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Planta Med 2019; 85(02): 94-102
DOI: 10.1055/a-0668-0962
Biological and Pharmacological Activity
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Diarylheptanoids from Curcuma phaeocaulis Suppress IL-6-Induced STAT3 Activation

Hyun-Jae Jang
Immunoregulatory Material Research Center, Korea Research Institute of Bioscience and Biotechnology, Jeongeup-si, Republic of Korea
,
Eun-Jae Park
Immunoregulatory Material Research Center, Korea Research Institute of Bioscience and Biotechnology, Jeongeup-si, Republic of Korea
,
Seung-Jae Lee
Immunoregulatory Material Research Center, Korea Research Institute of Bioscience and Biotechnology, Jeongeup-si, Republic of Korea
,
Hyung-Jin Lim
Immunoregulatory Material Research Center, Korea Research Institute of Bioscience and Biotechnology, Jeongeup-si, Republic of Korea
,
Jin Ha Jo
Immunoregulatory Material Research Center, Korea Research Institute of Bioscience and Biotechnology, Jeongeup-si, Republic of Korea
,
Seung Woong Lee
Immunoregulatory Material Research Center, Korea Research Institute of Bioscience and Biotechnology, Jeongeup-si, Republic of Korea
,
Mun-Chual Rho
Immunoregulatory Material Research Center, Korea Research Institute of Bioscience and Biotechnology, Jeongeup-si, Republic of Korea
› Author Affiliations
Further Information

Publication History

received 14 March 2018
revised 19 July 2018

accepted 27 July 2018

Publication Date:
10 August 2018 (online)

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Abstract

Three undescribed diarylheptanoids (3–5) and six known curcuminoids (1, 2, and 6–9) were obtained from the ethyl acetate-soluble fraction of an ethanolic extract of Curcuma phaeocaulis. Their chemical structures and absolute configurations were elucidated by high-resolution electrospray ionization mass spectrometry, nuclear magnetic resonance spectroscopy, circular dichroism spectroscopy, and the modified Mosherʼs method. Previous studies constructed Hep3B cells stably transfected with pSTAT3-Luc plasmid containing STAT3 binding site to discover STAT3 inhibitors from natural products. The STAT3 inhibitory activities of all isolates were measured in transfected Hep3B cells after treatment with IL-6. Compound 5 ((5R)-1,7-Bis(3,4-dimethoxyphenyl)-3-methoxy-1-hepten-5-ol), demethoxycurcumin (7), and curcumin (8) exhibited significant inhibitory activity (IC50 values: 11.1, 1.9, and 1.6 µM, respectively). Furthermore, IL-6-induced phosphorylation of STAT3, and the mRNA expression levels of inflammation-related genes such as CRP, IL-1β, ICAM-1, and SOCS3 were significantly reduced by exposure to compound 5. These data suggested that the inhibitory activity of 5 is associated with the suppression of STAT3 phosphorylation. Thus, compound 5 may be a promising candidate for the treatment of cancer or inflammatory diseases related to the IL-6/STAT3 signaling pathway.

Key words

Curcuma phaeocaulis - Zingiberaceae - NMR spectroscopy - diarylheptanoids - IL-6 - STAT3 - inflammation

Supporting Information

    1D and 2D NMR and HRESIMS spectroscopic data of compounds 2–5 are available as Supporting Information.

  • Supporting Information
 

  • References

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