MOLECULAR INTERACTION OF CURCUMIN, DEMETHOXYCURCUMIN, BISDEMETHOXYCURCUMIN, AND TURMERONE OF Curcuma longa WITH TYROSINASE AND TYROSINASE-RELATED PROTEIN-1

Firmansyah, Deni; Sumiwi, Sri Adi; Saptarini, Nyi Mekar; Levita, J.

doi:10.31788/rjc.2021.1446418

Cited by 6 publications

(4 citation statements)

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“…Two residues, Arg209 and Val218, located in the second outer layer of the active site, function a role in the binding of tyrosine (23). Our preliminary in silico study visualized that curcumin and other phenolic constituents of C. longa bound to tyrosinase and tyrosinase-related protein-1 with binding modes similar to those of kojic acid (24).…”

Section: Discussionmentioning

confidence: 78%

Curcuma longa extract inhibits the activity of mushroom tyrosinase and the growth of murine skin cancer B16F10 cells

Firmansyah

Sumiwi

Saptarini

et al. 2022

J Herbmed Pharmacol

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Introduction: Tyrosinase is considered an important target of melanin biosynthesis inhibitors. Curcuma longa L. has been used in the Javanese traditional whitening cosmetics. This work aimed to explore the effect of C. longa extracts on mushroom tyrosinase activity and the cytotoxicity of the extract towards murine skin cancer B16F10 cells. Methods: C. longa rhizomes were cold-extracted using ethanol 70% and yielded 15.3% w/w of extract (ECL). The presence of curcuminoids in ECL was determined by reversed-phase high-performance liquid chromatography (RP-HPLC). ECL was assessed for its inhibitory effects on mushroom tyrosinase activity using L-DOPA as substrate and kojic acid as the positive control drug. The cytotoxicity of ECL and curcumin was studied in B16F10 cells. Results: Triplet peaks of RP-HPLC chromatogram revealed that curcuminoids were available in ECL. The level of bisdemethoxycurcumin was 6.3306% (tR = 12.646 minutes), demethoxycurcumin was 3.1414% (tR = 13.675 minutes), and curcumin was 8.3754% (tR = 14.802 minutes). ECL had a weak inhibitory activity towards mushroom tyrosinase with IC50 = 564.8 µg/mL, while the IC50 = of kojic acid was 55.70 µg/mL. Both ECL and kojic acid had moderate toxicity to B16F10 cells (IC50 survival growth rates were 98.06 µg/mL and 65.54 µg/ mL, respectively). Curcumin was highly toxic to B16F10 cells (IC50 = 14.42 µg/mL). Conclusion: Taken together, ECL might be able to prevent melanogenesis via the inhibition of tyrosinase activity, and interestingly, it could inhibit the growth of murine skin cancer B16F10 cells. However, further studies are needed to verify its antimelanogenesis and anticancer properties.

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Section: Discussionmentioning

confidence: 78%

Curcuma longa extract inhibits the activity of mushroom tyrosinase and the growth of murine skin cancer B16F10 cells

Firmansyah

Sumiwi

Saptarini

et al. 2022

J Herbmed Pharmacol

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“…Notwithstanding these reports, the potent depigmentation effects of BDC in the absence of toxicity were confirmed in hormone-stimulated B16F10 cells and in an in vivo model of zebrafish in a recently published study [39]. In a previous study [70], the results of the molecular docking investigations using PC, DC, and BDC in conjunction with a bacterial tyrosinase revealed that all three compounds had binding capabilities towards tyrosinase and another melanogenic enzyme, namely, tyrosinase-related protein-1 (TRP-1). Notably, it was shown that their binding mechanisms closely resembled those of kojic acid.…”

Section: Discussionmentioning

confidence: 79%

Comparative Study of the Effects of Curcuminoids and Tetrahydrocurcuminoids on Melanogenesis: Role of the Methoxy Groups

