title: Structure-activity relationship of neuroprotective and reactive oxygen species scavenging activities for allium organosulfur compounds.
abstract: The neuroprotective and antioxidative activities of five organosulfur compounds with a thioallyl structure (-S-CH2CH=CH2) were characterized in terms of structure-activity relationships. Among five organosulfur compounds, only S-allyl-L-cysteine (SAC) having the alanyl group (-CH2CH-NH2-COOH) and lacking the oxo (O=) group with in between molecular properties, was effective in protecting cell death induced by both oxygen glucose deprivation and global cerebral ischemia. Conversely, lipophillic organosulfur compounds including diallyl sulfide, diallyl disulfide, and diallyl trisulfide were devoid of in vitro and in vivo neuroprotective activities. Furthermore, a significant correlation was only found between the in vivo neuroprotective activity and the OH- scavenging activity (gamma = 0.55 and p = 0.032) among reactive oxygen species scavenging activities. These results indicate that the presence of the alanyl group and the absence of the oxo group are essential for the manifestation of neuroprotective activity against ischemic insults and scavenging of OH radical, with SAC surfacing as a potent neuroprotectant.
authors.affiliation: Korea Food Research Institute, San 46-1, Backhyun, Bundang-gu, Sungnam, Kyonggi-do 463-746, Korea.
authors.forename: Ji-Myung
authors.initials: JM
authors.lastname: Kim
authors.forename: Hyun Joo
authors.initials: HJ
authors.lastname: Chang
authors.forename: Won-Ki
authors.initials: WK
authors.lastname: Kim
authors.forename: Namsoo
authors.initials: N
authors.lastname: Chang
authors.forename: Hyang Sook
authors.initials: HS
authors.lastname: Chun
mesh_terms: D000490:Allium / Q000737:chemistry*; D000818:Animals; D000975:Antioxidants / Q000494:pharmacology; D002545:Brain Ischemia; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D016166:Free Radical Scavengers / Q000737:chemistry / Q000494:pharmacology; D005849:Gerbillinae; D006801:Humans; D008297:Male; D009447:Neuroblastoma; D018696:Neuroprotective Agents / Q000737:chemistry / Q000494:pharmacology; D017382:Reactive Oxygen Species; D015427:Reperfusion Injury / Q000517:prevention & control; D013329:Structure-Activity Relationship; D013457:Sulfur Compounds / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000975:Antioxidants; D016166:Free Radical Scavengers; D018696:Neuroprotective Agents; D017382:Reactive Oxygen Species; D013457:Sulfur Compounds