Dihydrocoumarin is a compound found in Melilotus officinalis. Dihydrocoumarin is a yeast Sir2p inhibitor. Dihydrocoumarin also inhibits human SIRT1 and SIRT2 with IC50s of 208 μM and 295 μM, respectively.
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Quorum sensing (QS) is an intercellular signaling and gene regulatory mechanism that is implicated in food spoilage caused by bacteria. Thus, blocking QS may suppress QS-controlled phenotypes of these bacteria that are responsible for food spoilage. Biofilm formation is closely related to bacterial infection, and it is also a major mechanism responsible for the increased resistance of biofilm-associated bacteria to antimicrobial drugs. Food spoilage and biofilm formation caused by food-related bacteria have posed a significant problem for the food industry. Thus, adopting an antibiofilm approach would provide an alternative to an antibiotic strategy. Dihydrocoumarin is a compound that is derived from coumarin, a known natural QS inhibitor that has been used as an additive in food. Hafnia alvei is a spoilage bacterium; H. alvei H4 was isolated from ready-to-eat sea cucumber. Considering that QS and biofilm are often closely linked, this research aimed to detect the effect of dihydrocoumarin on the production of violacein by Chromobacterium violaceum 026 and to evaluate the inhibitory effect of dihydrocoumarin on the formation of biofilm by H. alvei H4 by using violacein and crystal violet assays. C. violaceum 026 treated with dihydrocoumarin showed as much as 70.1% reduction in QS-mediated production of violacein compared with untreated cells, while exhibiting no significant change in growth. H. alvei H4 treated with dihydrocoumarin displayed 75.8% reduction in swimming motility, and as much as 89.4% reduction in biofilm formation compared with the nontreated cells, with the reduction in both cases being dependent on the concentration of dihydrocoumarin. Scanning electron microscopy showed that dihydrocoumarin could effectively destroy the biofilm structure of H. alvei H4 and decrease biofilm density. These findings indicate that dihydrocoumarin can be developed into a new QS inhibitor or antibiofilm agent for controlling food spoilage and potentially investigated to increase food safety.
Antibiofilm; Dihydrocoumarin; Hafnia alvei H4; Quorum sensing.
Inhibition of Hafnia Alvei H4 Biofilm Formation by the Food Additive Dihydrocoumarin
Hong Man Hou 1 , Feng Jiang 1 , Gong Liang Zhang 1 , Jia Y Wang 1 , Ya H Zhu 1 , Xin Y Liu 1
2017 Apr 12
Coumarins are natural and synthetic active ingredients widely applied in diverse types of medicinal treatments, such as cancer, inflammation, infection, and enzyme inhibition (monoamine oxidase B). Dihydrocoumarin compounds are of great interest in organic chemistry due to their structural versatilities and, as part of our investigations concerning the structural characterization of small molecules, this work focuses on crystal structure and spectroscopic characterization of the synthesized and crystallized compound 4-(4-methoxyphenyl)-3,4-dihydro-chromen-2-one (C16H14O3). Additionally, a theoretical calculation was performed using density functional theory to analyze the sites where nucleophilic or electrophilic attack took place and to examine the molecular electrostatic potential surface. Throughout all of these calculations, both density functional theory and Car-Parrinello molecular dynamics were performed by fully optimized geometry. The spectroscopic analysis indicated the presence of aromatic carbons and hydrogen atoms, and also the carbonyl and methoxy groups that were confirmed by the crystallographic structure. The C16H14O3 compound has a non-classical intermolecular interaction of type C-H???O that drives the molecular arrangement and the crystal packing. Moreover, the main absorbent groups were characterized throughout calculated harmonic vibrational frequencies. Also, natural bond orbital analysis successfully locates the molecular orbital with π-bonding symmetry and the molecular orbital with π* antibonding symmetry. Finally, the gap between highest occupied and lowest unoccupied molecular orbitals implies in a high kinetic stability and low chemical reactivity of title molecule.
Coumarin; DFT analysis; NBO; X-ray diffraction.
A Novel Dihydrocoumarin Under Experimental and Theoretical Characterization
W F Vaz 1 2 , J M F Custodio 1 3 , N M N Rodrigues 1 , L G Santin 1 4 , S S Oliveira 1 , R Gargano 4 , F A P Osorio 3 5 , G L B Aquino 1 , A J Camargo 1 , M S Oliveira 1 , H B Napolitano 6
2017 Oct 18
Effective DNA repair enables cancer cells to survive DNA damage induced by chemotherapeutic or radiotherapeutic treatments. Therefore, inhibiting DNA repair pathways is a promising therapeutic strategy for increasing the efficacy of such treatments. In this study, we found that dihydrocoumarin (DHC), a flavoring agent, causes deficiencies in double-stand break (DSB) repair and prolonged DNA damage checkpoint recovery in yeast. Following DNA damage, Rad52 recombinase was revealed to be inhibited by DHC, which results in deficiencies in DSB repair and prolonged DNA damage checkpoint recovery. The deletion of RPD3, a class I histone deacetylase (HDAC), was found to mimic DHC-induced suppression of Rad52 expression, suggesting that the HDAC inhibitor activity of DHC is critical to DSB repair and DNA damage sensitivity. Overall, our findings delineate the regulatory mechanisms of DHC in DSB repair and suggest that it might potentially be used as an inhibitor of the DNA repair pathway in human cells.
DHC; DNA damage sensitivity; DSB; Rad52; homologous recombination; yeast.
Dihydrocoumarin, an HDAC Inhibitor, Increases DNA Damage Sensitivity by Inhibiting Rad52
Chin-Chuan Chen 1 2 3 , Ju-Sui Huang 4 , Tong-Hong Wang 5 6 7 , Chen-Hsin Kuo 8 , Chia-Jen Wang 9 , Shu-Huei Wang 10 , Yann-Lii Leu 11 12 13
2017 Dec 7