ケルセチン 化学特性,用途語,生産方法
定義
本品は、次の化学式で表される複素環式化合物である。
解説
ケルセチン，黄色の針状晶で2分子の水和水を含む．95～97 ℃ で無水和物となる．分解点314 ℃．λmax 258，375 nm(log ε 2.75，2.75．エタノール)．pKa 6.89±0.60．熱エタノール，氷酢酸に易溶，冷エタノール，エーテルに難溶，冷水にはほとんど不溶．FeCl3で暗緑色を呈する．配糖体のおもなものにクエルシトリン(3-ラムノシド)，クワMorus albaの葉などにあるイソクエルシトリン(3-グルコシド)，ソバFagopyrum esticulentumの全草，サンシキスミレViola tricolorの花などに含まれるルチン(3-ラムノシルグルコシド)がある．
森北出版「化学辞典（第2版）
化粧品の成分用途
皮膚コンディショニング剤、酸化防止剤
応用
ケルセチン，植物界にもっとも広く分布するフラボノール．多くの配糖体のアグリコンとして広く存在する．
説明
The name of quercetin has been used since 1857, which is derived from quercetum
(oak forest) after Quercus. Quercetin is widely found in flowers, leaves, and
fruits of various plants. Vegetables (such as onions, ginger, celery, etc.), fruits (such
as apples, strawberries, etc.), beverages (such as tea, coffee, red wine, fruit juice,
etc.), and more than 100 kinds of Chinese herbal medicines (such as Threevein
Aster, mountain white chrysanthemum, Huai rice, Apocynum, Ginkgo biloba, etc.)
contain this ingredient.
Threevein Aster is a Chinese herbal medicine and used in Jiangxi province,
China, for more than 30 years. Its plant name is three veins Mala, Compositae. It is
rich in drug sources, which can be found in Southern provinces of China. Clinical
practice proved that it has significant anti-inflammatory and expectorant effects, and
it is a good prescription for the treatment of elderly chronic bronchitis.
化学的特性
Yellow to green yellow crystalline powde
物理的性質
Appearance: yellow needle-like crystalline powder. Solubility: slightly soluble in
water; soluble in ethanol, acetone, pyridine, and acetic acid; easily soluble in ether
and methanol. Melting point: 314–317 °C.
来歴
In 1936, Szent-Gyorgyi firstly reported the separation and identification of biological
activity of quercetin. Usually quercetin is presented in the form of glycosides
such as lutin, quercitrin, and mycoside, which can be hydrolyzed to get the quercetin.
Quercetin has a polyphenol hydroxyl structure, which is of weak lipophilicity and poor hydrophilicity, resulting in its low bioavailability and limiting its clinical application. The synthesis of phenolic derivatives improves its bioavailability,
which are lipid-soluble quercetin derivatives such as 3-O-methylquercetin, hydrophilic
quercetin derivatives such as 3′-ON-carboxymethylformamide quercetin, and quercetin glycosides.
Threevein Aster, having quercetin as one of the main active ingredients, has been used for the domestic clinical treatment for chronic bronchitis in China since 1971.
使用
- Quercetin has been used as an antioxidant which reversed the immunosuppressive effects of high glucose and hyperglycemic sera in type 2 diabetic patients.
- It has been used as a detoxifying phytochemical in Apis mellifera.
- It has been used as a positive control in DPPH (2,2- diphenyl-1-picryhydrazyl) radical scavenging assay. It has also been used for the preparation of calibration curve to determine total flavonoid content.
適応症
It is mainly used for the treatment of chronic bronchitis.
一般的な説明
Yellow needles or yellow powder. Converts to anhydrous form at 203-207°F. Alcoholic solutions taste very bitter.
空気と水の反応
Sensitive to exposure to air and light. Insoluble in water.
反応プロフィール
3,3',4',5,7-Pentahydroxyflavone is a strong antioxidant and a metal chelator. Promotes the formation of nitrosamines .
危険性
Questionable carcinogen.
健康ハザード
ACUTE/CHRONIC HAZARDS: When heated to decomposition 3,3',4',5,7-Pentahydroxyflavone emits acrid smoke and irritating fumes.
