Linoleic acid and α-linolenic acid lightens ultraviolet-induced hyperpigmentation of the skin

Ando, Hironori; Ryu, Atsuko; Hashimoto, Akira; Oka, Masahiro; Ichihashi, Masamitsu

doi:10.1007/s004030050320

Cited by 163 publications

(101 citation statements)

References 28 publications

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“…Accordingly, melanogenesis is inhibited most effectively by a-linolenic acid, followed by linoleic acid and then oleic acid. 9) Consistent with these findings, the results of the present study revealed that methyl and ethyl linolenates exerted higher inhibitory activity against melanin synthesis than methyl and ethyl linoleates. In addition, these results suggest that methyl and ethyl group may act as a negative factor in the antimelanogenic effect.…”

Section: Resultssupporting

confidence: 91%

“…8) We found that Oxalis triangularis contains melanin biosynthesis inhibitors, which were isolated and identified as methyl linoleate, ethyl linoleate, methyl linolenate and ethyl linolenate. It has been reported that unsaturated fatty acids such as oleic acid, linoleic acid and alinolenic acid decrease melanin synthesis and tyrosinase activity, 9) and that these inhibitory effects occur in proportion to the number of unsaturated bonds. Accordingly, melanogenesis is inhibited most effectively by a-linolenic acid, followed by linoleic acid and then oleic acid.…”

Section: Resultsmentioning

confidence: 99%

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Melanogenesis Inhibitory Effect of Fatty Acid Alkyl Esters Isolated from Oxalis triangularis

Huh

Kim

Jung

et al. 2010

Biological & Pharmaceutical Bulletin

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Oxalis triangularis (purple shamrock or purple clover) in the family Oxalidaceae is an edible perennial plant that is easily cultivated. The leaves of Oxalis triangularis are especially appreciated due to their sour and exotic taste. Oxalis triangularis has intensely purple leaves with a monomeric anthocyanin content of 195 mg/100 g on a malvidin 3,5-diglucoside basis, which makes them a potential source of natural colorants.1) Additionally, it is known that treatment with the flavones, C-glycosides, as copigments effects the color and stability of anthocyanins. [2][3][4][5] To date, no studies have been conducted to investigate the inhibitory effect of Oxalis triangularis on melanogenesis. In this study, the fatty acid alkyl esters methyl linoleate, methyl linolenate, ethyl linoleate and ethyl linolenate from Oxalis triangularis were shown to play an active role in inhibition of the cellular production on melanin. MATERIALS AND METHODS General Methods1 H-and 13 C-NMR spectral data were determined using a Varian Unity Inova 500NB NMR instrument (500 MHz) using CDCl 3 as the solvent and tetramethylsilane (TMS) as an internal standard. The chemical shifts were reported in d (ppm) units relative to the TMS signal and coupling constants (J) in Hz. Gas chromatography-mass spectrometry (GC-MS) and GC-selected ion monitoring (SIM) were conducted using a 5972 Plus mass spectrometer (electron impact ionization, 70 electron volt, HewlettPackard, Palo Alto, CA, U.S.A.) connected to a 5890 gas chromatograph fitted with a fused silica capillary column (HP-5, 0.25ϫ30 m, 0.25 mm film thickness, HewlettPackard). The GC-conditions were as follows: on-column injection mode, He 1 ml/min; oven temperature 60°C for 2 min; and thermal gradient, 10°C/min to 260°C. Medium pressure liquid chromatography (MPLC) was conducted using a Combiflash Companion instrument with an UV/Vis detector (Teledyne ISCO, Inc., U.S.A.). Preparative HPLC (High Pressure Liquid Chromatography) was conducted Extraction and Isolation Whole bodies of Oxalis triangularis (1.6 kg dry weight) were homogenized and extracted with 80% ethanol (30 lϫ3). The extracts were then concentrated in vacuo, after which they were re-extracted with chloroform (2 lϫ3). After reducing to dryness in vacuo, the chloroform fraction (138 g) was solvent-partitioned between nhexane and 80% methanol (2 lϫ3). The concentrated nhexane soluble fraction (57.58 g) was then purified by silica gel column chromatography (100 g, Merck) and eluted stepwise with chloroform containing 0, 1, 2, 10 and 100% methanol (1 l each). The fractions eluted in 0% and 1% methanol in chloroform were combined and concentrated in vacuo (17.32 g), after which they were subjected to MPLC (RediSep, silica 40 g, 30ϫ140 mm; detection, UV at 254 nm; flow rate, 40 ml/min). The elution was performed stepwise in chloroform-methanol (0%, 2%, 10%, 100% methanol) for 10 min each to give 40 subfractions. Fraction 4 was subjected to reversed phase preparative HPLC (Phenomenex Luna C18(2), 21.2ϫ250 mm, 5 mm) and eluted with 40% a...

