In the course to find a stimulating compound for melanin biosynthesis, which should be useful for a gray and a white hair-preventive agent or tanning agent, we evaluated the effects of the methanol extract from mushroom of Pleurotus citrinopileatus on melanin production in B16 melanoma cells without theophylline. Activity-guided fractionation led to isolate myo -inositol (3) and D-mannitol (4) as the stimulating compounds on melanin production in B16 melanoma cells. Also, ergosterol (1), uracil (2), and D-glucose (5) have been isolated from the methanol extract of P. citrinopileatus and showed no effect on melanin production in B16 melanoma cells. These results indicated that myo -inositol (3) and D-mannitol (4) are potential candidates that could be useful such as a gray and a white hair-preventive agent or tanning agent.
K. D. Hyde, A. H. Bahkali and M. A. Moslem, “Fungi: An Unusual Source for Cosmetics,” Fungal Diversity, Vol. 43, No. 1, 2010, pp. 1-9. doi:10.1007/s13225-010-0043-3
T. X. Meng, H. Ishikawa, K. Shimizu, S. Ohga and R. Kondo, “Evaluation of Biological Activities of Extracts from the Fruiting Body of Pleurotus citrinopileatus for Skin Cosmetics,” Journal of Wood Science, Vol. 57, No. 5, 2011, pp. 452-458. doi:10.1007/s10086-011-1192-z
T. X. Meng, S. Furuta, S. Fukamizu, R. Yamamoto, H. Ishikawa, E. T. Arung, K. Shimizu, S. Ohga and R. Kondo, “A Glucosylceramide with Antimicrobial Activity from the Edible Mushroom Pleurotus citrinopileatus,” Journal of Wood Science, Vol. 58, No. 1, 2012, pp. 81-86. doi:10.1007/s10086-011-1213-y
J. H. Janga, S. C. Jeonga, J. H. Kimb, Y. H. Leeb, Y. C. Jub and J. S. Leea, “Characterization of a New AntiHypertensive Angiotensin I-Converting Enzyme Inhibitory Peptide from Pleurotus cornucopiae,” Food Chemistry, Vol. 127, No. 2, 2011, pp. 412-418.
Y. Takakura, N. Oka, H. Kajiwara, M. Tsunashima, S. Usami, H. Tsukamoto, Y. Ishida and T. Yamamoto, Tamavidin, “A Versatile Affinity Tag for Protein Purification and Immobilization,” Journal of Biotechnology, Vol. 145, No. 4 , 2010, pp. 317-322.
V. J. Hearing and K. Tsukamoto, “Enzymatic Control of Pigmentation in Mammals,” The Journal of the Federation of American Societies for Experimental Biology, Vol. 5, No. 14, 1991, pp. 2902-2909.
I. J. Jackson, D. M. Chambers, K. Tsukamoto, N. G. Copeland, D. J. Gilbert, N. A. Jenkins and V. Hearing, “A Second Tyrosinase-Related Protein, TRP-2, Maps to and Is Mutated at the Mouse Slaty Locus,” The EMBO Journal, Vol. 11, No. 2, 1992, pp. 527-535.
P. Aroca, F. Solano, C. Salinas, J. C. Garcia-Borron and J. A. Lozano, “Regulation of the Final Phase of Mammalian Melanogenesis: The Role of Dopachrome Tautomerase and the Ratio between 5,6-Dihydroxyindole-2-carboxylic Acid and 5,6-Dihydroxyindole,” European Journal of Biochemistry, Vol. 208, No. 1, 1992, pp. 155-163.
E. Steingrímsson, N. G. Copeland and N. A. Jenkins, “Melanocytes and the Microphthalmia Transcription Factor Network,” Annual Review of Genetics, Vol. 38, No. 1, 2004, pp. 365-411.
R. Busca and R. Ballotti, “Cyclic AMP: A Key Messenger in the Regulation of Skin Pigmentation,” Pigment Cell Research, Vol. 13, No. 2, 2000, pp. 60-69.
