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Erschienen in: Journal of Natural Medicines 4/2016

29.06.2016 | Note

Anti-melanin deposition activity of ceramicines from Chisocheton ceramicus

verfasst von: Chie Iijima, Chin Piow Wong, Alfarius Eko Nugroho, Yayoi Sotozono, Saki Someya, Yusuke Hirasawa, Toshio Kaneda, A. Hamid A. Hadi, Hiroshi Morita

Erschienen in: Journal of Natural Medicines | Ausgabe 4/2016

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Abstract

The ceramicines, a series of limonoids from Chisocheton ceramicus (Meliaceae), were evaluated for anti-melanin deposition activity on α-melanocyte stimulating hormone (α-MSH) and 3-isobutyl-1-methylxanthine (IBMX)-treated B16-F10 melanoma cell, and several ceramicines were found to be active. The structure–activity relationship of ceramicines as anti-melanin deposition inhibitors was deduced. Furthermore, the mechanism of anti-melanin deposition activity of ceramicine B, a major constituent of C. ceramicus that showed potent anti-melanin deposition activity, was investigated. Tyrosinase enzymatic activity and tyrosinase mRNA expression were not affected by ceramicine B. The anti-melanin deposition activity of ceramicine B was shown to be related to the downregulation of tyrosinase protein expression. These results suggest that ceramicines have potential to be used as depigmentation agents.
Literatur
1.
Zurück zum Zitat Kim YJ, Uyama H (2005) Tyrosinase inhibitors from natural and synthetic sources: structure, inhibition mechanism and perspective for the future. Cell Mol Life Sci 62:1707–1723CrossRefPubMed Kim YJ, Uyama H (2005) Tyrosinase inhibitors from natural and synthetic sources: structure, inhibition mechanism and perspective for the future. Cell Mol Life Sci 62:1707–1723CrossRefPubMed
2.
Zurück zum Zitat Morikawa T, Ninomiya K, Kuramoto H, Kamei I, Yoshikawa M, Muraoka O (2015) Phenylethanoid and phenylpropanoid glycosides with melanogenesis inhibitory activity from the flowers of Narcissus tazetta var. chinensis. J Nat Med 70:89–101CrossRef Morikawa T, Ninomiya K, Kuramoto H, Kamei I, Yoshikawa M, Muraoka O (2015) Phenylethanoid and phenylpropanoid glycosides with melanogenesis inhibitory activity from the flowers of Narcissus tazetta var. chinensis. J Nat Med 70:89–101CrossRef
3.
Zurück zum Zitat Bolognia J, Murray M, Pawelek J (1989) UVB-induced melanogenesis may be mediated through the MSH-receptor system. J Investig Dermatol 92:651–656CrossRefPubMed Bolognia J, Murray M, Pawelek J (1989) UVB-induced melanogenesis may be mediated through the MSH-receptor system. J Investig Dermatol 92:651–656CrossRefPubMed
4.
Zurück zum Zitat Yasumoto K, Yokoyama K, Shibata K, Tomota Y, Shibahara S (1994) Microphthalmia-associated transcription factor as a regulator for melanocyte-specific transcription of the human tyrosinase gene. Mol Cell Biol 14:8058–8070CrossRefPubMedPubMedCentral Yasumoto K, Yokoyama K, Shibata K, Tomota Y, Shibahara S (1994) Microphthalmia-associated transcription factor as a regulator for melanocyte-specific transcription of the human tyrosinase gene. Mol Cell Biol 14:8058–8070CrossRefPubMedPubMedCentral
5.
Zurück zum Zitat Hearing VJ, Jiménez M (1987) Mammalian tyrosinase—the critical regulatory control point in melanocyte pigmentation. Int J Biochem 19:1141–1147CrossRefPubMed Hearing VJ, Jiménez M (1987) Mammalian tyrosinase—the critical regulatory control point in melanocyte pigmentation. Int J Biochem 19:1141–1147CrossRefPubMed
6.
