Title:Discovery of Resveratrol and its Derivatives as Novel Antiviral and Anti-
Phytopathogenic-Fungus Agents
Volume: 20
Issue: 3
Author(s): Zongwei Xia, Xiuling Yu*, Feng Feng*, Pengfei Song, Wenqiang Yang, Jiacai Wang and Qingmin Wang*
Affiliation:
- College of Pharmacy,
Linyi University, Linyi 276000, People’s Republic of China
- College of Pharmacy,
Linyi University, Linyi 276000, People’s Republic of China
- College of Chemistry, State Key Laboratory of Elemento-
Organic Chemistry, Nankai University, Tianjin 300071, People’s Republic of China
Keywords:
Resveratrol, lead compound, structural modification, anti-TMV activity, fungicidal activity, structure-activity relationships.
Abstract:
Background: Plant diseases caused by viruses and pathogens have posed a serious threat to
global agricultural production and are difficult to control. Natural products have always been a valuable
source for lead discovery in medicinal and agricultural chemistry. The natural product resveratrol was
found to have good antiviral activity against the tobacco mosaic virus (TMV) and fungicidal activities
against 14 kinds of phytopathogenic fungi.
Objective: The aim of this work was to design, synthesize a series of derivatives of resveratrol, and
evaluate their antiviral and fungicidal activities systematically.
Methods: Novel resveratrol sulfonate derivatives were prepared by a convenient synthesis method from
resveratrol, alkyl sulfonyl chloride, aryl sulfonyl chloride, and heterocyclic sulfonyl chloride. Their
structures were also identified by nuclear magnetic resonance (NMR) spectroscopy and high-resolution
mass spectrometry (HRMS).
Results: Most of the targets were obtained at a high yield. Compounds I-2, I-5, I-10, II-2, and II-4, with
excellent antiviral activities, showed higher anti-TMV activities than those of lead compounds and
commercial ribavirin (inhibitory rates of 38, 37, and 38% at 500 μg/mL for inactivation, curative, and
protection activities in vivo, respectively). In particular, compounds I-5, I-10, II-2, and II-4 displayed
similar inhibitory effects as ningnanmycin (inhibitory rates of 54, 56, and 58% at 500 μg/mL for inactivation,
curative, and protection activities in vivo, respectively), the best antiviral agent at present,
thereby emerging as new antiviral pilot compounds. Further fungicidal activity tests showed that
resveratrol derivatives also displayed broad-spectrum fungicidal activities.
Conclusion: The anti-TMV activities of these compounds were discovered for the first time. Some of
these simply structured compounds showed higher TMV inhibitory effects than ribavirin. The current
study provided valuable insights into the antiviral and fungicidal activities of resveratrol derivatives,
but more modification of the structure should be conducted.