M. Brenner and V. J. Hearing, “The Protective Role of Melanin against UV Damage in Human Skin,” Photochemistry and Photobiology, Vol. 84, No. 3, 2008, pp. 539-549. doi:10.1111/j.1751-1097.2007.00226.x
M. D. Altschule and Z. L. Hegedus, “Commentary: The Importance of Studying Visceral Melanins,” Clinical Pharmacology and Therapeutics, Vol. 19, No. 2, 1976, pp. 124-134.
H. P. Wassermann, “Studies on Melanin-Labelled Cells in the Human Skin Window,” South African Journal of Laboratory and Clinical Medicine, Vol. 10, 1964, pp. 76-81.
A. S. Breathnach, “Extra-Cutaneous Melanin,” Pigment Cell Research, Vol. 1, No. 4, 1988, pp. 234-237. doi:10.1111/j.1600-0749.1988.tb00421.x
C. G. Summers, W. S. Oetting and R. A. King, “Diagnosis of Oculocutaneous Albinism with Molecular Analysis,” American Journal of Ophthalmology, Vol. 121, No. 6, 1996, pp. 724-726.
J. P. Ortonne and T. Passeron, “Melanin Pigmentary Disorders: Treatment Update,” Dermatologic Clinics, Vol. 23, No. 2, 2005, pp. 209-226. doi:10.1016/j.det.2005.01.001
D. B. Sgarbi, A. J. Silva, I. Z. Carlos, C. L. Silva, J. Angluster and C. S. Alviano, “Isolation of Ergosterol Peroxide and Its Reversion to Ergosterol in the Pathogenic Fungus Sporothrix schenckii,” Mycopathologia, Vol. 139, No. 1, 1997, pp. 9-14. doi:10.1023/A:1006803832164
A. Trigos and A. Ortega-Regules, “Selective Destruction of Microscopic Fungi through Photo-Oxidation of Ergosterol,” Mycologia, Vol. 94, No. 4, 2002, pp. 563-568. doi:10.2307/3761707
Y. S. Kim, I. K. Lee, S. J. Seok and B. S. Yun, “Chemical Constituents of the Fruiting Bodies of Clitocybe nebularis and Their Antifungal Activity,” Mycobiology, Vol. 36, No. 2, 2008, pp. 110-113. doi:10.4489/MYCO.2008.36.2.110
R. J. Abraham, J. Byrne, L. Griffiths and R. Koniotou, “ 1 H Chemical Shifts in NMR: Part 22-Prediction of the 1 H Chemical Shifts of Alcohols, Diols and Inositols in Solution, a Conformational and Solvation Investigation,” Magnetic Resonance in Chemistry, Vol. 43, No. 8, 2005, pp. 611-624. doi:10.1002/mrc.1611
R. Jennemann, B. L. Bauer, H. Bertalanffy, R. Geyer, R. M. Gschwind, T. Selmer and H. Wiegandt, “Novel Glycoinositolphosphosphingolipids, Basidiolipids, from Agaricus,” European Journal of Biochemistry, Vol. 259, No. 2, 1999, pp. 331-338.
S. Y. Hagiwara, M. Takahashi, Y. Shen, S. Kaihou, T. Tomiyama, M. Yazawa, Y. Tamai and M. Terazawa, “A Phytochemical in an Edible Tamogi-Take Mushroom (Pleurotus cornucopiae), D-Mannitol, Inhibits ACE Activity and Lowers the Blood Pressure of Spontaneously Hypertensive Rats,” Bioscience Biotechnology and Biochemistry, Vol. 69, No. 8, 2005, pp. 1603-1605. doi:10.1271/bbb.69.1603
A. Bagno, F. Rastrelli and G. Saielli, “Prediction of the 1 H and 13 C NMR Spectra of α-D-Glucose in Water by DFT Methods and MD Simulations,” The Journal of Organic Chemistry, Vol. 72, No. 19, 2007, pp. 7373-7381.