Zurück zum Zitat Matsuda H, Nakashima S, Oda Y, Nakamura S, Yoshikawa M (2009) Melanogenesis inhibitors from the rhizomes of Alpinia officinarum in B16 melanoma cells. Bioorg Med Chem 17:6048–6053CrossRefPubMed Matsuda H, Nakashima S, Oda Y, Nakamura S, Yoshikawa M (2009) Melanogenesis inhibitors from the rhizomes of Alpinia officinarum in B16 melanoma cells. Bioorg Med Chem 17:6048–6053CrossRefPubMed
7.
Zurück zum Zitat Naish-Byfield S, Cooksey CJ, Latter AM, Johnson CI, Riley PA (1991) In vitro assessment of the structure-activity relationship of tyrosinase-dependent cytotoxicity of a series of substituted phenols. Melanoma Res 1(4):273–287CrossRefPubMed Naish-Byfield S, Cooksey CJ, Latter AM, Johnson CI, Riley PA (1991) In vitro assessment of the structure-activity relationship of tyrosinase-dependent cytotoxicity of a series of substituted phenols. Melanoma Res 1(4):273–287CrossRefPubMed
8.
Zurück zum Zitat Smit NP, Peters K, Menko W, Westerhof W, Pavel S, Riley PA (1992) Cytotoxicity of a selected series of substituted phenols towards cultured melanoma cells. Melanoma Res 2(5–6):295–304CrossRefPubMed Smit NP, Peters K, Menko W, Westerhof W, Pavel S, Riley PA (1992) Cytotoxicity of a selected series of substituted phenols towards cultured melanoma cells. Melanoma Res 2(5–6):295–304CrossRefPubMed
9.
Zurück zum Zitat Jennifer C, Stephie CM, Abhishri SB, Shalini BU (2012) A review on skin whitening property of plant extracts. Int J Pharm Bio Sci 3(4):332–347 Jennifer C, Stephie CM, Abhishri SB, Shalini BU (2012) A review on skin whitening property of plant extracts. Int J Pharm Bio Sci 3(4):332–347
10.
Zurück zum Zitat Hosoya T, Nakata A, Yamasaki F, Abbas F, Shaari K, Lajis N, Morita H (2012) Curcumin-like diarylpentanoid analogues as melanogenesis inhibitors. J Nat Med 66:166–176CrossRefPubMed Hosoya T, Nakata A, Yamasaki F, Abbas F, Shaari K, Lajis N, Morita H (2012) Curcumin-like diarylpentanoid analogues as melanogenesis inhibitors. J Nat Med 66:166–176CrossRefPubMed
11.
Zurück zum Zitat Koyama K, Hirasawa Y, Hosoya T, Hoe TC, Chan KL, Morita H (2010) Alpneumines A–H, new anti-melanogenic indole alkaloids from Alstonia pneumatophora. Bioorg Med Chem 18:4415–4421CrossRefPubMed Koyama K, Hirasawa Y, Hosoya T, Hoe TC, Chan KL, Morita H (2010) Alpneumines A–H, new anti-melanogenic indole alkaloids from Alstonia pneumatophora. Bioorg Med Chem 18:4415–4421CrossRefPubMed
12.
Zurück zum Zitat Mohamad K, Hirasawa Y, Lim CS, Awang K, Hadi AHA, Takeya K, Morita H (2008) Ceramicine A and walsogyne A, novel limonoids from two species of Meliaceae. Tetrahedron Lett 49:4276–4278CrossRef Mohamad K, Hirasawa Y, Lim CS, Awang K, Hadi AHA, Takeya K, Morita H (2008) Ceramicine A and walsogyne A, novel limonoids from two species of Meliaceae. Tetrahedron Lett 49:4276–4278CrossRef
13.
Zurück zum Zitat Mohamad K, Hirasawa Y, Litaudon M, Awang K, Hadi AHA, Takeya K, Ekasari W, Widyawaruyanti A, Zaini NC, Morita H (2009) Ceramicines B–D, new antiplasmodial limonoids from Chisocheton ceramicus. Bioorg Med Chem 17:727–730CrossRefPubMed Mohamad K, Hirasawa Y, Litaudon M, Awang K, Hadi AHA, Takeya K, Ekasari W, Widyawaruyanti A, Zaini NC, Morita H (2009) Ceramicines B–D, new antiplasmodial limonoids from Chisocheton ceramicus. Bioorg Med Chem 17:727–730CrossRefPubMed
14.
Zurück zum Zitat Wong CP, Shimada M, Nagakura Y, Nugroho AE, Hirasawa Y, Kaneda T, Awang K, Hadi AHA, Mohamad K, Shiro M, Morita H (2011) Ceramicines E–I, new limonoids from Chisocheton ceramicus. Chem Pharm Bull 59:407–411CrossRefPubMed Wong CP, Shimada M, Nagakura Y, Nugroho AE, Hirasawa Y, Kaneda T, Awang K, Hadi AHA, Mohamad K, Shiro M, Morita H (2011) Ceramicines E–I, new limonoids from Chisocheton ceramicus. Chem Pharm Bull 59:407–411CrossRefPubMed
15.
