title: Compounds from the heartwood of Caesalpinia sappan and their anti-inflammatory activity.
abstract: Two new phenolics, (3S,4R)-3,7,2',3'-tetrahydroxy-3,4-dihydro-9H-indeno[6,5-c]chromene (caesalpiniaphenol E, 1), and (3R,4S)-3,7-dihydroxy-3-(3'-methoxy-4'-hydroxyphenyl)-4-methoxychroman (caesalpiniaphenol F, 2), together with eleven known compounds (3-13), were isolated from the heartwood of Caesalpinia sappan. Their chemical structures were established mainly by 1D and 2D NMR techniques and mass spectrometry. Their anti-inflammatory activity was evaluated against LPS-induced NO production in macrophage RAW264.7 cells. Among them, compounds 10 and 13 showed strong inhibitory activities toward the LPS-induced NO production in macrophage RAW264.7 cells, with IC(50) values of 12.5 and 8.1 μm, respectively. In addition, compounds 10 and 13 inhibited the inductions of iNOS mRNA in dose-dependent manners, indicating that these compounds attenuated the synthesis of these transcripts at the transcriptional level.
authors.affiliation: College of Pharmacy, Catholic University of Daegu, Gyeongbuk 712-702, Republic of Korea. bsmin@cu.ac.kr
authors.forename: Byung Sun
authors.initials: BS
authors.lastname: Min
authors.forename: To Dao
authors.initials: TD
authors.lastname: Cuong
authors.forename: Tran Manh
authors.initials: TM
authors.lastname: Hung
authors.forename: Bo Kyung
authors.initials: BK
authors.lastname: Min
authors.forename: Beom Soo
authors.initials: BS
authors.lastname: Shin
authors.forename: Mi Hee
authors.initials: MH
authors.lastname: Woo
mesh_terms: D000818:Animals; D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D001578:Benzopyrans / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D029911:Caesalpinia / Q000737:chemistry*; D002460:Cell Line; D002839:Chromans / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D008070:Lipopolysaccharides / Q000037:antagonists & inhibitors / Q000494:pharmacology; D008264:Macrophages / Q000187:drug effects* / Q000378:metabolism; D051379:Mice; D008968:Molecular Conformation; D009569:Nitric Oxide / Q000037:antagonists & inhibitors / Q000096:biosynthesis; D052247:Nitric Oxide Synthase Type II / Q000037:antagonists & inhibitors / Q000096:biosynthesis / Q000378:metabolism; D012333:RNA, Messenger / Q000037:antagonists & inhibitors / Q000096:biosynthesis / Q000378:metabolism; D013329:Structure-Activity Relationship
chemical_list: C581045:(3R,4S)-3,7-dihydroxy-3-(3'-methoxy-4'-hydroxyphenyl)-4-methoxychroman; C581044:(3S,4R)-3,7,2',3'-tetrahydroxy-3,4-dihydro-9H-indeno(6,5-c)chromene; D000893:Anti-Inflammatory Agents; D001578:Benzopyrans; D002839:Chromans; D004791:Enzyme Inhibitors; D008070:Lipopolysaccharides; D012333:RNA, Messenger; D009569:Nitric Oxide; D052247:Nitric Oxide Synthase Type II