1. Rare ginsenoside Ia synthesized from F1 by cloning and overexpression of the UDP-glycosyltransferase gene from Bacillus subtilis: synthesis, characterization, and in vitro melanogenesis inhibition activity in BL6B16 cells
- Author
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Ramya Mathiyalagan, Yan Jin, Nam-In Baek, Chao Wang, Yeon-Ju Kim, Deok-Chun Yang, Zuly Elizabeth Jimenez Perez, Dandan Wang, and Josua Markus
- Subjects
melanogenesis ,0301 basic medicine ,ginsenoside Ia ,Tyrosinase ,Bacillus subtilis ,Biochemistry, Genetics and Molecular Biology (miscellaneous) ,Melanin ,03 medical and health sciences ,chemistry.chemical_compound ,0302 clinical medicine ,lcsh:Botany ,Glycosyltransferase ,B16BL6 cell line ,biology ,Arbutin ,Biological activity ,biology.organism_classification ,Molecular biology ,In vitro ,lcsh:QK1-989 ,030104 developmental biology ,Complementary and alternative medicine ,chemistry ,Biochemistry ,ginsenoside F1 ,Ginsenoside ,030220 oncology & carcinogenesis ,biology.protein ,UDP-glycosyltransferase ,Biotechnology - Abstract
Background Ginsenoside F1 has been described to possess skin-whitening effects on humans. We aimed to synthesize a new ginsenoside derivative from F1 and investigate its cytotoxicity and melanogenesis inhibitory activity in B16BL6 cells using recombinant glycosyltransferase enzyme. Glycosylation has the advantage of synthesizing rare chemical compounds from common compounds with great ease. Methods UDP-glycosyltransferase (BSGT1) gene from Bacillus subtilis was selected for cloning. The recombinant glycosyltransferase enzyme was purified, characterized, and utilized to enzymatically transform F1 into its derivative. The new product was characterized by NMR techniques and evaluated by MTT, melanin count, and tyrosinase inhibition assay. Results The new derivative was identified as (20 S )-3 β ,6 α ,12 β ,20-tetrahydroxydammar-24-ene-20- O - β -D-glucopyranosyl-3- O - β -D-glucopyranoside (ginsenoside Ia), which possesses an additional glucose linked into the C-3 position of substrate F1. Ia had been previously reported; however, no in vitro biological activity was further examined. This study focused on the mass production of arduous ginsenoside Ia from accessible F1 and its inhibitory effect of melanogenesis in B16BL6 cells. Ia showed greater inhibition of melanin and tyrosinase at 100 μmol/L than F1 and arbutin. These results suggested that Ia decreased cellular melanin synthesis in B16BL6 cells through downregulation of tyrosinase activity. Conclusion To our knowledge, this is the first study to report on the mass production of rare ginsenoside Ia from F1 using recombinant UDP-glycosyltransferase isolated from B. subtillis and its superior melanogenesis inhibitory activity in B16BL6 cells as compared to its precursor. In brief, ginsenoside Ia can be applied for further study in cosmetics.
- Published
- 2018