title: ent-Abietane-Type and Related Seco-/Nor-diterpenoids from the Rare Chloranthaceae Plant Chloranthus sessilifolius and Their Antineuroinflammatory Activities.
abstract: Fourteen new ent-abietane-type diterpenoids, sessilifols A-N (1-14), and three related new norditerpenoids (15-17) were isolated from Chloranthus sessilifolius. The absolute configurations were determined by single-crystal X-ray diffraction analysis, the modified Mosher's method, and/or the observed Cotton effects in their electronic circular dichroism spectra. Sessilifols A (1) and B (2) possess an uncommon five-membered C-ring rearranged by oxidative cleavage of the C-13/C-14 bond in abieta-7,13-diene followed by the formation of a new C-C bond between C-12 and C-14. Sessilifol C (3) is a rare 7,8-seco-9-spiro-fused ent-abietane, whereas sessilifol O (15) represents the first example of a naturally occurring 14-norabietane-type diterpenoid. Compounds 6 and 9 were found to have moderate antineuroinflammatory activities by inhibiting the nitric oxide production in lipopolysaccharide-stimulated murine BV-2 microglial cells, with IC50 values of 8.3 and 7.4 μM, respectively.
authors.affiliation: †Department of Natural Products Chemistry and ‡Department of Pharmacology, School of Pharmacy, Fudan University, No. 826 Zhangheng Road, Shanghai 201203, People's Republic of China.
authors.forename: Li-Jun
authors.initials: LJ
authors.lastname: Wang
authors.affiliation: †Department of Natural Products Chemistry and ‡Department of Pharmacology, School of Pharmacy, Fudan University, No. 826 Zhangheng Road, Shanghai 201203, People's Republic of China.
authors.forename: Juan
authors.initials: J
authors.lastname: Xiong
authors.affiliation: †Department of Natural Products Chemistry and ‡Department of Pharmacology, School of Pharmacy, Fudan University, No. 826 Zhangheng Road, Shanghai 201203, People's Republic of China.
authors.forename: Shu-Ting
authors.initials: ST
authors.lastname: Liu
authors.affiliation: †Department of Natural Products Chemistry and ‡Department of Pharmacology, School of Pharmacy, Fudan University, No. 826 Zhangheng Road, Shanghai 201203, People's Republic of China.
authors.forename: Li-Long
authors.initials: LL
authors.lastname: Pan
authors.affiliation: †Department of Natural Products Chemistry and ‡Department of Pharmacology, School of Pharmacy, Fudan University, No. 826 Zhangheng Road, Shanghai 201203, People's Republic of China.
authors.forename: Guo-Xun
authors.initials: GX
authors.lastname: Yang
authors.affiliation: †Department of Natural Products Chemistry and ‡Department of Pharmacology, School of Pharmacy, Fudan University, No. 826 Zhangheng Road, Shanghai 201203, People's Republic of China.
authors.forename: Jin-Feng
authors.initials: JF
authors.lastname: Hu
mesh_terms: D045784:Abietanes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D000818:Animals; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D020128:Inhibitory Concentration 50; D008070:Lipopolysaccharides / Q000494:pharmacology; D019684:Magnoliopsida / Q000737:chemistry*; D051379:Mice; D015394:Molecular Structure; D009569:Nitric Oxide / Q000096:biosynthesis; D019906:Nuclear Magnetic Resonance, Biomolecular
chemical_list: D045784:Abietanes; D004224:Diterpenes; D004365:Drugs, Chinese Herbal; D008070:Lipopolysaccharides; D009569:Nitric Oxide