Bioactive constituents of Lindernia crustacea and its anti-EBV effect via Rta expression inhibition in the viral lytic cycle

Yu Chi Tsai, Judit Hohmann, Mohamed El-Shazly, Li Kwan Chang, Balázs Dankó, Norbert Kúsz, Chi Ting Hsieh, Attila Hunyadi, Fang Rong Chang

Research output: Contribution to journalArticle

Abstract

Ethnopharmacological relevance: Lindernia crustacea (L.) F.Muell. (Scrophulariaceae) was selected for phytochemical investigation owing to its traditional use against human herpes virus infection and its anti-Epstein–Barr virus (EBV) effect. Aims of the study: The present study focused on the phytochemical investigation of L. crustacea including the isolation and structure determination of its biologically active compounds. Compounds with anti-EBV effects were also investigated. Materials and methods: The EtOH extract of L. crustacea was subsequently partitioned using different solvents. The EtOAc fraction was subjected to several chromatographic methods to obtain pure compounds. The structures of all isolates were established by spectroscopic analysis and compared with previously reported physical data. The anti-EBV effect was evaluated in an EBV-containing Burkitt's lymphoma cell line (P3HR1) to study the expression of EBV lytic proteins. Results: Thirty-three compounds, including one diterpene (1), four anthraquinones (2–5), two ionones (6 and 7), fourteen phenylpropanoid glycosides (8–21), five flavonoids (22–26), one lignan glycoside (27), one phenethyl alcohol glycoside (28), one phenylpropene glycoside (29), one glucosyl glycerol derivative (30), one furanone (31), and two cinnamic acid derivatives (32 and 33), were isolated from the ethanolic extract of the plant. All isolated compounds were obtained for the first time from Lindernia sp. The evaluation of the anti-EBV activity of L. crustacea crude extract, partitioned fractions, and constituents was performed for the first time. Phytol (1), aloe-emodin (2), byzantionoside B (7), a mixture of trans-martynoside (8) and cis-martynoside (9), a mixture of trans-isomartynoside (10) and cis-isomartynoside (11), luteolin-7-O-β-D-glucopyranoside (24), and apigenin-7-O-[β-D-apiofuranosyl (1→6)-β-D-glucopyranoside] (25) exhibited significant inhibitory effects on the EBV lytic cycle at 20 μg/mL in the immunoblot analysis. On the other hand, (6R,7E,9R)-3-oxo-α-ionol-β-D-glucopyranoside (6) and a mixture of trans-dolichandroside A (12) and cis-dolichandroside A (13) showed moderate anti-EBV activity at 20 μg/mL. Conclusions: L. crustacea and its active isolates could be developed as potential candidates against EBV. Our findings provide scientific evidence for the traditional use of L. crustacea for its antiviral effects.

Original languageEnglish
Article number112493
JournalJournal of Ethnopharmacology
Volume250
DOIs
Publication statusPublished - Mar 25 2020

Fingerprint

Crustacea
Viruses
Glycosides
Phytochemicals
Scrophulariaceae
Phytol
Norisoprenoids
Phenylethyl Alcohol
Apigenin
Luteolin
Anthraquinones
Butylated Hydroxytoluene
Lignans
Diterpenes
Plant Extracts
Virus Diseases
Complex Mixtures
Human Herpesvirus 4
Flavonoids
Glycerol

Keywords

  • Anthranoid
  • Epstein–Barr virus
  • Flavonoid
  • Herpes virus
  • Ionone
  • Lindernia crustacea
  • Phenylpropanoid
  • Scrophulariaceae

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery

Cite this

Bioactive constituents of Lindernia crustacea and its anti-EBV effect via Rta expression inhibition in the viral lytic cycle. / Tsai, Yu Chi; Hohmann, Judit; El-Shazly, Mohamed; Chang, Li Kwan; Dankó, Balázs; Kúsz, Norbert; Hsieh, Chi Ting; Hunyadi, Attila; Chang, Fang Rong.

In: Journal of Ethnopharmacology, Vol. 250, 112493, 25.03.2020.

