title: Eleven new highly oxygenated triterpenoids from the leaves and stems of Schisandra chinensis.
abstract: Eleven new triterpenoids, schinchinenins A–H (1–8) and schinchinenlactones A–C (9–11) together with three known triterpenoids, henrischinins A–C (12–14), were isolated from the leaves and stems of Schisandra chinensis by bioassay-guided fractionation. Schinchinenin A (1) is the first example of a highly oxygenated triterpenoid characterized by a 5/5/7/6/5-fused pentacyclic ring and a 3-one-2-oxabicyclo[3.2.1]-octane moiety. Schinchinenins E and F (5 and 6) are highly oxygenated triterpenoids that contain a hydroperoxyl moiety, which is rare in compounds from the Schisandra genus. The structures and stereochemistry of 1–11 were elucidated using spectroscopic analysis, single-crystal X-ray diffraction, computational optical rotation, chemical transformation, and CD exciton chirality methods. The activities of compounds 1, 2, 7, and 12–14 against HSV-2 and adenovirus were evaluated for the first time, and of these compounds, 13 was the most active inhibitor of HSV-2, with a selectivity index value as high as 29.95.
authors: State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, People's Republic of China.
authors: Qiu-Yan
authors: QY
authors: Song
authors: Kan
authors: K
authors: Jiang
authors: Qian-Qian
authors: QQ
authors: Zhao
authors: Kun
authors: K
authors: Gao
authors: Xiao-Jie
authors: XJ
authors: Jin
authors: Xiao-Jun
authors: XJ
authors: Yao
mesh_terms: D008958:Models, Molecular; D008968:Molecular Conformation; D010100:Oxygen / Q000737:chemistry*; D018515:Plant Leaves / Q000737:chemistry*; D018547:Plant Stems / Q000737:chemistry*; D032141:Schisandra / Q000737:chemistry*; D013237:Stereoisomerism; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification*
chemical_list: D014315:Triterpenes; D010100:Oxygen