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Section: Resultssupporting

confidence: 91%

Section: Resultsmentioning

confidence: 99%

Melanogenesis Inhibitory Effect of Fatty Acid Alkyl Esters Isolated from Oxalis triangularis

Huh

Kim

Jung

et al. 2010

Biological & Pharmaceutical Bulletin

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“…GR was obtained from Sigma Chemical Co. (St. Louis, U.S.A.) and GA from Aldrich Chemical Co. (Milwaukee, U.S.A.). The cells were harvested three days later and the melanin contents and tyrosinase activities were determined in triplicate for each treatment (Ando et al, 1998).…”

Section: Cell Culturementioning

confidence: 99%

Stimulation of melanogenesis by glycyrrhizin in B16 melanoma cells

Jung

Yang²,

Song³

et al. 2001

Exp Mol Med

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Glycyrrhizin (GR), triterpenoid saponin composed of one glycyrrhetinic acid (GA) and two glucuronic acids, is a main constituent of the hydrophilic fraction of licorice (Glycyrrhiza glabra) extracts and is known to have a wide range of pharmacological actions. In this study, we investigated the mechanism of GR effect on melanogenesis in B16 murine melanoma cells. The cellular levels of tyrosinase mRNA, protein, enzyme activities and melanin contents were increased by GR in a dose dependent manner. Expression of tyrosinase-related protein-2 (TRP-2) mRNA was also increased by GR, however, no significant change was observed on TRP-1. No cytotoxicity was observed at the effective concentration range of GR. GA showed no effect on melanogenesis at the equivalent nontoxic concentrations, indicating that glycoside structure is important in the stimulatory effect of GR on melanogenesis. These results indicate that GR-induced stimulation of melanogenesis is likely to occur through the transcriptional activation.

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“…We previously reported the skin whitening effect of linoleic acid (LA), 1,2) the mechanism of the whitening effect involving a decrease in tyrosinase level by LA, 3) and clinical trials of liposomal LA for skin hyperpigmentary disorders, such as melasma. 4) Although these reports described the whitening effect of LA in transdermal application, and the stabilization of LA by liposomal formulation, it was not confirmed whether LA encapsulated in liposomes enhanced the skin whitening effect.…”

mentioning

confidence: 99%

Skin Whitening Effect of Linoleic Acid Is Enhanced by Liposomal Formulations

Shigeta

Imanaka²,

Ando³

et al. 2004

Biological & Pharmaceutical Bulletin

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Hyperpigmentation on faces is a highly anxiety-producing symptom, especially for women from the aspect of beauty. We previously reported the skin whitening effect of linoleic acid (LA), 1,2) the mechanism of the whitening effect involving a decrease in tyrosinase level by LA, 3) and clinical trials of liposomal LA for skin hyperpigmentary disorders, such as melasma.4) Although these reports described the whitening effect of LA in transdermal application, and the stabilization of LA by liposomal formulation, it was not confirmed whether LA encapsulated in liposomes enhanced the skin whitening effect. There have been number of reports that describe transdermal application using liposomes on cutaneous absorption, 5-7) on the transdermal delivey of encapsulated drugs 8) and on effective interaction of dermal skin cells with liposomes containing drugs in liposomes.9-11) The synergistic effect of liposomes on active reagents for whitening via transdermal application was also reported.12) Compared to those reagents previously reported, LA is not only effective in whitening but also quite safe.13) Although there are many examples of the transdermal applications of liposomal formulations, little is known about the enhancement of drug efficacy by liposomalization. From this point of view, we were interested in the possible enhancement of LA's whitening activity by encapsulating it in liposomes. The present study clearly demonstrated that LA encapsulation in liposomes significantly enhanced it's whitening efficacy by transdermal application for UV-induced hyperpigmented dorsal skin of brownish guinea pigs. We also observed enhanced whitening efficacy by liposomalization of LA in UV-induced hyperpigmented human skin. MATERIALS AND METHODSWhitening Assay UVB-induced hyperpigmentation was elicited on the backs of brownish guinea pigs weighing about 600 g each (Saitama Experimental Animal Supply Co., Japan) using a modification of the method reported by Imokawa et al.14) Guinea pigs were gently tethered, and four separate areas (2.5 cmϫ2 cm) on the back of each animal were exposed to UVB radiation (ToRex FL20S-E-30/DMR, Toshiba, Japan) three times a week (every other day) for two consecutive weeks. The UVB intensity was 2 mW/cm 2 , and total energy dose was 1 J/cm 2 per exposure. Groups of six or more animals were used in each experiment. The animals were then left for an additional week to allow the UVBinduced hyperpigmentation to stabilize. Test samples were then topically applied daily to the hyperpigmented areas (0.01 ml/cm 2 ) five times per week for 3 successive weeks. The degree of pigmentation was assessed as the L-value measured with a chromameter (CR-200, Minolta, Japan) once every week from the beginning of sample application. The animals were cared for according to the guidelines for the Care and Use of Laboratory Animals of the University of Shizuoka.In the case of human skin assay, persons being tested were 6 healthy men in their 20 s or 30 s. After obtaining informed consents from the volunteers, UVB-induced hyp...

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Linoleic acid and α-linolenic acid lightens ultraviolet-induced hyperpigmentation of the skin

Cited by 163 publications

References 28 publications

Melanogenesis Inhibitory Effect of Fatty Acid Alkyl Esters Isolated from Oxalis triangularis

Melanogenesis Inhibitory Effect of Fatty Acid Alkyl Esters Isolated from Oxalis triangularis

Stimulation of melanogenesis by glycyrrhizin in B16 melanoma cells

Skin Whitening Effect of Linoleic Acid Is Enhanced by Liposomal Formulations

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