Melanogenesis inhibitors from the rhizomes of Alpinia officinarum in B16 melanoma cells.

The 80% aqueous acetone extract from the rhizomes of Alpinia officinarum, a Chinese medicinal herb, were found to inhibit melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells. Among the constituents isolated, four diarylheptanoids [5-hydroxy-1,7-diphenyl-3-heptanone, 7-(4('')-hydroxy-3('')-methoxyphenyl)-1-phenylhept-4-en-3-one, 5-hydroxy-7-(4('')-hydroxy-3('')-methoxyphenyl)-1-phenyl-3-heptanone, and 3,5-dihydroxy-1,7-diphenylheptane] and two flavonol constituents (kaempferide and galangin) inhibited melanogenesis with IC(50) values of 10-48microM, and several structural requirements of the active constituents for the inhibition were clarified. In addition, 7-(4('')-hydroxy-3('')-methoxyphenyl)-1-phenylhept-4-en-3-one, kaempferide, and galangin inhibited mRNA expression of tyrosinase and tyrosinase-related proteins-1 and -2, and the protein level of a microphthalmia-associated transcription factor.

[1]  M. Choi,et al.  Whitening activity of luteolin related to the inhibition of cAMP pathway in α-MSH-stimulated B16 melanoma cells , 2008, Archives of pharmacal research.

[2]  Y. Asakawa.  A New Ketol, 1,7-Diphenyl-5-hydroxy-3-heptanone, and trans-Stilbene from Alnus firma Sieb. et Zucc. (BETULACEAE) , 1970 .

[3]  W. Au,et al.  Anti-genotoxicity of galangin as a cancer chemopreventive agent candidate. , 2001, Mutation research.

[4]  I. Kubo,et al.  Effects of quercetin on mushroom tyrosinase and B16-F10 melanoma cells. , 2007, Molecules.

[5]  B. Gilchrest,et al.  Ultraviolet radiation directly induces pigment production by cultured human melanocytes , 1987, Journal of cellular physiology.

[6]  Jun Sik Lee,et al.  Antimelanogenic Activity of 3,4-Dihydroxyacetophenone: Inhibition of Tyrosinase and MITF , 2006, Bioscience, biotechnology, and biochemistry.

[7]  M. Shimoyamada,et al.  Isolation and structural elucidation of some glycosides from the rhizomes of smaller galanga (Alpinia officinarum Hance). , 2002, Journal of agricultural and food chemistry.

[8]  T. Akihisa,et al.  Melanogenesis inhibitory and free radical scavenging activities of diarylheptanoids and other phenolic compounds from the bark of Acer nikoense. , 2006, Biological & pharmaceutical bulletin.

[9]  H. Matsuda,et al.  Inhibitors from the rhizomes of Alpinia officinarum on production of nitric oxide in lipopolysaccharide-activated macrophages and the structural requirements of diarylheptanoids for the activity. , 2006, Bioorganic & medicinal chemistry.

[10]  Y. Mishima.  Molecular and biological control of melanogenesis through tyrosinase genes and intrinsic and extrinsic regulatory factors. , 1994, Pigment cell research.

[11]  J. Chirikdjian,et al.  [Flavonoids from galanga rhizome (Alpinia officinarum Hance)]. , 1972, Planta medica.

[12]  Zhihua Liu,et al.  A Diarylheptanoid from Lesser Galangal (Alpinia officinarum) Inhibits Proinflammatory Mediators via Inhibition of Mitogen-Activated Protein Kinase, p44/42, and Transcription Factor Nuclear Factor-κB , 2003, Journal of Pharmacology and Experimental Therapeutics.

[13]  Dong-Hyun Kim,et al.  3-Methylethergalangin isolated from Alpinia officinarum inhibits pancreatic lipase. , 2003, Biological & pharmaceutical bulletin.

[14]  Masayuki Yoshikawa,et al.  Structural requirements of flavonoids and related compounds for aldose reductase inhibitory activity. , 2002, Chemical & pharmaceutical bulletin.

[15]  M. Shimoyamada,et al.  Antioxidative compounds isolated from the rhizomes of smaller galanga (Alpinia officinarum Hance) , 2004, BioFactors.

[16]  I. Kubo,et al.  Effects of phenolic compounds isolated from Rabdosia japonica on B16‐F10 melanoma cells , 2008, Phytotherapy research : PTR.

[17]  M. Steinberg,et al.  Stimulation of melanotic expression in a melanoma cell line by theophylline , 1976, Journal of cellular physiology.

[18]  V. Ferrans,et al.  Production of melanocyte-specific antibodies to human melanosomal proteins: expression patterns in normal human skin and in cutaneous pigmented lesions. , 2001, Pigment cell research.

[19]  V. Hearing,et al.  New regulators of melanogenesis are associated with purified tyrosinase isozymes. , 1982, The Journal of investigative dermatology.

