Modulative Effect of Human Hair Dermal Papilla Cell Apoptosis by Oregonin from the Braches of <i>Alnus japonica</i>

Gyeong Hwa Lee, Kwang Hyun Park and Sun Eun Choi*

doi:10.7732/kjpr.2018.31.4.322

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2018 Vol.31, Issue 4 Preview Page Next Page

Modulative Effect of Human Hair Dermal Papilla Cell Apoptosis by Oregonin from the Braches of Alnus japonica 오리나무 가지 유래 Oregonin의 인체 모유두 세포 Apoptosis 조절 효능: Gyeong Hwa Lee¹,Kwang Hyun Park² and Sun Eun Choi¹^*
이 경화¹,박 광현²,최 선은¹^*; ¹ Department of Cosmetology Science, Nambu University
² Department of Oriental Pharmaceutical Development, Nambu University

¹ 남부대학교 향장미용학과
² 남부대학교 한방제약개발학과; ^*Corresponding Author

August 2018. pp. 322-329

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Abstract

A diarylheptanoid, (5S)-1,7-bis-(3,4-dihydroxyphenyl)-5- hydroxyheptane-3-one-5-O-β-D-xylopyranoside, named oregonin (1), was isolated from the of Alnus japonica (A. japonica), which is a species of the genus Betulaceae, growing throughout Korea, Japan and China. The structure was elucidated by various spectroscopic methods including negative and positive LC/MS, 1H-NMR, and 13C-NMR techniques or by comparison with authentic samples. In order to evaluate the anti-oxidative activities of oregonin (1) isolated from A. japonica, 1,1-diphenyl-2-picryhydrazyl (DPPH) radical scavenging activity and 2,2'-azino-bis[3-ethylbenzothiazoline-6-sulphonic acid] (ABTS) radical scavenging activity were measured in vitro. Oregonin from A. japonica exhibited potent DPPH and ABTS radical scavenging activities. A. japonica shows not only 1,1-diphenyl-2-picryhydrazyl (DPPH) radical scavenging activity and ABTS radical scavenging activity, but also apoptosis modulative effects. The present results indicate that A. japonica could be a hair-growth-promoting agent for cosmetic products.

