title: Cassane-type diterpenoids from Caesalpinia echinata (Leguminosae) and their NF-κB signaling inhibition activities.
abstract: Fourteen cassane-type diterpenoids, echinalides H-U, were isolated from the stem of Caesalpinia echinata Lam. (Leguminosae). The structures of the echinalides were elucidated by spectroscopic investigation, including 2D NMR spectroscopic analysis. The structures of echinalide H and echinalide T were further confirmed by single-crystal X-ray diffraction. The absolute configurations of echinalides H, I, J and K were determined by CD spectroscopy. Additionally, the absolute configurations of echinalide L and M were determined by chemical conversion from echinalide H. These compounds were evaluated for inhibitory activity against nuclear factor κB (NF-κB). Echinalide M showed the most potent inhibitory activity (47±11% at 5μM) toward NF-κB-responsive gene expression.
authors.affiliation: Department of Biological Chemistry, Faculty of Science, Okayama University of Science, 1-1 Ridai-cho, Kita-ku, Okayama 700-0005, Japan.
authors.forename: Taichi
authors.initials: T
authors.lastname: Mitsui
authors.affiliation: Department of Biological Chemistry, Faculty of Science, Okayama University of Science, 1-1 Ridai-cho, Kita-ku, Okayama 700-0005, Japan.
authors.forename: Risa
authors.initials: R
authors.lastname: Ishihara
authors.affiliation: Department of Biological Chemistry, Faculty of Science, Okayama University of Science, 1-1 Ridai-cho, Kita-ku, Okayama 700-0005, Japan.
authors.forename: Ken-Ichiro
authors.initials: KI
authors.lastname: Hayashi
authors.affiliation: Department of Life Science, Faculty of Science, Okayama University of Science, 1-1 Ridai-cho, Kita-ku, Okayama 700-0005, Japan.
authors.forename: Nobuyasu
authors.initials: N
authors.lastname: Matsuura
authors.affiliation: Research Institute of Natural Sciences, Okayama University of Science, 1-1 Ridai-cho, Kita-ku, Okayama 700-0005, Japan.
authors.forename: Haruo
authors.initials: H
authors.lastname: Akashi
authors.affiliation: Department of Biological Chemistry, Faculty of Science, Okayama University of Science, 1-1 Ridai-cho, Kita-ku, Okayama 700-0005, Japan. Electronic address: nozaki@dbc.ous.ac.jp.
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Nozaki
mesh_terms: D001938:Brazil; D029911:Caesalpinia / Q000737:chemistry*; D018360:Crystallography, X-Ray; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D006367:HeLa Cells; D006801:Humans; D020672:I-kappa B Proteins; D008968:Molecular Conformation; D015394:Molecular Structure; D016328:NF-kappa B / Q000037:antagonists & inhibitors*; D019906:Nuclear Magnetic Resonance, Biomolecular; D018547:Plant Stems / Q000737:chemistry; D012639:Seeds / Q000737:chemistry; D015398:Signal Transduction / Q000187:drug effects
chemical_list: D004224:Diterpenes; D020672:I-kappa B Proteins; D016328:NF-kappa B; C000605022:echinalide M
keywords: Caesalpinia echinata; Caesalpiniaceae; Cassane diterpene; Echinalide; Nuclear factor κB