title: Biological evaluation of novel derivatives of the orange pigments from Monascus sp. as inhibitors of melanogenesis.
abstract: Nitrogenous derivatives of the two orange pigments from Monascus sp. with anti-melanogenic activities were prepared using fermentation and chemical synthesis. The pigments were produced in a 5 l jar fermentor. A total of 33 derivatives were synthesized via incorporation of L-amino acids and amines into the pigments. Two derivatives with high inhibitory melanin-synthesizing activities and low cell toxicities were selected based on testing using B16F10 cells. Glutamic acid and (S)-(+)-1-amino-2-propanol derivatives showed high inhibitory activities against melanogenesis. Both the reaction and expression of tyrosinase, an important enzyme in the melanin-synthesizing pathway, were inhibited by the glutamic acid derivative in a dose-dependent manner. The (S)-(+)-1-amino-2-propanol derivative inhibited expression of tyrosinase in cells, but not the tyrosinase reaction. TRP1 and TRP2, other important proteins in melanin-synthesis, were not affected by the two derivatives.
authors.affiliation: Department of Biotechnology, Yonsei University, Seodaemun-gu, Seoul, 120-749, South Korea, djminu@naver.com.
authors.forename: Dajung
authors.initials: D
authors.lastname: Jo
authors.forename: Deokyeong
authors.initials: D
authors.lastname: Choe
authors.forename: Kyunghwa
authors.initials: K
authors.lastname: Nam
authors.forename: Chul Soo
authors.initials: CS
authors.lastname: Shin
mesh_terms: D000588:Amines / Q000378:metabolism; D000818:Animals; D016923:Cell Death / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D018698:Glutamic Acid / Q000096:biosynthesis / Q000737:chemistry / Q000494:pharmacology; D019746:Intramolecular Oxidoreductases / Q000378:metabolism; D008543:Melanins / Q000037:antagonists & inhibitors* / Q000096:biosynthesis* / Q000737:chemistry; D008546:Melanoma, Experimental / Q000378:metabolism / Q000473:pathology; D051379:Mice; D032741:Monascus / Q000737:chemistry*; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors / Q000378:metabolism; D010088:Oxidoreductases / Q000378:metabolism; D010860:Pigments, Biological / Q000494:pharmacology*
chemical_list: D000588:Amines; D008543:Melanins; D010860:Pigments, Biological; D018698:Glutamic Acid; D010088:Oxidoreductases; C064056:tyrosinase-related protein-1; D014442:Monophenol Monooxygenase; D019746:Intramolecular Oxidoreductases; C042501:dopachrome isomerase