Chemical Constituents from the Aerial Parts of Elsholtzia ciliata and Their Protective Activities on Glutamate-Induced HT22 Cell Death

Young Hye Seo; Tuy An Trinh; Seung Mok Ryu; Hyo Seon Kim; Goya Choi; Byeong Cheol Moon; Sang Hee Shim; Dae Sik Jang; Dongho Lee; Ki Sung Kang; Jun Lee

doi:10.1021/acs.jnatprod.0c00756

Chemical Constituents from the Aerial Parts of Elsholtzia ciliata and Their Protective Activities on Glutamate-Induced HT22 Cell Death

Young Hye Seo, Tuy An Trinh, Seung Mok Ryu, Hyo Seon Kim, Goya Choi, Byeong Cheol Moon, Sang Hee Shim, Dae Sik Jang, Dongho Lee, Ki Sung Kang, Jun Lee

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

13 Citations (Scopus)

Abstract

A new phenolic glucoside, (7E,9E)-3-hydroxyavenalumic acid-3-O-[6′-O-(E)-caffeoyl]-β-d-glucopyranoside (1), and three new acetylated flavone glycosides, acacetin-7-O-[β-d-glucopyranosyl(1″″→2″)-4′-O-acetyl-α-l-rhamnopyranosyl(1′→6″)]-β-d-glucopyranoside (3), acacetin-7-O-[6″″-O-acetyl-β-d-glucopyranosyl(1″″→2″)-3′-O-acetyl-α-l-rhamnopyranosyl(1′→6″)]-β-d-glucopyranoside (5), and acacetin-7-O-[3″″,6″″-di-O-acetyl-β-d-glucopyranosyl(1″″→2″)-4′-O-acetyl-α-l-rhamnopyranosyl(1′→6″)]-β-d-glucopyranoside (7), as well as 34 known compounds (2, 4, 6, and 8-38) were isolated from the aerial parts of Elsholtzia ciliata. The chemical structures of the new compounds were determined by spectroscopic/spectrometric data interpretation using NMR and HRESIMS. The neuroprotective effect of the isolated compounds was evaluated by a cell viability assay on HT22 murine hippocampal neuronal cells. Among them, 23 compounds, including new substances 1 and 3, exhibited neuroprotective effects against glutamate-induced HT22 cell death. In particular, compounds 2, 16, 17, 20, 22, 28, 29, and 31 presented potent neuroprotective effects with EC50 values of 1.5-8.3 μM.

Original language	English
Pages (from-to)	3149-3155
Number of pages	7
Journal	Journal of Natural Products
Volume	83
Issue number	10
DOIs	https://doi.org/10.1021/acs.jnatprod.0c00756
Publication status	Published - 2020 Oct 23

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, G17290) and the projects entitled “Applicational Development of Standardized Herbal Resources” and “Development of Sustainable Application for Standard Herbal Resources” (grant nos. KSN1911420 and KSN2012320) from the KIOM. This study was also supported by the National Research Foundation of Korea (NRF) funded by the Ministry of Science and ICT (MSIT), Republic of Korea (grant no. 2019R1F1A1059173).

Publisher Copyright:
©

ASJC Scopus subject areas

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

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10.1021/acs.jnatprod.0c00756

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@article{2bcb5fdc409e4be69ab36c5dcb0f264b,

title = "Chemical Constituents from the Aerial Parts of Elsholtzia ciliata and Their Protective Activities on Glutamate-Induced HT22 Cell Death",

abstract = "A new phenolic glucoside, (7E,9E)-3-hydroxyavenalumic acid-3-O-[6′-O-(E)-caffeoyl]-β-d-glucopyranoside (1), and three new acetylated flavone glycosides, acacetin-7-O-[β-d-glucopyranosyl(1″″→2″)-4′-O-acetyl-α-l-rhamnopyranosyl(1′→6″)]-β-d-glucopyranoside (3), acacetin-7-O-[6″″-O-acetyl-β-d-glucopyranosyl(1″″→2″)-3′-O-acetyl-α-l-rhamnopyranosyl(1′→6″)]-β-d-glucopyranoside (5), and acacetin-7-O-[3″″,6″″-di-O-acetyl-β-d-glucopyranosyl(1″″→2″)-4′-O-acetyl-α-l-rhamnopyranosyl(1′→6″)]-β-d-glucopyranoside (7), as well as 34 known compounds (2, 4, 6, and 8-38) were isolated from the aerial parts of Elsholtzia ciliata. The chemical structures of the new compounds were determined by spectroscopic/spectrometric data interpretation using NMR and HRESIMS. The neuroprotective effect of the isolated compounds was evaluated by a cell viability assay on HT22 murine hippocampal neuronal cells. Among them, 23 compounds, including new substances 1 and 3, exhibited neuroprotective effects against glutamate-induced HT22 cell death. In particular, compounds 2, 16, 17, 20, 22, 28, 29, and 31 presented potent neuroprotective effects with EC50 values of 1.5-8.3 μM.",

