Details

Autor(en) / Beteiligte

• Bai, Ming
• Xi, Yu-Fei
• Mi, Si-Hui
• Yang, Pei-Yuan
• Lou, Li-Li
• Lv, Tian-Ming
• Zhang, Xin
• Yao, Guo-Dong
• Lin, Bin
• Huang, Xiao-Xiao
• Song, Shao-Jiang

Titel

Isatin-based spiro indolenine alkaloids from Isatis indigotica Fortune with anti-neuroinflammatory and acetylcholinesterase inhibitory effects

Ist Teil von

• Organic Chemistry Frontiers, 2024-01, Vol.11 (2), p.427-436

Ort / Verlag

London: Royal Society of Chemistry

Erscheinungsjahr

2024

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• Isatin-based spiro indolenine alkaloids are derived from mixed biosynthetic origins, and the C-2 and C-3 carbonyl groups of isatin could be spirocyclic, thus achieving a variable chemical diversity. Four novel alkaloids (1a/1b, 2, and 3), featuring an unusual isatin-based spiro indolenine system, were obtained from the leaves of Isatis indigotica Fortune. Compounds 1a/1b were a pair of enantiomers characterized by an unprecedented 6/5/6/5/6 N,O-heterocyclic scaffold with a unique spiro[4.5] core. Compound 2 was the first 6/5/6/5/5/6 hexacyclic skeleton fused with an unexpected dispiro[4.4.0.4] system of an isatin-based alkaloid. Their structures were elucidated by 1D and 2D NMR and HRESIMS techniques as well as density functional theory (DFT) calculations and computer-assisted structure elucidation (CASE). The possible biosynthetic pathways for compounds 1a/1b–3 are proposed. In addition, all alkaloids were evaluated for their anti-neuroinflammatory and acetylcholinesterase inhibitory effects.