Chemical constituents from the stems of Securidaca inappendiculata Hassk

• Published in: Fitoterapia 2019-09, Vol.137 (NA), p.104271, Article 104271
• Main Authors: Ji, Junyang, Wang, Qiwen, Wang, Maolin, Chen, Jianwei, Li, Xiang
• Format: Article
• Language: English
• Subjects: Glycosides; Hemiterpene glycoside; Neolignan glycoside; NMR; Nuclear magnetic resonance; Organic chemistry; Phenolic compounds; Phenolic glycoside; Phenols; Polygalaceae; Securidaca; Securidaca inappendiculata Hassk; Stems
• ISSN: 0367-326X; 1873-6971
• DOI: 10.1016/j.fitote.2019.104271

Three new neolignan glycosides, (7R,8S)-4-hydroxy-3,3′-dimethoxy-8,4′-oxyneoligna-7,9,9′-triol-4-O-β-d-glucopyranosyl-(1 → 4)-β-D-glucopyranoside (1), (7R,8S)-4-hydroxy-3,5′-dimethoxy-4′,7-epoxy-8,3′-neoligna-9,9′-diol-9’-O-β-d-glucopyranosyl-4-O-[β-d-glucopyranosyl-(1 → 4)]-β-D-glucopyranoside (2), and (7R,8S)-4-hydroxy-3,5,5′-trimethoxy-4′,7-epoxy-8,3′-neoligna-9,9′-diol-9’-O-β-d-glucopyranosyl-4-O-[β-d-glucopyranosyl-(1 → 4)]-β-D-glucopyranoside (3), one new phenolic glycoside, securiphenoside B (4) and two new hemiterpene glycosides, securiterpenoside E-F (5–6) were isolated from the stems of Securidaca inappendiculata Hassk. Their structures were elucidated on the basis of 1D and 2D NMR, HRESIMS, CD and chemical evidence. Furthermore, compound 2 showed moderate hepatoprotective activity compared with bicyclol in vitro. [Display omitted] •Three neolignan glycosides, one phenolic glycoside and two hemiterpene glycosides were isolated from S. inappendiculata.•The structures of the six compounds were solved by 1D and 2D NMR, HRESIMS, CD, chemical evidence and relevant literature.•Compound 2 showed moderate hepatoprotective activitiy compared with bicyclol in vitro.