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A new rearranged eudesmane sesquiterpene and bioactive sesquiterpenes from the twigs of Lindera glauca (Sieb. et Zucc.) Blume

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Abstract

A new rearranged eudesmane sesquiterpene, named eudeglaucone (1), and five known sesquiterpenes including (+)-faurinone (2) and four eudesmane-type sesquiterpenes (3–6), were isolated from the twigs of Lindera glauca (Sieb. et Zucc.) Blume. The structure of 1 was elucidated by a combination of extensive spectroscopic analyses, including extensive 2D NMR (1H-1H COSY, HMQC, HMBC, and NOESY) and HR-MS. Compound 1 was a relatively rare rearranged eudesmane sesquiterpene in terpenoids. All isolates were evaluated for their antiproliferative activities against four human tumor cell lines (A549, SK-OV-3, SK-MEL-2, and HCT-15). Compounds 3 and 6 showed significant cytotoxicity against SK-MEL-2 and HCT-15 cell lines with IC50 values ranging from 9.98 to 12.20 μM. We also investigated the anti-neuroinflammatory activities of the isolates (1–6) in the lipopolysaccharide (LPS)-stimulated murine microglia BV-2 cell line by measuring nitric oxide (NO) levels. All isolates significantly inhibited NO production with IC50 values of 3.67–26.48 μM without inducing cell toxicity.

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Acknowledgments

This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Science, ICT & Future Planning (2015R1C1A1A02037383) and by the Ministry of Education (NRF-2012R1A5A2A28671860).

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Authors and Affiliations

  1. School of Pharmacy, Sungkyunkwan University, Suwon, 440-746, Republic of Korea

    Jae Sik Yu, Jiwon Baek & Ki Hyun Kim

  2. Department of Chemistry, Yale University, New Haven, CT, 06520, USA

    Hyun Bong Park

  3. Charmzone R&D Center, Charmzone Co. LTD., 318 Yeongdong-daero, Gangnam-gu, Seoul, 06177, Republic of Korea

    Eunjung Moon

  4. College of Pharmacy, Gachon University, #191 Hambakmoero, Yeonsu-gu, Incheon, 406-799, Republic of Korea

    Sun Yeou Kim

  5. Korea Research Institute of Chemical Technology, Deajeon, 305-600, Republic of Korea

    Sang Un Choi

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  1. Jae Sik Yu
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  2. Jiwon Baek
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  3. Hyun Bong Park
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  4. Eunjung Moon
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  5. Sun Yeou Kim
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  7. Ki Hyun Kim
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Correspondence to Ki Hyun Kim.

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Yu, J.S., Baek, J., Park, H.B. et al. A new rearranged eudesmane sesquiterpene and bioactive sesquiterpenes from the twigs of Lindera glauca (Sieb. et Zucc.) Blume. Arch. Pharm. Res. 39, 1628–1634 (2016). https://doi.org/10.1007/s12272-016-0838-1

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  • DOI: https://doi.org/10.1007/s12272-016-0838-1

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