毡毛美洲茶素; 4',5-二羟基-3',7-二甲氧基黄酮 | 25739-41-7

• 物质功能分类: 天然产物 - 黄酮类化合物
• 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: 毡毛美洲茶素; 4',5-二羟基-3',7-二甲氧基黄酮
• 中文别名: 毡毛美洲茶素;4',5-二羟基-3',7-二甲氧基黄酮；4',5-二羟基-3',7-二甲氧基黄酮；毡毛美洲茶素
• 英文名称: velutin
• 英文别名: 5,4′-dihydroxy-7,3′-dimethoxyflavone；5,4'-dihydroxy-7,3'-dimethoxyflavone；5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-methoxychromen-4-one
• CAS: 25739-41-7
• 化学式: C₁₇H₁₄O₆
• 分子量: 314.295
• InChiKey: ROCUOVBWAWAQFD-UHFFFAOYSA-N

物化性质

• 熔点：
  298 °C
• 沸点：
  567.5±50.0 °C(Predicted)
• 密度：
  1.402±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 海关编码：
  2914509090
• 储存条件：
  2-8℃，干燥，密封保存。

制备方法与用途

生物活性方面，Velutin 是从槲寄生中提取的苷元，能够抑制黑色素的生物合成。此外，Velutin 还能通过 NF-κB 途径减少破骨细胞的分化，并下调 HIF-1α 的表达。

反应信息

• 作为反应物：
  描述：

  毡毛美洲茶素; 4',5-二羟基-3',7-二甲氧基黄酮 、 硫酸二甲酯 在 potassium carbonate 作用下， 生成 3,4,5,7-四甲氧基黄酮
  参考文献：
  名称：

  Tiwari; Sinha, Journal of the Indian Chemical Society, 1982, vol. 59, # 4, p. 526 - 526

  摘要：

  DOI：
• 作为产物：
  描述：

  5,4'-dihydroxy-7,3'-dimethoxyflavone-4'-O-β-D-xylopyranosyl-(2a→1b)-2a-O-β-D-xylopyranosyl-(2b→1c)-2b-O-β-D-xylopyranosyl-2c-octadecanoate 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 生成 毡毛美洲茶素; 4',5-二羟基-3',7-二甲氧基黄酮
  参考文献：
  名称：

  New Chemical Constituents from Oryza sativa Straw and Their Algicidal Activities against Blue-Green Algae

  摘要：

  Five new constituents, 5,4'-dihydroxy-7,3'-dimethoxyflavone-4'-O-beta-D-xylopyranosyl-(2a -> 1b)-2a-O-beta-D-xylopyranosyl-(2b -> 1c)-2b-O-beta-D-xylopyranosyl-2c-octadecanoate (1), 5,4'-dihydroxy-7,3'-dimethoxyflavone-4'-O-alpha-D-xylopyranosyl(2a -> 1b)-2a- O-alpha-u-xyl opyran osyl- (2b -> 1c)-2b-O-alpha-D-xylopyranosyl-(2c -> 1c)-2c- O-alpha-D-xylopyranosy1-2d-octadecanoate (2), kaempferol-3-O-alpha-D-xylopyranosyl- (2a -> 1b)-2a-O-alpha-D-xylopyranosyl-(2b -> 1c)-2b-O-alpha-D-xylopyranosyl-(2c -> 1d)-2c-O-alpha-D-xylopyranosy1-2d-hexadecanoate (3), methyl salicylate-2-O-alpha-u-xylopyranosyl-(2a -> 1b)-2a-O-alpha-D-xylopyranosyl-(2b -> 1c)-2b-O-alpha-D-xylopyranosyl-(2c -> 1d) -2c-O-alpha-D-xylopyranosyl-(2d -> 1e)-2c-O-alpha-D-xylopyranosyl-(2e -> 1b)-2a-O-alpha-a-D-xylopyranosyl- (2f -> 1g) 1g)-2f-O-alpha-D-xylopyranosyl-(2g -> 1h)-2g-O-alpha-D-xylopyranosyl-2h-geranilan-8',10'-dioic acid-1'-oate (4), and oleioyl-beta-D-arabinoside (5), along with eight known compounds, were isolated from a methanol extract of Oryza sativa straw. The structures of the new compounds were elucidated using one- and two-dimensional NMR spectroscopies in combination with IR, ESI/MS, and HR-ESI/FTMS. In bioassays with blue-green algae, the efficacies of the algicidal activities of the five new compounds (1-5) were evaluated at concentrations of 1, 10, and 100 mg/L. Compound S had the highest growth inhibition (92.6 +/- 0.3%) for Microcystis aeruginosa UTEX 2388 at a concentration of 100 ppm (mg/L). Compound 5 has high potential for the ecofriendly control of weeds and algae harmful to water-logged rice.

