Synthesis and Cytotoxicity Studies of Bioactive Benzofurans from Lavandula agustifolia and Modified Synthesis of Ailanthoidol, Homoegonol, and Egonol

Aneesh Sivaraman, Jin Sook Kim, Dipesh S. Harmalkar, Kyoung Ho Min, Joong Won Park, Yongseok Choi, Kyungtae Kim, Kyeong Lee

    Research output: Contribution to journalArticlepeer-review

    11 Citations (Scopus)

    Abstract

    2-Aryl/alkylbenzofurans, which constitute an important subclass of naturally occurring lignans and neolignans, have attracted extensive synthetic efforts due to their useful biological activities and significant pharmacological potential. Herein, we report a general and efficient approach to divergent 2-arylbenzofurans through a one-pot synthesis of versatile 2-bromobenzofurans as key intermediates. Using this approach, the first total synthesis of a series of trisubstituted and tetrasubstituted benzofurans bearing the hydroxyethyl unit, including the natural compounds isolated from Lavandula agustifolia (1-3) and their non-natural derivatives (4-8), was accomplished. We also report a modified synthesis of ailanthoidol, homoegonol, and egonol that enables the divergent synthesis of their derivatives for future exploration. Among these, the representative phenolic natural compound 2 and its derivatives 7 and 5 induced apoptotic cell death related poly(ADP-ribose) polymerase (PARP) cleavage in MCF74, A549, PC3, HepG2, and Hep3B cancer cell lines. Additionally, the tumor suppressor protein p53 was also induced in p53 wild type cancer cells.

    Original languageEnglish
    Pages (from-to)3354-3362
    Number of pages9
    JournalJournal of Natural Products
    Volume83
    Issue number11
    DOIs
    Publication statusPublished - 2020 Nov 25

    Bibliographical note

    Publisher Copyright:
    © 2020 American Chemical Society. All rights reserved.

    ASJC Scopus subject areas

    • Analytical Chemistry
    • Molecular Medicine
    • Pharmacology
    • Pharmaceutical Science
    • Drug Discovery
    • Complementary and alternative medicine
    • Organic Chemistry

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