[20]  Soo-Min Cho,et al.  Melanogenesis inhibitory activities of diarylheptanoids fromalnus hirsuta turcz in B16 mouse melanoma cell , 2002, Archives of pharmacal research.

[21]  G. Prota.  Progress in the chemistry of melanins and related metabolites , 1988, Medicinal research reviews.

[22]  D. Fisher,et al.  MITF: master regulator of melanocyte development and melanoma oncogene. , 2006, Trends in molecular medicine.

[23]  Masayuki Yoshikawa,et al.  Anastatins A and B, new skeletal flavonoids with hepatoprotective activities from the desert plant Anastatica hierochuntica. , 2003, Bioorganic & medicinal chemistry letters.

[24]  Y. Asakawa,et al.  Five new diarylheptanoids from the male flowers of Alnus sieboldiana. , 1986 .

[25]  K. Wakamatsu,et al.  Eumelanin biosynthesis is regulated by coordinate expression of tyrosinase and tyrosinase-related protein-1 genes. , 1993, Experimental cell research.

[26]  S. Uehara,et al.  Diarylheptanoids from the Rhizomes of Curcuma xanthorrhiza and Alpinia officinarum , 1987 .

[27]  U. Sankawa,et al.  Inhibition of prostaglandin and leukotriene biosynthesis by gingerols and diarylheptanoids. , 1992, Chemical & pharmaceutical bulletin.

[28]  M. Ahn,et al.  Inhibition of 5alpha-reductase activity by diarylheptanoids from Alpinia officinarum. , 2003, Planta medica.

[29]  V. Hearing,et al.  Mammalian tyrosinase--the critical regulatory control point in melanocyte pigmentation. , 1987, The International journal of biochemistry.

[30]  H. Morita,et al.  Diarylheptanoids from the Rhizome of Alpinia officinarum HANCE , 1985 .

[31]  T. Miyase,et al.  Chemical Studies on the Constituents of Polygonum nodosum , 1982 .

[32]  U. Sankawa,et al.  Inhibitors of prostaglandin biosynthesis from alpinia officinarum , 1982 .

[33]  M. Tachibana,et al.  Cochlear melanocytes and MITF signaling. , 2001, The journal of investigative dermatology. Symposium proceedings.

[34]  M. Shimoyamada,et al.  Isolation and characterization of some antioxidative compounds from the rhizomes of smaller galanga (Alpinia officinarum Hance). , 2003, Journal of agricultural and food chemistry.

[35]  A. Thody,et al.  Alpha-melanocyte stimulating hormone and its analogue Nle4DPhe7 alpha-MSH affect morphology, tyrosinase activity and melanogenesis in cultured human melanocytes. , 1994, Journal of cell science.

[36]  Se-Jae Kim,et al.  Involvement of Extracellular Signal-Regulated Kinase in Nobiletin-Induced Melanogenesis in Murine B16/F10 Melanoma Cells , 2007, Bioscience, biotechnology, and biochemistry.

[37]  Hyunsu Bae,et al.  Survey and mechanism of skin depigmenting and lightening agents , 2006, Phytotherapy research : PTR.

[38]  J. Pawelek,et al.  Melanocyte-stimulating hormone promotes activation of pre-existing tyrosinase molecules in Cloudman S91 melanoma cells , 1975, Nature.

[39]  Dong-Hyun Kim,et al.  5-Hydroxy-7-(4'-hydroxy-3'-methoxyphenyl)-1-phenyl-3-heptanone: a pancreatic lipase inhibitor isolated from Alpinia officinarum. , 2004, Biological & pharmaceutical bulletin.

[40]  I. Kubo,et al.  Flavonols from saffron flower: tyrosinase inhibitory activity and inhibition mechanism. , 1999, Journal of agricultural and food chemistry.

[41]  F. Camacho,et al.  Management of Facial Hyperpigmentation , 2000, American journal of clinical dermatology.

[42]  R. Buscà,et al.  Different cis-Acting Elements Are Involved in the Regulation of TRP1 and TRP2 Promoter Activities by Cyclic AMP: Pivotal Role of M Boxes (GTCATGTGCT) and of Microphthalmia , 1998, Molecular and Cellular Biology.

[43]  K. Kinoshita,et al.  Antiemetic principles of Alpinia officinarum. , 2002, Journal of natural products.

[44]  Zheng-Tao Wang,et al.  Mechanism and inhibitory effect of galangin and its flavonoid mixture from Alpinia officinarum on mushroom tyrosinase and B16 murine melanoma cells , 2007, Journal of enzyme inhibition and medicinal chemistry.

[45]  R. Yamauchi,et al.  Volatile Components of the Essential Oils in Galanga (Alpinia officinarum Hance) from Vietnam , 2001 .

[46]  A. Motoyama,et al.  A novel melanin inhibitor: hydroperoxy traxastane-type triterpene from flowers of Arnica montana. , 2007, Biological & pharmaceutical bulletin.