Zurück zum Zitat Wong C, Shimada M, Nugroho AE, Hirasawa Y, Kaneda T, Hadi AHA, Osamu S, Morita H (2012) Ceramicines J–L, new limonoids from Chisocheton ceramicus. J Nat Med 66:566–570CrossRefPubMed Wong C, Shimada M, Nugroho AE, Hirasawa Y, Kaneda T, Hadi AHA, Osamu S, Morita H (2012) Ceramicines J–L, new limonoids from Chisocheton ceramicus. J Nat Med 66:566–570CrossRefPubMed
16.
Zurück zum Zitat Wong CP, Deguchi J, Nugroho AE, Kaneda T, Hadi AHA, Morita H (2013) Ceramicines from Chisocheton ceramicus as lipid-droplets accumulation inhibitors. Bioorg Med Chem Lett 23:1786–1788CrossRefPubMed Wong CP, Deguchi J, Nugroho AE, Kaneda T, Hadi AHA, Morita H (2013) Ceramicines from Chisocheton ceramicus as lipid-droplets accumulation inhibitors. Bioorg Med Chem Lett 23:1786–1788CrossRefPubMed
17.
Zurück zum Zitat Wong CP, Kaneda T, Hadi AHA, Morita H (2014) Ceramicine B, a limonoid with anti-lipid droplets accumulation activity from Chisocheton ceramicus. J Nat Med 68:22–30CrossRefPubMed Wong CP, Kaneda T, Hadi AHA, Morita H (2014) Ceramicine B, a limonoid with anti-lipid droplets accumulation activity from Chisocheton ceramicus. J Nat Med 68:22–30CrossRefPubMed
18.
Zurück zum Zitat Roy A, Saraf S (2006) Limonoids: overview of significant bioactive triterpenes distributed in plants kingdom. Biol Pharm Bull 29:191–201CrossRefPubMed Roy A, Saraf S (2006) Limonoids: overview of significant bioactive triterpenes distributed in plants kingdom. Biol Pharm Bull 29:191–201CrossRefPubMed
19.
Zurück zum Zitat Akihisa T, Noto T, Takahashi A, Fujita Y, Banno N, Tokuda H, Koike K, Suzuki T, Yasukawa K, Kimura Y (2009) Melanogenesis inhibitory, anti-inflammatory, and chemopreventive effects of limonoids from the seeds of Azadirachta indiciai A. Juss. (neem). J Oleo Sci 58:581–594CrossRefPubMed Akihisa T, Noto T, Takahashi A, Fujita Y, Banno N, Tokuda H, Koike K, Suzuki T, Yasukawa K, Kimura Y (2009) Melanogenesis inhibitory, anti-inflammatory, and chemopreventive effects of limonoids from the seeds of Azadirachta indiciai A. Juss. (neem). J Oleo Sci 58:581–594CrossRefPubMed
20.
Zurück zum Zitat Akihisa T, Takahashi A, Kikuchi T, Takagi M, Watanabe K, Fukatsu M, Fujita Y, Banno N, Tokuda H, Yasukawa K (2011) The melanogenesis-inhibitory, anti-inflammatory, and chemopreventive effects of limonoids in n-hexane extract of Azadirachta indica A. Juss. (neem) seeds. J Oleo Sci 60:53–59CrossRefPubMed Akihisa T, Takahashi A, Kikuchi T, Takagi M, Watanabe K, Fukatsu M, Fujita Y, Banno N, Tokuda H, Yasukawa K (2011) The melanogenesis-inhibitory, anti-inflammatory, and chemopreventive effects of limonoids in n-hexane extract of Azadirachta indica A. Juss. (neem) seeds. J Oleo Sci 60:53–59CrossRefPubMed
21.
Zurück zum Zitat Takagi M, Tachi Y, Zhang J, Shinozaki T, Ishii K, Kikuchi T, Ukiya M, Banno N, Tokuda H, Akihisa T (2014) Cytotoxic and melanogenesis-inhibitory activities of limonoids from the leaves of Azadirachta indica (neem). Chem Biodiverse 11:451–468CrossRef Takagi M, Tachi Y, Zhang J, Shinozaki T, Ishii K, Kikuchi T, Ukiya M, Banno N, Tokuda H, Akihisa T (2014) Cytotoxic and melanogenesis-inhibitory activities of limonoids from the leaves of Azadirachta indica (neem). Chem Biodiverse 11:451–468CrossRef
Metadaten
Titel
Anti-melanin deposition activity of ceramicines from Chisocheton ceramicus
verfasst von
Chie Iijima
Chin Piow Wong
Alfarius Eko Nugroho
Yayoi Sotozono
Saki Someya
Yusuke Hirasawa
Toshio Kaneda
A. Hamid A. Hadi
Hiroshi Morita
Publikationsdatum
29.06.2016
Verlag
Springer Japan
Erschienen in
Journal of Natural Medicines / Ausgabe 4/2016
Print ISSN: 1340-3443
Elektronische ISSN: 1861-0293
DOI
https://doi.org/10.1007/s11418-016-1016-y

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