Copyright (c) 2014 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Physiological Activity of Chinese Lichen (Gyrophora esculenta) Component, Methyl 2,4-Dihydroxy-6-methylbenzoate and the Related Compounds
Corresponding Author(s) : Zhendong Zhao
Asian Journal of Chemistry,
Vol. 26 No. 3 (2014): Vol 26 Issue 3
Abstract
It was confirmed that there was a higher expression of antioxidant potential in methyl 2,4-dihydroxy-6-methylbenzoate (orsellinic acid methyl ester) (2), which was isolated from methanol extract oil of Chinese lichen Gyrophora esculenta rather than from commercialized ascorbic acid. Taking this into account, 4 types of compounds-(4-7) which are known to be related to compound (2)-have been synthesized by using 2,4-dihydroxy benzoic acid (3) as starting material. After that, some physiological activity tests on these compounds have been conducted in the following aspects: antioxidant potential, cytotoxicity, cytokine suppressant effect and histamine liberation inhibition and the effects have been evaluated, respectively. The result shows that (2) and methyl 2,4-dihydroxybenzoate (4) showed high radical expression in both antioxidant potential and histamine liberation inhibition. It was also found that none of these compounds expresses cytotoxicity.
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References
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S. Inoue and S. Kawanishi, FEBS Lett., 371, 86 (1995); doi:10.1016/0014-5793(95)00873-8.
V.P. Skulachev, FEBS Lett., 423, 275 (1998); doi:10.1016/S0014-5793(98)00061-1.
T. Yoshikawa, S. Kokura, K. Tainaka, K. Itani, H. Oyamada, T. Kaneko, Y. Naito and M. Kondo, Cancer Res., 53, 2326 (1993).
T. Yoshikawa, S. Kokura, H. Oyamada, S. Iinuma, S. Nishimura, T. Kaneko, Y. Naito and M. Kondo, Cancer Res., 54, 5033 (1994).
A. Ohta, Materials for Functional Food, CMC Publishing Co., Ltd., Tokyo, pp. 3-36 (2006).
Y. Yamamoto, Regulation of Plants, 35, 169 (2000).
Y. Ohmura, K. H. Moon and H. Kashiwadani, Bunrui, 8, 123 (2008).
C.H. Kim, Ass., 34, 531 (1982).
M. Nakagawa and H. Nagai, Fragrance J., 19, 44 (1991).
T. Hashimoto, K. Yoshikawa, N. Kokudo, Y. Asakawa, T. Kimura, T. Inose, A. Hirasawa and G. Tsujimoto, Search for antidiabetogenic principles from edible mushrooms and lichen, 3rd Symposium on Pharmaceutical Food Science, Osaka, Japan, pp. 98-100 (2009).
T. Hashimoto, N. Kokudo, H. Yano, K. Yoshikawa, A. Umeyama and S. Arihara, Lichenology, 6, 168 (2007).
I.B. Repinskaya, Zh. Organicheskoi Khim., 16, 1508 (1980).
G. Just, G. Sacripante and L. Zamir, Synth. Commun., 15, 1007 (1985); doi:10.1080/00397918508076833.
N. Nakatani, C.H. Kim, H. Kikuzaki, T. Muroi and Y. Matsumura, Chemistry Express, 6, 587 (1991).
K. Tangdenpaisal, S. Sualek, S. Ruchirawat and P. Ploypradith, Tetrahedron, 65, 4316 (2009); doi:10.1016/j.tet.2009.03.089.
P. Ploypradith, P. Cheryklin, N. Niyomtham, D.R. Bertoni and S. Ruchirawat, Org. Lett., 9, 2637 (2007); doi:10.1021/ol070781+.
M.C. Matos and V.P. Murphy, J. Org. Chem., 72, 1803 (2007); doi:10.1021/jo062159l.
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T. Abe and M. Nomura, Aroma Res., 7, 56 (2006).
S. Ode, Dokkyo J. Medical Sci., 37, 69 (2010).
H. Kato and T. Nakatu, Low Temperature and Materials Sciences (Kyoto Univ.), 11, 44 (2007).
Z. Woldehiwet and B.K. Horrocks, J. Comp. Pathol., 132, 322 (2005); doi:10.1016/j.jcpa.2004.12.002.
T. Inoue, Y. Sugimoto, H. Masuda and C. Kamei, Biol. Pharm. Bull., 25, 256 (2002); doi:10.1248/bpb.25.256.
M.A. Hossen, T. Inoue, Y. Shinmei, K. Minami, Y. Fujii and C. Kamei, Biol. Pharm. Bull., 29, 64 (2006); doi:10.1248/bpb.29.64.
A.T. Gomes, N.K. Honda, F.M. Roese, R.M. Muzzi and L. Sauer, Z. Naturforsch. C, 61, 653 (2006).
T.I.B. Lopes, R.G. Coelho, N.C. Yoshida and N.K. Honda, Chem. Pharm. Bull., 56, 1551 (2008); doi:10.1248/cpb.56.1551.
J.F. Sanchez, Y.-M. Chiang, E. Szewczyk, A.D. Davidson, M. Ahuja, C. Elizabeth Oakley, J. Woo Bok, N. Keller, B.R. Oakley and C.C.C. Wang, Mol. Biosyst., 6, 587 (2010); doi:10.1039/b904541d.
Y. Sawai, Yasai Chagyo Kenkyusho, 6, 23 (2007).
T. Katsu, H. Ono, K. Tasaka and Y. Fujita, Chem. Pharm. Bull. (Tokyo), 32, 4185 (1984); doi:10.1248/cpb.32.4185.
A.M. Quílez, M.T. Saenz, M.D. García and R. de la Puerta, J. Pharm. Pharmacol., 56, 1185 (2004); doi:10.1211/0022357044102.
T. Tanaka, T. Hirano, S. Higa, J. Arimitsu and M. Kawai, Soc. Comple. Alter. Med., 3, 1 (2006).
E.M. Marinova, N.V. Yanishlieva and I.R. Totseva, J. Food Sci. Technology, 37, 145 (2002); doi:10.1046/j.1365-2621.2002.00551.x.
S.I. Rizvi and K.B. Pandey, Pharmacol. Rep., 62, 726 (2010).