Phenanthrenes from juncus compressus jacq. With promising antiproliferative and anti-HSV-2 activities

Csaba Bús, Norbert Kúsz, Gusztáv Jakab, Seyyed Ashkan Senobar Tahaei, I. Zupkó, Valéria Endrész, Anita Bogdanov, K. Burián, Boglárka Csupor-Lffler, J. Hohmann, A. Vasas

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Juncaceae species are rich sources of phenanthrenes. The present study has focused on the isolation and structure determination of biologically active components from Juncus compressus. Eleven compounds (nine phenanthrenes and two flavonoids) have been isolated from the plant by the combination of different chromatographic methods. Two compounds (compressins A (Compound 1) and B (Compound 2)) are novel natural products, while seven phenanthrenes (effusol (Compound 3), effususol (Compound 4), juncusol (Compound 5), 2-hydroxy-1-methyl-4-oxymethylene-5-vinyl-9,10-dihydrophenanthrene (Compound 6), 7-hydroxy-1-methyl-2-methoxy-5-vinyl-9,10-dihydrophenanthrene (Compound 7), effususin A (Compound 8), and dehydroeffusol (Compound 9)), and two flavonoids (apigenin (Compound 10) and luteolin (Compound 11) were isolated for the first time from the plant. Compressin B (Compound 2) is a dimeric phenanthrene, in which two juncusol monomers (Compound 5) are connecting through their C-3 atoms. The structure elucidation of the isolated compounds was carried out using 1D, 2D NMR spectroscopic methods and HR-MS measurements. In vitro investigation of the antiproliferative effect of the phenanthrenes on two cervical (HeLa and SiHa) and an ovarian human tumor cell line (A2780) revealed that compounds have remarkable antiproliferative activity, mainly on the HeLa cell line. Moreover, juncusol (Compound 5) proved to possess significant antiviral activity against the herpes simplex 2 virus (HSV-2).

Original languageEnglish
Article number2085
JournalMolecules
Volume23
Issue number8
DOIs
Publication statusPublished - Aug 20 2018

Fingerprint

Phenanthrenes
phenanthrene
Human Herpesvirus 2
Flavonoids
cultured cells
Cells
Apigenin
Luteolin
Tumor Cell Line
Biological Products
Viruses
HeLa Cells
Antiviral Agents
Tumors
viruses
Monomers
Nuclear magnetic resonance
isolation
Cell Line
tumors

Keywords

  • Anti-HSV-2
  • Antiproliferative
  • Flavonoid
  • Juncus compressus
  • Phenanthrene

ASJC Scopus subject areas

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

Cite this

Phenanthrenes from juncus compressus jacq. With promising antiproliferative and anti-HSV-2 activities. / Bús, Csaba; Kúsz, Norbert; Jakab, Gusztáv; Tahaei, Seyyed Ashkan Senobar; Zupkó, I.; Endrész, Valéria; Bogdanov, Anita; Burián, K.; Csupor-Lffler, Boglárka; Hohmann, J.; Vasas, A.

In: Molecules, Vol. 23, No. 8, 2085, 20.08.2018.

Research output: Contribution to journalArticle

Bús, Csaba ; Kúsz, Norbert ; Jakab, Gusztáv ; Tahaei, Seyyed Ashkan Senobar ; Zupkó, I. ; Endrész, Valéria ; Bogdanov, Anita ; Burián, K. ; Csupor-Lffler, Boglárka ; Hohmann, J. ; Vasas, A. / Phenanthrenes from juncus compressus jacq. With promising antiproliferative and anti-HSV-2 activities. In: Molecules. 2018 ; Vol. 23, No. 8.
@article{adc3902879e448b68b10825a0dae0683,
title = "Phenanthrenes from juncus compressus jacq. With promising antiproliferative and anti-HSV-2 activities",
abstract = "Juncaceae species are rich sources of phenanthrenes. The present study has focused on the isolation and structure determination of biologically active components from Juncus compressus. Eleven compounds (nine phenanthrenes and two flavonoids) have been isolated from the plant by the combination of different chromatographic methods. Two compounds (compressins A (Compound 1) and B (Compound 2)) are novel natural products, while seven phenanthrenes (effusol (Compound 3), effususol (Compound 4), juncusol (Compound 5), 2-hydroxy-1-methyl-4-oxymethylene-5-vinyl-9,10-dihydrophenanthrene (Compound 6), 7-hydroxy-1-methyl-2-methoxy-5-vinyl-9,10-dihydrophenanthrene (Compound 7), effususin A (Compound 8), and dehydroeffusol (Compound 9)), and two flavonoids (apigenin (Compound 10) and luteolin (Compound 11) were isolated for the first time from the plant. Compressin B (Compound 2) is a dimeric phenanthrene, in which two juncusol monomers (Compound 5) are connecting through their C-3 atoms. The structure elucidation of the isolated compounds was carried out using 1D, 2D NMR spectroscopic methods and HR-MS measurements. In vitro investigation of the antiproliferative effect of the phenanthrenes on two cervical (HeLa and SiHa) and an ovarian human tumor cell line (A2780) revealed that compounds have remarkable antiproliferative activity, mainly on the HeLa cell line. Moreover, juncusol (Compound 5) proved to possess significant antiviral activity against the herpes simplex 2 virus (HSV-2).",
keywords = "Anti-HSV-2, Antiproliferative, Flavonoid, Juncus compressus, Phenanthrene",
author = "Csaba B{\'u}s and Norbert K{\'u}sz and Guszt{\'a}v Jakab and Tahaei, {Seyyed Ashkan Senobar} and I. Zupk{\'o} and Val{\'e}ria Endr{\'e}sz and Anita Bogdanov and K. Buri{\'a}n and Bogl{\'a}rka Csupor-Lffler and J. Hohmann and A. Vasas",
year = "2018",
month = "8",
day = "20",
doi = "10.3390/molecules23082085",
language = "English",
volume = "23",
journal = "Molecules",
issn = "1420-3049",
publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",
number = "8",

