Lignans from guaiac resin decrease nitric oxide production in interleukin 1β-treated hepatocytes
- 258 Downloads
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.
KeywordsGuaiac resin Guaiacum officinale Lignan Anti-inflammatory effect Nitric oxide Hepatocyte
High-performance liquid chromatography
- MALDI-TOF MS
Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry
Electron ionization mass spectrometry
Nuclear magnetic resonance
Heteronuclear multiple-bond connectivity
Nuclear Overhauser effect
Nuclear Overhauser effect spectroscopy
Half-maximal inhibitory concentration
Inducible nitric oxide synthase
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.
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.
- 1.King FE, Wilson JG (1964) The chemistry of extractives from hardwoods. Part XXXVI. The lignans of Guaiacum officinale L. J Chem Soc, pp 4011–4024Google Scholar
- 5.Ahmad VU, Saba N, Ali Z, Zahid M, Alam L (2000) A new triterpenoidal saponin from the bark of Guaiacum officinale L. Z Naturforsh 55b:227–230Google Scholar
- 7.Bartram T (1998) Bartram’s Encyclopedia of herbal medicine: the definitive guide to the herbal treatments of diseases. Marlowe & Company, New York, p 208Google Scholar
- 13.Kitade H, Sakitani K, Inoue K, Masu Y, Kawada N, Hiramatsu Y, Kamiyama Y, Okumura T, Ito S (1996) Interleukin 1 β markedly stimulates nitric oxide formation in the absence of other cytokines or lipopolysaccharide in primary cultured rat hepatocytes but not in Kupffer cells. Hepatology 23:797–802PubMedGoogle Scholar
- 14.Ohno N, Yoshigai E, Okuyama T, Yamamoto Y, Okumura T, Sato K, Ikeya Y, Nishizawa M (2012) Chlorogenic acid from the Japanese herbal medicine Kinginka (Flos Lonicerae japonicae) suppresses the expression of inducible nitric oxide synthase in rat hepatocytes. HOAJ Biol 1:2. doi: 10.7243/2050-0874-1-2 CrossRefGoogle Scholar
- 16.Tanemoto R, Okuyama T, Matsuo H, Okumura T, Ikeya Y, Nishizawa M (2015) The constituents of licorice (Glycyrrhiza uralensis) differentially suppress nitric oxide production in interleukin-1β-treated hepatocytes. Biochem Biophys Rep 2:153–159. doi: 10.1016/j.bbrep.2015.06.004 PubMedPubMedCentralGoogle Scholar
- 17.Nakajima A, Yamamoto Y, Yoshinaka N, Namba M, Matsuo H, Okuyama T, Yoshigai E, Okumura T, Nishizawa M, Ikeya Y (2015) A new flavanone and other flavonoids from green perilla leaf extract inhibit nitric oxide production in interleukin 1β-treated hepatocytes. Biosci Biotechnol Biochem 79:138–146CrossRefPubMedGoogle Scholar