Phytosphingosine

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Sanghee Kim - One of the best experts on this subject based on the ideXlab platform.

  • anti melanogenic activity of Phytosphingosine via the modulation of the microphthalmia associated transcription factor signaling pathway
    Journal of Dermatological Science, 2017
    Co-Authors: Eun Jeong Jang, Sanghee Kim, Yoonho Shin, Hyen Joo Park, Donghwa Kim, Cholomi Jung, Jiyoung Hong, Sang Kook Lee
    Abstract:

    Abstract Background Microphthalmia-associated transcription factor (MITF) suppresses the expression of enzymes controlling the production of melanin. Phytosphingosine is a well-known cosmetic agent, but its anti-melanogenic activity and mechanism of action remain unclear. Objective This study was designed to investigate the effects of Phytosphingosine on melanin synthesis and elucidate the plausible mechanism of actions in vitro and ex vivo systems. Methods Melanin content, cell viability, tyrosinase activity, p-CREB DNA binding activity, and the protein gene expression levels of the enzymes and proteins involved in melanogenesis were measured with the treatment of Phytosphingosine. Results Phytosphingosine inhibits melanin synthesis in cultured melan-a cells and a reconstructed human skin model. One possible mechanism of the anti-melanogenic activity of Phytosphingosine appears to be associated with the modulation of MITF, which suppresses the expression of tyrosinase, tyrosinase-related protein-1 (TRP-1), and TRP-2. Further analysis revealed that Phytosphingosine suppressed paired box 3 and SRY-related HMG-box 10, critical transcription factors of MITF. Phytosphingosine also effectively downregulated the protein levels of β-catenin and the phospho-cAMP response element binding protein, an upstream regulatory factor of MITF. These results are closely related to the suppression of MITF gene expression. In addition, treatment with Phytosphingosine for over 12 h, which is a relatively long period of time, did not directly suppress these MITF transcriptional factors. Instead, Phytosphingosine induced ERK activation, which led to MITF phosphorylation, followed by its degradation. Therefore, the downregulation of MITF protein levels by Phytosphingosine with a long time exposure is in part associated with MITF protein degradation through the MAPK kinase activation pathway. Conclusion The modulation of MITF by Phytosphingosine is closely related with the signaling pathways, such as the suppression of the MITF gene expression and the degradation of the MITF protein, depending on the duration of treatment time. These results suggest that Phytosphingosine might serve as an effective melanogenesis inhibitor in melanocytes via the regulation of the MITF signaling pathways.

  • Phytosphingosine derivatives ameliorate skin inflammation by inhibiting nf κb and jak stat signaling in keratincoytes and mice
    Journal of Investigative Dermatology, 2014
    Co-Authors: Byung Hak Kim, Sanghee Kim, Ji Min Lee, Yonggyu Jung, Taeyoon Kim
    Abstract:

    Phytosphingosine is abundant in plants and fungi and is found in mammalian epidermis, including the stratum corneum. Phytosphingosine and its derivatives N -acetyl Phytosphingosine and tetraacetyl Phytosphingosine are part of the natural defense system of the body. However, these molecules exhibit strong toxicities at high concentrations. We synthesized Phytosphingosine derivatives, mYG-II-6 (( Z )-4-oxo-4-(((2 S ,3 S ,4 R )-1,3,4-trihydroxyoctadecan-2-yl)amino)but-2-enoic acid) and fYG-II-6 (( E )-4-oxo-4-(((2 S ,3 S ,4 R )-1,3,4-trihydroxyoctadecan-2-yl)amino)but-2-enoic acid), to increase efficacy and decrease toxicity, and the biological activities of the derivatives in the inflammatory response were examined. Both YG-II-6 compounds effectively suppressed 12- O -tetradecanoylphorbol-13-acetate (TPA)–induced inflammatory skin damage and inflammatory response in a mouse model. In addition, topical application of fYG-II-6 suppressed ear swelling and psoriasiform dermatitis in the ears of IL-23-injected mice. Anti-inflammatory and antipsoriatic activities of the Phytosphingosine derivatives inhibited NF-κB, JAK/signal transducer and activator of transcription (JAK/STAT), and mitogen-activated protein kinase (MAPK) signaling. Finally, the YG-II-6 compounds induced programmed cell death in keratinocytes and mouse skin and were less toxic than Phytosphingosine. Our study demonstrated that the Phytosphingosine-derived YG-II-6 compounds have much stronger biological potencies than the lead compounds. The YG-II-6 compounds ameliorated inflammatory skin damage. Thus, YG-II-6 compounds are potential topical agents for treating chronic inflammatory skin diseases, such as psoriasis.

