title: (+)- and (-)-Spiroreticulatine, A Pair of Unusual Spiro Bisheterocyclic Quinoline-imidazole Alkaloids from the South China Sea Sponge Fascaplysinopsis reticulata.
abstract: A pair of novel bisheterocyclic quinoline-imidazole alkaloids, (+)- and (-)-spiroreticulatine (1), were isolated from the South China Sea sponge Fascaplysinopsis reticulata. The structures and absolute configurations were elucidated by comprehensive spectroscopic analysis, single-crystal X-ray diffraction, and quantum chemical calculation methods. Spiroreticulatine is the first example of a sponge-derived natural spiro quinoline-imidazole alkaloid that may derive from tryptophan and 1,3-dimethylurea. Compound 1 showed inhibitory activity on IL-2 production but inactive against normal tumor cell lines.
authors.affiliation: †Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, People's Republic of China.
authors.forename: Qi
authors.initials: Q
authors.lastname: Wang
authors.affiliation: ‡College of Chemistry and Chemical Engineering, Ocean University of China, Qingdao 266100, People's Republic of China.
authors.forename: Xuli
authors.initials: X
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, People's Republic of China.
authors.forename: Xiangchao
authors.initials: X
authors.lastname: Luo
authors.affiliation: §National Museum of Natural History, 2300 RA Leiden, 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, People's Republic of China.
authors.forename: Pinglin
authors.initials: P
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, People's Republic of China.
authors.forename: Guoqiang
authors.initials: G
authors.lastname: Li
mesh_terms: D000470:Alkaloids / Q000737:chemistry* / Q000302:isolation & purification; D000818:Animals; D045744:Cell Line, Tumor; D002681:China; D018360:Crystallography, X-Ray; D004354:Drug Screening Assays, Antitumor; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D007376:Interleukin-2 / Q000037:antagonists & inhibitors / Q000737:chemistry*; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry*; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification
chemical_list: D000470:Alkaloids; D007093:Imidazoles; D007376:Interleukin-2; D011804:Quinolines; D013141:Spiro Compounds; C000602281:spiroreticulatine; C029899:imidazole; C037219:quinoline