Research output: Contribution to journalArticle

Tsai, Yu Chi ; Hohmann, Judit ; El-Shazly, Mohamed ; Chang, Li Kwan ; Dankó, Balázs ; Kúsz, Norbert ; Hsieh, Chi Ting ; Hunyadi, Attila ; Chang, Fang Rong. / Bioactive constituents of Lindernia crustacea and its anti-EBV effect via Rta expression inhibition in the viral lytic cycle. In: Journal of Ethnopharmacology. 2020 ; Vol. 250.
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abstract = "Ethnopharmacological relevance: Lindernia crustacea (L.) F.Muell. (Scrophulariaceae) was selected for phytochemical investigation owing to its traditional use against human herpes virus infection and its anti-Epstein–Barr virus (EBV) effect. Aims of the study: The present study focused on the phytochemical investigation of L. crustacea including the isolation and structure determination of its biologically active compounds. Compounds with anti-EBV effects were also investigated. Materials and methods: The EtOH extract of L. crustacea was subsequently partitioned using different solvents. The EtOAc fraction was subjected to several chromatographic methods to obtain pure compounds. The structures of all isolates were established by spectroscopic analysis and compared with previously reported physical data. The anti-EBV effect was evaluated in an EBV-containing Burkitt's lymphoma cell line (P3HR1) to study the expression of EBV lytic proteins. Results: Thirty-three compounds, including one diterpene (1), four anthraquinones (2–5), two ionones (6 and 7), fourteen phenylpropanoid glycosides (8–21), five flavonoids (22–26), one lignan glycoside (27), one phenethyl alcohol glycoside (28), one phenylpropene glycoside (29), one glucosyl glycerol derivative (30), one furanone (31), and two cinnamic acid derivatives (32 and 33), were isolated from the ethanolic extract of the plant. All isolated compounds were obtained for the first time from Lindernia sp. The evaluation of the anti-EBV activity of L. crustacea crude extract, partitioned fractions, and constituents was performed for the first time. Phytol (1), aloe-emodin (2), byzantionoside B (7), a mixture of trans-martynoside (8) and cis-martynoside (9), a mixture of trans-isomartynoside (10) and cis-isomartynoside (11), luteolin-7-O-β-D-glucopyranoside (24), and apigenin-7-O-[β-D-apiofuranosyl (1→6)-β-D-glucopyranoside] (25) exhibited significant inhibitory effects on the EBV lytic cycle at 20 μg/mL in the immunoblot analysis. On the other hand, (6R,7E,9R)-3-oxo-α-ionol-β-D-glucopyranoside (6) and a mixture of trans-dolichandroside A (12) and cis-dolichandroside A (13) showed moderate anti-EBV activity at 20 μg/mL. Conclusions: L. crustacea and its active isolates could be developed as potential candidates against EBV. Our findings provide scientific evidence for the traditional use of L. crustacea for its antiviral effects.",
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author = "Tsai, {Yu Chi} and Judit Hohmann and Mohamed El-Shazly and Chang, {Li Kwan} and Bal{\'a}zs Dank{\'o} and Norbert K{\'u}sz and Hsieh, {Chi Ting} and Attila Hunyadi and Chang, {Fang Rong}",
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doi = "10.1016/j.jep.2019.112493",
language = "English",
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TY - JOUR

T1 - Bioactive constituents of Lindernia crustacea and its anti-EBV effect via Rta expression inhibition in the viral lytic cycle

