Depigmenting activity of new kojic acid derivative obtained as a side product in the synthesis of cinnamate of kojic acid

Cho, Jun-Cheol; Rho, Ho Sik; Baek, Hye Jin; Ahn, Soo Mi; Woo, Byoung Young; Hong, Yong Deog; Cheon, Jong Woo; Heo, Jung Mi; Shin, Song Seok; Suh, Kyung‐Do

doi:10.1016/j.bmcl.2012.01.032

Cited by 28 publications

(8 citation statements)

References 14 publications

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“…To determine the appropriate non-cytotoxic concentration of various compounds including SG and newly selected derivatives (KCED-1 and KCED-2) (Figure 1), hSCFs were treated with each compound and cell viability was measured at 24 and 72 h. KA and cinnamic acid (CA), which are structural moieties for KCEDs [10], and glibenclamide (GC), a well-known adiponectin inducer [13], were used as negative or positive controls. These control compounds did not cause severe changes in cell viability at tested concentrations (Figure 2).…”

Section: Resultsmentioning

confidence: 99%

“…Previously, we synthesized kojyl cinnamate ester derivatives (KCEDs) via the sequential reaction of kojic acid (KA) with thionyl chloride and then with 3,4-(methylenedioxy) cinnamic acid (CA), generating Seletinoid G (SG; Compound 4b) [10,11], which shows anti-aging activity and promotes APN production in adipose tissue-derived stem cells (ADSCs) [11,12]. Similar to SG, two derivatives (Compounds 4a and 4c) were verified to show improved activity for APN production during adipogenesis, importantly indicating that an α,β-unsaturated carbonyl ester structure and intact KA moiety in the derivatives are essential for promoting adipogenesis.…”

Section: Introductionmentioning

confidence: 99%

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Kojyl Cinnamate Ester Derivatives Increase Adiponectin Expression and Stimulate Adiponectin-Induced Hair Growth Factors in Human Dermal Papilla Cells

Park

Cho

2019

IJMS

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Adiponectin (APN), released mainly from adipose tissue, is a well-known homeostatic factor for regulating glucose levels, lipid metabolism, and insulin sensitivity. A recent study showed that human hair follicles express APN receptors and the presence of APN-mediated hair growth signaling, thereby suggesting that APN is a potent hair growth-promoting adipokine. Previously, kojyl cinnamate ester derivatives (KCEDs) were synthesized in our institute as new anti-aging or adiponectin-/adipogenesis-inducing compounds. Here, we tested the activity of these derivatives to induce endogenous APN secretion. Among the derivatives, KCED-1 and KCED-2 showed improved activity in inducing APN mRNA expression, secretion of APN protein, and adipogenesis in human subcutaneous fat cells (hSCFs) when compared with the effects of Seletinoid G, a verified APN inducer. When human follicular dermal papilla cells were treated with the culture supernatant of KCED-1- or KCED-2-treated hSCFs, the mRNA expression of APN-induced hair growth factors such as insulin-like growth factor, hepatocyte growth factor, and vascular endothelial growth factor was upregulated compared with that in the control. Taken together, our study shows that among kojyl cinnamate ester derivatives, KCED-1, KCED-2, as well as Seletinoid G are effective inducers of endogenous APN production in subcutaneous fat tissues, which may in turn contribute to the promotion of hair growth in the human scalp.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Kojyl Cinnamate Ester Derivatives Increase Adiponectin Expression and Stimulate Adiponectin-Induced Hair Growth Factors in Human Dermal Papilla Cells

Park

Cho

2019

IJMS

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“…It is known to be capable of preventing excess melanogenesis by inhibiting tyrosinase via chelation of two copper ions in the active site of the enzyme. Therefore, KA is employed as an ingredient of dermocosmetics used for the treatment of hyperpigmentation of the skin (Cho et al, ; Kahn, Ben‐Shalom, & Zakin, ; Sharma & Davids, ; Wang et al, ). Numerous other studies proved that KA and its derivatives also exhibit anti‐oxidant, anti‐neoplastic, anti‐inflammatory, anti‐bacterial, anti‐viral, anti‐convulsant, anti‐tyrosinase, and anti‐aging properties (Aytemir & Calis, ; Aytemir & Ozcelik, ; Aytemir, Ozcelik, Erdogan, Karakaya, & Senol, ; Aytemir, Septioglu, & Calis, ; Dung et al, ; Karakaya, Ercan, Oncul, & Aytemir, ; Mohammadpour, Behjati, Sadeghi, & Fassihi, ; Rho et al, ; Smith & Lindsay, ; Zhang et al, ).…”

