Four undescribed sulfur-containing indole alkaloids with nitric oxide inhibitory activities from Isatis tinctoria L. roots. (June 2020)

• Record Type: Journal Article
• Authors: Zhang, Dongdong; Ruan, Deqing; Li, Jingyi; Chen, Zhaoqiang; Zhu, Weiliang; Guo, Fujiang; Chen, Kaixian; Li, Yiming; Wang, Rui
• Is Part Of: Phytochemistry. Volume 174(2020)
• Publication Date: 2020-06
• Subjects: Isatis tinctoria L. -- Brassicaceae -- Indole alkaloids -- Isatisindigoticanines H and I -- Isatindigosides F and G -- Nitric oxide inhibition; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2020.112337
• Languages: English
• ISSNs: 0031-9422

Abstract

Abstract: Four undescribed sulfur-containing indole alkaloids, isatisindigoticanines H, I and isatindigosides F, G along with three known analogues were obtained from Isatis tinctoria L. roots. Isatisindigoticanines H and I contained an unusual 1-(thiazol-4-yl)butane-1, 2, 3, 4-tetraol moiety while isatindigosides F and G possessed a new 3-[3-(1 H -indole-2-yl)azet-2-yl]-1 H -indole skeleton. The putative biosynthetic pathways of isatisindigoticanines H, I and isatindigosides F, G are proposed. The isolated compounds showed nitric oxide inhibitory effects with IC50 values ranging from 4.3 to 70.3 μ M. Graphical abstract: Four undescribed sulfur-containing indole alkaloids along with three known ones were obtained from Isatis tinctoria L. roots. The isolated compounds showed nitric oxide inhibitory effects with IC50 values ranging from 4.3 to 70.3 μ M. Image 1 Highlights: Four undescribed sulfur-containing indole alkaloids and three known ones were isolated from Isatis tinctoria L. roots. Their structures were elucidated by 1D, 2D NMR, IR, HRESIMS, X-ray crystallography, specific rotation and ECD data. 3-[3-(1 H -indole-2-yl)azet-2-yl]-1 H -indole skeleton was reported for the first time. All the compounds were tested for their NO inhibitory effects in LPS-induced RAW264.7 cells.