First Discovery and Stucture-Activity Relationship Study of Phenanthroquinolizidines as Novel Antiviral Agents against Tobacco Mosaic Virus (TMV)

Abstract

A series of phenanthroquinolizidine alkaloids 1–24 were prepared and first evaluated for their antiviral activity against tobacco mosaic virus (TMV). The bioassay results showed that most of these compounds exhibited good to excellent in vivo anti-TMV activity, of which compounds 1, 2, 15 and 16 displayed significantly higher activity than (R)-antofine and commercial Ningnanmycin at the same test condition. The substituents on the phenanthrene moiety play an important role for maintaining high in vivo antiviral activity. The introduction of 6-hydroxyl, which is proposed to interact with TMV RNA, did increased anti-TMV activity. The 14aR-configuration was confirmed to be the preferred antiviral configuration for phenanthroquinolizidine alkaloids. Introduction of hydroxy group at 15-position of phenanthroquinolizidine alkaloids increased activity for S-configuration but decreased activity for R-configuration. Present study provides fundamental support for development and optimization of phenanthroquinolizidine alkaloids as potential inhibitors of plant virus.

Facile synthesis of novel dithioacetal–naphthalene derivatives as potential activators for plant resistance induction

“…First, compounds S1-S16 were measured for their phytotoxic activity against tobacco. 24 The data of phytotoxic activity at 500 mg mL À1 indicated that compounds S1-S16 showed no toxicity to the tested plant.…”

“…The biological activity of the title compounds against tobacco mosaic virus (TMV) and cucumber mosaic virus (CMV) respectively were evaluated using a half-leaf method according to the previously references. 24 Virus purication and activity evaluation of the compounds were performed as previously reported. 27,28 In vitro antibacterial activity.…”

First Discovery of Polycarpine, Polycarpaurines A and C, and Their Derivatives as Novel Antiviral and Antiphytopathogenic Fungus Agents

“…The reaction mixture was stirred for 1 h at 0°C and then warmed to room temperature. After stirring for another 2 h at room temperature, the mixture was concentrated in vacuo to 40 mL, kept at 0°C for 3 h, and then filtered to give 2-bromo-1-(4-methoxyphenyl)ethanone (11,31 Synthesis of 1-(4-Methoxyphenyl)-2-(methylamino)-ethanone Hydrochloride (12). To a solution of methylamine (30% solution in absolute ethanol, 104 mL, 0.68 mol) in acetonitrile (200 mL) was added dropwise a solution of 2-bromo-1-(4-methoxyphenyl)ethanone (11,31.0 g, 0.14 mol) in acetonitrile (150 mL) and dichloromethane (50 mL) at −30°C, and then the mixture was stirred for 10 min.…”

“…The test procedures and method have been reported in our previous work. 11,12 Antifungal Biological Assay. The test method of antifungal activity of the synthesized compounds was described in previous work.…”

Marine‐natural‐products for biocides development: first discovery of meridianin alkaloids as antiviral and anti‐phytopathogenic‐fungus agents

“…Detailed procedures for the phytotoxic-activity, 21,22 anti-TMV 21,22 and fungicidal [23][24][25] activities were carried out using reported methods, which can also be found in the Supporting Information. wileyonlinelibrary.com/journal/ps…”