Keywords

Alnus japonica

Anti-oxidant

Hair growth

Oregonin

References

Alnemri, E.S., D.J. Livingston, D.W. Nicholson, G. Salvesen, N.A. Thornberry, W.W. Wong and J. Yuan. 1996. Human ICE/CED-3 protease nomenclature. Cell 87:171.10.1016/S0092-8674(00)81334-3
Alnermri, E.S. 1997. Mammalian cell death proteases: a family of highly conserved aspartate specific cystein proteases. J. Cell. Biochem. 64:32-42.
Boericke, W. 1927. Pocket Manual of Homeopathic Materia Medica with Repertory (Ninth Edition). Boericke & Tafel, INC. Santa Rosa, CA (USA). p. 24.
Boivin, W.A., H. Jiang, O.B. Utting and D.W.C. Hunt. 2006. Influence of interleukin-1α on androgen receptor expression and cytokine secretion by cultured human dermal papilla cells. Exp. Dermatol. 15:784-793.10.1111/j.1600-0625.2006.00462.x16984260
Burnette, W.N. 1981. Western blotting: electrophoretic transfer of proteins from sodium dodecyl sulfate—polyacrylamide gels to unmodified nitrocellulose and radiographic detection with antibody and radioiodinated protein A. Anal. Biochem. 112:195-203.10.1016/0003-2697(81)90281-5
Choi, S.E. 2013. Chemotaxonomic significance of oregonin in Alnus species. Asian J. Chem. 25:6989.
Choi, S.E. 2013. K.H. Park, M.H. Kim, J.H. Song, H.Y. Jin and M.W. Lee. 2012. Diarylheptanoids from the Bark of Alnus pendula Matsumura. Nat. Prod. Sci. 18:106.
Choi, S.E. 2013. M.S. Jeong, M.J. Kang, D.I. Lee, S.S. Joo, C.S. Lee, H. Bang, M.K. Lee, S.C. Myung, Y.W. Choi, K. Lee, S.J. Seo and M.W. Lee. 2010. Effect of topical application and intraperitoneal injection of oregonin on atopic dermatitis in NC/Nga mice. Exp. Dermatol. 19:37-43.10.1111/j.1600-0625.2009.00961.x19849716
Clarke, P.G. and S. Clarke. 1995. Historic apoptosis. Nature 378:230.10.1038/378230c07477334
Cleary, M. L., S.D. Smith and J. Sklar. 1986 Cloning and structural analysis of cDNAs for bcl-2 and a hybrid bcl-2/immunoglobulin transcript resulting from the t(14;18) translocation. Cell 47:19-28.10.1016/0092-8674(86)90362-4
Godon, C., F.P. Cordelieres, D. Biard, N. Giocanti, F. Megnin- Chanet, J. Hall and V. Favaudon. 2008. PARP inhibition versus PARP-1 silencing: different outcomes in terms of single-strand break repair and radiation susceptibility. Nucleic Acids Res. 36:4454-4464.10.1093/nar/gkn40318603595PMC2490739
Harrington, H.A., L.K. Ho, S. Ghosh and K.C. Tung. 2008. Construction and analysis of a modular model of caspase activation in apoptosis. Theor. Biol. Med. Model. 5:1-15.10.1186/1742-4682-5-2619077196PMC2672941
Hatano, T., R. Edamatsu, M. Hiramatsu, A. Mori, Y. Fujita, T. Yasuhara, T. Yoshida and T. Okuda. 1989. Effects of the interaction of tannins with co-existing substances. Ⅵ. Effects of tannins and ralated polyphenols on superoxide anion radical, and on 1,1-diphenyl-2-picrylhydrazyl radical. Chem. Pharm. Bull. 37:2016-2021.
Kim, H.J., K.H. Kim, S.H. Yeom, M.K. Kim, J.G. Shim, H.W. Lim and M.W. Lee. 2005. New diarylheptanoids from the barks of Alnus japonica Steudel, Chin. Chem. Lett. 16:1337-1340.
Lee, S.J. 1966. Korea Folk Medicine. Seoul National University Publishing Center Press, Seoul, Korea. p. 40.
Lim, H.W., M.K. Kim, H.J. Kim, J.G. Shim, G.H. Kim, H.K. Choi and M.W. Lee. 2004. Quantitative determination of diarylheptanoid compounds from Korean Alnus. Kor. J. Pharmacogn. 35:384-387.
Muller, S., J.P. Briand, S. Barakat, J. Lagueux, G.G. Poirier, G. De Murcia and D.A. Isenberg. 1994. Autoantibodies reacting with poly(ADP-ribose) and with a zinc-finger functional domain of poly(ADP-ribose) polymerase involved in the recognition of damaged DNA. Clin. Immunol. Immunopathol. 73:187-196.10.1006/clin.1994.11877923925
Oltvai, Z.N., C.L. Milliman and S.J. Korsmeyer. 1993. Bcl-2 heterodimerizes in vivo with a conserved homolog, Bax, that accelerates programmed cell death. Cell 74:609-619.10.1016/0092-8674(93)90509-O
Re, R., N. Pellegrini, A. Proteggente, A. Pannala, M. Yang and C. Rice-Evans. 1999. Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free. Radic. Biol. Med. 26:1231-1237.10.1016/S0891-5849(98)00315-3
Schultz, N., E. Lopez, N. Saleh-Gohari and T. Helleday. 2003. Poly(ADP-ribose) polymerase (PARP-1) has a controlling role in homologous recombination. Nucleic Acids Res. 31:4959-4964.10.1093/nar/gkg70312930944PMC212803
Sedlak, T.W., Z.N. Oltvai, E. Yang, K. Wang, L.H. Boise, C.B. Thompson and S.J. Korsmeyer. 1995. Multiple Bcl-2 family members demonstrate selective dimerizations with Bax. PNASU. 92:7834-7838.10.1073/pnas.92.17.7834
Tsujimoto, Y., L.R. Finger, J. Yunis, P.C. Nowell and C.M. Croce. 1984. Cloning of the chromosome breakpoint of neoplastic B cells with the t(14;18) chromosome translocation. Science 226:1097-1099. 10.1126/science.60932636093263
Xie, G.H., S.E. Choi, M.J. Mun, J.H. Jeong and K.H. Park. 2018. Ameliorative effects of combinative injection of Ginko biloba leaves extract and vitamin C on ischemia/ reperfusion liver damages model. Korean J. Plant Res. 31:268-273.
Zhap, Z.Q., J.M. Budde, C. Morris, N.P. Wang, D.A. Velez, S. Murak, R.A. Guyton and J.J. Vinten. 2001. Adenosine attenuated reperfusion induced apoptotic cell death by modulation expression of Bcl-2 and Bax proteins. J. Mol. Cell Cardiol. 33:57-68.10.1006/jmcc.2000.127511133223