  • regioselective inversion of the hydroxyl group in d ribo Phytosphingosine via a cyclic sulfate and bis sulfonate intermediate
    Journal of Organic Chemistry, 2011
    Co-Authors: Yun Mi Lee, Dong Jae Baek, Seokwoo Lee, Deukjoon Kim, Sanghee Kim
    Abstract:

    The selective synthesis of d-xylo- and d-lyxo-Phytosphingosines from commercially available d-ribo-Phytosphingosine is described. Thermolysis of the N-carbonyl protected cyclic sulfate led to an in...

  • efficient and selective synthesis of d arabino d lyxo and d xylo Phytosphingosine from d ribo Phytosphingosine
    Journal of Organic Chemistry, 2008
    Co-Authors: Sanghee Kim, Nakyong Lee, Sukjin Lee, Taeho Lee, Yun Mi Lee
    Abstract:

    A new high-yield approach to the regio- and stereoselective synthesis of d-arabino-, d-lyxo-, and d-xylo-Phytosphingosines from inexpensive d-ribo-Phytosphingosine is described. The synthetic methodologies mainly rely on the selective configurational inversion of the stereocenter through a neighboring group participation mechanism.

  • synthesis of pachastrissamine from Phytosphingosine a comparison of cyclic sulfate vs an epoxide intermediate in cyclization
    Organic Letters, 2007
    Co-Authors: Taeho Lee, Deukjoon Kim, Sukjin Lee, Young Shin Kwak, Sanghee Kim
    Abstract:

    The syntheses of the cytotoxic natural product pachastrissamine and its unnatural 4-epi-congener were accomplished starting from a natural Phytosphingosine. The relatively unstrained cyclic sulfate intermediate smoothly underwent the 5-endo cyclization to yield the 2,3,4-trisubstituted tetrahydrofuran ring system of pachastrissamine. The corresponding epoxy alcohol afforded the 4-epi-congener via a tosylate-mediated double inversion process.

Deukjoon Kim - One of the best experts on this subject based on the ideXlab platform.

Luigi Panza - One of the best experts on this subject based on the ideXlab platform.

  • a versatile synthesis of αgalcer and its analogues exploiting a cyclic carbonate as Phytosphingosine 3 4 diol protecting group
    Carbohydrate Research, 2019
    Co-Authors: Luigi Panza, Federica Compostella, Daniela Imperio
    Abstract:

    Abstract A convenient synthetic strategy to αGalCer and some relevant analogues by using a handily protected Phytosphingosine is reported here. The conversion of the Phytosphingosine amino group to azide and the protection of 3,4-diol as cyclic carbonate group, cleavable in mild basic conditions but resistant to acidic treatment, afforded quickly an excellent glycosyl acceptor. Its glycosylation with a proper galactosyl donor, gave a versatile intermediate in high yield and excellent stereoselectivity. To demonstrate the potentiality of the intermediate, three immunologically relevant compounds were chosen as model targets: αGalCer, dansyl alpha-galactosylceramide and 7DW8-5. These products were easily obtained in few steps and high yields to validate the synthetic route.

