Lindenane Disesquiterpenoids with Anti-HIV-1 Activity from Chloranthus japonicus
| Autor: | Yang Lu, Ning-Bo Gong, Chang-Xiang Chen, Ping-Lei Fang, Li-Li Pan, Shucong Liu, Ying Guo, Huan Yan, Hai-Yang Liu, Hui-Min Zhong, Ying-li Cao |
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| Rok vydání: | 2011 |
| Předmět: |
Double bond
Anti-HIV Agents Stereochemistry Molecular Conformation Pharmaceutical Science Biology Pharmacognosy Crystallography X-Ray Sesquiterpene Analytical Chemistry Magnoliopsida Structure-Activity Relationship chemistry.chemical_compound Drug Discovery Humans Structure–activity relationship Pharmacology chemistry.chemical_classification Molecular Structure Organic Chemistry Absolute configuration Biological activity Terpenoid Complementary and alternative medicine chemistry HIV-1 Molecular Medicine Sesquiterpenes Lactone |
| Zdroj: | Journal of Natural Products. 74:1408-1413 |
| ISSN: | 1520-6025 0163-3864 |
| DOI: | 10.1021/np200087d |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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