Synthesis and biological evaluation of novel coumarin derivatives in rhabdoviral clearance

Hu, Yang; Shan, Li-Peng; Qiu, Tian-Xiu; Liu, Lei; Chen, Jiong

doi:10.1016/j.ejmech.2021.113739

Cited by 28 publications

(24 citation statements)

References 48 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Coumarins, on the other hand, are easier to synthesize than arctigenin (Liu et al, 2016(Liu et al, , 2021(Liu et al, , 2022. And our previous research has shown the anti-parasitic activity of several newly synthesized coumarin derivatives Hu, Shan, Qiu, et al, 2021;Wang et al, 2021). These derivatives were tested against D. intermedius, and based on structure-activity relationship, a new coumarin derivative with a triazole substitute group, N11, was synthesized and found to have superior anthelmintic activity compared to the previous coumarins.…”

Section: Discussionmentioning

confidence: 99%

“…Preventing the horizontal transmission of parasites can greatly reduce the likelihood of fish disease outbreaks. Previous research has shown that coumarin derivatives, such as infectious haematopoietic necrosis virus and spring viremia of carp virus (Hu, Shan, Qiu, et al, 2021; Liu et al, 2020; Qiu et al, 2020), can inhibit the horizontal transmission of rhabdovirus. Our study is consistent with these findings and demonstrates that N11 can effectively inhibit the horizontal transmission of D. intermedius , indicating its potential as a prophylactic agent against parasites.…”

Section: Discussionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis and anti‐parasites efficacy of coumarin derivatives against Dactylogyrus intermedius

Liu,

Zhang,

Zhu

et al. 2023

Journal of Fish Diseases

Self Cite

View full text Add to dashboard Cite

Dactylogyrus is one of the most common parasitic diseases in fish and causes huge losses to the aquaculture industry. With the advantages of safety, low toxicity and easy degradation, plant‐derived drugs are ideal for the creation of green aquatic ingredients. The use of plant‐derived drugs in aquaculture is limited by their low content and high processing costs, which is a challenge that can be solved by the chemical synthesis of plant‐derived drugs. Eleven new coumarin derivatives were synthesized and assessed for their anthelmintic activity in this study. Among them, the derivative 7‐((1‐tosyl‐1H‐1,2,3‐triazol‐4‐yl)methoxy)‐2H‐chromen‐2‐one (N11) has good anthelmintic activity and its mean anthelmintic efficacy against D. intermedius at a concentration of 10 μM reached 99.84%, which is even better than the anthelmintic activity of the positive control mebendazole. Further studies showed that N11 had concentration values of 3.31 and 1.94 μM for 50% maximal effect (EC50) against D. intermedius at 24 and 48 h, respectively. Furthermore, scanning electron microscopy revealed that N11 caused damage to D. intermedius. What is more noteworthy is that a substantial reduction in the ATP content of the parasite was observed following in vitro and in vivo administration of N11. Moreover, it was also found that N11 was able to inhibit the horizontal transmission of D. intermedius. Furthermore, real‐time quantitative PCR analysis was utilized to determine the expression profile of genes associated with anti‐inflammatory cytokines (IL‐10, TGF‐β and IL‐4) in goldfish. In all examined organs, it was observed that the expression of anti‐inflammatory cytokines increased subsequent to treatment with N11, according to the results. Thus, these results all suggest that N11 possesses good anthelmintic activity and is a potentially effective agent for the control of D. intermedius.

show abstract

Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Synthesis and anti‐parasites efficacy of coumarin derivatives against Dactylogyrus intermedius

Liu,

Zhang,

Zhu

et al. 2023

Journal of Fish Diseases

Self Cite

View full text Add to dashboard Cite

show abstract

“…Moreover, like MSRV, other fish rhabdoviruses, including spring viremia carp virus (SVCV), viral hemorrhagic septicemia virus (VHSV), pike fry rhabdovirus (PFRV), perch rhabdovirus (PRV), ulcerative disease rhabdovirus (UDRV), hirame rhabdovirus (HIRRV), and Siniperca chuatsi rhabdovirus (SCRV), can infect marine and freshwater fish, causing great economic losses in the aquaculture industry [ 23 , 24 , 25 , 26 , 27 ]. Currently, no drugs are available to prevent and control MSRV infection [ 28 , 29 ]. The discovery and the development of new antiviral drugs are usually costly and time-consuming processes.…”

Section: Discussionmentioning

confidence: 99%

Synthesized Magnolol Derivatives Improve Anti-Micropterus salmoides Rhabdovirus (MSRV) Activity In Vivo

