Antityrosinase and Antimicrobial Activities of <i>trans</i>-Cinnamaldehyde Thiosemicarbazone

Zhu, Yujing; Song, Kangkang; Li, Zhi-Cong; Pan, Zhiyong; Guo, Yun-Ji; Zhou, Jingjing; Wang, Qin; Liu, Bo; Chen, Qing‐Xi

doi:10.1021/jf9007554

Cited by 47 publications

(28 citation statements)

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“…Some inhibitors of tyrosinase were also found in the antimicrobial activities [16,17]. Some inhibitors have been applied in cosmetic and medicine, but the effects of fatty acids as inhibitors of tyrosinase were rarely investigated.…”

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confidence: 99%

Inhibitory Effects of Fatty Acids on the Activity of Mushroom Tyrosinase

Guo

Pan

Chen

et al. 2010

Appl Biochem Biotechnol

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The effects of fatty acids, octanoic acid, (2E, 4E)-hexa-2,4-dienoic acid, hexanoic acid, (2E)-but-2-enoic acid, and butyric acid on the activities of mushroom tyrosinase have been investigated. The results showed that the fatty acids can potently inhibit both monophenolase activity and diphenolase activity of tyrosinase, and that the unsaturated fatty acids exhibited stronger inhibitory effect against tyrosinase than the corresponding saturated fatty acids, and the inhibitory effects were enhanced with the extendability of the fatty acid chain. For the monophenolase activity, the fatty acids could not only lengthen the lag period, but also decrease the steady-state activities. For the diphenolase activity, fatty acids displayed reversible inhibition. Kinetic analyses showed that octanoic acid and hexanoic acid were mixed-type inhibitors and (2E,4E)-hexa-2,4-dienoic acid and (2E)-but-2-enoic acid were noncompetitive inhibitors. The inhibition constants have been determined and compared.

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confidence: 99%

Inhibitory Effects of Fatty Acids on the Activity of Mushroom Tyrosinase

Guo

Pan

Chen

et al. 2010

Appl Biochem Biotechnol

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“…As for therapeutic agent, the production of cinnamaldehyde is from the bark of cinnamon tree was steamed to get the oil for their various applications. The proof from the previous article using trans-cinnamaldehyde thosemicarbazone could develop novel of tyrosinase inhibitors and could develop new cosmetics additive 57 . Cinnamaldehyde itself also act as fungicides/ insecticides, corrosion inhibitors it also helps relieve congestion.…”

Section: Other Therapeutics Usesmentioning

confidence: 92%

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2017

IJPSR

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“…The copper ions chelation ability Many substances have been reported to act as an tyrosinase inhibitor due to their innate function in chelating metal ions, maybe as a chelator to the copper ions in the tyrosinase (Kim et al, 2006;Khatib et al, 2005;Zhu et al, 2009). In order to explore and illustrate the underlying mechanism better, the direct interactions between the inhibitors and the copper ions were assessed routinely by UV-2450 spectrophotometer at pH 6.8.…”

Section: Methodsmentioning

confidence: 99%

“…The behaviour observed showed that the inhibitor could combine with both the free enzyme and the enzymesubstrate complex. The inhibition constants (K I and K IS ) can be obtained from a plot of the vertical intercept versus the inhibitor concentration as showed in Table 1.It is evident to summarize that the above compounds with methoxy exhibited non-competitive inhibition type, showed competitive inhibition with mono-or dihydroxy, displayed mixed-type inhibition when both methoxy and hydroxyl existed.The copper ions chelation ability Many substances have been reported to act as an tyrosinase inhibitor due to their innate function in chelating metal ions, maybe as a chelator to the copper ions in the tyrosinase (Kim et al, 2006;Khatib et al, 2005;Zhu et al, 2009). In order to explore and illustrate the underlying mechanism better, the direct interactions between the inhibitors and the copper ions were assessed routinely by UV-2450 spectrophotometer at pH 6.8.…”

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confidence: 99%

Tyrosinase Inhibitory Effects and Antioxidant Properties of Paeonol and Its Analogues

Zhu

Cao

2013

FSTR

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With the aim to find out structural features for the tyrosinase inhibitory activity, the inhibitory effects of seven paeonol analogues on the diphenolase of mushroom tyrosinase, the interaction between the inhibitors and the copper ions, and the antioxidant activity by DPPH radical were investigated. These paeonol analogues had suggested remarkable inhibition toward tyrosinase. Among them, paeonol (a) exhibited the strongest inhibition activity (IC 50 =0.21 mM) as well as showed potent scavenging activity on the DPPH radical. The inhibition kinetics revealed that paeonol (a) was a mixed-type inhibitor, 2′-hydroxy acetophenone (c), 4′-hydroxy acetophenone (d), and 2,4′-dihydroxy acetophenone (e) were competitive inhibitors, while acetophenone (b), 2′-methoxyacetophenone (f), and 4′-methoxy acetophenone (g) behaved as noncompetitive inhibitors. The maximum absorbing wavelengths of compounds (c), (d), and (e) showed different significant blue shifts, which could explain that they exhibited competitive inhibition by forming a chelate with the copper ions at the catalytic domain of the tyrosinase.Keywords: paeonol, acetophenone, tyrosinase inhibitor, DPPH radical, copper ions chelation *To whom correspondence should be addressed. E-mail: yuyanying@ncu.edu.cn IntroductionTyrosinase (EC 1.14.18.1), known as polyphenol oxidase, is a multifunctional copper-containing metalloenzyme widely distributed in nature. It mainly catalyzes the o-hydroxylation of monophenols to the corresponding catechols, and the oxidation of monophenols to the corresponding o-quinones (Yoon et al., 2009). Consequently, a series of high reactive quinones are produced to initiate the pigmentation and excessive activation of tyrosinase can cause various dermatological disorders, such as Parkinson and other degenerative diseases (Asanuma et al., 2003).One of the reactions catalyzed by the tyrosinase is the oxidation of L-dopa to L-dopaquinone by utilising molecular oxygen. In addition, reactive oxygen species (ROS) and free radical-mediated reactions are associated with various diseases, such as diabetes mellitus, cancer, ageing, skin disorders, and neurodegenerative diseases (Pham-Huy et al., 2008). If the inhibitors we have designed can weaken the tyrosinase activity as well as scavenge ROS effectively, the production of melanin and the damage of ROS to our human beings will be decreased to a great extent. Hence, tyrosinase inhibitors have become increasingly important in cosmetic (Guevara and Pandya, 2001) and medicinal (Kanost et al., 2004) industry, the food industry (Lunadei et al., 2011) and agriculture (Guerrero and Rosell, 2005) to prevent hyperpigmentation.In recent years, a large number of naturally occurring and synthetic tyrosinase inhibitors have been reported. There are many tyrosinase inhibitors, such as hydroquinone (Garcia and Fulton Jr, 1996), ascorbic acid (Kameyama et al., 1996), arbutin (Nakajima et al., 1998), kojic acid (Mishima et al., 1994, aromatic aldehydes (Jimenez et al., 2001;, aromatic acids (Chen et al., 2005;Si et a...

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Antityrosinase and Antimicrobial Activities of trans-Cinnamaldehyde Thiosemicarbazone

Cited by 47 publications

References 17 publications

Inhibitory Effects of Fatty Acids on the Activity of Mushroom Tyrosinase

Inhibitory Effects of Fatty Acids on the Activity of Mushroom Tyrosinase

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Tyrosinase Inhibitory Effects and Antioxidant Properties of Paeonol and Its Analogues

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