  • A versatile synthesis of αGalCer and its analogues exploiting a cyclic carbonate as Phytosphingosine 3,4-diol protecting group
    'Elsevier BV', 2019
    Co-Authors: Luigi Panza, Federica Compostella, Daniela Imperio
    Abstract:

    A convenient synthetic strategy to \u3b1GalCer and some relevant analogues by using a handily protected Phytosphingosine is reported here. The conversion of the Phytosphingosine amino group to azide and the protection of 3,4-diol as cyclic carbonate group, cleavable in mild basic conditions but resistant to acidic treatment, afforded quickly an excellent glycosyl acceptor. Its glycosylation with a proper galactosyl donor, gave a versatile intermediate in high yield and excellent stereoselectivity. To demonstrate the potentiality of the intermediate, three immunologically relevant compounds were chosen as model targets: \u3b1GalCer, dansyl alpha-galactosylceramide and 7DW8-5. These products were easily obtained in few steps and high yields to validate the synthetic route

  • protected sphingosine from Phytosphingosine as an efficient acceptor in glycosylation reaction
    Organic Letters, 2014
    Co-Authors: Roberta Di Benedetto, Luca Zanetti, Monica Varese, Mehdi Rajabi, Riccardo Di Brisco, Luigi Panza
    Abstract:

    A convenient, simple, and high-yielding five-step synthesis of a sphingosine acceptor from Phytosphingosine is reported, and its behavior in glycosylation reactions is described. Different synthetic paths to sphingosine acceptors using tetrachlorophthalimide as a protecting group for the sphingosine amino function and different glycosylation methods have been explored. Among the acceptors tested, the easiest accessible acceptor, unprotected on the two hydroxyl groups in positions 1 and 3, was regioselectively glycosylated on the primary position, the regioselectivity depending on the donor used.

Andrew Sutherland - One of the best experts on this subject based on the ideXlab platform.

Daniela Imperio - One of the best experts on this subject based on the ideXlab platform.

  • a versatile synthesis of αgalcer and its analogues exploiting a cyclic carbonate as Phytosphingosine 3 4 diol protecting group
    Carbohydrate Research, 2019
    Co-Authors: Luigi Panza, Federica Compostella, Daniela Imperio
    Abstract:

    Abstract A convenient synthetic strategy to αGalCer and some relevant analogues by using a handily protected Phytosphingosine is reported here. The conversion of the Phytosphingosine amino group to azide and the protection of 3,4-diol as cyclic carbonate group, cleavable in mild basic conditions but resistant to acidic treatment, afforded quickly an excellent glycosyl acceptor. Its glycosylation with a proper galactosyl donor, gave a versatile intermediate in high yield and excellent stereoselectivity. To demonstrate the potentiality of the intermediate, three immunologically relevant compounds were chosen as model targets: αGalCer, dansyl alpha-galactosylceramide and 7DW8-5. These products were easily obtained in few steps and high yields to validate the synthetic route.

  • A versatile synthesis of αGalCer and its analogues exploiting a cyclic carbonate as Phytosphingosine 3,4-diol protecting group
    'Elsevier BV', 2019
    Co-Authors: Luigi Panza, Federica Compostella, Daniela Imperio
    Abstract:

    A convenient synthetic strategy to \u3b1GalCer and some relevant analogues by using a handily protected Phytosphingosine is reported here. The conversion of the Phytosphingosine amino group to azide and the protection of 3,4-diol as cyclic carbonate group, cleavable in mild basic conditions but resistant to acidic treatment, afforded quickly an excellent glycosyl acceptor. Its glycosylation with a proper galactosyl donor, gave a versatile intermediate in high yield and excellent stereoselectivity. To demonstrate the potentiality of the intermediate, three immunologically relevant compounds were chosen as model targets: \u3b1GalCer, dansyl alpha-galactosylceramide and 7DW8-5. These products were easily obtained in few steps and high yields to validate the synthetic route

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