title: Anti-inflammatory terpenylated coumarins from the leaves of Zanthoxylum schinifolium with α-glucosidase inhibitory activity.
abstract: Nine terpenylated coumarins, namely 7-[(E)-3',7'-dimethyl-6'-oxo-2',7'-octadienyl]oxy-coumarin (1), schinilenol (2), schinindiol (3), collinin (4), 7-[(E)-7'-hydroxy-3',7'-dimethy-locta-2',5'-dienyloxy]-coumarin (5), 8-methoxyanisocoumarin (6), 7-(6'R-hydroxy-3',7'-dimethyl-2'E,7'-octadienyloxy)coumarin (7), (E)-4-methyl-6-(coumarin-7'-yloxy)hex-4-enal (8), and aurapten (9), along with a 4-quinolone alkaloid (10) and integrifoliodiol (11), were isolated from the leaves of Zanthoxylum schinifolium. Of the isolates, compounds 4 and 7 potentially inhibited NO production in lipopolysaccharide (LPS)-stimulated macrophage RAW264.7 cells, with IC50 values of 5.9 ± 0.8 and 18.2 ± 1.8 μM, respectively. Furthermore, compounds 4 and 7 dose-dependently reduced the LPS-induced iNOS expression. Moreover, pre-incubation of cells with 4 and 7 significantly suppressed LPS-induced COX-2 protein expression. In addition, compounds 4, 7, 8, and 10 showed strong α-glucosidase inhibitory effects, with IC50 values of 92.1 ± 0.7, 90.6 ± 0.9, 78.2 ± 0.2, and 82.4 ± 0.8 μM, respectively. Compounds 1, 5, and 11 displayed moderate effects with IC50 values of 161.6 ± 0.3, 164.4 ± 1.1, and 155.4 ± 0.9 μM, while acarbose, a positive control, possessed an IC50 value of 121.5 ± 1.0 μM. This is the first investigation on the α-glucosidase inhibitory effect of components from Zanthoxylum schinifolium. Further studies should be made on active compounds.
authors.affiliation: College of Pharmacy, Catholic University of Daegu, Hayang, Gyeongbuk, 38430, Republic of Korea.
authors.forename: Phi-Hung
authors.initials: PH
authors.lastname: Nguyen
authors.affiliation: College of Pharmacy, Catholic University of Daegu, Hayang, Gyeongbuk, 38430, Republic of Korea.
authors.forename: Bing Tian
authors.initials: BT
authors.lastname: Zhao
authors.affiliation: College of Natural Science, Kangwon National University, Kangwon, 24341, Republic of Korea.
authors.forename: Okhwa
authors.initials: O
authors.lastname: Kim
authors.affiliation: College of Natural Science, Kangwon National University, Kangwon, 24341, Republic of Korea.
authors.forename: Jeong Hyung
authors.initials: JH
authors.lastname: Lee
authors.affiliation: Faculty of Food Science and Biotechnology, Pukyong National University, Busan, 48513, Republic of Korea.
authors.forename: Jae Sue
authors.initials: JS
authors.lastname: Choi
authors.affiliation: College of Pharmacy, Catholic University of Daegu, Hayang, Gyeongbuk, 38430, Republic of Korea.
authors.forename: Byung Sun
authors.initials: BS
authors.lastname: Min
authors.affiliation: College of Pharmacy, Catholic University of Daegu, Hayang, Gyeongbuk, 38430, Republic of Korea. woomh@cu.ac.kr.
authors.forename: Mi Hee
authors.initials: MH
authors.lastname: Woo
mesh_terms: D000470:Alkaloids / Q000302:isolation & purification / Q000494:pharmacology; D000818:Animals; D000893:Anti-Inflammatory Agents / Q000302:isolation & purification / Q000494:pharmacology*; D003374:Coumarins / Q000302:isolation & purification / Q000494:pharmacology*; D051546:Cyclooxygenase 2 / Q000378:metabolism; D065089:Glycoside Hydrolase Inhibitors / Q000302:isolation & purification / Q000494:pharmacology*; D007093:Imidazoles / Q000302:isolation & purification / Q000494:pharmacology; D007249:Inflammation / Q000378:metabolism*; D008070:Lipopolysaccharides; D008264:Macrophages / Q000187:drug effects; D051379:Mice; D009569:Nitric Oxide / Q000096:biosynthesis; D052247:Nitric Oxide Synthase Type II / Q000378:metabolism; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology*; D018515:Plant Leaves / Q000737:chemistry; D000067996:RAW 264.7 Cells; D032106:Zanthoxylum / Q000737:chemistry*; D000520:alpha-Glucosidases / Q000378:metabolism*
chemical_list: D000470:Alkaloids; D000893:Anti-Inflammatory Agents; D003374:Coumarins; D065089:Glycoside Hydrolase Inhibitors; D007093:Imidazoles; D008070:Lipopolysaccharides; D010936:Plant Extracts; C533975:collinin; C517283:coumarin 7; D009569:Nitric Oxide; C030123:coumarin; D052247:Nitric Oxide Synthase Type II; C496317:Nos2 protein, mouse; D051546:Cyclooxygenase 2; D000520:alpha-Glucosidases; C105832:aurapten
keywords: Anti-inflammation; Terpenylated coumarins; Zanthoxylum schinifolium; α-Glucosidase