Chemical Constituents from the Aerial Parts of Agastache rugosa and Their Inhibitory Activities on Prostaglandin E2 Production in Lipopolysaccharide-Treated RAW 264.7 Macrophages

Young H. Seo; Shin Young Kang; Ji Sun Shin; Seung M. Ryu; A. Y. Lee; Goya Choi; Byeong C. Moon; Dae Sik Jang; Sang H. Shim; Dongho Lee; Kyung Tae Lee; Jun Lee

doi:10.1021/acs.jnatprod.9b00697

Chemical Constituents from the Aerial Parts of Agastache rugosa and Their Inhibitory Activities on Prostaglandin E₂ Production in Lipopolysaccharide-Treated RAW 264.7 Macrophages

Young H. Seo, Shin Young Kang, Ji Sun Shin, Seung M. Ryu, A. Y. Lee, Goya Choi, Byeong C. Moon, Dae Sik Jang, Sang H. Shim, Dongho Lee, Kyung Tae Lee, Jun Lee^*

^*Corresponding author for this work

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

23 Citations (Scopus)

Abstract

A new flavone glucoside, acacetin-7-O-(3″-O-acetyl-6″-O-malonyl)-β-d-glucopyranoside (1), two new phenolic glucosides, (3R,7R)-tuberonic acid-12-O-[6′-O-(E)-feruloyl]-β-d-glucopyranoside (14) and salicylic acid-2-O-[6′-O-(E)-feruloyl]-β-d-glucopyranoside (15), and two new phenylpropanoid glucosides, chavicol-1-O-(6′-O-methylmalonyl)-β-d-glucopyranoside (17) and chavicol-1-O-(6′-O-acetyl)-β-d-glucopyranoside(18), as well as 26 known compounds, 2-13, 16, and 19-31, were isolated from the aerial parts of Agastache rugose. The structures of the new compounds were established by spectroscopic/spectrometric methods such as HRESIMS, NMR, and ECD. The anti-inflammatory effect of the isolated compounds was evaluated by measuring their inhibitory activities on prostaglandin E₂ (PGE₂) in lipopolysaccharide (LPS)-treated RAW 264.7 macrophages. New compounds 1, 15, 17, and 18 inhibited LPS-induced PGE₂ production with IC₅₀ values of 16.8 ± 0.8, 33.9 ± 4.8, 14.3 ± 2.1, and 48.8 ± 4.4 μM, respectively. Compounds 5, 7, 9-11, 13, 19, 20, 22, and 27-30 showed potent inhibitory activities with IC₅₀ values of 1.7-8.4 μM.

Original language	English
Pages (from-to)	3379-3385
Number of pages	7
Journal	Journal of Natural Products
Volume	82
Issue number	12
DOIs	https://doi.org/10.1021/acs.jnatprod.9b00697
Publication status	Published - 2019 Dec 27

Bibliographical note

Funding Information:
This work was supported by a National Research Council of Science & Technology (NST) grant by the Korean government (MSIP) (No. CRC-15-04-KIST, G16230) and the projects entitled “Applicational Development of Standardized Herbal Resources” (grant number: KSN1911420) from the Korea Institute of Oriental Medicine (KIOM).

Publisher Copyright:
© 2019 American Chemical Society and American Society of Pharmacognosy.

ASJC Scopus subject areas

Analytical Chemistry
Molecular Medicine
Pharmacology
Pharmaceutical Science
Drug Discovery
Complementary and alternative medicine
Organic Chemistry

Access to Document

10.1021/acs.jnatprod.9b00697

Cite this

Seo, Y. H., Kang, S. Y., Shin, J. S., Ryu, S. M., Lee, A. Y., Choi, G., Moon, B. C., Jang, D. S., Shim, S. H., Lee, D., Lee, K. T., & Lee, J. (2019). Chemical Constituents from the Aerial Parts of Agastache rugosa and Their Inhibitory Activities on Prostaglandin E₂ Production in Lipopolysaccharide-Treated RAW 264.7 Macrophages. Journal of Natural Products, 82(12), 3379-3385. https://doi.org/10.1021/acs.jnatprod.9b00697

Chemical Constituents from the Aerial Parts of Agastache rugosa and Their Inhibitory Activities on Prostaglandin E₂ Production in Lipopolysaccharide-Treated RAW 264.7 Macrophages. / Seo, Young H.; Kang, Shin Young; Shin, Ji Sun et al.
In: Journal of Natural Products, Vol. 82, No. 12, 27.12.2019, p. 3379-3385.

