title: Neuroprotective coumarins from the root of Angelica gigas: structure-activity relationships.
abstract: An n-butanol-soluble fraction of the root of Angelica gigas Nakai (Umbelliferae) exhibited significant protection against glutamate-induced toxicity in primary cultured rat cortical cells. Using neuroprotective activity-guided fractionation, nine coumarins; marmesinin (1), nodakenin (2), columbianetin-O-beta-D-glucopyranoside (3), (S)-peucedanol-7-O-beta-D-glucopyranoside (4), (S)-peucedanol-3'-O-beta-D-glucopyranoside (5), skimmin (6), apiosylskimmin (7), isoapiosylskimmin (8) and magnolioside (9), were isolated from the n-butanol fraction. Of these nine coumarins, three dihydrofuranocoumarins; 1, 2 and 3, exhibited significant neuroprotective activities against glutamate-induced toxicity, exhibiting cell viabilities of about 50% at concentrations ranging from 0.1 to 10 microM. To explore the structure-activity relationships of coumarins, sixteen previously isolated compounds; 10-25, were simultaneously evaluated in the same system. Our results revealed that cyclization of the isoprenyl group, such as dihydropyran or dihydrofuran, or the furan ring at the C-6 position of coumarin, as well as lipophilicity played an important role in the neuroprotective activity of coumarins.
authors: Division of Food Science and Aqualife Medicine, Chonnam National University, Yeosu, Chonnam 550-749, Korea. sykang1@chonnam.ac.kr
authors: So Young
authors: SY
authors: Kang
authors: Young Choong
authors: YC
authors: Kim
mesh_terms: D029969:Angelica / Q000737:chemistry*; D000818:Animals; D002478:Cells, Cultured; D002540:Cerebral Cortex / Q000187:drug effects; D003374:Coumarins / Q000302:isolation & purification / Q000494:pharmacology*; D018698:Glutamic Acid / Q000633:toxicity; D018696:Neuroprotective Agents / Q000302:isolation & purification / Q000494:pharmacology*; D018517:Plant Roots / Q000737:chemistry*; D051381:Rats; D013329:Structure-Activity Relationship
chemical_list: D003374:Coumarins; D018696:Neuroprotective Agents; D018698:Glutamic Acid