Tyrosinase inhibitory study of flavonolignans from the seeds of Silybum marianum (Milk thistle)

Kim, Ji Yeong; Kim, Jeong‐Yoon; Jenis, Janar; Li, Zuo Peng; Ban, Yeong Jun; Baiseitova, Aizhamal; Park, Ki Hun

doi:10.1016/j.bmc.2019.03.013

Cited by 33 publications

(17 citation statements)

References 23 publications

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“…The most efficient was silybin AB (unfortunately authors failed to test separated silybin diastereomers), followed by isosilybin A and silydianin, all with a mixed type of inhibition. The tyrosinase activity of the tested flavonolignans is rather potent compared to the positive control-kojic acid-with IC50 15.3/37.1 µM (L-Tyr/L-DOPA) [142].…”

Section: Other Biological Activitiesmentioning

confidence: 91%

Chirality Matters: Biological Activity of Optically Pure Silybin and Its Congeners

Křen

2021

IJMS

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This review focuses on the specific biological effects of optically pure silymarin flavo-nolignans, mainly silybins A and B, isosilybins A and B, silychristins A and B, and their 2,3-dehydro derivatives. The chirality of these flavonolignans is also discussed in terms of their analysis, preparative separation and chemical reactions. We demonstrated the specific activities of the respective diastereomers of flavonolignans and also the enantiomers of their 2,3-dehydro derivatives in the 3D anisotropic systems typically represented by biological systems. In vivo, silymarin flavonolignans do not act as redox antioxidants, but they play a role as specific ligands of biological targets, according to the “lock-and-key” concept. Estrogenic, antidiabetic, anticancer, antiviral, and antiparasitic effects have been demonstrated in optically pure flavonolignans. Potential application of pure flavonolignans has also been shown in cardiovascular and neurological diseases. Inhibition of drug-metabolizing enzymes and modulation of multidrug resistance activity by these compounds are discussed in detail. The future of “silymarin applications” lies in the use of optically pure components that can be applied directly or used as valuable lead structures, and in the exploration of their true molecular effects.

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Section: Other Biological Activitiesmentioning

confidence: 91%

Chirality Matters: Biological Activity of Optically Pure Silybin and Its Congeners

Křen

2021

IJMS

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“…Particularly active were prodelphinidins and procyanidins from the fruit pericarp of Clausena lansium Skeels [102], as well as the complex mixtures isolated from Persea Americana [106], Longan bark [99], and from leaves and fruit of Leucaena leucocephala [97]. Very potent (IC 50 values in the range 0.10-7.5 µM) mushroom tyrosinase inhibitors have been isolated from licorice (Figure 12), the most active belonging to the isoflavan class [108][109][110] IC50 values in the range 28-42 μM have been reported for two lignans isolated from Opilia amentacea leaves [112] (Figure 13), whereas particularly effective against the monophenolase activity of the enzyme were flavonolignans from the seeds of Silybum marianum (IC50 in the range 1.7-4.9 μM) ( Figure 13) [113] as well as, although with a lower strength, hydroxylated phenones from Syzygium polyanthum leaves [114] (Figure 14). IC 50 values in the range 28-42 µM have been reported for two lignans isolated from Opilia amentacea leaves [112] (Figure 13), whereas particularly effective against the monophenolase activity of the enzyme were flavonolignans from the seeds of Silybum marianum (IC 50 in the range 1.7-4.9 µM) ( Figure 13) [113] as well as, although with a lower strength, hydroxylated phenones from Syzygium polyanthum leaves [114] (Figure 14).…”

Section: Natural Phenolic Inhibitors Of Mushroom Tyrosinasementioning

confidence: 99%

Natural and Bioinspired Phenolic Compounds as Tyrosinase Inhibitors for the Treatment of Skin Hyperpigmentation: Recent Advances

2019

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One of the most common approaches for control of skin pigmentation involves the inhibition of tyrosinase, a copper-containing enzyme which catalyzes the key steps of melanogenesis. This review focuses on the tyrosinase inhibition properties of a series of natural and synthetic, bioinspired phenolic compounds that have appeared in the literature in the last five years. Both mushroom and human tyrosinase inhibitors have been considered. Among the first class, flavonoids, in particular chalcones, occupy a prominent role as natural inhibitors, followed by hydroxystilbenes (mainly resveratrol derivatives). A series of more complex phenolic compounds from a variety of sources, first of all belonging to the Moraceae family, have also been described as potent tyrosinase inhibitors. As to the synthetic compounds, hydroxycinnamic acids and chalcones again appear as the most exploited scaffolds. Several inhibition mechanisms have been reported for the described inhibitors, pointing to copper chelating and/or hydrophobic moieties as key structural requirements to achieve good inhibition properties. Emerging trends in the search for novel skin depigmenting agents, including the development of assays that could distinguish between inhibitors and potentially toxic substrates of the enzyme as well as of formulations aimed at improving the bioavailability and hence the effectiveness of well-known inhibitors, have also been addressed.

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“…None demonstrated [94] *Other topical preparations that have been proven effective and safe in melasma and to have an effect on active melanocytes are arbutin, azelaic acid 20%, kojic acid 2%, silymarin 1%-2%, glycolic acid 20%-70%, trichloroacetic acid 10%-20%, tretinoin 1%, salicylic acid 30%, lactic acid peel, and Jessner's peel [90][91][92][93]. Currently being developed for cancer treatment [33] compared to normal skin.…”

Section: Modulates P53 Expressionmentioning

confidence: 99%

The pathogenesis of melasma and implications for treatment

Artzi

Horovitz

Bar‐Ilan

et al. 2021

J of Cosmetic Dermatology

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Melasma is an acquired disorder of hyperpigmentation affecting millions of individuals worldwide. It is mostly observed in the facial area of darker-complexioned individuals (skin types IV-VI) exposed to intense ultraviolet (UV) radiation 1 and shorter wavelengths of visible light (VL). 2 At least 90% of those affected are women. 1 Melasma is characterized by symmetrically oriented hyperpigmented macules and patches, with varying presentations including blotchy, irregular, arcuate, and polycyclic. 3 One way of dividing the disorder into different subtypes is based on the distribution pattern: centrofacial (the most common), malar, and mandibular. Another division is

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Tyrosinase inhibitory study of flavonolignans from the seeds of Silybum marianum (Milk thistle)

Cited by 33 publications

References 23 publications

Chirality Matters: Biological Activity of Optically Pure Silybin and Its Congeners

Chirality Matters: Biological Activity of Optically Pure Silybin and Its Congeners

Natural and Bioinspired Phenolic Compounds as Tyrosinase Inhibitors for the Treatment of Skin Hyperpigmentation: Recent Advances

The pathogenesis of melasma and implications for treatment

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