Synthesis, Antioxidative and Whitening Effects of Novel Cysteine Derivatives

• Published in: Bulletin of the Korean Chemical Society 2017, 38(1), , pp.78-84
• Main Authors: Ha, Ji Hoon, Kim, Kyoung Mi, Jeong, Yoon Ju, Park, Young Min, Lee, Jae‐Young, Park, Jino, Park, Soo Nam
• Format: Article
• Language: English
• Subjects: Antioxidative activity; l‐cysteine ethyl ester; N‐acetyl cysteine ethyl ester; N‐acetyl cysteine methyl ester; Whitening effect; 화학
• ISSN: 1229-5949; 0253-2964; 1229-5949
• DOI: 10.1002/bkcs.11050

Recently, development of biocompatibility functional cosmetic agents as antioxidant or whitening agent has increased. In this study, synthetic cysteine derivatives (DBLS‐21, ‐24, and ‐33) were developed containing syringic acid and cysteine moieties (l‐cysteine ethyl ester, N‐acetyl cysteine methyl ester, and N‐acetyl cysteine ethyl ester), and their antioxidative and whitening activities were evaluated. The cellular protective effect (τ50) of DBLS‐21 was 51.1 min at 50 μM on 1O2 ‐induced hemolysis of erythrocytes. This activity was slightly higher than that of α‐tocopherol (43.6 min) as a lipophilic antioxidant. In the melanogenesis inhibitory effect, DBLS‐21, ‐24, and ‐33 was 1.6‐, 1.8‐, and 2.5‐fold higher than arbutin, respectively. In particular, DBLS‐21 and ‐33 was 112.8‐ and 6.1‐fold higher than arbutin, respectively (293.4 μM) on tyrosinase inhibition activity (IC50 ). But DBLS‐24 had no tyrosinase inhibitory activity. These results suggest that cysteine derivatives possess potential for use as an antioxidant agent (DBLS‐21) and whitening agents (all derivatives) in cosmetics. The three‐dimensional structures and dipole moments of DBLS‐21 (a), DBLS‐24 (b), and DBLS‐33 (c) on ground states geometries.