1. Aconicumines A–D, an advanced class of norditerpenoid alkaloids with an unprecedented N,O-diacetal motif from Aconitum taipeicum Hand.-Mazz., exhibit anti-inflammatory properties in vitro.
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Zhang, Dong-Bo, Liang, Yan-Ni, Wang, Zheng, Shi, Li-Ke, Zhang, Zhen, Tang, Zhi-Shu, and Huang, Lu-Qi
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MONKSHOODS , *ISOQUINOLINE alkaloids , *NITRIC oxide , *STRUCTURE-activity relationships , *ALKALOIDS , *X-ray diffraction , *RANUNCULACEAE - Abstract
Aconicumines A–D, an advanced class of norditerpenoid alkaloids, and seven known alkaloids, were isolated from Aconitum taipaicum Hand.-Mazz. (Ranunculaceae). The structures of the previously undescribed compounds, including their absolute configurations, were fully elucidated based on spectroscopic and single-crystal X-ray diffraction data analysis. Aconicumines A–D exhibit interesting cage-like structure, characterised by an unprecedented N,O- diacetal moiety (C6–O–C19–N–C17–O–C7) that has not been previously observed in diterpenoid alkaloids. Possible biosynthetic pathways for aconicumines A–D were proposed. Aconitine, hypaconitine, and aconicumine A showed significant inhibition of nitric oxide production in RAW 264.7 macrophages induced by lipopolysaccharide with IC 50 values ranging from 4.1 to 19.7 μM compared to positive control (dexamethasone, IC 50 = 12.5 μM). Furthermore, the primary structure–activity relationships for aconicumines A–D were also represented. [Display omitted] • Four undescribed diterpenoid alkaloids (DAs) were isolated from Aconitum taipaicum. • All structures with their absolute configurations were completely determined. • Aconicumines A–D possessed rare 7,17-seco-DAs carbon skeleton in natural. • Aconicumines A–D presented an unprecedented N,O -diacetal residue in DAs. • Aconicumine A showed significant (nitric oxide) NO inhibitory activity. [ABSTRACT FROM AUTHOR]
- Published
- 2023
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