Update on naturally occurring novel arylnaphthalenes from plants

Li, Shoujie; Liang, Zizhen; Li, Jinjie; Zhang, Xuan; Zheng, Ruihong; Zhao, Changqi

doi:10.1007/s11101-020-09668-7

Cited by 28 publications

(14 citation statements)

References 172 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Compound 23a was obtained as a white solid (42. 6 Dimethyl 1 8 ,2 3 -Dimethoxy-4,11-dioxo-3,12-dioxa-1(1,7)-naphthalena-2(1,4)-benzenacyclododecaphane-1 2 ,1 3 -dicarboxylate (24a). The photo reactant 22a (100.0 mg, 181.63 μmol) dissolved in DCM (36.33 mL, 5 mM) was subjected to the reaction conditions described in GP4.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…Between 1999 and 2019 alone, more than 300 representatives of this class have been reported exhibiting a variety of biological activities. 3 Among others, cytotoxicity, antimicrobial, and antiviral activity should be mentioned. In view of the interesting biological activities and the poor accessibility of plant raw materials, it is hardly surprising that total syntheses for a number of ANLs were already published.…”

Section: ■ Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Studies toward the Total Synthesis of Arylnaphthalene Lignans via a Photo-Dehydro-Diels–Alder (PDDA) Reaction

et al. 2022

View full text Add to dashboard Cite

An efficient method for the preparation of arylnaphthalene lignans (ANLs) was developed, which is based on the Photo-Dehydro-Diels–Alder (PDDA) reaction. While intermolecular PDDA reactions turned out to be inefficient, the intramolecular variant using suberic acid as tether linking two aryl propiolic esters smoothly provided naphthalenophanes. The irradiations were performed with a previously developed annular continuous-flow reactor and UVB lamps. In this way, the natural products Alashinol D, Taiwanin C, and an unnamed ANL could be prepared.

show abstract

Section: ■ Experimental Sectionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Studies toward the Total Synthesis of Arylnaphthalene Lignans via a Photo-Dehydro-Diels–Alder (PDDA) Reaction

et al. 2022

View full text Add to dashboard Cite

show abstract

“…Natural derivatives of diphyllin are known that have methyl or glycosyl linkages to the phenol group. 57 An example is a 6-deoxyglucosyl-diphyllin derivative, which showed in vivo efficacy in a Zika infection model. 40 However, adding glycosyl groups can enhance activities associated with cytotoxic effects.…”

Section: Results and Discussionmentioning

confidence: 99%

Evaluation of Phenol-Substituted Diphyllin Derivatives as Selective Antagonists for Ebola Virus Entry

Plescia¹,

Lindstrom²,

Quintero

et al. 2022

ACS Infect. Dis.

View full text Add to dashboard Cite

Ebola virus (EBOV) is an aggressive filoviral pathogen that can induce severe hemorrhagic fever in humans with up to 90% fatality rate. To date, there are no clinically effective small-molecule drugs for postexposure therapies to treat filoviral infections. EBOV cellular entry and infection involve uptake via macropinocytosis, navigation through the endocytic pathway, and pH-dependent escape into the cytoplasm. We report the inhibition of EBOV cell entry via selective inhibition of vacuolar (V)-ATPase by a new series of phenol-substituted derivatives of the natural product scaffold diphyllin. In cells challenged with Ebola virus, the diphyllin derivatives inhibit viral entry dependent upon structural variations to low nanomolar potencies. Mechanistically, the diphyllin derivatives had no effect on uptake and colocalization of viral particles with endocytic marker LAMP1 but directly modulated endosomal pH. The most potent effects were reversible exhibiting higher selectivity than bafilomycin or the parent diphyllin. Unlike general lysosomotrophic agents, the diphyllin derivatives showed no major disruptions of endocytic populations or morphology when examined with Rab5 and LAMP1 markers. The dilated vacuole phenotype induced by apilimod treatment or in constitutively active Rab5 mutant Q79L-expressing cells was both blocked and reversed by the diphyllin derivatives. The results are consistent with the action of the diphyllin scaffold as a selective pH-dependent viral entry block in late endosomes. Overall, the compounds show improved selectivity and minimal cytotoxicity relative to classical endosomal acidification blocking agents.

show abstract

“…Although the isolation and chemistry of natural lignan products has been broadly reviewed (Teponno et al 2016;Li et al 2020), a focused and comprehensive review on the structures and beneficial biological activities of natural arylnaphthalene lignan lactones has not been published. The purpose of this review is to provide a compilation of naturally occurring arylnaphthalene lignan lactones in terms of structure, isolation, and pharmacological activity.…”

Section: Introductionmentioning

confidence: 99%

Arylnaphthalene lactones: structures and pharmacological potentials

2021

View full text Add to dashboard Cite

Natural arylnaphthalene lactones are representative lignans that are found in various dietary and medicinal plants. Their unique structural features and significant pharmacological activity have attracted considerable attention from both synthetic and medicinal chemists. Owing to their unique structural features such as relative rigid tetracyclic skeleton, structural diversity of more than five substituents, and no chiral center, arylnaphthalene lactones are recognized as a valuable scaffold for drug discovery, in addition to their significant pharmacological activities. This review covers the structures and isolation of all naturally occurring arylnaphthalene lactone congeners reported. Based on the aryl substituents, they were categorized as Type I and Type II and further classified according to the oxidation state of the ring and glycosylation level. Special attention has been paid to natural arylnaphthalene lactones owing to their broad spectrum of biological activities such as cytotoxic, antiplatelet, antiviral, anti-HIV, antifungal, neuroprotective, and anti-inflammatory properties. All the products were reorganized based on their biological activities, and selected data are presented.

show abstract

Update on naturally occurring novel arylnaphthalenes from plants

Cited by 28 publications

References 172 publications

Studies toward the Total Synthesis of Arylnaphthalene Lignans via a Photo-Dehydro-Diels–Alder (PDDA) Reaction

Studies toward the Total Synthesis of Arylnaphthalene Lignans via a Photo-Dehydro-Diels–Alder (PDDA) Reaction

Evaluation of Phenol-Substituted Diphyllin Derivatives as Selective Antagonists for Ebola Virus Entry

Arylnaphthalene lactones: structures and pharmacological potentials

Contact Info

Product

Resources

About