Jin

Yang

Zhang³

et al. 2022

Viruses

View full text Add to dashboard Cite

Micropterus salmoides rhabdovirus (MSRV) is a primary viral pathogen in largemouth bass aquaculture, which leads to tremendous economic losses yearly. Currently, there are no approved drugs for the treatment and control of this virus. Our previous studies screened the herb Magnolia officinalis from many traditional Chinese medicines, and we isolated and identified magnolol as its main active compound against multiple rhabdoviruses, including MSRV. On the basis of the structure–activity relationship and pharmacophore model of magnolol, two new magnolol derivatives, namely, hydrogenated magnolol and 2,2′-dimethoxy-magnolol, were designed and synthesized. Their anti-MSRV activities were systematically investigated both in vitro and in vivo. By comparing the half-maximal inhibitory concentration (IC50), it was found that hydrogenated magnolol possessed a higher anti-MSRV activity than magnolol and 2,2′-dimethoxy-magnolol, with an IC50 of 13.37 μM. Furthermore, hydrogenated magnolol exhibited a protective effect on the grass carp ovary (GCO) cell line by reducing the cytopathic effect induced by MSRV. Further studies revealed that hydrogenated magnolol did not directly impact virions or interfere with MSRV adsorption. It worked within the 6–8 h of the phase of virus replication. In vivo treatment of MSRV infection with magnolol and hydrogenated magnolol showed that they significantly improved the survival rate by 44.6% and 62.7%, respectively, compared to MSRV-infected groups. The viral load measured by the expression of viral glycoprotein in the organs including the liver, spleen, and kidney also significantly decreased when fish were intraperitoneally injected at a dose of 20 mg/kg. Altogether, the structural optimization of magnolol via hydrogenation of the propylene groups increased its anti-MSRV activity both in vitro and in vivo. These results may provide a valuable reference for anti-MSRV drug discovery and development in aquaculture.

show abstract

“…Osthole ( 1 , Figure ), known as methoxy parsley, belongs to the coumarin-type compounds and has a high content in the plant Cnidium monnieri, , which possesses antitumor activity, , anti-inflammatory activity, , neuroprotective effect, and other biological properties. , Recent studies have found that it has potential application value in agriculture. , According to the China Pesticide Information Network (), 20 different osthole-type fungicides and insecticides were registered in China. In recent years, structural optimization of natural products as precursors has become the crucial means to obtain pesticide candidates.…”

Section: Introductionmentioning

confidence: 99%

Optimization of Osthole in the Lactone Ring as an Agrochemical Candidate: Synthesis, Characterization, and Pesticidal Activities of Osthole Amide/Ester Derivatives and Their Effects on Morphological Changes of Mite Epidermis

et al. 2023

J. Agric. Food Chem.

View full text Add to dashboard Cite

Structural modification of natural products is one of the important ways in the discovery of novel pesticides. Based on a diversity-oriented synthesis strategy, herein, two series of amide/ester derivatives (52 compounds) were obtained by opening the lactone of osthole. Interestingly, the effect of different concentrations of aq. sodium hydroxide on the ratio of two isomers (cis - and trans -2) was investigated, and a magical phenomenon of ultraviolet (UV) light irradiation on intertransformation of two isomers (cis - and trans -2) was observed. Against Mythimna separata, when compared with the precursor osthole, compounds 4b, 4l, 5l, 5m, 7h, 7l, and 7m displayed more pronounced growth inhibitory activity with the final mortality rates of 62.0–68.9%. Compounds 4b, 4i, and 5m showed 5.7–6.6 times stronger acaricidal activity against Tetranychus cinnabarinus than osthole, and notably, control effects of compounds 4i and 5m were 2.4- and 2.7-fold that of osthole in the management of T. cinnabarinus in the greenhouse. Scanning electron microscopy (SEM) images of the epidermis of 5m-treated T. cinnabarinus indicated that compound 5m can destroy the mite cuticle layer. Compounds 4b and 5m can be used as leads to further explore more promising pesticidal agents.

show abstract

Synthesis and biological evaluation of novel coumarin derivatives in rhabdoviral clearance

Cited by 28 publications

References 48 publications

Synthesis and anti‐parasites efficacy of coumarin derivatives against Dactylogyrus intermedius

Synthesis and anti‐parasites efficacy of coumarin derivatives against Dactylogyrus intermedius

Synthesized Magnolol Derivatives Improve Anti-Micropterus salmoides Rhabdovirus (MSRV) Activity In Vivo

Optimization of Osthole in the Lactone Ring as an Agrochemical Candidate: Synthesis, Characterization, and Pesticidal Activities of Osthole Amide/Ester Derivatives and Their Effects on Morphological Changes of Mite Epidermis

Contact Info

Product

Resources

About