Sesquiterpene coumarins from Ferula fukanensis and nitric oxide production inhibitory effects.
Six new sesquiterpene coumarin derivatives, 2,3-dihydro-7-hydroxy-2R,3R-dimethyl-2-[4,8-dimethyl-3(E),7-nonadien-6-onyl]furo[3,2-c]coumarin (4), fukanefuromarin A (5), fukanefuromarin B (6), fukanefuromarin C (7), fukanefuromarin D (8), and fukanemarin A (9), were isolated from a 80% aqueous methanol extract of the roots of Ferula fukanensis. The structures were elucidated on the basis of spectral evidence, especially heteronuclear multiple-bond connectivity (HMBC), nuclear Overhauser exchange spectroscopy (NOESY), and high-resolution MS. An extract of F. fukanensis (FFE) and the sesquiterpene coumarin derivatives inhibited nitric oxide (NO) production and inducible NO synthase (iNOS) gene expression by a murine macrophage-like cell line (RAW 264.7), which was activated by lipopolysaccharide (LPS) and recombinant mouse interferon-gamma (IFN-gamma).
Motai
Tsunetake
T
College of Pharmacy, Nihon University, 7-7-1 Narashinodai, Funabashi, Chiba 274-8555, Japan.
Daikonya
Akihiro
A
Kitanaka
Susumu
S
D000818:Animals; D002681:China; D003374:Coumarins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D005309:Ferula / Q000737:chemistry*; D007371:Interferon-gamma / Q000494:pharmacology; D008070:Lipopolysaccharides / Q000494:pharmacology; D008264:Macrophages / Q000378:metabolism; D051379:Mice; D009569:Nitric Oxide / Q000378:metabolism; D019001:Nitric Oxide Synthase / Q000037:antagonists & inhibitors*; D052247:Nitric Oxide Synthase Type II; D009573:Nitrites / Q000032:analysis; D018517:Plant Roots / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D012333:RNA, Messenger / Q000032:analysis; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
D003374:Coumarins; D004791:Enzyme Inhibitors; D008070:Lipopolysaccharides; D009573:Nitrites; D012333:RNA, Messenger; D012717:Sesquiterpenes; D009569:Nitric Oxide; D007371:Interferon-gamma; D019001:Nitric Oxide Synthase; D052247:Nitric Oxide Synthase Type II; C496317:Nos2 protein, mouse