Goenka

2024

Future Pharmacology

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Curcuminoids are naturally occurring yellow-colored compounds that, when hydrogenated to remove their conjugated double bond, become colorless and are referred to as tetrahydrocurcuminoids. Curcuminoids consist of pure curcumin (PC) in major amounts and demethoxycurcumin (DC) and bisdemethoxycurcumin (BDC) in minor amounts. Tetrahydrocurcuminoids similarly consist mainly of tetrahydrocurcumin (THC), along with minor amounts of tetrahydrodemethoxycurcumin (THDC) and tetrahydrobisdemethoxycurcumin (THBDC). Previous studies have shown the inhibitory effects of PC, DC, and BDC on melanin production, but there are contradictory findings about THC. In addition, there are currently no reports on the effects of THDC and THBDC on melanogenesis. Our previous report described that, in contrast to PC, which suppressed melanin production, THC stimulated melanin production in B16F10 and MNT-1 cells; this effect was ascribed to the loss of the conjugated heptadiene moiety of PC. However, whether this finding can be generalized to the two curcumin derivatives (DC and BDC), such that THDC and THBDC might also stimulate melanogenesis, has not been addressed. Herein, a comparative study of six curcumin derivatives (PC, DC, BDC, THC, THDC, and THBDC) was undertaken to identify their effects on melanogenesis with the goal of elucidating the structure–activity relationships (SARs) focused on assessing the two regions of the parent curcumins’ structure: (i) the hydrogenation of the two double bonds bridging the phenyl rings to the β-diketone moiety, and (ii) the effect of the ortho-methoxy substituent (-OCH3) on the two phenyl rings. To determine the direct effects of the six compounds, antioxidant activity and tyrosinase activity were assessed in cell-free systems before cellular experiments utilizing the B16F10 mouse melanoma cells, MNT-1 human melanoma cells, and primary cells. Evaluations were made on cytotoxicity, melanin concentration, and cellular tyrosinase activity. The results showed that BDC inhibited melanogenesis in B16F10 and MNT-1 cells. However, it was ineffective in primary human melanocytes, while THBDC continued to exhibit anti-melanogenic capacity in normal human melanocytes. Moreover, these findings provide a novel perspective into the role of the methoxy groups of PC on the biological effects of melanogenesis and also confirm that the removal of the conjugated double bonds abolishes the anti-melanogenic capacity of PC and DC only, but not BDC, as THBDC maintained anti-melanogenic activity that was greater than BDC. However, the outcome is contingent upon the specific kind of cell involved. To the best of our knowledge, this work presents novel findings indicating that the anti-melanogenic capacity of the colored BDC is not only intact but enhanced after its hydrogenation as observed in THBDC. The findings show potential for using colorless THBDC as a pharmacological candidate to diminish the increased pigmentation characteristic of skin hyperpigmentation disorders. Future pharmacological therapeutics that incorporate pure THBDC or THBDC-enriched extracts, which retain both a colorless appearance and potent anti-melanogenic activity, can be applied to compounds for anti-melanoma therapeutics where the demand for nontoxic novel molecules is desired for established efficacies.

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“…To date, there are no reports on the enzyme-inhibitory activity of C. alismatifolia essential oil. Extensive studies on tyrosinase inhibitors in C. longa have been made at in silico, in vitro and in vivo levels [63][64][65][66], whereas the remaining species have only been worked on a basic level. Thus, the present observations about the three Curcuma species might improve our knowledge on the anti-tyrosinase activity of different species of the genus Curcuma and lead to the development of plant-based skin whitening cosmetics.…”

Section: Anti-tyrosinase Activitymentioning

confidence: 99%

Variation in Yield, Chemical Composition and Biological Activities of Essential Oil of Three Curcuma Species: A Comparative Evaluation of Hydrodistillation and Solvent-Free Microwave Extraction Methods

et al. 2023

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The essential oils of three medicinally important Curcuma species (Curcuma alismatifolia, Curcuma aromatica and Curcuma xanthorrhiza) were extracted using conventional hydro-distillation (HD) and solvent free microwave extraction (SFME) methods. The volatile compounds from the rhizome essential oils were subsequently analysed by GC–MS. The isolation of essential oils of each species was carried out following the six principles of green extraction and comparison was made between their chemical composition, antioxidant, anti-tyrosinase and anticancer activities. SFME was found to be more efficient than HD in terms of energy savings, extraction time, oil yield, water consumption and waste production. Though the major compounds of essential oils of both the species were qualitatively similar, there was a significant difference in terms of quantity. The essential oils extracted through HD and SFME methods were dominated by hydrocarbon and oxygenated compounds, respectively. The essential oils of all Curcuma species exhibited strong antioxidant activity, where SFME was significantly better than HD with lower IC50 values. The anti-tyrosinase and anticancer properties of SFME-extracted oils were relatively better than that of HD. Further, among the three Curcuma species, C. alismatifolia essential oil showed the highest rates of inhibition in DPPH and ABTS assay, significantly reduced the tyrosinase activity and exhibited significant selective cytotoxicity against MCF7 and PC3 cells. The current results suggested that the SFME method, being advanced, green and fast, could be a better alternative for production of essential oils with better antioxidant, anti-tyrosinase and anticancer activities for application in food, health and cosmetic industries.

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MOLECULAR INTERACTION OF CURCUMIN, DEMETHOXYCURCUMIN, BISDEMETHOXYCURCUMIN, AND TURMERONE OF Curcuma longa WITH TYROSINASE AND TYROSINASE-RELATED PROTEIN-1

Cited by 6 publications

References 0 publications

Curcuma longa extract inhibits the activity of mushroom tyrosinase and the growth of murine skin cancer B16F10 cells

Curcuma longa extract inhibits the activity of mushroom tyrosinase and the growth of murine skin cancer B16F10 cells

Comparative Study of the Effects of Curcuminoids and Tetrahydrocurcuminoids on Melanogenesis: Role of the Methoxy Groups

Variation in Yield, Chemical Composition and Biological Activities of Essential Oil of Three Curcuma Species: A Comparative Evaluation of Hydrodistillation and Solvent-Free Microwave Extraction Methods

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