author = "Seo, {Young Hye} and Trinh, {Tuy An} and Ryu, {Seung Mok} and Kim, {Hyo Seon} and Goya Choi and Moon, {Byeong Cheol} and Shim, {Sang Hee} and Jang, {Dae Sik} and Dongho Lee and Kang, {Ki Sung} 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, G17290) and the projects entitled “Applicational Development of Standardized Herbal Resources” and “Development of Sustainable Application for Standard Herbal Resources” (grant nos. KSN1911420 and KSN2012320) from the KIOM. This study was also supported by the National Research Foundation of Korea (NRF) funded by the Ministry of Science and ICT (MSIT), Republic of Korea (grant no. 2019R1F1A1059173). Publisher Copyright: {\textcopyright} ",

year = "2020",

month = oct,

day = "23",

doi = "10.1021/acs.jnatprod.0c00756",

language = "English",

volume = "83",

pages = "3149--3155",

journal = "Journal of Natural Products",

issn = "0163-3864",

publisher = "American Chemical Society",

number = "10",

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T1 - Chemical Constituents from the Aerial Parts of Elsholtzia ciliata and Their Protective Activities on Glutamate-Induced HT22 Cell Death

AU - Seo, Young Hye

AU - Trinh, Tuy An

AU - Ryu, Seung Mok

AU - Kim, Hyo Seon

AU - Choi, Goya

AU - Moon, Byeong Cheol

AU - Shim, Sang Hee

AU - Jang, Dae Sik

AU - Lee, Dongho

AU - Kang, Ki Sung

AU - Lee, Jun

N1 - 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, G17290) and the projects entitled “Applicational Development of Standardized Herbal Resources” and “Development of Sustainable Application for Standard Herbal Resources” (grant nos. KSN1911420 and KSN2012320) from the KIOM. This study was also supported by the National Research Foundation of Korea (NRF) funded by the Ministry of Science and ICT (MSIT), Republic of Korea (grant no. 2019R1F1A1059173). Publisher Copyright: ©

PY - 2020/10/23

Y1 - 2020/10/23

N2 - A new phenolic glucoside, (7E,9E)-3-hydroxyavenalumic acid-3-O-[6′-O-(E)-caffeoyl]-β-d-glucopyranoside (1), and three new acetylated flavone glycosides, acacetin-7-O-[β-d-glucopyranosyl(1″″→2″)-4′-O-acetyl-α-l-rhamnopyranosyl(1′→6″)]-β-d-glucopyranoside (3), acacetin-7-O-[6″″-O-acetyl-β-d-glucopyranosyl(1″″→2″)-3′-O-acetyl-α-l-rhamnopyranosyl(1′→6″)]-β-d-glucopyranoside (5), and acacetin-7-O-[3″″,6″″-di-O-acetyl-β-d-glucopyranosyl(1″″→2″)-4′-O-acetyl-α-l-rhamnopyranosyl(1′→6″)]-β-d-glucopyranoside (7), as well as 34 known compounds (2, 4, 6, and 8-38) were isolated from the aerial parts of Elsholtzia ciliata. The chemical structures of the new compounds were determined by spectroscopic/spectrometric data interpretation using NMR and HRESIMS. The neuroprotective effect of the isolated compounds was evaluated by a cell viability assay on HT22 murine hippocampal neuronal cells. Among them, 23 compounds, including new substances 1 and 3, exhibited neuroprotective effects against glutamate-induced HT22 cell death. In particular, compounds 2, 16, 17, 20, 22, 28, 29, and 31 presented potent neuroprotective effects with EC50 values of 1.5-8.3 μM.

AB - A new phenolic glucoside, (7E,9E)-3-hydroxyavenalumic acid-3-O-[6′-O-(E)-caffeoyl]-β-d-glucopyranoside (1), and three new acetylated flavone glycosides, acacetin-7-O-[β-d-glucopyranosyl(1″″→2″)-4′-O-acetyl-α-l-rhamnopyranosyl(1′→6″)]-β-d-glucopyranoside (3), acacetin-7-O-[6″″-O-acetyl-β-d-glucopyranosyl(1″″→2″)-3′-O-acetyl-α-l-rhamnopyranosyl(1′→6″)]-β-d-glucopyranoside (5), and acacetin-7-O-[3″″,6″″-di-O-acetyl-β-d-glucopyranosyl(1″″→2″)-4′-O-acetyl-α-l-rhamnopyranosyl(1′→6″)]-β-d-glucopyranoside (7), as well as 34 known compounds (2, 4, 6, and 8-38) were isolated from the aerial parts of Elsholtzia ciliata. The chemical structures of the new compounds were determined by spectroscopic/spectrometric data interpretation using NMR and HRESIMS. The neuroprotective effect of the isolated compounds was evaluated by a cell viability assay on HT22 murine hippocampal neuronal cells. Among them, 23 compounds, including new substances 1 and 3, exhibited neuroprotective effects against glutamate-induced HT22 cell death. In particular, compounds 2, 16, 17, 20, 22, 28, 29, and 31 presented potent neuroprotective effects with EC50 values of 1.5-8.3 μM.

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U2 - 10.1021/acs.jnatprod.0c00756

DO - 10.1021/acs.jnatprod.0c00756

M3 - Article

C2 - 32991171

AN - SCOPUS:85094219694

SN - 0163-3864

VL - 83

SP - 3149

EP - 3155

JO - Journal of Natural Products

JF - Journal of Natural Products

IS - 10

ER -

Chemical Constituents from the Aerial Parts of Elsholtzia ciliata and Their Protective Activities on Glutamate-Induced HT22 Cell Death

Abstract

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