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Melanogenesis inhibitors from the desert plant Anastatica hierochuntica in B16 melanoma cells.

Bioorganic & medicinal chemistry (2010-03-02)
Souichi Nakashima, Hisashi Matsuda, Yoshimi Oda, Seikou Nakamura, Fengming Xu, Masayuki Yoshikawa
ABSTRACT

The methanolic extract from the whole plants of Anastatica hierochuntica, an Egyptian herbal medicine, was found to inhibit melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells. Among the constituents isolated, anastatin A, silybin A, isosilybins A and B, eriodictyol, luteolin, kaempferol, quercetin, hierochins A and B, (2R,3S)-2,3-dihydro-2-(3,4-dimethoxyphenyl)-3-hydroxymethyl-5-(2-formylvinyl)-7-hydroxybenzofuran, (+)-dehydrodiconiferyl alcohol, (+)-balanophonin, 1-(4-hydroxy-3-methoxyphenyl)-2-{4-[(E)-3-hydroxy-1-propenyl]-2-methoxyphenoxy}-1,3-propanediol, and 3,4-dihydroxybenzaldehyde substantially inhibited melanogenesis with IC(50) values of 6.1-32 microM. With regard to the mechanism of action of silybins and isosilybins, the inhibition of tyrosinase activity suggested to be important. In addition, isosilybins A and B inhibited the mRNA expression of TRP-2, but silybins A and B oppositely enhanced the mRNA expression of tyrosinase and TRP-1 and -2 at 10 and/or 30 microM, and the inhibition of phosphorylation of extracellular signal-regulated kinases (ERK1/2) is involved in the enhanced expression of mRNA, at least in part, similar to that of PD98059.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Vanillin, ReagentPlus®, 99%
Sigma-Aldrich
trans-Cinnamic acid, ≥99%
Sigma-Aldrich
trans-Ferulic acid, 99%
Sigma-Aldrich
4-Hydroxybenzaldehyde, 98%
Sigma-Aldrich
Kaempferol, ≥97.0% (HPLC)
Sigma-Aldrich
4-Hydroxybenzoic acid, ReagentPlus®, ≥99%
Sigma-Aldrich
4-Hydroxybenzoic acid, ReagentPlus®, 99%
Sigma-Aldrich
Luteolin, ≥98% (TLC), powder
Sigma-Aldrich
Vanillin, natural, ≥97%, FCC, FG
Sigma-Aldrich
3,4-Dihydroxybenzoic acid, ≥97.0% (T)
Sigma-Aldrich
Vanillin, ≥97%, FCC, FG
Sigma-Aldrich
Kaempferol, ≥90% (HPLC), powder
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Vanillic acid, purum, ≥97.0% (HPLC)
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Kojic acid
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3,4-Dihydroxybenzaldehyde, 97%
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Vanillic acid, 97%
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trans-Cinnamic acid, 97%
Sigma-Aldrich
4-Methoxybenzoic acid, ReagentPlus®, 99%
Sigma-Aldrich
trans-Cinnamic acid, natural, ≥99%, FCC, FG
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trans-Ferulic acid, ≥99%
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4′-Hydroxy-3′-methoxyacetophenone, 98%
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4-Hydroxybenzaldehyde, ≥97%, FG
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Acetovanillone, ≥98%, FG
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Vanillin, tested according to Ph. Eur.
Supelco
Mettler-Toledo Calibration substance ME 51143093, Vanillin, traceable to primary standards (LGC)
Supelco
Melting point standard 182-184°C, analytical standard
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Vanillic acid, ≥97%, FG
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p-Anisic acid, ≥99%, FG
Supelco
trans-Ferulic acid, matrix substance for MALDI-MS, ≥99.0% (HPLC)
Sigma-Aldrich
trans-Cinnamic acid, ≥99%, FG