六羟黄酮/栎草亭 | 90-18-6

• 物质功能分类: 生物化工 - 提取物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 六羟黄酮/栎草亭
• 中文别名: 栎草亭；槲皮万寿菊素；槲皮万寿菊素栎草亭；槲皮素；槲皮；6-羟黄酮；六羟黄酮(RG)；六羟黄酮
• 英文名称: quercetagetin
• 英文别名: 3,3‘,4’,5,6,7-hexahydroxyflavone；3,5,6,7,3',4'-hexahydroxyflavonol；3,3',4',5,6,7-hexahydroxyflavone；3,5,6,7,3',4'-hexahydroxyflavone；6-hydroxyquercetin；2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxychromen-4-one
• CAS: 90-18-6
• 化学式: C₁₅H₁₀O₈
• mdl: MFCD00017428
• 分子量: 318.24
• InChiKey: ZVOLCUVKHLEPEV-UHFFFAOYSA-N

物化性质

• 熔点：
  >300°C
• 沸点：
  732.4±60.0 °C(Predicted)
• 密度：
  1.912±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO：125 mg/mL（392.79 mM；需要超声波）
• LogP：
  2.230 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  148
• 氢给体数：
  6
• 氢受体数：
  8

安全信息

• WGK Germany：
  3
• 储存条件：
  | 2-8℃ |

制备方法与用途

生物活性

Quercetagetin（6-羟基山柰酚）是从柚子（Citrus unshiu）果皮中分离出的主要类黄酮。Quercetagetin 是一种中等强度和选择性的 PIm-1 激酶抑制剂，IC50 为 0.34 μM，并且具有抗炎及抗肿瘤活性。

靶点

PIM1	IC50 (μM)	0.34
PIM2	IC50 (μM)	3.45
RSK2	IC50 (μM)	2.82
PKA	IC50 (μM)	21.2

体外研究

Quercetagetin 还抑制 PIM2、PKA 和 RSK2，IC50 分别为 3.45、21.2 和 2.82 μM。Quercetagetin（浓度分别为 0.1、1、10 和 100 μM，作用时间 72 小时）对 RWPE2 前列腺癌细胞的抑制生长效果平均半数有效剂量 (ED50) 为 3.8 μM。

细胞活力测定

参数	详细信息
细胞系	RWPE2前列腺癌细胞
浓度（μM）	0.1、1、10 和 100
孵育时间（小时）	72
结果	抑制了 RWPE2 前列腺癌细胞的生长，平均 ED50 为 3.8 μM

体内研究

Quercetagetin 显著抑制紫外线 B (UVB) 引起的皮肤癌症发展。外用 4 或 20 nmol 的 Quercetagetin 涂抹在小鼠皮肤上，分别减少了 32.0% 和 46.7% 的肿瘤发生率。

实验结果

动物模型	SKH-1 去毛小鼠模型
剂量（nmol）	4 或 20
给药方式	外用；28 周
结果	抑制了紫外线 B 引起的皮肤肿瘤形成，延缓了 SKH-1 去毛小鼠模型中的肿瘤发展并减少了肿瘤体积

化学性质

来源于万寿菊。

反应信息

• 作为反应物：
  描述：

  六羟黄酮/栎草亭 在 1,1-二苯-2-苦基肼 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Kinetic Study of Flavonoid Reactions with Stable Radicals

  摘要：

  The antiradical activities of some flavonols (kaempferol, quercetin, robinetin, quercetagetin, and myricetin), flavones (apigenin, baicalein, and luteolin), flavanones (naringenin and dihydroquercetin), and flavanols [(+)-catechin and (-)-epicatechin] were determined by measuring the reaction kinetics with 2,2-diphenyl-1-picrylhydrazyl (DPPH) and alpha,gamma-bisdiphenylene-beta-phenylallyl (BDPA) radicals. The reactions, which follow the mixed second-order rate law, were investigated under pseudo-first-order conditions by use of a large excess of flavonoids, and their stoichiometry was determined by spectrophotometric titration. The results confirm stoichiometric factors of 1, 2, and 3 for flavonoids with one, two, and three hydroxyl groups in the B-ring, respectively, excluding kaempferol, which, despite a single OH group in the B-ring, has a factor of 2, which is explained by the 3-OH group supporting the reaction with free radicals. Structure- activity considerations indicate for the present series of flavonoids the importance of multiple OH substitutions and conjugation. The logarithms of reaction rate constants with the OH, DPPH, and BDPA radicals correlate well with the reduction potential of the flavonoids.

