Sesquiterpenoids from the rhizomes of Atractylodes macrocephala and their protection against lipopolysaccharide-induced neuroinflammation in microglia BV-2 cells

• Published in: Journal of functional foods Vol. 83; p. 104541
• Main Authors: Si, Jin-Guang, Zhang, Hai-Xin, Yu, Meng, Li, Ling-Yu, Zhang, Hong-Wu, Jia, Hong-Mei, Ma, Li-Yan, Qin, Ling-Ling, Zhang, Tao, Zou, Zhong-Mei
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 01.08.2021; Elsevier
• Subjects: Atractylodes macrocephala; BV-2 microglia; Chiral-phase HPLC resolution; Sesquiterpenoids; BV-2 microglia; Atractylodes macrocephala; Sesquiterpenoids; Chiral-phase HPLC resolution
• ISSN: 1756-4646; 2214-9414
• DOI: 10.1016/j.jff.2021.104541

[Display omitted] •Eight new sesquiterpenoids were isolated from the rhizome of Atractylodes macrocephala.•Three pairs of enantiomers formed a complete stereoisomer library.•Twelve X-ray crystallographic data confirmed the relative and absolute configurations.•Compounds 4 and 6 exhibited potential anti-neuroinflammatory. The rhizomes of Atractylodes macrocephala have been widely used in both functional foods and herbal medicines for a long history. A phytochemical investigation of its 95% ethanol extract offered twenty-three sesquiterpenoids, including eight new ones named (4S,5S)-atractylmacrene A (1a), atractylmacrenes B–C (2–3), 4R,5R,8S,9S-diepoxylatractylenolide Ⅱ (4), 4-oxo-8S,9S-epoxylatractylenolide Ⅱ (5), and 8S,9S-epoxylatractylenolide Ⅱ (6), among which three pairs of enantiomers (1a/1b, 2a/2b, and 3a/3b) were successfully isolated by the chiral-phase HPLC resolution. Their structures were elucidated using NMR and HRESIMS analyses, electronic circular dichroism (ECD) and X-ray diffraction analyses. Neuroprotective activity in LPS induced BV-2 microglia cells were performed, and compounds 4 and 6 showed significant NO inhibition with IC50 values of 15.8, and 17.8 μΜ, respectively. Mechanism study showed that 4 exerted its protective effect through inhibiting the production of interleukin-6 (IL-6). The findings disclosed the potential of A. macrocephala to be developed as new neuroprotective functional food and medicine.