A unique spiro-beta-triazinedione-gamma-hydantoin type alkaloid with antiviral activity against tobacco mosaic virus from Streptomyces gamaensis

Chemical investigation of a soil actinomycete strain Streptomyces gamaensis NEAU-Gz11 led to the isolation of three alkaloids 1-3 with antiviral activity. Their structures were determined by extensive spectroscopic and X-ray crystallographic analyses. Compound 1 possesses a new and unique spiro-beta...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 6; no. 18; pp. 3215 - 3219
Main Authors Guo, Xiaowei, Wang, Jidong, Su, Can, Liu, Chongxi, Ma, Xiao-Yan, Yu, Zhiyin, Li, Jiansong, Wang, Xiangjing, Xiang, Wensheng, Huang, Sheng-Xiong
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 21.09.2019
Royal Society of Chemistry
Subjects
Alkaloids
Antiviral activity
Chemistry
Chemistry, Organic
Crystallography
Host plants
Hydantoin
NMR
Nuclear magnetic resonance
Organic chemistry
Peppers
Physical Sciences
Science & Technology
Soil investigations
Streptomyces
Tobacco
Tomatoes
Uniqueness
Viruses
EVOLUTION
ANTI-TMV ACTIVITY
PRODUCT
BIOSYNTHESIS
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Summary:Chemical investigation of a soil actinomycete strain Streptomyces gamaensis NEAU-Gz11 led to the isolation of three alkaloids 1-3 with antiviral activity. Their structures were determined by extensive spectroscopic and X-ray crystallographic analyses. Compound 1 possesses a new and unique spiro-beta-triazinedione-gamma-hydantoin skeleton. The racemic feature and the chemical conversion experiments led us to propose a biosynthetic pathway for 1. Compound 1 (100 mg L-1) showed a strong anti-TMV (tobacco mosaic virus, TMV) activity on the host plants of tomatoes and peppers with inhibition rates of 72.34% and 62.09%, respectively.
ISSN:2052-4129
2052-4110
2052-4110
DOI:10.1039/c9qo00742c