title: Neolignans with a Rare 2-Oxaspiro[4.5]deca-6,9-dien-8-one Motif from the Stem Bark of Cinnamomum subavenium.
abstract: Two pairs of racemic spirodienone neolignans with a rare 2-oxaspiro[4.5]deca-6,9-dien-8-one motif, named (±)-subaveniumins A (1) and B (2), were isolated from the bark of Cinnamomum subavenium. The chiral separation of the (+)-1, (-)-1, (+)-2, and (-)-2 enantiomers was accomplished via high-performance liquid chromatography on a chiral column. Their structures were elucidated using single-crystal X-ray diffraction and spectroscopic analyses (UV, IR, HRESIMS, and 1D and 2D NMR). The absolute configurations of the enantiomers were determined by comparing the experimental and calculated electronic circular dichroic spectra. The (+)-1, (-)-1, (+)-2, and (-)-2 enantiomers exhibited moderate inhibitory effects against NO production in RAW264.7 mouse macrophages induced by lipopolysaccharide, with IC50 values of 17.9, 5.6, 15.1, and 4.3 μM, respectively.
authors.affiliation: †Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China.|§Department of Pharmacy, The Central Hospital of Wuhan, Wuhan 430014, People's Republic of China.
authors.forename: Yongji
authors.initials: Y
authors.lastname: Lai
authors.affiliation: †Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China.
authors.forename: Tingting
authors.initials: T
authors.lastname: Liu
authors.affiliation: ‡Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002, People's Republic of China.
authors.forename: Rongjian
authors.initials: R
authors.lastname: Sa
authors.affiliation: †Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China.
authors.forename: Xialan
authors.initials: X
authors.lastname: Wei
authors.affiliation: †Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China.
authors.forename: Yongbo
authors.initials: Y
authors.lastname: Xue
authors.affiliation: †Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China.
authors.forename: Zhaodi
authors.initials: Z
authors.lastname: Wu
authors.affiliation: †Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China.
authors.forename: Zengwei
authors.initials: Z
authors.lastname: Luo
authors.affiliation: †Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China.
authors.forename: Ming
authors.initials: M
authors.lastname: Xiang
authors.affiliation: †Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China.
authors.forename: Yonghui
authors.initials: Y
authors.lastname: Zhang
authors.affiliation: †Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China.
authors.forename: Guangmin
authors.initials: G
authors.lastname: Yao
mesh_terms: D000818:Animals; D002851:Chromatography, High Pressure Liquid; D027424:Cinnamomum / Q000737:chemistry*; D018360:Crystallography, X-Ray; D004365:Drugs, Chinese Herbal / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D017705:Lignans / Q000737:chemistry* / Q000302:isolation & purification*; D008070:Lipopolysaccharides / Q000494:pharmacology; D008264:Macrophages / Q000187:drug effects; D051379:Mice; D008968:Molecular Conformation; D015394:Molecular Structure; D009569:Nitric Oxide / Q000096:biosynthesis; D019906:Nuclear Magnetic Resonance, Biomolecular; D024301:Plant Bark / Q000737:chemistry; D018547:Plant Stems / Q000737:chemistry; D017434:Protein Structure, Tertiary; D013141:Spiro Compounds / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D013237:Stereoisomerism
chemical_list: D004365:Drugs, Chinese Herbal; D017705:Lignans; D008070:Lipopolysaccharides; D013141:Spiro Compounds; D009569:Nitric Oxide