HRESIMS-guided isolation of aspidosperma-scandine type bisindole alkaloids from Melodinus cochinchinensis and their anti-inflammatory and cytotoxic activities

• Published in: Phytochemistry (Oxford) Vol. 184; p. 112673
• Main Authors: Li, Fang-Ru, Liu, Lu, Liu, Ya-Ping, Wang, Jin-Tang, Yang, Mei-Lian, Khan, Afsar, Qin, Xu-Jie, Wang, Yu-Dan, Cheng, Gui-Guang
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 01.04.2021; Elsevier
• Subjects: Alkaloids - pharmacology; Anti-inflammatory; Anti-Inflammatory Agents - pharmacology; Apocynaceae; Aspidosperma; Biochemistry & Molecular Biology; Bisindole alkaloids; Cytotoxicity; Indole Alkaloids - pharmacology; Life Sciences & Biomedicine; Melodinus cochinchinensis (Lour.) Merr. (Apocynaceae); melokhanines; Molecular Structure; Plant Sciences; Science & Technology; Melodinus cochinchinensis (Lour.) Merr. (Apocynaceae); melokhanines; Cytotoxicity; Anti-inflammatory; Bisindole alkaloids; MONOTERPENOID INDOLE ALKALOIDS; FRUITS; CHEMISTRY
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2021.112673

The Melodinus species have been proved to be good resources of bisindole alkaloids. Six bisindole alkaloids were isolated from the leaves and stems of Melodinus cochinchinensis (Lour.) Merr. guided by HRESIMS data analysis. Among them, melokhanines K-M, epi-scandomelonine, and epi-scandomeline possessed aspidosperma-scandine skeleton linked by a C–C bond while meloyine II had a scandine-scandine skeleton. The structures were established by extensive spectroscopic analysis of their HRESIMS and NMR data. Melokhanines K-M were undescribed compounds, while epi-scandomelonine, epi-scandomeline and meloyine II were known compounds, which were reported from Melodinus species for the first time. The anti-inflammatory and cytotoxic activities of the isolates were also evaluated in vitro. Melokhanine K and meloyine II showed potent inhibitory activity on the production of nitric oxide, interleukin-6, and tumor necrosis factor-α in LPS-induced RAW 264.7 macrophages, whereas epi-scandomelonine and epi-scandomeline exhibited certain cytotoxic activity against MOLT-4 cells with IC50 values 5.2 and 1.5 μM, respectively. Six bisindole alkaloids were isolated from the leaves and stems of Melodinus cochinchinensis guided by HRESIMS data analysis. Among them, melokhanines K-M were undescribed compounds, while epi-scandomelonine, epi-scandomeline and meloyine II were known compounds, which were reported from Melodinus species for the first time. The anti-inflammatory and cytotoxic activities of the isolates were also evaluated in vitro. [Display omitted] •Six bisindole alkaloids were isolated from M. cochinchinensis guided by HRESIMS data analysis.•Anti-inflammatory and cytotoxic activities of the isolated alkaloids were evaluated.•Melokhanine K and meloyine Ⅱ showed potent inhibitory anti-inflammatory activities.•Episcandomelonine and episcandomeline showed certain cytotoxic activity against MOLT-4 cells.