A bisresorcinol, (8′Z)-3,5-dihydroxy-1-[16′-(3″,5″-dihydroxyphenyl)-8′-hexadecen-1′-yl]benzene (I), was isolated as an abundant constituent from the Vietnamese medicinal plant Heliciopsis terminalis (Kurz) Sleumer (Proteaceae). The antioxidant, hepatoprotective, and anti-inflammatory activities of compound I were tested in correlation with the use of H. terminalis as a hepatoprotective drug by ethnic people in Vietnam. Bisresorcinol I showed weak scavenging activity against DPPH radical at an EC50 value of 156.9 mg/mL. At a concentration of 100 mg/mL, compound I inhibited 19,78% of MDAproduction as one of the biomarkers for lipid peroxidation. Bisresorcinol I protected HepG2 cells against harmful CCl4. The hepatoprotective ability was observed at a concentration of 100 mg/mL with up to 44.42% cells alive, which was significantly higher than that in the control treated with CCl4 (29.93 %). The NO scavenging activity of I was determined in RAW 264.7 cells with an IC50 value of 71.15 mg/mL. Bisresorcinol I exhibited its anti-inflammatory activity through modulation of proinflammatory cytokines IL-6 and TNF-α as well as anti-inflammatory IL-10 in RAW264.7 cells.
Similar content being viewed by others
References
J. Goad and T. Akihisa, Analysis of Sterols, Springer Science & Business Media, Berlin (2012).
W. M. N. H. W. Salleh, F. Ahmad, and K. H. Yen, J. Appl. Pharm. Sci., 4, 087 – 091 (2014).
V. P. Chaturvedula, J. K. Schilling, J. S. Miller, et al., J. Nat. Prod., 65, 1627 – 1632 (2002).
Y. Suzuki, Y. Esumi, and I. Yamaguchi, Phytochemistry, 52, 281 – 289 (1999).
Y.-C. Chen, Y. Sugiyama, N. Abe, et al., Biosci. Biotechnol. Biochem., 69, 999 – 1006 (2005).
M. J. Simirgiotis, M. Silva, J. Becerra and G. Schmeda-Hirschmann, Food Chem., 131, 318 – 327 (2012).
T. Mello, F. Zanieri, E. Ceni, and A. Galli, Oxid. Med. Cell. Longevity, 2016, 8327410 (2016).
S. Li, H. Y. Tan, N. Wang, et al., Int. J. Mol. Sci., 16, 26087 – 26124 (2015).
M. M. Gaschler and B. R. Stockwell, Biochem. Biophys. Res. Commun., 482, 419 – 425 (2017).
P. J. Tsai, T. H. Tsai, C. H. Yu, and S. C. Ho, Food Chem., 103, 181 – 187 (2007).
N. R. Bernardes, M. Heggdorne-Araújo, I. F. Borges, et al., Rev. Bras. Farmacogn., 24, 644 – 650 (2014).
J. Rajangam, J. Appl. Pharm. Sci., 3, 069 – 076 (2013).
M. Boll, L. W. Weber, E. Becker, and A. Stampfl, Zeitschr. Naturforsch. C, 56, 649 – 659 (2001).
G. Ramadori and T. Armbrust, Eur. J. Gastroenterol. Hepatol., 13, 777 – 784 (2001).
L. Niederreiter and H. Tilg, Liver Res., 2, 14 – 20 (2018).
H. Tilg, Can. J. Gastroenterol., 15, 661 – 668 (2001).
S. Lacour, J.-C. Gautier, M. Pallardy, and R. Roberts, Cancer Biomarkers, 1, 29 – 39 (2005).
H. Tilg, A. Kaser and A. R. Moschen, Liver Int.,26, 1029 – 1039 (2006).
R. E. Rossi, I. Parisi, E. J. Despott, et al., World J. Gastroenterol., 20, 17352 – 17359 (2014).
K. Streetz, T. Luedde, M. Manns, and C. Trautwein, Gut, 47, 309 – 312 (2000).
S. C. Sahu (Ed.), Hepatotoxicity: From Genomics to In Vitro and In Vivo Models, John Wiley & Sons (2008).
J. A. Badmus, T. O. Adedosu, J. O. Fatoki, et al., Acta Polon. Pharm.,68, 23 – 29 (2011).
S. Cheenpracha, E. J. Park, B. Rostama, et al., Marine Drugs, 8, 429 – 437 (2010).
D. Ozerkan, N. Ozsoy and E. Yilmaz, Cytotechnology, 67, 995 – 1002 (2015).
L. T. González, N. W. Minsky, L. E. M. Espinosa, et al., BMC Complem. Altern. Med., 17, 39 (2017).
Acknowledgments
This research was funded by the National Program “Science and Technology for Sustainable Development of the Northwest Region” (Grant No. KHCN-TB. IIC/I3-I8). P.M.G. thanks Professor Hideaki Otsuka and Dr. Susumu Kawakami (Yasuda Women’s University, Hiroshima, Japan) for the measurements of HR-ESI-MS and 2D NMR spectra of compound I.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Giang, P.M., Thao, D.T., Nga, N.T. et al. Evaluation of the Antioxidant, Hepatoprotective, and Anti-Inflammatory Activities of Bisresorcinol Isolated from the Trunk of Heliciopsis Terminalis. Pharm Chem J 53, 628–634 (2019). https://doi.org/10.1007/s11094-019-02051-7
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11094-019-02051-7