Journal
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
Volume 60, Issue 41, Pages 10212-10219Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jf303550a
Keywords
Phenanthroindolizidines; diazepines; antiviral activity; tobacco mosaic virus; structure-activity relationship; TMV; SAR
Funding
- National Key Project for Basic Research [2010CB126100]
- National Natural Science Foundation of China [21132003, 21121002]
- China Postdoctoral Science Foundation [2011M500519, 2012T50207]
- National Key Technology Research and Development Program [2011BAE06B02-17, 2012BAK25B03-3]
- Tianjin Natural Science Foundation [11JCZDJC20500]
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On the basis of our previous structure-activity relationship (SAR) and antiviral mechanism studies, a series of phenanthroindolizidines and their analogues 3-20 were designed, targeting tobacco mosaic virus (TMV) RNA, synthesized, and systematically evaluated for their antiviral activity against TMV. The bioassay results showed that most of these compounds displayed good anti-TMV activity, and some of them exhibited higher antiviral activity than that of commercial Ningnanmycin (perhaps the most successful registered antiplant viral agent). Especially, (S)-deoxytylophorinine (5) with excellent anti-TMV activity (inactivation activity, 59.8%/500 mu g mL(-1) and 40.3%/100 mu g mL(-1); curative activity, 65.1%/500 mu g mL(-1) and 43.7%/100 mu g mL(-1); and protection activity, 70.2%/500 mu g mL(-1) and 51.3%/100 mu g mL(-1)) emerged as a potential inhibitor of the plant virus. Compound 20 exhibited a strong in vivo protection effect against TMV at 100 mu g mL(-1), which indicated that phenanthroindolizidine analogues with a seven-membered D ring have a new and interesting structural scaffold and have great potential for further development as tobacco protection agents.
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