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Five New Oxylipins from Chaenomeles sinensis

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  • Published:
Lipids

Abstract

In the course of our continuing search for bioactive constituents of Korean medicinal plants, we isolated five new oxylipins, chaenomic acid A–E (1–5), and six known ones (6–11) from the twigs of Chaenomeles sinensis. The structures of the new compounds (1–5) were determined by spectroscopic methods, including 1D and 2D NMR (1H and 13C NMR, 1H–1H COSY, HMQC, HMBC, and NOESY), olefin cross-metathesis, and LC/MS analysis. The known compounds (6–11) were identified by comparison of their spectroscopic data and specific optical rotation with the reported data. The isolated compounds (1–11) were tested for their inhibitory effects on nitric oxide production in lipopolysaccharide-activated murine microglial cells and for their cytotoxic activities against four human cancer cell lines (A549, SK-OV-3, A498, and HCT-15).

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Abbreviations

COSY:

Correlation spectroscopy

DMEM:

Dulbecco’s modified Eagle’s medium

FAB:

Fast atom bombardment

HMBC:

Heteronuclear multiple bond correlation

HMQC:

Heteronuclear multiple quantum correlation

HPLC:

High-performance liquid chromatography

HR:

High resolution

LPLC:

Low-pressure liquid chromatography

LPS:

Lipopolysaccharide

MS:

Mass spectrometry

l-NMMA:

N G-Monomethyl-l-arginine

NMR:

Nuclear magnetic resonance

NOESY:

Nuclear Overhauser effect spectroscopy

NO:

Nitric oxide

SRB:

Sulforhodamine B

TLC:

Thin-layer chromatography

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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 Education, Science and Technology (2013R1A1A2A10005315). We are thankful to the Korea Basic Science Institute (KBSI) for the measurements of NMR and MS spectra.

Conflict of interest

All authors declare that there are no conflicts of interest.

Author information

Authors and Affiliations

  1. Natural Products Laboratory, School of Pharmacy, Sungkyunkwan University, 300 Chonchon-dong, Jangan-ku, Suwon, 440-746, Republic of Korea

    Chung Sub Kim, Ki Hyun Kim & Kang Ro Lee

  2. Graduate School of East-West Medical Science, Kyung Hee University, Yongin, 446-701, Republic of Korea

    Oh Wook Kwon

  3. Gachon Institute of Pharmaceutical Science, Gachon University, Incheon, 406-799, Republic of Korea

    Oh Wook Kwon & Sun Yeou Kim

  4. College of Pharmacy, Gachon University, Incheon, 406-799, Republic of Korea

    Sun Yeou Kim

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

    Sang Un Choi

Authors
  1. Chung Sub Kim
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  2. Oh Wook Kwon
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  3. Sun Yeou Kim
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  4. Sang Un Choi
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  5. Ki Hyun Kim
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  6. Kang Ro Lee
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Correspondence to Kang Ro Lee.

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Kim, C.S., Kwon, O.W., Kim, S.Y. et al. Five New Oxylipins from Chaenomeles sinensis . Lipids 49, 1151–1159 (2014). https://doi.org/10.1007/s11745-014-3953-0

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  • DOI: https://doi.org/10.1007/s11745-014-3953-0

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