}

TY - JOUR

T1 - Phenanthrenes from juncus compressus jacq. With promising antiproliferative and anti-HSV-2 activities

AU - Bús, Csaba

AU - Kúsz, Norbert

AU - Jakab, Gusztáv

AU - Tahaei, Seyyed Ashkan Senobar

AU - Zupkó, I.

AU - Endrész, Valéria

AU - Bogdanov, Anita

AU - Burián, K.

AU - Csupor-Lffler, Boglárka

AU - Hohmann, J.

AU - Vasas, A.

PY - 2018/8/20

Y1 - 2018/8/20

N2 - Juncaceae species are rich sources of phenanthrenes. The present study has focused on the isolation and structure determination of biologically active components from Juncus compressus. Eleven compounds (nine phenanthrenes and two flavonoids) have been isolated from the plant by the combination of different chromatographic methods. Two compounds (compressins A (Compound 1) and B (Compound 2)) are novel natural products, while seven phenanthrenes (effusol (Compound 3), effususol (Compound 4), juncusol (Compound 5), 2-hydroxy-1-methyl-4-oxymethylene-5-vinyl-9,10-dihydrophenanthrene (Compound 6), 7-hydroxy-1-methyl-2-methoxy-5-vinyl-9,10-dihydrophenanthrene (Compound 7), effususin A (Compound 8), and dehydroeffusol (Compound 9)), and two flavonoids (apigenin (Compound 10) and luteolin (Compound 11) were isolated for the first time from the plant. Compressin B (Compound 2) is a dimeric phenanthrene, in which two juncusol monomers (Compound 5) are connecting through their C-3 atoms. The structure elucidation of the isolated compounds was carried out using 1D, 2D NMR spectroscopic methods and HR-MS measurements. In vitro investigation of the antiproliferative effect of the phenanthrenes on two cervical (HeLa and SiHa) and an ovarian human tumor cell line (A2780) revealed that compounds have remarkable antiproliferative activity, mainly on the HeLa cell line. Moreover, juncusol (Compound 5) proved to possess significant antiviral activity against the herpes simplex 2 virus (HSV-2).

AB - Juncaceae species are rich sources of phenanthrenes. The present study has focused on the isolation and structure determination of biologically active components from Juncus compressus. Eleven compounds (nine phenanthrenes and two flavonoids) have been isolated from the plant by the combination of different chromatographic methods. Two compounds (compressins A (Compound 1) and B (Compound 2)) are novel natural products, while seven phenanthrenes (effusol (Compound 3), effususol (Compound 4), juncusol (Compound 5), 2-hydroxy-1-methyl-4-oxymethylene-5-vinyl-9,10-dihydrophenanthrene (Compound 6), 7-hydroxy-1-methyl-2-methoxy-5-vinyl-9,10-dihydrophenanthrene (Compound 7), effususin A (Compound 8), and dehydroeffusol (Compound 9)), and two flavonoids (apigenin (Compound 10) and luteolin (Compound 11) were isolated for the first time from the plant. Compressin B (Compound 2) is a dimeric phenanthrene, in which two juncusol monomers (Compound 5) are connecting through their C-3 atoms. The structure elucidation of the isolated compounds was carried out using 1D, 2D NMR spectroscopic methods and HR-MS measurements. In vitro investigation of the antiproliferative effect of the phenanthrenes on two cervical (HeLa and SiHa) and an ovarian human tumor cell line (A2780) revealed that compounds have remarkable antiproliferative activity, mainly on the HeLa cell line. Moreover, juncusol (Compound 5) proved to possess significant antiviral activity against the herpes simplex 2 virus (HSV-2).

KW - Anti-HSV-2

KW - Antiproliferative

KW - Flavonoid

KW - Juncus compressus

KW - Phenanthrene

UR - http://www.scopus.com/inward/record.url?scp=85052819123&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85052819123&partnerID=8YFLogxK

U2 - 10.3390/molecules23082085

DO - 10.3390/molecules23082085

M3 - Article

C2 - 30127296

AN - SCOPUS:85052819123

VL - 23

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 8

M1 - 2085

ER -