title: Structurally Diverse Metabolites from the Soft Coral Sinularia verruca Collected in the South China Sea.
abstract: Nineteen metabolites with diverse structures, including the rare pyrroloindoline alkaloid verrupyrroloindoline (1), the unprecedented highly fused benzosesquiterpenoid verrubenzospirolactone (2), the new asteriscane-type sesquiterpenoid 10-deoxocapillosanane D (3), and the two new cyclopentenone derivatives (4S*,5S*)-4-hydroxy-5-(hydroxymethyl)-2,3-dimethyl-4-pentylcyclopent-2-en-1-one (4) and (S)-4-hydroxy-5-methylene-2,3-dimethyl-4-pentylcyclopent-2-en-1-one (5), were isolated from a South China Sea collection of the soft coral Sinularia verruca. Eleven previously described marine metabolites (7-15, 18, and 19) were also obtained as well as three new EtOH-adduct artifacts (6, 16, and 17). The structures of the new compounds were elucidated by extensive spectroscopic analysis and by comparison with previously reported data. Compounds 4, 5, and 16 showed protection against the cytopathic effects of HIV-1 infection with EC50 values of 5.8-34 μM, and 4, 6, and 16 exhibited inhibition against LPS-induced NO production with IC50 values of 24-28 μM.
authors.affiliation: School of Pharmaceutical Sciences, Wenzhou Medical University , Wenzhou, Zhejiang 325035, People's Republic of China.
authors.forename: Weiping
authors.initials: W
authors.lastname: Yuan
authors.affiliation: The Fifth Affiliated Hospital, Wenzhou Medical University , Lishui, Zhejiang 323000, People's Republic of China.
authors.forename: Shimiao
authors.initials: S
authors.lastname: Cheng
authors.affiliation: School of Pharmaceutical Sciences, Wenzhou Medical University , Wenzhou, Zhejiang 325035, People's Republic of China.
authors.forename: Weitao
authors.initials: W
authors.lastname: Fu
authors.affiliation: School of Pharmaceutical Sciences, Wenzhou Medical University , Wenzhou, Zhejiang 325035, People's Republic of China.
authors.forename: Min
authors.initials: M
authors.lastname: Zhao
authors.affiliation: Key Laboratory of Marine Bio-resources Sustainable Utilization, South China Sea Institute of Oceanology, Chinese Academy of Sciences , Guangzhou, Guangdong 510301, People's Republic of China.
authors.forename: Xiubao
authors.initials: X
authors.lastname: Li
authors.affiliation: School of Pharmaceutical Sciences, Wenzhou Medical University , Wenzhou, Zhejiang 325035, People's Republic of China.
authors.forename: Yuepiao
authors.initials: Y
authors.lastname: Cai
authors.affiliation: School of Pharmaceutical Sciences, Wenzhou Medical University , Wenzhou, Zhejiang 325035, People's Republic of China.
authors.forename: Jianyong
authors.initials: J
authors.lastname: Dong
authors.affiliation: School of Pharmaceutical Sciences, Wenzhou Medical University , Wenzhou, Zhejiang 325035, People's Republic of China.
authors.forename: Kexin
authors.initials: K
authors.lastname: Huang
authors.affiliation: Molecular Targets Laboratory, Center for Cancer Research, National Cancer Institute , Frederick, Maryland 21702-1201, United States.
authors.forename: Kirk R
authors.initials: KR
authors.lastname: Gustafson
authors.affiliation: School of Pharmaceutical Sciences, Wenzhou Medical University , Wenzhou, Zhejiang 325035, People's Republic of China.|Molecular Targets Laboratory, Center for Cancer Research, National Cancer Institute , Frederick, Maryland 21702-1201, United States.
authors.forename: Pengcheng
authors.initials: P
authors.lastname: Yan
mesh_terms: D000818:Animals; D037421:Anthozoa / Q000737:chemistry*; D002681:China; D003517:Cyclopentanes / Q000737:chemistry / Q000302:isolation & purification; D015497:HIV-1 / Q000187:drug effects; D026121:Indole Alkaloids / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D008070:Lipopolysaccharides / Q000494:pharmacology; D017737:Macrophages, Peritoneal / Q000187:drug effects; D051379:Mice; D015394:Molecular Structure; D009569:Nitric Oxide / Q000096:biosynthesis; D019906:Nuclear Magnetic Resonance, Biomolecular; D009792:Oceans and Seas; D012717:Sesquiterpenes / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology
chemical_list: C000610611:10-deoxocapillosanane D; D003517:Cyclopentanes; D026121:Indole Alkaloids; D008070:Lipopolysaccharides; D012717:Sesquiterpenes; C000610610:verrubenzospirolactone; C000610609:verrupyrroloindoline; D009569:Nitric Oxide; C013905:cyclopentenone