ウルソール酸

危険有害性情報のコード(GHS)

• 絵表示(GHS)

  

• 注意喚起語

  Warning

• 危険有害性情報

  H302：飲み込むと有害

• 注意書き

  P280：保護手袋/保護衣/保護眼鏡/保護面を着用するこ と。

  P305+P351+P338：眼に入った場合：水で数分間注意深く洗うこと。次にコ ンタクトレンズを着用していて容易に外せる場合は外す こと。その後も洗浄を続けること。

ウルソール酸 価格

ウルソール酸 化学特性,用途語,生産方法

• 外観

  白色～うすい黄褐色、結晶性粉末～粉末

• 定義

  本品は、セージ Salvia officinalis の葉のエキスである。

• 溶解性

  エーテル、エタノール、クロロホルム、酢酸に可溶。ベンゼン、リグロインに不溶。

• 解説

  ウルソール酸，ウルソールサン．ウルサン骨格をもつ五環式トリテルペン系カルボン酸．はじめツツジ科ウワウルシArctostaphylos uvaursiから単離されたが，リンゴ，サクランボなどの果実，葉のろう状物質などに広汎に存在している．融点288 ℃．＋70°(クロロホルム)．エタノール，熱酢酸に易溶，ほかの有機溶媒に可溶，水，石油エーテルに不溶．

• 化粧品の成分用途

  口腔ケア剤、皮膚コンディショニング剤、香料

• 効能

  アセタート〔mp. 295～296 °C〕；メチルエステル〔mp. 171～172 °C〕

• 化学的特性

  white to light yellow crystal powde

• 使用

  Ursolic Acid is a Triterpene acid used in cosmetics, that also has STAT3 pathway inhibiting properties. It inhibits endothelial cell proliferation and migration (IC50=5 μM) and angiogenesis. Promotes skeletal muscle rejuvenation via enhanced SIRT1 expression. Induces apoptosis in malignant mesothelioma cells. Ursolic acid protects against muscle atrophy and boosts muscle growth (see also tomatidine T538500).

• 主な応用

  ursolic acid helps maintain the look and feel of the skin, acts as a perfume and helps mask odor. Therapeutic benefits in skin care include anti-inflammatory activity. ursolic acid has demonstrated anti-microbial, anti-bacterial, and anti-fungal action as well.

• 定義

  ChEBI: Ursolic acid is a pentacyclic triterpenoid that is urs-12-en-28-oic acid substituted by a beta-hydroxy group at position 3. It has a role as a plant metabolite and a geroprotector. It is a pentacyclic triterpenoid and a hydroxy monocarboxylic acid. It derives from a hydride of an ursane.

• 一般的な説明

  Ursolic acid (UA) is a hydroxyl pentacyclic triterpenoic acid (HPTA), which exhibits anti-bacterial, anti-cancer, anti-oxidative and anti-inflammatory effects. It can also promote neuroregeneration after peripheral nerve injury. UA can enhance sleep duration by activating the GABAergic neurotransmitter system. [GABA= γ-aminobutyric acid]

• 抗がん研究

  It is a triterpenoid, derived from basil, and suppresses the activation of NF-κB byinhibiting a kinase that activates NF-κB(IKK) (Aggarwal and Shishodia 2004). It suppresses tumorigenesis, tumor promotion, and angiogenesis by downregulationof the expression of lipoxygenases (LOX), MMP-9, and COX-2. It is reported toinduce apoptosis in breast cancer, melanoma, hepatoma, prostate cancer, andacute myelogenous leukemia by preventing replication of DNA, inhibition of proteintyrosine kinases, activation of caspases, induction of calcium release, anddownregulating apoptosis gene cellular inhibitor. Ursolic acid inhibits IκBαkinase activity, degradation of IκBα, phosphorylation, NF-κB-dependent reportergene expression, p65 nuclear translocation, and p65 phosphorylation. Inhibitionof NF-κB leads to the reduction of cyclin D1, COX-2, and MMP9 expression.This downregulates STAT-3 activation and its regulated gene products such ascyclin D1, Mcl-1, Bcl-xL, survivin, Bcl-2, and VEGF. It also induces the expressionof tyrosine phosphatase SHP-1 protein and of mRNA (Aggarwal et al. 2008;Hsu et al. 2004).

• 副作用

  Adverse effects of Ursolic acid include reduction of sperm viability and inhibition of spermatogenesis, leading to infertility. Ursolic acid is capable of inducing endothelial cell death at concentrations above 12.5uM, and the mechanism of death is related to apoptosis. In addition, it also appears to cause DNA strand breaks.

• 細胞毒性(Cytotoxicity)

  IC₅₀ (μg/mL): 6.7 (518A2), 5.3 (A2780), 7(A549), 6.4 (FaDu), 4.8 (HT29), 5.8(MCF-7), 8.5 (NIH3T3) (Wiemann et al.2016)
  IC₅₀ (μg/mL): 12.38 (MGC-803),17.12(HCT-116), 13.39 (T24), 13.81(HepG2), 16.36 (A549), >45.7 (HL-7702)(Hua et al. 2015).

• 参考文献

  J.R. Mendive, J. Org. Chem., 5, 235 (1940), DOI: 10.1021/jo01209a003.

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ウルソール酸 スペクトルデータ(¹HNMR)

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