A seco -laurane sesquiterpene and related laurane derivatives from the red alga Laurencia okamurai Yamada
| Autor: | Yi Fang, Wen-Fei He, Feng Meitang, Ding-Quan Liu, Mao Shuichun, Yue-Wei Guo, Xiao-Qing Yu, Li-Hua Feng, Bin Wang |
|---|---|
| Rok vydání: | 2014 |
| Předmět: |
Antifungal Agents
Cell Survival Stereochemistry Candida glabrata Plant Science Trichophyton rubrum Horticulture Sesquiterpene Laurencia Biochemistry Aspergillus fumigatus chemistry.chemical_compound Trichophyton Cell Line Tumor Humans Organic chemistry Molecular Biology Cryptococcus neoformans Molecular Structure biology General Medicine biology.organism_classification Rhodomelaceae chemistry Oxidative cleavage Sesquiterpenes |
| Zdroj: | Phytochemistry. 103:162-170 |
| ISSN: | 0031-9422 |
| DOI: | 10.1016/j.phytochem.2014.03.021 |
| Popis: | A ring-cleaved sesquiterpene, named seco-laurokamurone, four laurane-type sesquiterpenes, laurepoxyene, 3β-hydroperoxyaplysin, 3α-hydroperoxy-3-epiaplysin, and 8,10-dibromoisoaplysin, one laurokamurane-type sesquiterpene, laurokamurene D, and one bisabolane-type sesquiterpene, (5S)-5-acetoxy-β-bisabolene, have been isolated from a re-collection of the red alga Laurencia okamurai Yamada, together with six other known sesquiterpenes. Their structures, including relative configuration, were elucidated by detailed analysis of spectroscopic data, and by comparison with data for related known compounds. In addition, on the basis of chemical conversions, degradation results, and biogenetic considerations, the absolute configurations of several of these compounds were also tentatively proposed. seco-Laurokamurone possesses an unprecedented carbon skeleton, formed from an oxidative cleavage of the laurokamurane skeleton, and laurokamurene D represents the fourth example of a laurokamurane-type sesquiterpene from a natural source. The in vitro antifungal activity of many of these compounds was evaluated against four fungi (Cryptococcus neoformans, Candida glabrata, Trichophyton rubrum, and Aspergillus fumigatus), as well as assessing cytotoxicity against HL-60 and A-549 human cancer cell lines. The compounds studied displayed moderate activities, relative to controls. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Full Text from ScienceDirect