Information

Publisher :The Plant Resources Society of Korea
Publisher(Ko) :한국자원식물학회
Journal Title :Korean Journal of Plant Resources
Journal Title(Ko) :한국자원식물학회지
Volume : 31
No :4
Pages :322-329
Received Date :2018. 02. 08
Accepted Date : 2018. 05. 18
DOI :https://doi.org/10.7732/kjpr.2018.31.4.322

[1] Alnemri, E.S., D.J. Livingston, D.W. Nicholson, G. Salvesen, N.A. Thornberry, W.W. Wong and J. Yuan. 1996. Human ICE/CED-3 protease nomenclature. Cell 87:171.10.1016/S0092-8674(00)81334-3

[2] Alnermri, E.S. 1997. Mammalian cell death proteases: a family of highly conserved aspartate specific cystein proteases. J. Cell. Biochem. 64:32-42.

[3] Boericke, W. 1927. Pocket Manual of Homeopathic Materia Medica with Repertory (Ninth Edition). Boericke & Tafel, INC. Santa Rosa, CA (USA). p. 24.

[4] Boivin, W.A., H. Jiang, O.B. Utting and D.W.C. Hunt. 2006. Influence of interleukin-1α on androgen receptor expression and cytokine secretion by cultured human dermal papilla cells. Exp. Dermatol. 15:784-793.10.1111/j.1600-0625.2006.00462.x16984260

[5] Burnette, W.N. 1981. Western blotting: electrophoretic transfer of proteins from sodium dodecyl sulfate—polyacrylamide gels to unmodified nitrocellulose and radiographic detection with antibody and radioiodinated protein A. Anal. Biochem. 112:195-203.10.1016/0003-2697(81)90281-5

[6] Choi, S.E. 2013. Chemotaxonomic significance of oregonin in Alnus species. Asian J. Chem. 25:6989.

[7] Choi, S.E. 2013. K.H. Park, M.H. Kim, J.H. Song, H.Y. Jin and M.W. Lee. 2012. Diarylheptanoids from the Bark of Alnus pendula Matsumura. Nat. Prod. Sci. 18:106.

[8] Choi, S.E. 2013. M.S. Jeong, M.J. Kang, D.I. Lee, S.S. Joo, C.S. Lee, H. Bang, M.K. Lee, S.C. Myung, Y.W. Choi, K. Lee, S.J. Seo and M.W. Lee. 2010. Effect of topical application and intraperitoneal injection of oregonin on atopic dermatitis in NC/Nga mice. Exp. Dermatol. 19:37-43.10.1111/j.1600-0625.2009.00961.x19849716

[9] Clarke, P.G. and S. Clarke. 1995. Historic apoptosis. Nature 378:230.10.1038/378230c07477334

[10] Cleary, M. L., S.D. Smith and J. Sklar. 1986 Cloning and structural analysis of cDNAs for bcl-2 and a hybrid bcl-2/immunoglobulin transcript resulting from the t(14;18) translocation. Cell 47:19-28.10.1016/0092-8674(86)90362-4

[11] Godon, C., F.P. Cordelieres, D. Biard, N. Giocanti, F. Megnin- Chanet, J. Hall and V. Favaudon. 2008. PARP inhibition versus PARP-1 silencing: different outcomes in terms of single-strand break repair and radiation susceptibility. Nucleic Acids Res. 36:4454-4464.10.1093/nar/gkn40318603595PMC2490739

