Neuroprotective schinortriterpenoids with diverse scaffolds from Schisandra henryi

• Published in: Bioorganic chemistry Vol. 105; p. 104353
• Main Authors: He, Tao-Bin, Yan, Bing-Chao, Hu, Kun, Li, Xiao-Nian, Sun, Han-Dong, Puno, Pema-Tenzin
• Format: Journal Article
• Language: English
• Published: SAN DIEGO Elsevier Inc 01.12.2020; Elsevier
• Subjects: Animals; Biochemistry & Molecular Biology; Chemistry; Chemistry, Organic; Corticosterone - metabolism; Drug Evaluation, Preclinical; Humans; Lactones - chemistry; Life Sciences & Biomedicine; Molecular Structure; Neuroprotective activity; Neuroprotective Agents - chemistry; Neuroprotective Agents - pharmacology; Oxygen - chemistry; PC12 Cells; Physical Sciences; Plant Extracts - chemistry; Plant Leaves - chemistry; Plant Stems - chemistry; Rats; Schinortriterpenoids; Schisandra - chemistry; Schisandra henryi; Science & Technology; Triterpenes - chemistry; Triterpenes - pharmacology; Schisandra henryi; Neuroprotective activity; Schinortriterpenoids; NORTRITERPENOIDS; CELLS; TRITERPENOIDS; CONSTITUENTS
• ISSN: 0045-2068; 1090-2120
• DOI: 10.1016/j.bioorg.2020.104353

[Display omitted] •Eleven new schinortriterpenoids (SNTs) were isolated from Schisandra henryi.•Four SNT types: preschisanartane, 18-norschiartane, schiartane, and schisanartane.•Four SNTs involving three skeleton types showed effectively neuroprotective activities. Eleven undescribed schinortriterpenoids (SNTs) and one known analogue (12) were isolated from the stems and leaves of Schisandra henryi. Their diverse structures included preschisanartane (1), 18-norschiartane (2–5, 12), schiartane (6 and 7), and schisanartane (8–11) skeletons, which were elucidated by comprehensive NMR, MS, electronic circular dichroism analyses, single crystal X-ray diffraction and biogenetic considerations. 1 was the first case of preschisanartane-type SNT with six-membered lactone ring, and 2 was one of the most highly oxygenated 18-norschiartane SNTs. Three types of the highly oxygenated SNTs, 1, 4, 10 and 11, effectively prevent apoptosis induced by corticosterone in PC12 cells. In addition, 11 showed neurite outgrowth-promoting activity.