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杜鹃醇对映体在人皮肤匀浆中的代谢

Metabolism of Enantiomers of Rhododendrol in Human Skin Homogenate.

作者信息

Gu Lihao, Maeda Kazuhisa

机构信息

Bionics Program, Tokyo University of Technology Graduate School, 1404-1 Katakura-machi, Hachioji City 192-0982, Tokyo, Japan.

School of Bioscience and Biotechnology, Tokyo University of Technology, 1404-1 Katakura-machi, Hachioji City 192-0982, Tokyo, Japan.

出版信息

Metabolites. 2022 May 3;12(5):412. doi: 10.3390/metabo12050412.

DOI:10.3390/metabo12050412
PMID:35629916
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9143848/
Abstract

We reported that raspberry ketone (RK) is produced from rhododendrol (RD) in excised mouse skin. We confirmed that RK is also produced from RD in human skin homogenates. We also observed more conversion of RD to RK when the oxidized form of nicotinamide adenine dinucleotide (NAD), a coenzyme of alcohol dehydrogenase (ADH), was added to human skin homogenates. Chiral column analysis of the consumption of RD enantiomers in human skin homogenates also showed that more of the R enantiomers of RD remained than the S enantiomers of RD. This suggests that the S-enantiomer of RD is more easily oxidized in human skin. We confirmed that RD is partially metabolized to RK in human skin, thus suggesting that ADH in the skin may be the main cause of the appearance of this oxidation product.

摘要

我们报道了在切除的小鼠皮肤中,杜鹃醇(RD)可生成树莓酮(RK)。我们证实,在人皮肤匀浆中,RD也可生成RK。当将酒精脱氢酶(ADH)的辅酶烟酰胺腺嘌呤二核苷酸(NAD)的氧化形式添加到人皮肤匀浆中时,我们还观察到RD向RK的转化率更高。对人皮肤匀浆中RD对映体消耗情况的手性柱分析也表明,剩余的RD的R对映体比S对映体更多。这表明RD的S对映体在人皮肤中更容易被氧化。我们证实,RD在人皮肤中会部分代谢为RK,因此表明皮肤中的ADH可能是这种氧化产物出现的主要原因。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fea0/9143848/eb8b13620dff/metabolites-12-00412-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fea0/9143848/c90d1ab098bc/metabolites-12-00412-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fea0/9143848/eb8b13620dff/metabolites-12-00412-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fea0/9143848/c90d1ab098bc/metabolites-12-00412-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fea0/9143848/eb8b13620dff/metabolites-12-00412-g002.jpg

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本文引用的文献

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Age-related NAD decline.与年龄相关的烟酰胺腺嘌呤二核苷酸(NAD)水平下降。
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Skin Metabolism: Relevance of Skin Enzymes for Rational Drug Design.皮肤代谢:皮肤酶在合理药物设计中的相关性。
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Tyrosinase-Catalyzed Oxidation of the Leukoderma-Inducing Agent Raspberry Ketone Produces (E)-4-(3-Oxo-1-butenyl)-1,2-benzoquinone: Implications for Melanocyte Toxicity.酪氨酸酶催化的白癜风诱导剂覆盆子酮氧化生成(E)-4-(3-氧代-1-丁烯基)-1,2-苯醌:对黑素细胞毒性的影响。
Chem Res Toxicol. 2017 Mar 20;30(3):859-868. doi: 10.1021/acs.chemrestox.7b00006. Epub 2017 Mar 6.
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Chemical Leukoderma.化学性白斑病
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Rhododenol and raspberry ketone impair the normal proliferation of melanocytes through reactive oxygen species-dependent activation of GADD45.玫瑰醇和树莓酮通过依赖活性氧的GADD45激活来损害黑素细胞的正常增殖。
Toxicol In Vitro. 2016 Apr;32:339-46. doi: 10.1016/j.tiv.2016.02.003. Epub 2016 Feb 8.
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Human tyrosinase is able to oxidize both enantiomers of rhododendrol.人酪氨酸酶能够氧化杜鹃素的两种对映异构体。
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