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Sulfur-enriched alkaloids from the root of Isatis indigotica.

ABSTRACT: Five new sulfur-enriched alkaloids isatithioetherins A-E (1-5), and two pairs of scalemic enantiomers (+)- and (-)-isatithiopyrin B (6a and 6b) and isoepigoitrin and isogoitrin (7a and 7b), along with the known scalemic enantiomers epigoitrin and goitrin (8a and 8b), were isolated and characterized from an aqueous extract of the Isatis indigotica roots. Their structures were determined by extensive spectroscopic data analysis, including 2D NMR and theoretical calculations of electronic circular dichroism (ECD) spectra based on the quantum-mechanical time-dependent density functional theory (TDDFT). Compounds 1-5 represent a novel group of sulfur-enriched alkaloids, biogenetically originating from stereoselective assemblies of epigoitrin-derived units. Isolation and structure characterization of 6a and 6b support the postulated biosynthetic pathways for the diastereomers 9a and 9bvia a rare thio-Diels-Alder reaction. Compounds 2 and 4 showed antiviral activity against the influenza virus A/Hanfang/359/95 (H3N2, IC50 0.60 and 1.92 ?mol/L) and the herpes simplex virus 1 (HSV-1, IC50 3.70 and 2.87??mol/L), and 2 also inhibited Coxsackie virus B3 (IC50 0.71??mol/L).

SUBMITTER: Guo Q

PROVIDER: S-EPMC6251858 | biostudies-other | 2018 Oct

REPOSITORIES: biostudies-other

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Sulfur-enriched alkaloids from the root of Isatis indigotica.

Guo Qinglan Q Xu Chengbo C Chen Minghua M Lin Sheng S Li Yuhuan Y Zhu Chenggen C Jiang Jiandong J Yang Yongchun Y Shi Jiangong J

Acta pharmaceutica Sinica. B 20180823 6

Five new sulfur-enriched alkaloids isatithioetherins A-E (1-5), and two pairs of scalemic enantiomers (+)- and (-)-isatithiopyrin B (6a and 6b) and isoepigoitrin and isogoitrin (7a and 7b), along with the known scalemic enantiomers epigoitrin and goitrin (8a and 8b), were isolated and characterized from an aqueous extract of the Isatis indigotica roots. Their structures were determined by extensive spectroscopic data analysis, includ ...[more]

PMID: 30505662

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Project description:BACKGROUND:Nitrogen (N), the primary limiting factor for plant growth and yield in agriculture, has a patchy distribution in soils due to fertilizer application or decomposing organic matter. Studies in solution culture over-simplify the complex soil environment where microbial competition and spatial and temporal heterogeneity challenge roots' ability to acquire adequate amounts of nutrients required for plant growth. In this study, various ammonium treatments (as 15N) were applied to a discrete volume of soil containing tomato (Solanum lycopersicum) roots to simulate encounters with a localized enriched patch of soil. Transcriptome analysis was used to identify genes differentially expressed in roots 53 hrs after treatment. RESULTS:The ammonium treatments resulted in significantly higher concentrations of both ammonium and nitrate in the patch soil. The plant roots and shoots exhibited increased levels of 15N over time, indicating a sustained response to the enriched environment. Root transcriptome analysis identified 585 genes differentially regulated 53 hrs after the treatments. Nitrogen metabolism and cell growth genes were induced by the high ammonium (65 mug NH4+-N g-1 soil), while stress response genes were repressed. The complex regulation of specific transporters following the ammonium pulse reflects a simultaneous and synergistic response to rapidly changing concentrations of both forms of inorganic N in the soil patch. Transcriptional analysis of the phosphate transporters demonstrates cross-talk between N and phosphate uptake pathways and suggests that roots increase phosphate uptake via the arbuscular mycorrhizal symbiosis in response to N. CONCLUSION:This work enhances our understanding of root function by providing a snapshot of the response of the tomato root transcriptome to a pulse of ammonium in a complex soil environment. This response includes an important role for the mycorrhizal symbiosis in the utilization of an N patch.

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Sulfur-enriched alkaloids from the root of Isatis indigotica.

Publications

Sulfur-enriched alkaloids from the root of <i>Isatis indigotica</i>.

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