Abstract
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.
| Original language | English |
|---|---|
| Article number | 642 |
| Journal | Molecules |
| Volume | 21 |
| Issue number | 5 |
| DOIs | |
| Publication status | Published - 2016 May 1 |
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Keywords
- Ailanthus altissima
- Canthinone type alkaloids
- Inflammation
- Nitric oxide
- Simaroubaceae
ASJC Scopus subject areas
- Organic Chemistry
Cite this
A new canthinone-type alkaloid isolated from Ailanthus altissima Swingle. / Kim, Hye Mi; Lee, Jin Su; Sezirahiga, Jurdas; Kwon, Jaeyoung; Jeong, Miran; Lee, Dongho; Choi, Jung Hye; Jang, Dae Sik.
In: Molecules, Vol. 21, No. 5, 642, 01.05.2016.Research output: Contribution to journal › Article
}
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
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
UR - http://www.scopus.com/inward/record.url?scp=84973622080&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84973622080&partnerID=8YFLogxK
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 -