  DOI：

  10.1021/jf049880h
• 作为产物：
  描述：

  山奈酚 在 氧气 、 NADP+ 、 腺嘌呤黄素 作用下， 生成 六羟黄酮/栎草亭
  参考文献：
  名称：

  Formation of UV-honey guides in Rudbeckia hirta

  摘要：

  The UV-honey guides of Rudbeckia hirta were investigated by UV-photography, reflectance spectroscopy, LC-MS analysis and studies of the enzymes involved in the formation of the W-absorbing flavonols present in the petals. It was shown for the first time that the typical bull's eye pattern is already established at the early stages of flower anthesis on the front side of the petal surface, but is hidden to pollinators until the buds are open and the petals are unfolded. The rear side of the petals remains W-reflecting during the whole flower anthesis. Studies on the local distribution of 19 flavonols across the petals confirmed that the majority are concentrated in the basal part of the ray flower. However, in contrast to the earlier studies, eupatolitin 3-O-glucoside (6,7-dimethoxyquercetin 3-O-glucoside) was present in both the basal and apical parts of the petals, whereas eupatolin (6,7-dimethoxyquercetin 3-O-rhamnoside) was exclusively found in the apical parts. The enzymes involved in the formation of the flavonols in R. hirta were demonstrated for the first time. These include a rare flavonol 6-hydroxylase, which was identified as cytochrome P450-dependent monooxygenase and did not accept any methylated flavonol as substrate. All enzymes were present in the basal and apical parts of the petals, although some of them clearly showed higher activities in the basal part. This indicates that the local accumulation of flavonols in R. hirta is not achieved by a locally restricted presence of the enzymes involved in flavonol formation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2009.04.017

文献信息

• O-methylation of flavonoids by cell-free extracts of calamondin orange
  作者：Gunter Brunet、Ragai K. Ibrahim

  DOI：10.1016/0031-9422(80)85102-8

  日期：——

  hydroxyls of a number of flavonoids, indicating the existence in citrus tissues of ortho, meta, para and 3-O-methyltransferases. The latter, hitherto unreported enzyme, catalysed the formation of 3-O-methyl ethers of galangin and quercetin. The stepwise O-methylation of a number of compounds, especially quercetin and quercetagetin, tends to suggest a coordinated sequence of O-methylations on the surface

  摘要 柑桔（Citrus mitis）的无细胞提取物催化了许多类黄酮的几乎所有羟基的O-甲基化，表明柑橘组织中存在邻位、间位、对位和3-O-甲基转移酶。后者，迄今未报道的酶，催化高良姜素和槲皮素的 3-O-甲基醚的形成。许多化合物的逐步 O-甲基化，尤其是槲皮素和槲皮素，往往表明多酶复合物表面上存在协调的 O-甲基化序列。所使用的类黄酮底物的甲基受体能力与它们的羟基取代模式和它们的负电子密度分布有关。
• METHOD OF IMPROVING STABILITY OF SWEET ENHANCER AND COMPOSITION CONTAINING STABILIZED SWEET ENHANCER
  申请人：TACHDJIAN Catherine

  公开号：US20120041078A1

  公开（公告）日：2012-02-16

  The present invention includes methods of stabilizing one or more sweet enhancers when they are exposed to a light source as well as liquid compositions containing one or more sweet enhancers and one or more photostabilizers.

  本发明包括在甜味增强剂暴露于光源时稳定一个或多个甜味增强剂的方法，以及包含一个或多个甜味增强剂和一个或多个光稳定剂的液体组合物。
• Controlled Release of Nitric Oxide And Drugs From Functionalized Macromers And Oligomers
  申请人：Bezwada Rao S.

  公开号：US20120035259A1

  公开（公告）日：2012-02-09

  The present invention provides NO and, optionally, drug releasing macromers and oligomers wherein the drug molecule and NO releasing moiety are linked an absorbable macromer or oligomeric chain susceptible to hydrolytic degradation and wherein the macromer or oligomer comprises of repeat units derived from safe and biocompatible molecules such as glycolic acid, lactic acid, caprolactone and p-dioxanone. Furthermore, the present invention relates to controlled release of nitric oxide (NO) and/or drug molecule from a NO and drug releasing macromer or oligomer. Moreover, the present invention also relates to medical devices, medical device coatings and therapeutic formulations comprising of nitric oxide and drug releasing macromers and oligomers of the present invention.