AU - Tsai, Yu Chi

AU - Hohmann, Judit

AU - El-Shazly, Mohamed

AU - Chang, Li Kwan

AU - Dankó, Balázs

AU - Kúsz, Norbert

AU - Hsieh, Chi Ting

AU - Hunyadi, Attila

AU - Chang, Fang Rong

PY - 2020/3/25

Y1 - 2020/3/25

N2 - Ethnopharmacological relevance: Lindernia crustacea (L.) F.Muell. (Scrophulariaceae) was selected for phytochemical investigation owing to its traditional use against human herpes virus infection and its anti-Epstein–Barr virus (EBV) effect. Aims of the study: The present study focused on the phytochemical investigation of L. crustacea including the isolation and structure determination of its biologically active compounds. Compounds with anti-EBV effects were also investigated. Materials and methods: The EtOH extract of L. crustacea was subsequently partitioned using different solvents. The EtOAc fraction was subjected to several chromatographic methods to obtain pure compounds. The structures of all isolates were established by spectroscopic analysis and compared with previously reported physical data. The anti-EBV effect was evaluated in an EBV-containing Burkitt's lymphoma cell line (P3HR1) to study the expression of EBV lytic proteins. Results: Thirty-three compounds, including one diterpene (1), four anthraquinones (2–5), two ionones (6 and 7), fourteen phenylpropanoid glycosides (8–21), five flavonoids (22–26), one lignan glycoside (27), one phenethyl alcohol glycoside (28), one phenylpropene glycoside (29), one glucosyl glycerol derivative (30), one furanone (31), and two cinnamic acid derivatives (32 and 33), were isolated from the ethanolic extract of the plant. All isolated compounds were obtained for the first time from Lindernia sp. The evaluation of the anti-EBV activity of L. crustacea crude extract, partitioned fractions, and constituents was performed for the first time. Phytol (1), aloe-emodin (2), byzantionoside B (7), a mixture of trans-martynoside (8) and cis-martynoside (9), a mixture of trans-isomartynoside (10) and cis-isomartynoside (11), luteolin-7-O-β-D-glucopyranoside (24), and apigenin-7-O-[β-D-apiofuranosyl (1→6)-β-D-glucopyranoside] (25) exhibited significant inhibitory effects on the EBV lytic cycle at 20 μg/mL in the immunoblot analysis. On the other hand, (6R,7E,9R)-3-oxo-α-ionol-β-D-glucopyranoside (6) and a mixture of trans-dolichandroside A (12) and cis-dolichandroside A (13) showed moderate anti-EBV activity at 20 μg/mL. Conclusions: L. crustacea and its active isolates could be developed as potential candidates against EBV. Our findings provide scientific evidence for the traditional use of L. crustacea for its antiviral effects.

AB - Ethnopharmacological relevance: Lindernia crustacea (L.) F.Muell. (Scrophulariaceae) was selected for phytochemical investigation owing to its traditional use against human herpes virus infection and its anti-Epstein–Barr virus (EBV) effect. Aims of the study: The present study focused on the phytochemical investigation of L. crustacea including the isolation and structure determination of its biologically active compounds. Compounds with anti-EBV effects were also investigated. Materials and methods: The EtOH extract of L. crustacea was subsequently partitioned using different solvents. The EtOAc fraction was subjected to several chromatographic methods to obtain pure compounds. The structures of all isolates were established by spectroscopic analysis and compared with previously reported physical data. The anti-EBV effect was evaluated in an EBV-containing Burkitt's lymphoma cell line (P3HR1) to study the expression of EBV lytic proteins. Results: Thirty-three compounds, including one diterpene (1), four anthraquinones (2–5), two ionones (6 and 7), fourteen phenylpropanoid glycosides (8–21), five flavonoids (22–26), one lignan glycoside (27), one phenethyl alcohol glycoside (28), one phenylpropene glycoside (29), one glucosyl glycerol derivative (30), one furanone (31), and two cinnamic acid derivatives (32 and 33), were isolated from the ethanolic extract of the plant. All isolated compounds were obtained for the first time from Lindernia sp. The evaluation of the anti-EBV activity of L. crustacea crude extract, partitioned fractions, and constituents was performed for the first time. Phytol (1), aloe-emodin (2), byzantionoside B (7), a mixture of trans-martynoside (8) and cis-martynoside (9), a mixture of trans-isomartynoside (10) and cis-isomartynoside (11), luteolin-7-O-β-D-glucopyranoside (24), and apigenin-7-O-[β-D-apiofuranosyl (1→6)-β-D-glucopyranoside] (25) exhibited significant inhibitory effects on the EBV lytic cycle at 20 μg/mL in the immunoblot analysis. On the other hand, (6R,7E,9R)-3-oxo-α-ionol-β-D-glucopyranoside (6) and a mixture of trans-dolichandroside A (12) and cis-dolichandroside A (13) showed moderate anti-EBV activity at 20 μg/mL. Conclusions: L. crustacea and its active isolates could be developed as potential candidates against EBV. Our findings provide scientific evidence for the traditional use of L. crustacea for its antiviral effects.

KW - Anthranoid

KW - Epstein–Barr virus

KW - Flavonoid

KW - Herpes virus

KW - Ionone

KW - Lindernia crustacea

KW - Phenylpropanoid

KW - Scrophulariaceae

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