Synthesis and Cytotoxicity Studies of Bioactive Benzofurans from Lavandula agustifolia and Modified Synthesis of Ailanthoidol, Homoegonol, and Egonol
- Authors
- Sivaraman, Aneesh; Kim, Jin Sook; Harmalkar, Dipesh S.; Min, Kyoung Ho; Park, Joong-Won; Choi, Yongseok; Kim, Kyungtae; Lee, Kyeong
- Issue Date
- 25-11월-2020
- Publisher
- AMER CHEMICAL SOC
- Citation
- JOURNAL OF NATURAL PRODUCTS, v.83, no.11, pp.3354 - 3362
- Indexed
- SCIE
SCOPUS
- Journal Title
- JOURNAL OF NATURAL PRODUCTS
- Volume
- 83
- Number
- 11
- Start Page
- 3354
- End Page
- 3362
- URI
- https://scholar.korea.ac.kr/handle/2021.sw.korea/51449
- DOI
- 10.1021/acs.jnatprod.0c00697
- ISSN
- 0163-3864
- 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.
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