Cassane-type diterpenoids from Caesalpinia echinata (Leguminosae) and their NF-κB signaling inhibition activities. (August 2015)

• Record Type: Journal Article
• Authors: Mitsui, Taichi; Ishihara, Risa; Hayashi, Ken-ichiro; Matsuura, Nobuyasu; Akashi, Haruo; Nozaki, Hiroshi
• Is Part Of: Phytochemistry. Volume 116(2015:Aug.)
• Page Start: 349
• Page End: 358
• Publication Date: 2015-08
• Subjects: Caesalpinia echinata -- Caesalpiniaceae -- Cassane diterpene -- Echinalide -- Nuclear factor κB; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2015.03.012
• Languages: English
• ISSNs: 0031-9422

Abstract

Abstract : Graphical abstract: Fourteen cassane-type diterpenoids, echinalides H–U, were isolated from the stem of Caesalpinia echinata Lam. (Leguminosae). Highlights: Fourteen cassane-type diterpenoids, echinalides H–U, were isolated from the stem of Caesalpinia echinata . The structures of echinalides H–U were determined by spectroscopic analyses including 2D NMR spectroscopy. Echinalide T and U appear to be rare cassane-type diterpenes, as both contain an unusual γ-spiro lactone ring. Echinalides H–U were evaluated for inhibitory activity against nuclear factor-κB (NF-κB). 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 5 μM) toward NF-κB-responsive gene expression.