10 μg/mL, 1−4 exhibited the inhibition rates with 81.5% ± 2.0, 76.4% ± 0.8, 79.6% ± 1.1, and 80.0 ± 1.8%, respectively, even better than the commonly used synthetic herbicide of acetochlor with 76.1 ± 1.4%. Further greenhouse bioassay revealed that 4 showed pre-emergence herbicidal activity against E. crusgalli with the fresh-weight inhibition rate of 74.1% at a dosage of 400 g ai/ha, also better than acetochlor, while the other isolated metabolites (5−11) exhibited moderate herbicidal activities. The structure−activity differences of isolated polyketides indicated that the heptaketide skeleton, characterized by a trans-fused decalin ring with 8-CH 3 substitution, should be the key factor of their herbicidal activities, which could give new insights for the bioherbicide developments.

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Structure–activity relationship studies of the phytotoxic properties of the diterpenic moiety of breviones

Cited by 5 publications

References 32 publications

CHFR Promoter Hypermethylation Is Associated with Gastric Cancer and Plays a Protective Role in Gastric Cancer Process

CHFR Promoter Hypermethylation Is Associated with Gastric Cancer and Plays a Protective Role in Gastric Cancer Process

Phytotoxicity evaluation of sesquiterpene lactones and diterpenes from species of the Decachaeta , Salvia and Podachaenium genera

Herbicidal Polyketides and Diketopiperazine Derivatives fromPenicillium viridicatum

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