Tyrosinase inhibitory activity of flavonoids from Artocarpus heterophyllous

Chemistry Central Journal

Hai Xuan Nguyen²  Nhan Trung Nguyen¹  Mai Ha Khoa Nguyen²  Tho Huu Le²  Truong Nhat Van Do²  Tran Manh Hung³  Mai Thanh Thi Nguyen¹ 

[1] Cancer Research Laboratory, Vietnam National University, 227 Nguyen Van Cu, District 5, Ho Chi Minh, Vietnam

[2] Faculty of Chemistry, University of Science, 227 Nguyen Van Cu, District 5, Ho Chi Minh, Vietnam

[3] Department of Biomedical Sciences, Institute for Research and Executive Education (VNUK), The University of Danang, 41 Le Duan, Haichau District, Danang, Vietnam

关键词: Tyrosinase inhibitors;    Chalcones;    Flavonoids;    Artocarpus heterophyllous;   

Others  :  1235789
DOI  :  10.1186/s13065-016-0150-7

 received in 2015-10-30, accepted in 2016-01-10,  发布年份 2016

【 摘 要 】

Background

Tyrosinase is an oxidoreductase that is very important in medicine and cosmetics because the excessive production of melanin causes hyperpigmentation. The development of novel, effective tyrosinase inhibitors has long been pursued. In preliminary tests, we found that an extract of the wood of Artocarpus heterophyllous (AH) potently inhibited tyrosinase activity.

Results

Two new flavonoids, artocaepin E (1) and artocaepin F (2), were isolated from the wood of AH, together with norartocarpetin (3), artocarpanone (4), liquiritigenin (5), steppogenin (6), and dihydromorin (7). Their structures were elucidated using one-dimensional (1D) and two-dimensional (2D) nuclear magnetic resonance (NMR) and mass spectrometry. The absolute configuration of 2 was determined from the circular dichroism (CD) spectrum. Artocarpanone (4) had the most potent tyrosinase inhibitory effect, with an IC ₅₀of 2.0 ± 0.1 μM, followed by artocaepin E (1) and steppogenin (6), with IC ₅₀values of 6.7 ± 0.8 and 7.5 ± 0.5 μM, respectively. A kinetic investigation indicated that 1 showed competitive inhibition, with an inhibition constant (K_i ) of 6.23 μM.

Conclusions

These results demonstrate that extracts of the wood of AH and its phytochemical constituents are potential sources for skin-whitening agents.

【 授权许可】

   
2016 Nguyen et al.

【 图 表 】

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