Anti-Epstein-Barr Viral Agents from the Medicinal Herb-Derived Fungus Alternaria alstroemeriae Km2286

Chia Hao Chang; Yi Chieh Lee; George Hsiao; Li Kwan Chang; Wei Chiung Chi; Yuan Chung Cheng; Shu Jung Huang; Tai Chou Wang; Yi Shan Lu; Tzong Huei Lee

doi:10.1021/acs.jnatprod.2c00783

Anti-Epstein-Barr Viral Agents from the Medicinal Herb-Derived Fungus Alternaria alstroemeriae Km2286

Chia Hao Chang, Yi Chieh Lee, George Hsiao, Li Kwan Chang, Wei Chiung Chi, Yuan Chung Cheng, Shu Jung Huang, Tai Chou Wang, Yi Shan Lu, Tzong Huei Lee

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

2 Citations (Scopus)

Abstract

Chromatographic separation on the liquid-state fermented products produced by the fungal strain Alternaria alstroemeriae Km2286 isolated from the littoral medicinal herb Atriplex maximowicziana Makino resulted in the isolation of compounds 1-9. Structures were determined by spectroscopic analysis as four undescribed perylenequinones, altertromins A-D (1-4), along with altertoxin IV (5), altertoxin VIII (6), stemphyperylenol (7), tenuazonic acid (8), and allo-tenuazonic acid (9). Compounds 1-6 exhibited antiviral activities against Epstein-Barr virus (EBV) with EC₅₀values ranging from 0.17 ± 0.07 to 3.13 ± 0.31 μM and selectivity indices higher than 10. In an anti-neuroinflammatory assay, compounds 1-4, 6, and 7 showed inhibitory activity of nitric oxide production in lipopolysaccharide-induced microglial BV-2 cells, with IC₅₀values ranging from 0.33 ± 0.04 to 4.08 ± 0.53 μM without significant cytotoxicity. This is the first report to describe perylenequinone-type compounds with potent anti-EBV and anti-neuroinflammatory activities.

Original language	English
Pages (from-to)	2667-2674
Number of pages	8
Journal	Journal of Natural Products
Volume	85
Issue number	11
DOIs	https://doi.org/10.1021/acs.jnatprod.2c00783
Publication status	Published - Nov 25 2022

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.2c00783

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title = "Anti-Epstein-Barr Viral Agents from the Medicinal Herb-Derived Fungus Alternaria alstroemeriae Km2286",

abstract = "Chromatographic separation on the liquid-state fermented products produced by the fungal strain Alternaria alstroemeriae Km2286 isolated from the littoral medicinal herb Atriplex maximowicziana Makino resulted in the isolation of compounds 1-9. Structures were determined by spectroscopic analysis as four undescribed perylenequinones, altertromins A-D (1-4), along with altertoxin IV (5), altertoxin VIII (6), stemphyperylenol (7), tenuazonic acid (8), and allo-tenuazonic acid (9). Compounds 1-6 exhibited antiviral activities against Epstein-Barr virus (EBV) with EC50values ranging from 0.17 ± 0.07 to 3.13 ± 0.31 μM and selectivity indices higher than 10. In an anti-neuroinflammatory assay, compounds 1-4, 6, and 7 showed inhibitory activity of nitric oxide production in lipopolysaccharide-induced microglial BV-2 cells, with IC50values ranging from 0.33 ± 0.04 to 4.08 ± 0.53 μM without significant cytotoxicity. This is the first report to describe perylenequinone-type compounds with potent anti-EBV and anti-neuroinflammatory activities.",

author = "Chang, {Chia Hao} and Lee, {Yi Chieh} and George Hsiao and Chang, {Li Kwan} and Chi, {Wei Chiung} and Cheng, {Yuan Chung} and Huang, {Shu Jung} and Wang, {Tai Chou} and Lu, {Yi Shan} and Lee, {Tzong Huei}",

note = "Funding Information: We thank Ms. Andrea Gu in the Instrumentation Center of Taipei Medical University for the NMR data acquisition. This work was supported by a grant from the National Science and Technology Council (MOST 110-2320-B-002-023-MY3) of Taiwan to T.-H.L. Publisher Copyright: {\textcopyright} 2022 Authors. All rights reserved.",

year = "2022",

month = nov,

day = "25",

doi = "10.1021/acs.jnatprod.2c00783",

language = "English",

volume = "85",

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journal = "Journal of Natural Products",

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T1 - Anti-Epstein-Barr Viral Agents from the Medicinal Herb-Derived Fungus Alternaria alstroemeriae Km2286

AU - Chang, Chia Hao

AU - Lee, Yi Chieh

AU - Hsiao, George

AU - Chang, Li Kwan

AU - Chi, Wei Chiung

AU - Cheng, Yuan Chung

AU - Huang, Shu Jung

AU - Wang, Tai Chou

AU - Lu, Yi Shan

AU - Lee, Tzong Huei

N1 - Funding Information: We thank Ms. Andrea Gu in the Instrumentation Center of Taipei Medical University for the NMR data acquisition. This work was supported by a grant from the National Science and Technology Council (MOST 110-2320-B-002-023-MY3) of Taiwan to T.-H.L. Publisher Copyright: © 2022 Authors. All rights reserved.

PY - 2022/11/25

Y1 - 2022/11/25

N2 - Chromatographic separation on the liquid-state fermented products produced by the fungal strain Alternaria alstroemeriae Km2286 isolated from the littoral medicinal herb Atriplex maximowicziana Makino resulted in the isolation of compounds 1-9. Structures were determined by spectroscopic analysis as four undescribed perylenequinones, altertromins A-D (1-4), along with altertoxin IV (5), altertoxin VIII (6), stemphyperylenol (7), tenuazonic acid (8), and allo-tenuazonic acid (9). Compounds 1-6 exhibited antiviral activities against Epstein-Barr virus (EBV) with EC50values ranging from 0.17 ± 0.07 to 3.13 ± 0.31 μM and selectivity indices higher than 10. In an anti-neuroinflammatory assay, compounds 1-4, 6, and 7 showed inhibitory activity of nitric oxide production in lipopolysaccharide-induced microglial BV-2 cells, with IC50values ranging from 0.33 ± 0.04 to 4.08 ± 0.53 μM without significant cytotoxicity. This is the first report to describe perylenequinone-type compounds with potent anti-EBV and anti-neuroinflammatory activities.

AB - Chromatographic separation on the liquid-state fermented products produced by the fungal strain Alternaria alstroemeriae Km2286 isolated from the littoral medicinal herb Atriplex maximowicziana Makino resulted in the isolation of compounds 1-9. Structures were determined by spectroscopic analysis as four undescribed perylenequinones, altertromins A-D (1-4), along with altertoxin IV (5), altertoxin VIII (6), stemphyperylenol (7), tenuazonic acid (8), and allo-tenuazonic acid (9). Compounds 1-6 exhibited antiviral activities against Epstein-Barr virus (EBV) with EC50values ranging from 0.17 ± 0.07 to 3.13 ± 0.31 μM and selectivity indices higher than 10. In an anti-neuroinflammatory assay, compounds 1-4, 6, and 7 showed inhibitory activity of nitric oxide production in lipopolysaccharide-induced microglial BV-2 cells, with IC50values ranging from 0.33 ± 0.04 to 4.08 ± 0.53 μM without significant cytotoxicity. This is the first report to describe perylenequinone-type compounds with potent anti-EBV and anti-neuroinflammatory activities.

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Anti-Epstein-Barr Viral Agents from the Medicinal Herb-Derived Fungus Alternaria alstroemeriae Km2286

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