[12] Harrington, H.A., L.K. Ho, S. Ghosh and K.C. Tung. 2008. Construction and analysis of a modular model of caspase activation in apoptosis. Theor. Biol. Med. Model. 5:1-15.10.1186/1742-4682-5-2619077196PMC2672941

[13] Hatano, T., R. Edamatsu, M. Hiramatsu, A. Mori, Y. Fujita, T. Yasuhara, T. Yoshida and T. Okuda. 1989. Effects of the interaction of tannins with co-existing substances. Ⅵ. Effects of tannins and ralated polyphenols on superoxide anion radical, and on 1,1-diphenyl-2-picrylhydrazyl radical. Chem. Pharm. Bull. 37:2016-2021.

[14] Kim, H.J., K.H. Kim, S.H. Yeom, M.K. Kim, J.G. Shim, H.W. Lim and M.W. Lee. 2005. New diarylheptanoids from the barks of Alnus japonica Steudel, Chin. Chem. Lett. 16:1337-1340.

[15] Lee, S.J. 1966. Korea Folk Medicine. Seoul National University Publishing Center Press, Seoul, Korea. p. 40.

[16] Lim, H.W., M.K. Kim, H.J. Kim, J.G. Shim, G.H. Kim, H.K. Choi and M.W. Lee. 2004. Quantitative determination of diarylheptanoid compounds from Korean Alnus. Kor. J. Pharmacogn. 35:384-387.

[17] Muller, S., J.P. Briand, S. Barakat, J. Lagueux, G.G. Poirier, G. De Murcia and D.A. Isenberg. 1994. Autoantibodies reacting with poly(ADP-ribose) and with a zinc-finger functional domain of poly(ADP-ribose) polymerase involved in the recognition of damaged DNA. Clin. Immunol. Immunopathol. 73:187-196.10.1006/clin.1994.11877923925

[18] Oltvai, Z.N., C.L. Milliman and S.J. Korsmeyer. 1993. Bcl-2 heterodimerizes in vivo with a conserved homolog, Bax, that accelerates programmed cell death. Cell 74:609-619.10.1016/0092-8674(93)90509-O

[19] Re, R., N. Pellegrini, A. Proteggente, A. Pannala, M. Yang and C. Rice-Evans. 1999. Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free. Radic. Biol. Med. 26:1231-1237.10.1016/S0891-5849(98)00315-3

[20] Schultz, N., E. Lopez, N. Saleh-Gohari and T. Helleday. 2003. Poly(ADP-ribose) polymerase (PARP-1) has a controlling role in homologous recombination. Nucleic Acids Res. 31:4959-4964.10.1093/nar/gkg70312930944PMC212803

[21] Sedlak, T.W., Z.N. Oltvai, E. Yang, K. Wang, L.H. Boise, C.B. Thompson and S.J. Korsmeyer. 1995. Multiple Bcl-2 family members demonstrate selective dimerizations with Bax. PNASU. 92:7834-7838.10.1073/pnas.92.17.7834

[22] Tsujimoto, Y., L.R. Finger, J. Yunis, P.C. Nowell and C.M. Croce. 1984. Cloning of the chromosome breakpoint of neoplastic B cells with the t(14;18) chromosome translocation. Science 226:1097-1099. 10.1126/science.60932636093263

[23] Xie, G.H., S.E. Choi, M.J. Mun, J.H. Jeong and K.H. Park. 2018. Ameliorative effects of combinative injection of Ginko biloba leaves extract and vitamin C on ischemia/ reperfusion liver damages model. Korean J. Plant Res. 31:268-273.

[24] Zhap, Z.Q., J.M. Budde, C. Morris, N.P. Wang, D.A. Velez, S. Murak, R.A. Guyton and J.J. Vinten. 2001. Adenosine attenuated reperfusion induced apoptotic cell death by modulation expression of Bcl-2 and Bax proteins. J. Mol. Cell Cardiol. 33:57-68.10.1006/jmcc.2000.127511133223

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