H. Asaoka, “ 1 H- and 13 C-N.M.R. Spectroscopy of α-D-Glucose and α-D-Mannose with Boron (III) Oxide as Shift Reagent,” Carbohydrate Research, Vol. 118, 1983, pp. 302-307. doi:10.1016/0008-6215(83)88060-4
A. Hussein, N. Al-Wadei, T. Takahashi and H. M. Schuller, “Theophylline Stimulates cAMP-Mediated Signaling Associated with Growth Regulation in Human Cells from Pulmonary Adenocarcinoma and Small Airway Epithelia,” International Journal of Oncology, Vol. 27, No. 1, 2005, pp. 155-160.
N. Saito, U. Kikkawa and Y. Nishizuka, “The Family of Protein Kinase C and Membrane Lipid Mediators,” Journal of Diabetes and Its Complications, Vol. 16, No. 1, 2002, pp. 4-8. doi:10.1016/S1056-8727(01)002008
M. Y. Choi, H. S. Song, H. S. Hur and S. Sim, “Whitening Activity of Luteolin Related to the Inhibition of cAMP Pathway in Alpha-MSH Stimulated B16 Melanoma Cells,” Archives of Pharmacal Research, Vol. 31, No. 9, 2008, pp. 1166-1171. doi:10.1007/s12272-009-1309-8
M. Perluigi, F. De-Marco, C. Foppoli, R. Coccia, C. Blarzino, M. L. Marcante and C. Cini, “Tyrosinase Protects Human Melanocytes from ROS-Generating Compounds,” Biochemical and Biophysical Research Communications, Vol. 305, No. 2, 2003, pp. 250-256.
J. Yamakoshi, F. Otsuka, A. Sano, S. Tokutake, M. Saito, M. Kikuchi and Y. Kubota, “Lightening Effect on Ultraviolet-Induced Pigmentation of Guinea Pig Skin by Oral Administration of a Proanthocyanidin Rich Extract from Grape Seeds,” Pigment Cell Research, Vol. 16, No. 6, 2003, pp. 629-638. doi:10.1046/j.16000749.2003.00093.x
B. Shen, R. G. Jensen and H. J. Bohnert, “Mannitol Protects against Oxidation by Hydroxyl Radicals,” Plant Physiology, Vol. 115, No. 2, 1997, pp. 527-532.
D. J. Tobin and R. P. Graying, “Gerontobiology of the Hair Follicle Pigmentary Unit,” Experimental Gerontology, Vol. 36, No. 1, 2001, pp. 29-54.
T. Horikawa, D. A. Norris, T. W. Johnson, T. Zekman, N. Dunscomb, S. D. Bennion, R. L. Jackson and J. G. Morelli, “DOPA-Negative Melanocytes in the Outer Root Sheath of Human Hair Follicles Express Premelanosomal Antigens but Not a Melanosomal Antigen or the Melanosome-Associated Glycoproteins Tyrosinase, TRP-1, and TRP-2,” Journal of Investigative Dermatology, Vol. 106, No. 1, 1996, pp. 28-35. doi:10.1111/1523-1747.ep12326989
H. Matsuda, Y. Kawaguchi, M. Yamazaki, N. Hirata, S. Naruto, Y. Asanuma, T. Kaihatsu and M. Kubo, “Melanogenesis Stimulation in Murine B16 Melanoma Cells by Pipernigrum Leaf Extract and Its Lignan Constituents,” Biological Pharmaceutical Bulletin, Vol. 27, No. 10, 2004, pp. 1611-1616. doi:10.1248/bpb.27.1611
M. J. Berridge, P. Lipp and M. D. Bootman, “The Versatility and Universality of Calcium Signaling,” Nature Reviews Molecular Cell Biology, Vol. 1, No. 1, 2000, pp. 11-21. doi:10.1038/35036035
