Eudesmane−type sesquiterpenes from the rhizomes of Atractylodes macrocephala and their bioactivities

• Published in: Phytochemistry (Oxford) 2023-02, Vol.206, p.113545-113545, Article 113545
• Main Authors: Zhang, Hai-Xin, Si, Jin-Guang, Li, Jing-Rong, Yu, Meng, Qin, Ling-Ling, Zhao, Chen-Xu, Zhang, Tao, Zou, Zhong-Mei
• Format: Article
• Language: English
• Subjects: Atractylodes - chemistry; Atractylodes macrocephala Koidz; Bioactivities; Compositae; Isolation; Molecular Structure; Rhizome - chemistry; Sesquiterpene; Sesquiterpenes - chemistry; Sesquiterpenes, Eudesmane - analysis; Sesquiterpenes, Eudesmane - chemistry; Sesquiterpenes, Eudesmane - pharmacology
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2022.113545

Fifteen undescribed eudesmane−type sesquiterpenes, named atramacronoids D−R, along with fourteen known analogues were isolated from the rhizomes of Atractylodes macrocephala. The structures of atramacronoids D−R were elucidated based on extensive spectroscopic data analysis, Snatzke's rule, electronic circular dichroism (ECD) calculations, and X-ray crystallographic analysis. Notably, of the undescribed isolates, atramacronoids D and E are the first example of eudesmanolactam−phenol and eudesmanolactam−ethyl hybrids obtained from plants, respectively. A pair of enantiomers, (+)- and (−)-atramacronoids F, were successfully resolved by chiral-phase HPLC. Atramacronoid D exhibited weak cytotoxicity against SGC-7901 cells. Atramacronoid E significantly promoted the proliferation of LPS-induced IEC-6 cells. Undescribed eudesmane sesquiterpenes were isolated from the rhizomes of Atractylodes macrocephala and were confirmed by the single-crystal. [Display omitted] •Fifteen undescribed sesquiterpenes were obtained from A. macrocephala.•Atramacronoids D and E are rare eudesmanolactam−phenol/−ethyl hybrids.•Atramacronoid D exhibited weak cytotoxicity against SGC-7901 cells.•Atramacronoid E had the capacity of promoting IEC-6 cells proliferation.