  本发明提供了一氧化氮(NO)和可选的药物释放的大分子和寡聚物，其中药物分子和一氧化氮释放部分通过可吸收的大分子或可水解降解的寡聚物链连接，并且大分子或寡聚物由来自诸如乙醇酸、乳酸、己内酰胺和对二恶烷等安全且生物相容的分子的重复单元组成。此外，本发明还涉及从一氧化氮和/或药物分子释放的大分子或寡聚物控制释放一氧化氮(NO)。此外，本发明还涉及包含本发明的一氧化氮和药物释放大分子和寡聚物的医疗器械、医疗器械涂层和治疗方法。
• ABSORBABLE BRANCHED POLYESTERS AND POLYURETHANES
  申请人：Bezwada Biomedical, LLC

  公开号：US20140142199A1

  公开（公告）日：2014-05-22

  The present invention relates to the discovery of a new class of hydrolysable isocyanates, hydrolysable branched polyols and branched absorbable polyesters and polyurethanes prepared therefrom. The resultant absorbable polymers are useful for drug delivery, stents, highly porous foam, reticulated foam, tissue engineering, tissue adhesives, adhesion prevention, bone wax formulations, medical device coatings, surface modifying agents and other implantable medical devices. In addition, these absorbable polymers can have a controlled hydrolytic degradation profile.

  本发明涉及一种新型可水解异氰酸酯、可水解支链多元醇及其制备的支链可吸收聚酯和聚氨酯的发现。由此得到的可吸收聚合物可用于药物输送、支架、高孔隙率泡沫、网状泡沫、组织工程、组织粘合剂、防止粘连、骨蜡制剂、医疗设备涂层、表面改性剂以及其他可植入医疗设备。此外，这些可吸收聚合物可以具有受控的水解降解特性。
• Functionalized drugs and polymers derived therefrom
  申请人：Bezwada S. Rao

  公开号：US20060172983A1

  公开（公告）日：2006-08-03

  Compounds selected from: where DRUG-OH, DRUG-COOH and DRUG-NH 2 are biologically active compounds; each X is independently selected from —CH 2 COO— (glycolic acid moiety), —CH(CH 3 )COO— (lactic acid moiety), —CH 2 CH 2 OCH 2 COO— (dioxanone moiety), —CH 2 CH 2 CH 2 CH 2 CH 2 COO— (caprolactone moiety), —(CH 2 ) y COO—, where y is 2-4 or 6-24 and —(CH 2 CH 2 O) z CH 2 COO—, where z is 2-24; each Y is independently selected from —COCH 2 O— (glycolic ester moiety), —COCH(CH 3 )O— (lactic ester moiety), —COCH 2 OCH 2 CH 2 O— (dioxanone ester moiety), —COCH 2 CH 2 CH 2 CH 2 CH 2 O— (caprolactone ester moiety), —CO(CH 2 ) m O—, where m is 2-4 or 6-24 and —COCH 2 O(CH 2 CH 2 O) n — where n is between 2-24; R′ is hydrogen, benzyl or an alkyl group, the alkyl group being either straight-chained or branched; and p is 1-6. Multi-functional compounds and drug dimers, oligomers and polymers are also disclosed.

  从中选择的化合物：其中DRUG-OH，DRUG-COOH和DRUG-NH2是生物活性化合物；每个X独立地从— COO—（乙二酸基团），—CH(CH3)COO—（乳酸基团），— O COO—（二氧杂环己酮基团），— COO—（己内酯基团），—(CH2)yCOO—中选择，其中y为2-4或6-24和—( O)z COO—，其中z为2-24；每个Y独立地从—CO O—（乙二酸酯基团），—COCH( )O—（乳酸酯基团），—CO O O—（二氧杂环己酮酯基团），—CO O—（己内酯酯基团），—CO( )mO—，其中m为2-4或6-24和—CO O( O)n—，其中n为2-24；R′为氢，苄基或烷基，烷基可以是直链或支链；p为1-6。还披露了多功能化合物和药物二聚体、寡聚体和聚合物。