title: Lindenane disesquiterpenoids with anti-HIV-1 activity from Chloranthus japonicus.
abstract: Five new lindenane disesquiterpenoids, chlorajaponilides A-E (1-5), together with 11 known analogues were isolated from whole plants of Chloranthus japonicus. The structure and absolute configuration of 1 was confirmed by X-ray crystallography. Compounds 1 and 2 represent the first examples of lindenane disesquiterpenoids with a C-5 hydroxy group and a C-4-C-15 double bond. Compounds 8, 9, 11, and 12 showed anti-HIV-1 replication activities in both wild-type HIV-1 and two NNRTIs-resistant strains. Shizukaol B (8) exhibited the best activity against HIV(wt), HIV(RT-K103N), and HIV(RT-K103N) with EC₅₀ values of 0.22, 0.47, and 0.50 μM, respectively. Compounds 8, 9, 11, and 12 had significant cytotoxicities against C8166 cells with CC₅₀ values of 0.020, 0.089, 0.047, and 0.022, respectively, and exhibited inhibitory activities against HIV-1 with EC₅₀ values of 0.0014, 0.016, 0.0043, and 0.0033 μM, respectively.
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, People's Republic of China.
authors.forename: Ping-Lei
authors.initials: PL
authors.lastname: Fang
authors.forename: Ying-Li
authors.initials: YL
authors.lastname: Cao
authors.forename: Huan
authors.initials: H
authors.lastname: Yan
authors.forename: Li-Li
authors.initials: LL
authors.lastname: Pan
authors.forename: Shu-Cong
authors.initials: SC
authors.lastname: Liu
authors.forename: Ning-Bo
authors.initials: NB
authors.lastname: Gong
authors.forename: Yang
authors.initials: Y
authors.lastname: Lü
authors.forename: Chang-Xiang
authors.initials: CX
authors.lastname: Chen
authors.forename: Hui-Min
authors.initials: HM
authors.lastname: Zhong
authors.forename: Ying
authors.initials: Y
authors.lastname: Guo
authors.forename: Hai-Yang
authors.initials: HY
authors.lastname: Liu
mesh_terms: D019380:Anti-HIV Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D018360:Crystallography, X-Ray; D015497:HIV-1 / Q000187:drug effects*; D006801:Humans; D019684:Magnoliopsida / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D019380:Anti-HIV Agents; D012717:Sesquiterpenes