A new canthinone-type alkaloid isolated from Ailanthus altissima Swingle

Hye Mi Kim; Jin Su Lee; Jurdas Sezirahiga; Jaeyoung Kwon; Miran Jeong; Dongho Lee; Jung Hye Choi; Dae Sik Jang

doi:10.3390/molecules21050642

A new canthinone-type alkaloid isolated from Ailanthus altissima Swingle

Hye Mi Kim, Jin Su Lee, Jurdas Sezirahiga, Jaeyoung Kwon, Miran Jeong, Dongho Lee, Jung Hye Choi, Dae Sik Jang

Department of Biosystems and Biotechnology

Research output: Contribution to journal › Article › peer-review

19 Citations (Scopus)

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	https://doi.org/10.3390/molecules21050642
Publication status	Published - 2016 May 1

Keywords

Ailanthus altissima
Canthinone type alkaloids
Inflammation
Nitric oxide
Simaroubaceae

ASJC Scopus subject areas

Analytical Chemistry
Chemistry (miscellaneous)
Molecular Medicine
Pharmaceutical Science
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry

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10.3390/molecules21050642

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title = "A new canthinone-type alkaloid isolated from Ailanthus altissima Swingle",

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.",

keywords = "Ailanthus altissima, Canthinone type alkaloids, Inflammation, Nitric oxide, Simaroubaceae",

author = "Kim, {Hye Mi} and Lee, {Jin Su} and Jurdas Sezirahiga and Jaeyoung Kwon and Miran Jeong and Dongho Lee and Choi, {Jung Hye} and Jang, {Dae Sik}",

note = "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: {\textcopyright} 2016 by the authors; licensee MDPI.",

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AU - Kim, Hye Mi

AU - Lee, Jin Su

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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.

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.

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KW - Inflammation

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KW - Simaroubaceae

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A new canthinone-type alkaloid isolated from Ailanthus altissima Swingle

Abstract

Keywords

ASJC Scopus subject areas

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