title: Pyrrole Derivatives and Diterpene Alkaloids from the South China Sea Sponge Agelas nakamurai.
abstract: Two pairs of new non-brominated racematic pyrrole derivatives, (±)-nakamurine D (1) and (±)-nakamurine E (2), two new diterpene alkaloids, isoagelasine C (16) and isoagelasidine B (21), together with 13 known pyrrole derivatives ((±)-3 - 15), five known diterpene alkaloids (17 - 20, 22) were isolated from the South China Sea sponge Agelas nakamurai. The racemic mixtures, compounds 1 - 4, were resolved into four pairs of enantiomers, (+)-1 and (-)-1, (+)-2 and (-)-2, (+)-3 and (-)-3, and (+)-4 and (-)-4, by chiral HPLC. The structures and absolute configurations were elucidated on the basis of comprehensive spectroscopic analyses, quantum chemical calculations, quantitative measurements of molar rotations, application of van't Hoff's principle of optical superposition, and comparison with the literature data. The NMR and MS data of compound 3 are reported for the first time, as the structure was listed in SciFinder Scholar with no associated reference. These non-brominated pyrrole derivatives were found in this species for the first time. Compound 18 showed valuable cytotoxicities against HL-60, K562, and HCT-116 cell lines with IC50values of 12.4, 16.0, and 19.8 μm, respectively. Compounds 16 - 19, 21, and 22 showed potent antifungal activities against Candida albicans with MIC values ranging from 0.59 to 4.69 μg/ml. Compounds 16 - 19 exhibited moderate antibacterial activities against Proteusbacillus vulgaris (MIC values ranging from 9.38 to 18.75 μg/ml).
authors.affiliation: Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, 266003, P. R. China.|Laboratory of Marine Drugs and Biological Products, National Laboratory for Marine Science and Technology, Qingdao, 266235, P. R. China.
authors.forename: Mei-Jun
authors.initials: MJ
authors.lastname: Chu
authors.affiliation: Laboratory of Marine Drugs and Biological Products, National Laboratory for Marine Science and Technology, Qingdao, 266235, P. R. China.
authors.forename: Xu-Li
authors.initials: XL
authors.lastname: Tang
authors.affiliation: Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, 266003, P. R. China.|Laboratory of Marine Drugs and Biological Products, National Laboratory for Marine Science and Technology, Qingdao, 266235, P. R. China.
authors.forename: Guo-Fei
authors.initials: GF
authors.lastname: Qin
authors.affiliation: Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, 266003, P. R. China.|Laboratory of Marine Drugs and Biological Products, National Laboratory for Marine Science and Technology, Qingdao, 266235, P. R. China.
authors.forename: Yan-Ting
authors.initials: YT
authors.lastname: Sun
authors.affiliation: Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, 266003, P. R. China.|Laboratory of Marine Drugs and Biological Products, National Laboratory for Marine Science and Technology, Qingdao, 266235, P. R. China.
authors.forename: Lei
authors.initials: L
authors.lastname: Li
authors.affiliation: National Museum of Natural History, Leiden, 2300 RA, The Netherlands.
authors.forename: Nicole J
authors.initials: NJ
authors.lastname: de Voogd
authors.affiliation: Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, 266003, P. R. China.|Laboratory of Marine Drugs and Biological Products, National Laboratory for Marine Science and Technology, Qingdao, 266235, P. R. China.
authors.forename: Ping-Lin
authors.initials: PL
authors.lastname: Li
authors.affiliation: Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, 266003, P. R. China.|Laboratory of Marine Drugs and Biological Products, National Laboratory for Marine Science and Technology, Qingdao, 266235, P. R. China.
authors.forename: Guo-Qiang
authors.initials: GQ
authors.lastname: Li
mesh_terms: D047230:Agelas / Q000737:chemistry*; D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification*; D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification; D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification*; D045325:HCT116 Cells; D018922:HL-60 Cells; D006801:Humans; D020014:K562 Cells; D015394:Molecular Structure; D011758:Pyrroles / Q000737:chemistry / Q000302:isolation & purification*
chemical_list: D000470:Alkaloids; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D000970:Antineoplastic Agents; D004224:Diterpenes; D011758:Pyrroles
keywords: 
  Agelas nakamurai
  ; Antimicrobial activity; Cytotoxic activity; Diterpene alkaloids; Pyrrole alkaloids