TY - JOUR
T1 - A new canthinone-type alkaloid isolated from Ailanthus altissima Swingle
AU - Kim, Hye Mi
AU - Lee, Jin Su
AU - Sezirahiga, Jurdas
AU - Kwon, Jaeyoung
AU - Jeong, Miran
AU - Lee, Dongho
AU - Choi, Jung Hye
AU - Jang, Dae Sik
N1 - Funding Information:
This work was supported by the Bio-Synergy Research Project (NRF-2014M3A9C4066594) of the Ministry of Science, ICT, and Future Planning through the National Research Foundation and by High Value-added Food Technology Development Program, Korea Institute of Planning and Evaluation for Technology in Food, Agriculture, Forestry, and Fisheries (113036-04-1-HD020).
Publisher Copyright:
© 2016 by the authors; licensee MDPI.
Copyright:
Copyright 2016 Elsevier B.V., All rights reserved.
PY - 2016/5/1
Y1 - 2016/5/1
N2 - The present investigation of the chemical constituents of the stem barks of Ailanthus altissima has resulted in the isolation of six canthinone-type alkaloids, including a new compound, (R)-5-(1-hydroxyethyl)-canthine-6-one (1), and five known compounds (2-6). Moreover, four phenyl propanoids (7-10), two lignans (11 and 12), two triterpenoids (13 and 14) and a fatty acid (15) having previously known chemical structures were isolated during the same course of this study. The structure of the new compound was elucidated by physical (m.p., [α]D) and spectroscopic data (1H-NMR, 13C-NMR, 2D NMR, and HR-DART-MS) interpretation and its absolute configuration was determined by electronic circular dichroism (ECD) data and quantum chemical calculations. The inflammatory activities of the isolates were screened on lipopolysaccharide (LPS)-induced nitric oxide (NO), a proinflammatory mediator, in RAW 264.7 cells. Among these isolated compounds, six compounds exhibited significant inhibition of NO production, with IC50 values in the range of 5.92 ± 0.9 to 15.09 ± 1.8 μM.
AB - The present investigation of the chemical constituents of the stem barks of Ailanthus altissima has resulted in the isolation of six canthinone-type alkaloids, including a new compound, (R)-5-(1-hydroxyethyl)-canthine-6-one (1), and five known compounds (2-6). Moreover, four phenyl propanoids (7-10), two lignans (11 and 12), two triterpenoids (13 and 14) and a fatty acid (15) having previously known chemical structures were isolated during the same course of this study. The structure of the new compound was elucidated by physical (m.p., [α]D) and spectroscopic data (1H-NMR, 13C-NMR, 2D NMR, and HR-DART-MS) interpretation and its absolute configuration was determined by electronic circular dichroism (ECD) data and quantum chemical calculations. The inflammatory activities of the isolates were screened on lipopolysaccharide (LPS)-induced nitric oxide (NO), a proinflammatory mediator, in RAW 264.7 cells. Among these isolated compounds, six compounds exhibited significant inhibition of NO production, with IC50 values in the range of 5.92 ± 0.9 to 15.09 ± 1.8 μM.
KW - Ailanthus altissima
KW - Canthinone type alkaloids
KW - Inflammation
KW - Nitric oxide
KW - Simaroubaceae
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U2 - 10.3390/molecules21050642
DO - 10.3390/molecules21050642
M3 - Article
C2 - 27196883
AN - SCOPUS:84973622080
VL - 21
JO - Molecules
JF - Molecules
SN - 1420-3049
IS - 5
M1 - 642
ER -