Tyrosinase inhibitory activity of flavonoids from Artocarpus heterophyllous

Chemistry Central Journal
Hai Xuan NguyenMai Thanh Thi Nguyen

Abstract

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. 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 IC50 of 2.0 ± 0.1 μM, followed by artocaepin E (1) and steppogenin (6), with IC50 values 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. These results demonstrate that extracts of the wood of AH and its phytochemical constituents are potential sources f...Continue Reading

References

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Citations

Dec 7, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Dong-Cheol KimYoun-Chul Kim
Nov 10, 2017·Natural Product Research·Phu H DangNhan T Nguyen
Oct 9, 2018·Natural Product Research·Phu H DangNhan T Nguyen
May 23, 2020·Critical Reviews in Biochemistry and Molecular Biology·Mark-Anthony McLarin, Ivanhoe K H Leung
Jun 28, 2019·Mini Reviews in Medicinal Chemistry·Kamal Uddin ZaidiIshrat Naaz
Jul 17, 2020·Zeitschrift Für Naturforschung. C, a Journal of Biosciences·Phu Hoang DangNhan Trung Nguyen
Jan 19, 2021·Natural Product Research·Nhan Trung NguyenMai Thanh Thi Nguyen
May 4, 2021·Natural Product Research·Nhan Trung NguyenMai Thanh Thi Nguyen
Jul 25, 2021·International Journal of Molecular Sciences·Wonmin KoDong-Sung Lee

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Methods Mentioned

BETA
column chromatography
NMR

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