火災危険
Flash point data for 3,3',4',5,7-Pentahydroxyflavone are not available; however, 3,3',4',5,7-Pentahydroxyflavone is probably combustible.
生物活性
Anti-tumor agent; induces apoptosis and inhibits synthesis of heat shock proteins. Inhibits many enzyme systems including tyrosine protein kinase, phospholipase A 2 , phosphodiesterases, mitochondrial ATPase, PI 3-kinase and protein kinase C. Can also activate Ca 2+ and K + channels and behaves as an agonist at estrogen (GPR30) receptors.
薬理学
Experimental studies showed that quercetin had antitumor, anti-inflammatory, anti-oxidation, hypoglycemic, anti-obesity, antidepressant, and other effects. In vitro cell experiments and in vivo animal experiments have shown that quercetin could
inhibit the growth of various malignant tumor cells such as human ovarian cancer,
breast cancer, gastrointestinal tumor cells, and leukemia, and it could induce cancer
cell apoptosis and had a reversal of tumor multidrug resistance (MDR) effect, while,
combined with other anticancer drugs, it could enhance the effect of anticancer
drugs.
Quercetin could alleviate the inflammatory response that was aggravated by the activation of the central granulocytes. In the experimental study on the treatment of non-bacterial prostatitis and acute gouty arthritis, quercetin also showed a good
anti-inflammatory effect.
The experimental results showed that quercetin had a good direct scavenging effect on free radicals and exhibited antioxidant activity. In addition, it also had the anti-hepatic fibrosis, pulmonary fibrosis, keloid hyperplasia and glaucoma filtering bubble scarring and other effects, its mechanism involving the inhibition of fibroblast proliferation, inhibition of collagen synthesis, preventing oxidative damage and so on. Moreover, studies have shown that quercetin also had antibacterial, antiaging, antidepressant, antileukemia, antidiabetic, and other pharmacological effects.
臨床応用
Since the first clinical phase I trial of quercetin in 1996 found that it had antitumor
activity, quercetin has also been reported in early clinical trials of cardiovascular
disease, diabetes, and other diseases. However, there is still insufficient evidence shown that quercetin has a significant effect on the treatment of the disease in clinic.The US FDA has issued a warning, emphasizing that quercetin is not a definite
nutrient, unable to determine its content in the diet, nor can it be used as a drug.
China’s Threevein Aster consists of a single Chinese herb, which was released by
the Pharmacopoeia of the People’s Republic of China (1977) Part I. One of the main active ingredients obtained following the hydrolysis of Threevein Aster is quercetin, which has the function of relieving cough and eliminating phlegm and can be used for the treatment of chronic bronchitis. The anti-inflammatory effect of Threevein Aster is poor. Side effects after use include stomach discomfort, dizziness, and abdominal pain, while withdrawal can make them disappear.
安全性プロファイル
Poison by ingestion, subcutaneous, and intravenous routes. Experimental teratogenic and reproductive effects. Questionable carcinogen with experimental carcinogenic, neoplastigenic, and tumorigenic data. Human mutation data reported. Used as a pharmaceutical and veterinary drug. When heated to decomposition it emits acrid smoke and irritating fumes
ケルセチン 上流と下流の製品情報
原材料
準備製品
2-(3,4-DIMETHOXY-PHENYL)-5,7-DIHYDROXY-3-METHOXY-CHROMEN-4-ONE
5,7,4'-トリヒドロキシ-3,3'-ジメトキシフラボン
3,7-ジ-O-メチルケルセチン
2-(4-ヒドロキシ-3-メトキシフェニル)-5-ヒドロキシ-3,7-ジメトキシ-4H-1-ベンゾピラン-4-オン
トリヒドロキシ-3,4'-ジメトキシフラボン, 3',5,7-
3,4',5-トリヒドロキシ-3',7-ジメトキシフラボン
2-(3-ヒドロキシ-4-メトキシフェニル)-3-ヒドロキシ-5-ヒドロキシ-7-メトキシ-4H-1-ベンゾピラン-4-オン
2-(3-ヒドロキシ-4-メトキシフェニル)-3,7-ジメトキシ-5-ヒドロキシ-4H-1-ベンゾピラン-4-オン