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

Seo, YH, Kang, SY, Shin, JS, Ryu, SM, Lee, AY, Choi, G, Moon, BC, Jang, DS, Shim, SH, Lee, D, Lee, KT & Lee, J 2019, 'Chemical Constituents from the Aerial Parts of Agastache rugosa and Their Inhibitory Activities on Prostaglandin E₂ Production in Lipopolysaccharide-Treated RAW 264.7 Macrophages', Journal of Natural Products, vol. 82, no. 12, pp. 3379-3385. https://doi.org/10.1021/acs.jnatprod.9b00697

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title = "Chemical Constituents from the Aerial Parts of Agastache rugosa and Their Inhibitory Activities on Prostaglandin E2 Production in Lipopolysaccharide-Treated RAW 264.7 Macrophages",

abstract = "A new flavone glucoside, acacetin-7-O-(3″-O-acetyl-6″-O-malonyl)-β-d-glucopyranoside (1), two new phenolic glucosides, (3R,7R)-tuberonic acid-12-O-[6′-O-(E)-feruloyl]-β-d-glucopyranoside (14) and salicylic acid-2-O-[6′-O-(E)-feruloyl]-β-d-glucopyranoside (15), and two new phenylpropanoid glucosides, chavicol-1-O-(6′-O-methylmalonyl)-β-d-glucopyranoside (17) and chavicol-1-O-(6′-O-acetyl)-β-d-glucopyranoside(18), as well as 26 known compounds, 2-13, 16, and 19-31, were isolated from the aerial parts of Agastache rugose. The structures of the new compounds were established by spectroscopic/spectrometric methods such as HRESIMS, NMR, and ECD. The anti-inflammatory effect of the isolated compounds was evaluated by measuring their inhibitory activities on prostaglandin E2 (PGE2) in lipopolysaccharide (LPS)-treated RAW 264.7 macrophages. New compounds 1, 15, 17, and 18 inhibited LPS-induced PGE2 production with IC50 values of 16.8 ± 0.8, 33.9 ± 4.8, 14.3 ± 2.1, and 48.8 ± 4.4 μM, respectively. Compounds 5, 7, 9-11, 13, 19, 20, 22, and 27-30 showed potent inhibitory activities with IC50 values of 1.7-8.4 μM.",

author = "Seo, \{Young H.\} and Kang, \{Shin Young\} and Shin, \{Ji Sun\} and Ryu, \{Seung M.\} and Lee, \{A. Y.\} and Goya Choi and Moon, \{Byeong C.\} and Jang, \{Dae Sik\} and Shim, \{Sang H.\} and Dongho Lee and Lee, \{Kyung Tae\} and Jun Lee",

note = "Funding Information: This work was supported by a National Research Council of Science \& Technology (NST) grant by the Korean government (MSIP) (No. CRC-15-04-KIST, G16230) and the projects entitled “Applicational Development of Standardized Herbal Resources” (grant number: KSN1911420) from the Korea Institute of Oriental Medicine (KIOM). Publisher Copyright: {\textcopyright} 2019 American Chemical Society and American Society of Pharmacognosy.",

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AU - Ryu, Seung M.

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AU - Choi, Goya

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PY - 2019/12/27

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N2 - A new flavone glucoside, acacetin-7-O-(3″-O-acetyl-6″-O-malonyl)-β-d-glucopyranoside (1), two new phenolic glucosides, (3R,7R)-tuberonic acid-12-O-[6′-O-(E)-feruloyl]-β-d-glucopyranoside (14) and salicylic acid-2-O-[6′-O-(E)-feruloyl]-β-d-glucopyranoside (15), and two new phenylpropanoid glucosides, chavicol-1-O-(6′-O-methylmalonyl)-β-d-glucopyranoside (17) and chavicol-1-O-(6′-O-acetyl)-β-d-glucopyranoside(18), as well as 26 known compounds, 2-13, 16, and 19-31, were isolated from the aerial parts of Agastache rugose. The structures of the new compounds were established by spectroscopic/spectrometric methods such as HRESIMS, NMR, and ECD. The anti-inflammatory effect of the isolated compounds was evaluated by measuring their inhibitory activities on prostaglandin E2 (PGE2) in lipopolysaccharide (LPS)-treated RAW 264.7 macrophages. New compounds 1, 15, 17, and 18 inhibited LPS-induced PGE2 production with IC50 values of 16.8 ± 0.8, 33.9 ± 4.8, 14.3 ± 2.1, and 48.8 ± 4.4 μM, respectively. Compounds 5, 7, 9-11, 13, 19, 20, 22, and 27-30 showed potent inhibitory activities with IC50 values of 1.7-8.4 μM.

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