title: A seco-laurane sesquiterpene and related laurane derivatives from the red alga Laurencia okamurai Yamada.
abstract: 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.
authors.affiliation: School of Pharmacy, Nanchang University, 461 Bayi Road, Nanchang 330006, People's Republic of China.
authors.forename: Xiao-Qing
authors.initials: XQ
authors.lastname: Yu
authors.affiliation: State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, People's Republic of China.
authors.forename: Wen-Fei
authors.initials: WF
authors.lastname: He
authors.affiliation: School of Pharmacy, Nanchang University, 461 Bayi Road, Nanchang 330006, People's Republic of China.
authors.forename: Ding-Quan
authors.initials: DQ
authors.lastname: Liu
authors.affiliation: School of Pharmacy, Nanchang University, 461 Bayi Road, Nanchang 330006, People's Republic of China.
authors.forename: Mei-Tang
authors.initials: MT
authors.lastname: Feng
authors.affiliation: School of Pharmacy, Nanchang University, 461 Bayi Road, Nanchang 330006, People's Republic of China.
authors.forename: Yi
authors.initials: Y
authors.lastname: Fang
authors.affiliation: School of Pharmacy, Nanchang University, 461 Bayi Road, Nanchang 330006, People's Republic of China.
authors.forename: Bin
authors.initials: B
authors.lastname: Wang
authors.affiliation: School of Pharmacy, Nanchang University, 461 Bayi Road, Nanchang 330006, People's Republic of China.
authors.forename: Li-Hua
authors.initials: LH
authors.lastname: Feng
authors.affiliation: State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, People's Republic of China.
authors.forename: Yue-Wei
authors.initials: YW
authors.lastname: Guo
authors.affiliation: School of Pharmacy, Nanchang University, 461 Bayi Road, Nanchang 330006, People's Republic of China; Institute of Translational Medicine, Nanchang University, Nanchang 330031, People's Republic of China. Electronic address: maoshuichun@ncu.edu.cn.
authors.forename: Shui-Chun
authors.initials: SC
authors.lastname: Mao
mesh_terms: D000935:Antifungal Agents / Q000009:adverse effects / Q000737:chemistry* / Q000494:pharmacology; D001232:Aspergillus fumigatus / Q000187:drug effects; D041221:Candida glabrata / Q000187:drug effects; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D003455:Cryptococcus neoformans / Q000187:drug effects; D006801:Humans; D044722:Laurencia / Q000737:chemistry*; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000009:adverse effects / Q000737:chemistry* / Q000494:pharmacology; D014249:Trichophyton / Q000187:drug effects
chemical_list: D000935:Antifungal Agents; D012717:Sesquiterpenes
keywords: Antifungal activity; Bisabolane sesquiterpene; Cytotoxicity; Laurane sesquiterpene; Laurencia; Laurencia okamurai; Laurokamurane sesquiterpene; Rhodomelaceae; seco-Laurokamurane sesquiterpene