title: Compositacins A-K: Bioactive chamigrane-type halosesquiterpenoids from the red alga Laurencia composita Yamada.
abstract: Eleven highly halogenated chamigrane sesquiterpenoids, compositacins A-K, including one unusual rearranged chamigrane sesquiterpenoid, compositacin A, were isolated from the red alga Laurencia composita Yamada, along with seven known structural analogues. Compositacins B and D are the first examples of chamigranes bearing an ether bridge involving C-5/C-9 and C-3/C-5, respectively, while compositacins B and C represent the first chamigranes with a C-10 carbonyl group. Their structures were elucidated on the basis of extensive spectroscopic analysis. The absolute configuration of compositacin B was determined by ECD calculation, whereas the absolute configurations of compositacins A and C-L were proposed on biosynthetic grounds by comparison to compositacin B and the related known sesquiterpenoids johnstonol and yicterpene A. We also suggest that the structure of the previously reported sesquiterpenoid laurokamin A should be revised. Cytotoxicity and antifungal activity of these isolates were also investigated. The results showed that compositacin G exhibited good antifungal activity against Microsporum gypseum (Cmccfmza) with a MIC80value of 4 μg/mL relative to positive controls. Four of the chamigrane halosesquiterpenoids showed marginal cytotoxicity against the A-549 human lung adenocarcinoma cell line with IC50values ranging from 48.6 to 85.2 μM.
authors.affiliation: School of Pharmacy, Nanchang University, 461 Bayi Road, Nanchang 330006, People's Repulic of China.
authors.forename: Xiao-Qing
authors.initials: XQ
authors.lastname: Yu
authors.affiliation: School of Pharmacy, Nanchang University, 461 Bayi Road, Nanchang 330006, People's Repulic of China.
authors.forename: Chang-Sheng
authors.initials: CS
authors.lastname: Jiang
authors.affiliation: School of Pharmacy, Nanchang University, 461 Bayi Road, Nanchang 330006, People's Repulic of China.
authors.forename: Yi
authors.initials: Y
authors.lastname: Zhang
authors.affiliation: School of Pharmacy, Nanchang University, 461 Bayi Road, Nanchang 330006, People's Repulic of China.
authors.forename: Pan
authors.initials: P
authors.lastname: Sun
authors.affiliation: Department of Organic Chemistry, University of Debrecen, PO Box 400, H-4002 Debrecen, Hungary.
authors.forename: Tibor
authors.initials: T
authors.lastname: Kurtán
authors.affiliation: Department of Organic Chemistry, University of Debrecen, PO Box 400, H-4002 Debrecen, Hungary.
authors.forename: Attila
authors.initials: A
authors.lastname: Mándi
authors.affiliation: State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, People's Repulic of China.
authors.forename: Xiao-Lu
authors.initials: XL
authors.lastname: Li
authors.affiliation: State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, People's Repulic of China.
authors.forename: Li-Gong
authors.initials: LG
authors.lastname: Yao
authors.affiliation: Center of Analysis and Testing, Nanchang University, Nanchang 330047, People's Repulic of China.
authors.forename: Ai-Hong
authors.initials: AH
authors.lastname: Liu
authors.affiliation: School of Pharmacy, Nanchang University, 461 Bayi Road, Nanchang 330006, People's Repulic of China.
authors.forename: Bin
authors.initials: B
authors.lastname: Wang
authors.affiliation: State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, People's Repulic 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 Repulic of China. Electronic address: maoshuichun@ncu.edu.cn.
authors.forename: Shui-Chun
authors.initials: SC
authors.lastname: Mao
mesh_terms: D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D002460:Cell Line; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D006846:Hydrocarbons, Halogenated / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D044722:Laurencia / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*
chemical_list: D000935:Antifungal Agents; D000970:Antineoplastic Agents; D006846:Hydrocarbons, Halogenated; D012717:Sesquiterpenes; C000614679:compositacin B; C000614680:compositacin D
keywords: Antifungal activity; Chamigrane sesquiterpenoid; Compositacins A–K; Cytotoxicity; ECD calculation; Laurencia composita; Rearranged chamigrane sesquiterpenoid; Rhodomelaceae; X-ray diffraction