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Inhibitory effects of a novel ascorbic derivative, disodium isostearyl 2-O-L-ascorbyl phosphate on melanogenesis.

Abstract
We investigated the inhibitory effects of a novel amphiphilic ascorbic derivative, disodium isostearyl 2-O-L-ascorbyl phosphate (VCP-IS-2Na), synthesized from a hydrophilic ascorbic derivative, sodium-2-O-L-ascorbyl phosphate (VCP-Na), on melanogenesis in cultured human melanoma cells, normal human melanocytes, and three-dimensional cultured human skin models. Melanin synthesis in melanoma cells treated with VCP-IS-2Na at 300 muM and melanocytes treated with VCP-IS-2Na at 100 muM decreased to 23% and 52% of that in non-treated cells, respectively, and the cell viability was not affected. VCP-IS-2Na also significantly suppressed the cellular tyrosinase activity of melanoma cells and melanocytes. Melanin synthesis in human skin models was evaluated by macro- and microscopic observations of its pigmentation and quantitative measurements of melanin. Treatment of the human skin models with 1.0% VCP-IS-2Na did not inhibit cell viability, while melanin synthesis was decreased to 21% of that in the control. In contrast, L-ascorbic acid (VC) and VCP-Na did not seem to inhibit melanin synthesis and cellular tyrosinase activity. These results indicate that VCP-IS-2Na may be an effective whitening agent for the skin, and we expect the application of VCP-IS-2Na in the cosmetic industry.
AuthorsSanae Matsuda, Hiroharu Shibayama, Masayoshi Hisama, Mamitaro Ohtsuki, Masahiro Iwaki
JournalChemical & pharmaceutical bulletin (Chem Pharm Bull (Tokyo)) Vol. 56 Issue 3 Pg. 292-7 (Mar 2008) ISSN: 0009-2363 [Print] Japan
PMID18310938 (Publication Type: Journal Article)
Chemical References
  • Indicators and Reagents
  • Melanins
  • Tetrazolium Salts
  • Thiazoles
  • disodium isostearyl 2-O-L-ascorbyl phosphate
  • Monophenol Monooxygenase
  • thiazolyl blue
  • Ascorbic Acid
Topics
  • Ascorbic Acid (analogs & derivatives, pharmacology)
  • Cell Line, Tumor
  • Cell Proliferation (drug effects)
  • Humans
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Melanins (antagonists & inhibitors, biosynthesis)
  • Melanoma (metabolism)
  • Monophenol Monooxygenase (antagonists & inhibitors)
  • Skin (cytology, metabolism)
  • Spectrometry, Mass, Fast Atom Bombardment
  • Spectrophotometry, Ultraviolet
  • Tetrazolium Salts
  • Thiazoles

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