14-Noreudesmanes and a phenylpropane heterodimer from sea buckthorn berry inhibit Herpes simplex type 2 virus replication

Dóra Rédei, Norbert Kúsz, Tímea Rafai, Anita Bogdanov, Katalin Burián, Attila Csorba, Attila Mándi, Tibor Kurtán, Andrea Vasas, Judit Hohmann

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Two new 14-noreudesmane sesquiterpenes, one new phenylpropane heterodimer, caulilexin C, and uvaol were isolated from the 70% MeOH extract of the fruit peel of Elaeagnus rhamnoides. The structures of the compounds were elucidated by HRESIMS and advanced NMR methods. The absolute configuration of (R)-6,9-dihydroxy-1-oxo-14-noreudesm-5,7,9-triene was determined by the TDDFT-ECD method. The new compounds, together with structurally similar naphthalenes (musizin, musizin-8-O-glucoside, torachrysone-8-O-glucoside) and 1,4-naphthoquinone (2-methylstipandrone), isolated previously from Rumex aquaticus, were investigated for their antiviral activity against Herpes simplex virus type 2 (HSV-2) using two different methods. Applying the traditional virus yield reduction test, (R)-6,9-dihydroxy-1-oxo-14-noreudesm-5,7,9-triene, 1-[3-methoxy-4-(2-methoxy-4-(1E)-propenyl-phenoxy)-phenyl]-propane-1,2-diol, and musizin caused a 2.00 log 10 , 3.49 log 10 , and 2.33 log 10 reduction of HSV-2 yield, respectively, at a concentration of 12.5 μM. 2-Hydroxy-1-methoxy-6,9-dioxo-14-noreudesm-1,3,5(10),7-tetraene exhibited an antiviral effect at concentration of 50 μM only. Similar results were obtained when the qPCR method was used to test the antiviral activity of the compounds.

Original languageEnglish
Pages (from-to)1364-1370
Number of pages7
JournalTetrahedron
Volume75
Issue number10
DOIs
Publication statusPublished - Mar 8 2019

Keywords

  • Anti-HSV2-activity
  • Elaeagnus rhamnoides
  • Hippophae rhamnoides
  • Noreudesmane
  • Phenylpropane dimer
  • Sea buckthorn

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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