Section: Introductionmentioning

confidence: 99%

A kojic acid derivative promotes intrinsic apoptotic pathway of hepatocellular carcinoma cells without incurring drug resistance

et al. 2019

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Hepatocellular carcinoma is one of the most pervasive cancers with low prognosis, high frequency of recurrence, and metastasis. Studies conducted have focused on extricating novel strategies for successful treatment. Kojic acid and its derivatives are already proven to have depigmenting, anti‐inflammatory, and anti‐neoplastic properties. In the present study, kojic acid and its 10 distinct derivatives were tested on HEPG2 cell line for their possible anti‐cancer effect and seven of them were observed to be cytotoxic. Compound 6 was chosen to proceed as the IC50 dosage for HEPG2 cells was lower in comparison with the other derivatives and kojic acid itself. Further experiments pointed out that intrinsic apoptotic pathway was triggered with the exposure of the cells to IC50 concentration of the derivative as the treatment led to escalation of intracellular ROS, induction of TP53 gene, and activation of caspase 3/7. Pro‐apoptotic Jnk and Bax genes were not triggered suggesting that the apoptotic pathway advance through an alternative route. Complementary experiments are in need; howbeit, the current findings suggest that the derivative offers a novel promising approach against hepatocellular carcinoma as it is not detrimental to healthy cells within the concentrations applied, and it does not induce drug resistance.

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“…The excessive accumulation of melanin can lead to hyperpigmentation or even skin cancer (2,3). Many inhibitors of melanin synthesis have been isolated from natural sources, including flavonoids, kojic acid, arbutin, and hydroquinone (4)(5)(6)(7)(8)(9). Previous findings have shown that arbutin increases the pigmentation of cultured human melanocytes, while kojic acid has toxic and mutagenic effects when used for prolonged periods of time (10)(11)(12).…”

Section: Introductionmentioning

confidence: 99%

Berberine regulates melanin synthesis by activating PI3K/AKT, ERK and GSK3β in B16F10 melanoma cells

Song

Lee

Kim

et al. 2015

International Journal of Molecular Medicine

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Berberine, an isoquinoline alkaloid, has a wide range of beneficial properties, including anti-bacterial, anti-inflammatory, anti-cancer, and cholesterol-lowering effects. Recently findings suggest that berberine improves glucose and lipid metabolism disorders. In the present study, we examined the mechanism underlying the inhibitory effect of berberine on α-melanocyte-stimulating hormone (α-MSH)-stimulated B16F10 melanoma cells. The results showed that berberine attenuated α-MSH induction of the microphthalmia-associated transcription factor (MITF) and tyrosinase in a dose-dependent manner. To elucidate the mechanism underlying the inhibitory effect of berberine, we examined the effect of α-MSH-stimulated phosphorylation of PI3K/AKT, ERK, and GSK3β. The results showed that treatment with berberine resulted in a reduction in the phosphorylation of PI3K/AKT, ERK, and GSK3β. Taken together, the results suggested that berberine inhibits melanin synthesis and tyrosinase activity by downregulating the expression of MITF and tyrosinase. Thus, these findings may contribute to the potential application of berberine in the prevention and treatment of skin pigmentation disorders.

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Depigmenting activity of new kojic acid derivative obtained as a side product in the synthesis of cinnamate of kojic acid

Cited by 28 publications

References 14 publications

Kojyl Cinnamate Ester Derivatives Increase Adiponectin Expression and Stimulate Adiponectin-Induced Hair Growth Factors in Human Dermal Papilla Cells

Kojyl Cinnamate Ester Derivatives Increase Adiponectin Expression and Stimulate Adiponectin-Induced Hair Growth Factors in Human Dermal Papilla Cells

A kojic acid derivative promotes intrinsic apoptotic pathway of hepatocellular carcinoma cells without incurring drug resistance

Berberine regulates melanin synthesis by activating PI3K/AKT, ERK and GSK3β in B16F10 melanoma cells

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