Anti-Tobacco Mosaic Virus Quassinoids from Ailanthus altissima (Mill.) Swingle

J Agric Food Chem. 2018 Jul 18;66(28):7347-7357. doi: 10.1021/acs.jafc.8b01280. Epub 2018 Jul 10.

Abstract

Quassinoids are bitter constituents characteristic of the family Simaroubaceae. A total of 18 C20 quassinoids, including nine new quassinoid glycosides, named chuglycosides A-I (1-6 and 8-10), were identified from the samara of Ailanthus altissima (Mill.) Swingle. All of the quassinoids showed potent anti-tobacco mosaic virus (TMV) activity. A preliminary structure-anti-TMV activity relationship of quassinoids was discussed. The effects of three quassinoids, including chaparrinone (12), glaucarubinone (15), and ailanthone (16), on the accumulation of TMV coat protein (CP) were studied by western blot analysis. Ailanthone (16) was further investigated for its influence on TMV spread in the Nicotiana benthamiana plant.

Keywords: Ailanthus altissima (Mill.) Swingle; quassinoids; structure−activity relationship (SAR); tobacco mosaic virus (TMV).

MeSH terms

  • Ailanthus / chemistry*
  • Antiviral Agents / chemistry
  • Antiviral Agents / isolation & purification
  • Antiviral Agents / pharmacology*
  • Nicotiana / virology
  • Plant Diseases / virology
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification
  • Plant Extracts / pharmacology*
  • Quassins / chemistry
  • Quassins / isolation & purification
  • Quassins / pharmacology*
  • Structure-Activity Relationship
  • Tobacco Mosaic Virus / drug effects*
  • Tobacco Mosaic Virus / physiology

Substances

  • Antiviral Agents
  • Plant Extracts
  • Quassins