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Proanthocyanidins purified from fruit pericarp of Clausena lansium (Lour.) Skeels as efficient tyrosinase inhibitors: structure evaluation, inhibitory activity and molecular mechanism.
Food Funct. 2017 Mar 22; 8(3):1043-1051.FF

Abstract

Fruit pericarp of Clausena lansium (Lour.) Skeels, a food waste, was selected as a raw material for proanthocyanidins. The proanthocyanidins' structures were integrally analyzed using three methods: matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS), high performance liquid chromatography electrospray ionization mass spectrometry (HPLC-ESI-MS) and 13C nuclear magnetic resonance (NMR). The results elucidated that these compounds were composed of prodelphinidin (75%) and procyanidin (25%) with a degree of polymerization (DP) up to the 20-mers. They were proved to be remarkable, reversible and mixed competitive inhibitors of tyrosinase according to results from enzyme experiments. The IC50 values were calculated to be 23.6 ± 1.2 and 7.0 ± 0.2 μg mL-1 for the monophenolase and diphenolase activities, respectively. In addition, the proanthocyanidins had a good inhibitory effect on cell proliferation, cellular tyrosinase activity and melanin production of B16 mouse melanoma cells. Chelation between the hydroxyl group on the B ring of the proanthocyanidins and dicopper irons of the enzyme provided one of the feasible mechanisms for the inhibition on the basis of fluorescence quenching and molecular docking analyses. This research would supply the scientific basis to these compounds application in the pharmaceutical, insecticides, and preservative fields.

Authors+Show Affiliations

College of Life Science and Key Laboratory of Poyang Lake Wetland and Watershed Research, Ministry of Education, Jiangxi Normal University, Nanchang, Jiangxi 330022, China. chaiweiming@jxnu.edu.cn zouzhr@163.com and Key Laboratory of Small Functional Organic Molecule, Ministry of Education, Jiangxi Normal University, Nanchang, Jiangxi 330022, China.College of Life Science and Key Laboratory of Poyang Lake Wetland and Watershed Research, Ministry of Education, Jiangxi Normal University, Nanchang, Jiangxi 330022, China. chaiweiming@jxnu.edu.cn zouzhr@163.com.Zigong Innovation Center of Zhejiang University, Zigong, Sichuan 643000, China.College of Life Science and Key Laboratory of Poyang Lake Wetland and Watershed Research, Ministry of Education, Jiangxi Normal University, Nanchang, Jiangxi 330022, China. chaiweiming@jxnu.edu.cn zouzhr@163.com.College of Life Science and Key Laboratory of Poyang Lake Wetland and Watershed Research, Ministry of Education, Jiangxi Normal University, Nanchang, Jiangxi 330022, China. chaiweiming@jxnu.edu.cn zouzhr@163.com.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

28128839

Citation

Chai, Wei-Ming, et al. "Proanthocyanidins Purified From Fruit Pericarp of Clausena Lansium (Lour.) Skeels as Efficient Tyrosinase Inhibitors: Structure Evaluation, Inhibitory Activity and Molecular Mechanism." Food & Function, vol. 8, no. 3, 2017, pp. 1043-1051.
Chai WM, Lin MZ, Feng HL, et al. Proanthocyanidins purified from fruit pericarp of Clausena lansium (Lour.) Skeels as efficient tyrosinase inhibitors: structure evaluation, inhibitory activity and molecular mechanism. Food Funct. 2017;8(3):1043-1051.
Chai, W. M., Lin, M. Z., Feng, H. L., Zou, Z. R., & Wang, Y. X. (2017). Proanthocyanidins purified from fruit pericarp of Clausena lansium (Lour.) Skeels as efficient tyrosinase inhibitors: structure evaluation, inhibitory activity and molecular mechanism. Food & Function, 8(3), 1043-1051. https://doi.org/10.1039/c6fo01320a
Chai WM, et al. Proanthocyanidins Purified From Fruit Pericarp of Clausena Lansium (Lour.) Skeels as Efficient Tyrosinase Inhibitors: Structure Evaluation, Inhibitory Activity and Molecular Mechanism. Food Funct. 2017 Mar 22;8(3):1043-1051. PubMed PMID: 28128839.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Proanthocyanidins purified from fruit pericarp of Clausena lansium (Lour.) Skeels as efficient tyrosinase inhibitors: structure evaluation, inhibitory activity and molecular mechanism. AU - Chai,Wei-Ming, AU - Lin,Mei-Zhen, AU - Feng,Hui-Ling, AU - Zou,Zheng-Rong, AU - Wang,Ying-Xia, PY - 2017/1/28/pubmed PY - 2017/7/14/medline PY - 2017/1/28/entrez SP - 1043 EP - 1051 JF - Food & function JO - Food Funct VL - 8 IS - 3 N2 - Fruit pericarp of Clausena lansium (Lour.) Skeels, a food waste, was selected as a raw material for proanthocyanidins. The proanthocyanidins' structures were integrally analyzed using three methods: matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS), high performance liquid chromatography electrospray ionization mass spectrometry (HPLC-ESI-MS) and 13C nuclear magnetic resonance (NMR). The results elucidated that these compounds were composed of prodelphinidin (75%) and procyanidin (25%) with a degree of polymerization (DP) up to the 20-mers. They were proved to be remarkable, reversible and mixed competitive inhibitors of tyrosinase according to results from enzyme experiments. The IC50 values were calculated to be 23.6 ± 1.2 and 7.0 ± 0.2 μg mL-1 for the monophenolase and diphenolase activities, respectively. In addition, the proanthocyanidins had a good inhibitory effect on cell proliferation, cellular tyrosinase activity and melanin production of B16 mouse melanoma cells. Chelation between the hydroxyl group on the B ring of the proanthocyanidins and dicopper irons of the enzyme provided one of the feasible mechanisms for the inhibition on the basis of fluorescence quenching and molecular docking analyses. This research would supply the scientific basis to these compounds application in the pharmaceutical, insecticides, and preservative fields. SN - 2042-650X UR - https://www.unboundmedicine.com/medline/citation/28128839/Proanthocyanidins_purified_from_fruit_pericarp_of_Clausena_lansium__Lour___Skeels_as_efficient_tyrosinase_inhibitors:_structure_evaluation_inhibitory_activity_and_molecular_mechanism_ L2 - https://doi.org/10.1039/c6fo01320a DB - PRIME DP - Unbound Medicine ER -