R. F. Irvine and S. J. Michael, “Back in the Water: The Return of the Inositol Phosphates,” Nature Reviews Molecular Cell Biology, Vol. 2, No. 1, 2001, pp. 327-338. doi:10.1038/35073015
M. J. Iqbal, A. J. Afzal, S. Yaegashi, E. Ruben, K. Triwitayakorn, V. N. Njiti, R. Ahsan, A. J. Wood and D. A. Lightfoot, “A Pyramid of Loci for Partial Resistance to Fusarium solani f. sp. Glycines Maintains Myo-inositol-1-phosphate Synthase Expression in Soybean Roots,” Theoretical and Applied Genetics, Vol. 105, 2002, pp. 1115-1123. doi:10.1007/s00122-002-0987-0
R. M. Deranieh and M. L. Greenberg, “Cellular Consequences of Inositol Depletion,” Biochemical Society Transactions, Vol. 37, No. 5, 2009, pp. 1099-1103. doi:10.1042/BST0371099
J. Larner, “D-Chiro-Inositol—Its Functional Role in Insulin Action and Its Deficit in Insulin Resistance,” International Journal of Experimental Diabetes Research, Vol. 3, No. 3, 2002, pp. 47-60. doi:10.1080/15604280212528
P. A. Brex, B. Gomez-Anson, G. J. Parker, P. D. Molyneux, K. A. Miszkiel, G. J. Barker, D. G. MacManus, C. A. Davie and G. T. Plant, “Proton NMR Spectroscopy in Clinically Isolated Syndromes Suggestive of Multiple Sclerosis,” Journal of the Neurological Sciences, Vol. 166, No. 1, 1999, pp. 16-22. doi:10.1016/S0022-510X(99)00105-7
J. McLaurin, T. Franklin, A. Chakrabartty and P. E. Fraser, “Phosphatidylinositol and Inositol Involvement in Alzheimer Amyloid-β Fibril Growth and Arrest,” Journal of Molecular Biology, Vol. 278, No. 1, 1998, pp. 183-194. doi:10.1006/jmbi.1998.1677
T. P. Thomas, F. Porcellati, K. Kato, M. J. Stevens, W. R. Sherman and D. A. Greene, “Effects of Glucose on Sorbitol Pathway Activation, Cellular Redox, and Metabolism of Myo-Inositol, Phosphoinositide, and Diacylglycerol in Cultured Human Retinal Pigment Epithelial Cells,” Journal of Clinical Investigation, Vol. 93, No. 6, 1994, pp. 2718-2724. doi:10.1172/JCI117286
B. C. Saha and F. M. Racine, “Biotechnological Production of Mannitol and Its Applications,” Applied Microbiology and Biotechnology, Vol. 89, No. 4, 2011, pp. 879-891. doi:10.1007/s00253-010-2979-3
W. Soetaert, K. Buchholz and E. J. Vandamme, “Production of D-Mannitol and D-Lactic Acid by Fermentation with Leuconostoc mesenteroides,” Agrofood Industry Hi-Tech, Vol. 6, 1995, pp. 41-44. doi:10.1002/bit.10638
S. I. Rapoport, “Advances in Osmotic Opening of the Blood-Brain Barrier to Enhance CNS Chemotherapy,” Expert Opinion on Investigational Drugs, Vol. 10, No. 10, 2001, pp. 1809-1818. doi:10.1517/13543784.10.10.1809
G. Miller, “Drug Targeting. Breaking Down Barriers,” Science, Vol. 297, No. 5584, 2002, pp. 1116-1118. doi:10.1126/science.297.5584.1116
J. C. Johnson, “Sugar Alcohols and Derivatives,” In: J. C. Johnson, Ed., Specialized Sugars for the Food Industry, Noyes Data Corporation, New Jersey, 1976, pp. 313-323.