Anti-Tobacco Mosaic Virus Chromone Derivatives from the Stems of Nicotiana tabacum

Zhou, Tao; Fan, Yang; Cai, Bing-Biao; Wu, Fan; Zhu, Yanyan; Liu, Lu; Liu, Chunbo; Ling, Jun; Kong, Wei-Song; Yang, Guangyu; Hu, Qiu‐Fen; Liu, Xin

doi:10.1007/s10600-021-03540-6

Cited by 6 publications

(2 citation statements)

References 22 publications

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“…The structures of the isolated compounds are shown in Figure 1 , their 1 H and 13 C NMR data are listed in Table 1 , Table 2 and Table 3 , and the Figures for NMR see supplementary (Figures S1–S16) . By a comparison with other studies, the known compounds were identified as 5-(hydroxymethyl)-2-methyl- 6-prenylisoindolin-1-one (6) [ 14 ], 8-(3-hydroxy- propyl)-2,2,6-trimethylchroman-4-one (7) [ 15 ], 5-methoxy-2,2-dimethyl-7-(2-oxopropyl)-chroman-4-one (8) [ 16 ], and 5-methoxy- 2,2-dimethyl-8-(2-oxopropyl)-2,3-dihydro- chromen-4-one (9) [ 16 ]. To the best of our knowledge, compound 5 represents a novel type of dimeric alkaloid, which might be biosynthetically formed via an intermolecular nucleophilic substitution reaction between an indole alkaloid and a chromone.…”

Section: Resultsmentioning

confidence: 99%

“…Since certain alkaloids and chromones from the Cassia genus exhibit potential anti-TMV activities [ 7 , 10 , 12 , 15 , 16 , 17 , 18 ], the anti-TMV activities for compounds 1–5 were tested using the half-leaf method [ 21 , 22 ] at a concentration of 20 μM. Ningnanmycin (a commercial product for plant disease in China, with inhibition rate of 32.8%) was used as a positive control.…”

Section: Resultsmentioning

confidence: 99%

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Indole Alkaloids and Chromones from the Stem Bark of Cassia alata and Their Antiviral Activities

Yang

Dai

et al. 2022

Molecules

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The Cassia (Leguminosae) genus has attracted a lot of attention as a prolific source of alkaloids and chromones with diverse structures and biological properties. The aim of this study is to screen the antiviral compounds from Cassia alata. The extract of the stem bark of this plant was separated using silica gel, MCI, ODS C18, and Sephadex LH-20 column chromatography, as well as semi-preparative HPLC. As a result, three new indole alkaloids, alataindoleins A–C (1–3); one new chromone, alatachromone A (4); and a new dimeric chromone-indole alkaloid, alataindolein D (5) were isolated. Their structures were determined by means of HRESIMS and extensive 1D and 2D NMR spectroscopic studies. Interestingly, alataindolein D (5) represents a new type of dimeric alkaloid with an unusual N-2−C-16’ linkage, which is biogenetically derived from a chromone and an indole alkaloid via an intermolecular nucleophilic substitution reaction. Compounds 1–5 were tested for their anti-tobacco mosaic virus (TMV) and anti-rotavirus activities, and the results showed that compounds 2–4 showed high anti-TMV activities with inhibition rates of 44.4%, 66.5%, and 52.3%, respectively. These rates were higher than those of the positive control (with inhibition rate of 32.8%). Compounds 1 and 5 also showed potential anti-TMV activities with inhibition rates of 26.5% and 31.8%, respectively. In addition, compounds 1–5 exhibited potential anti-rotavirus activities with therapeutic index (TI) values in the range of 9.75~15.3. The successful isolation and structure identification of the above new compounds provided materials for the screening of antivirus drugs, and contributed to the development and utilization of C. alata.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Indole Alkaloids and Chromones from the Stem Bark of Cassia alata and Their Antiviral Activities

Yang

Dai

et al. 2022

Molecules

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Synthesis and characterization of the novel heteroannulated chromeno[2,3‐d]pyrimidines and chromeno[2,3‐d][1,3]thiazolo[3,2‐a] pyrimidines

Ibrahim

2022

Journal of Heterocyclic Chem

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2‐Amino‐6,8‐dibromo‐7‐hydroxychromone‐3‐carboxamide (2) was synthesized and utilized as synthetic intermediate for the synthesis of novel heteroannulated chromones namely chromeno[2,3‐d]pyrimidines and chromeno[2,3‐d][1,3]thiazolo [3,2‐a]pyrimidines. Condensation of carboxamide 2 with formic acid, acetyl chloride, benzoyl chloride, isonicotinic acid, diethyl carbonate, and carbon disulfide furnished the novel chromeno[2,3‐d]pyrimidine derivatives, respectively. Reaction of 7,9‐dibromo‐8‐hydroxy‐2‐thioxo‐2H‐chromeno[2,3‐d]pyrimidine‐4,5(1H,3H)‐dione (8) with some bielectrophilic reagents afforded the first known chromeno[2,3‐d] [1, 3] thiazolo[3,2‐a]pyrimidines, respectively. Spectral and analytical data confirmed the structures of the new synthesized products.

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Chromones from the Tobacco Derived Fungus Aspergillus versicolor and Their Antiviral Activity

Shen,

Xiong,

et al. 2023

Chem Nat Compd

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Anti-Tobacco Mosaic Virus Chromone Derivatives from the Stems of Nicotiana tabacum

Cited by 6 publications

References 22 publications

Indole Alkaloids and Chromones from the Stem Bark of Cassia alata and Their Antiviral Activities

Indole Alkaloids and Chromones from the Stem Bark of Cassia alata and Their Antiviral Activities

Synthesis and characterization of the novel heteroannulated chromeno[2,3‐d]pyrimidines and chromeno[2,3‐d][1,3]thiazolo[3,2‐a] pyrimidines

Chromones from the Tobacco Derived Fungus Aspergillus versicolor and Their Antiviral Activity

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