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

D. Rédei, Norbert Kúsz, Tímea Rafai, Anita Bogdanov, K. Burián, Attila Csorba, Attila Mándi, T. Kurtán, A. Vasas, J. Hohmann

Research output: Article

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 log10, 3.49 log10, and 2.33 log10 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
JournalTetrahedron
DOIs
Publication statusAccepted/In press - jan. 1 2019

Fingerprint

Hippophae
Herpes Simplex
Virus Replication
Viruses
Antiviral Agents
Fruit
Glucosides
Human Herpesvirus 2
Naphthalenes
Elaeagnaceae
Propane
Sesquiterpenes
Rumex
Fruits
Nuclear magnetic resonance

Keywords

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

    Cite this

    @article{f479be5e18eb45e5960a93e4e068dbb7,
    title = "14-Noreudesmanes and a phenylpropane heterodimer from sea buckthorn berry inhibit Herpes simplex type 2 virus replication",
    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 log10, 3.49 log10, and 2.33 log10 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.",
    keywords = "Anti-HSV2-activity, Elaeagnus rhamnoides, Hippophae rhamnoides, Noreudesmane, Phenylpropane dimer, Sea buckthorn",
    author = "D. R{\'e}dei and Norbert K{\'u}sz and T{\'i}mea Rafai and Anita Bogdanov and K. Buri{\'a}n and Attila Csorba and Attila M{\'a}ndi and T. Kurt{\'a}n and A. Vasas and J. Hohmann",
    year = "2019",
    month = "1",
    day = "1",
    doi = "10.1016/j.tet.2019.01.050",
    language = "English",
    journal = "Tetrahedron",
    issn = "0040-4020",
    publisher = "Elsevier Limited",

    }

    TY - JOUR

    T1 - 14-Noreudesmanes and a phenylpropane heterodimer from sea buckthorn berry inhibit Herpes simplex type 2 virus replication

    AU - Rédei, D.

    AU - Kúsz, Norbert

    AU - Rafai, Tímea

    AU - Bogdanov, Anita

    AU - Burián, K.

    AU - Csorba, Attila

    AU - Mándi, Attila

    AU - Kurtán, T.

    AU - Vasas, A.

    AU - Hohmann, J.

    PY - 2019/1/1

    Y1 - 2019/1/1

    N2 - 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 log10, 3.49 log10, and 2.33 log10 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.

    AB - 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 log10, 3.49 log10, and 2.33 log10 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.

    KW - Anti-HSV2-activity

    KW - Elaeagnus rhamnoides

    KW - Hippophae rhamnoides

    KW - Noreudesmane

    KW - Phenylpropane dimer

    KW - Sea buckthorn

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    SN - 0040-4020

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