Journal of Natural Medicines

, Volume 71, Issue 1, pp 190–197 | Cite as

Lignans from guaiac resin decrease nitric oxide production in interleukin 1β-treated hepatocytes

  • Yuki Nakano
  • Masaaki Nasu
  • Mana Kano
  • Hiroshi Kameoka
  • Tetsuya Okuyama
  • Mikio Nishizawa
  • Yukinobu Ikeya
Original Paper
First Online:
Received:
Accepted:

Abstract

Guaiac resin, extracted from the heartwood of Guaiacum officinale L. or G. sanctum L., is speculated to have anti-inflammatory effects. Lignans were purified from guaiac resin (also known as gum guaiacum) by monitoring the nitric oxide (NO) production in rat hepatocytes treated with an inflammatory cytokine interleukin-1β (IL-1β). Six lignans were purified from guaiac resin and identified as: dehydroguaiaretic acid (1), (+)-trans-1,2-dihydrodehydroguaiaretic acid (2), furoguaiaoxidin (3), meso-dihydroguaiaretic acid (4), furoguaiacin (i.e., α-guaiaconic acid) (5), and nectandrin B (6). To our knowledge, this is the first time that 1 has been isolated from guaiac resin as a non-derivative. Compounds 2 and 6 were first found in guaiac resin. Compound 3 was first isolated from a natural source as a non-derivative. Furthermore, 1–6 significantly suppressed NO production in IL-1β-treated hepatocytes. Because anti-inflammatory compounds suppress NO production, this system is often used to measure the anti-inflammatory effects of Kampo drugs and herbal constituents. The NO-suppressing activity of the six lignans isolated in this study indicates that guaiac resin has anti-inflammatory effects and that these lignans may be responsible for the anti-inflammatory effects of guaiac resin.

Keywords

Guaiac resin Guaiacum officinale Lignan Anti-inflammatory effect Nitric oxide Hepatocyte 

Abbreviations

EtOAc

Ethyl acetate

CDCl3

Deuterochloroform

CD3OD

Methanol-d 4

ODS

Octadecylsilyl

HPLC

High-performance liquid chromatography

IR

Infrared

UV

Ultraviolet

CD

Circular dichroism

MALDI-TOF MS

Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry

EI-MS

Electron ionization mass spectrometry

NMR

Nuclear magnetic resonance

HMBC

Heteronuclear multiple-bond connectivity

COSY

Correlation spectroscopy

NOE

Nuclear Overhauser effect

NOESY

Nuclear Overhauser effect spectroscopy

br

Broad

d

Doublet

m

Multiplet

s

Singlet

t

Triplet

TLC

Thin-layer chromatography

IC50

Half-maximal inhibitory concentration

IL-1β

Interleukin-1β

LDH

Lactate dehydrogenase

NO

Nitric oxide

iNOS

Inducible nitric oxide synthase

CC

Column chromatography

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Notes

Acknowledgments

We thank Drs. Hiromitsu Maeda (College of Life Sciences, Ritsumeikan University) and Yuji Hasegawa (Central Equipment Room, Daiichi University of Pharmacy) for the MS measurements.

Compliance with ethical standards

Conflict of interest

No potential conflict of interest was reported by the authors.

Authors’ contributions

M. Nishizawa and Y. Ikeya designed the experiments and wrote the manuscript. Y. Nakano, M. Nasu, M. Kano, and H. Kameoka performed the experiments as students. T. Okuyama performed the experiments and analyzed the data.

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Copyright information

© The Japanese Society of Pharmacognosy and Springer Japan 2016

Authors and Affiliations

  1. 1.Department of Biomedical Sciences, College of Life SciencesRitsumeikan UniversityKusatsuJapan
  2. 2.Department of Pharmacy, College of Pharmaceutical SciencesRitsumeikan UniversityKusatsuJapan
  3. 3.Department of Pharmacy Educational Assist CenterDaiichi University of PharmacyFukuokaJapan

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