  DOI：

  10.1021/jf402145u

文献信息

• Anti-Melanogenic Properties of Velutin and Its Analogs
  作者：Se-Hui Jung、Hee-Young Heo、Jung-Won Choe、Jaehyun Kim、Kooyeon Lee

  DOI：10.3390/molecules26103033

  日期：——

  chemical synthesis, to perform SAR analysis of velutin structural analogues. The SAR study revealed that the substitution of functional groups at C5, C7, C3′, and C4′ of the flavone backbone affects biological activities related to melanin synthesis. The coexistence of hydroxyl and methoxy at the C5 and C7 position is essential for inhibiting tyrosinase activity. However, 1,2-diol compounds substituted

  Velutin是天然植物中的一种黄酮，具有多种有益的活性，例如美白皮肤，以及抗炎，抗过敏，抗氧化和抗菌活性。但是，尚未研究velutin的结构与其抗黑素生成活性之间的关系。在这项研究中，我们通过化学合成获得了12种维他汀衍生物，这些化合物在黄酮骨架的C5，C7，C3'和C4'处被氢，羟基和甲氧基官能团取代，以进行维他汀结构类似物的SAR分析。SAR研究表明，黄酮骨架的C5，C7，C3'和C4'处的官能团取代会影响与黑色素合成有关的生物学活性。羟基和甲氧基在C5和C7位置的共存对于抑制酪氨酸酶活性至关重要。然而，在黄酮骨架的C3'和C4'处取代的1,2-二醇化合物诱导黑素瘤细胞凋亡。此外，在C3'和C4'处被甲氧基或氢取代对于抑制黑色素生成是必不可少的。因此，这项研究将有助于开发天然来源的功能材料，以调节黑色素的合成。
• 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。
• Acidic rearrangement of benzyl group in flavone benzyl ethers and its regioselectivity
  作者：Chong-Qing Wang、Xin Chen、Jun-Hang Jiang、Hui Tang、Kong-Kai Zhu、You-Jun Zhou、Can-Hui Zheng、Ju Zhu

  DOI：10.1016/j.cclet.2015.03.035

  日期：2015.6

  synthesis of benzyl-substituted flavone derivatives via the acidic rearrangement of benzyl groups in flavone benzyl ethers, and the complicated regioselectivity of the rearrangement were reported. The regioselectivity was proposed to be determined by the steric hindrance as well as the ease of electrophilic substitution reaction for benzyl cations at different positions of corresponding debenzylated flavone

  摘要苄基取代的黄酮类化合物在自然界中很少见，其中一些具有令人感兴趣的生物学活性。据报道，通过黄酮苄基醚中苄基的酸性重排，可以合成苄基取代的黄酮衍生物，并具有复杂的区域选择性。提议通过区域位阻以及在相应的脱苄基黄酮化合物的不同位置上苄基阳离子的亲电取代反应的容易性来确定区域选择性。
• WT1 peptide cancer vaccine composition for transdermal administration
  申请人：NITTO DENKO CORPORATION

  公开号：EP2762159A1

  公开（公告）日：2014-08-06

  The present invention provides a cancer vaccine composition for transdermal administration for inducing cellular immunity, comprising (i) a WT1 peptide and/or a modified WT1 peptide; and (ii) a cellular immunity induction promoter. The composition efficiently induces cellular immunity against a cancer in a subject.

  本发明提供了一种用于透皮给药的诱导细胞免疫的癌症疫苗组合物，该组合物包含(i) WT1 肽和/或修饰的 WT1 肽；以及(ii) 细胞免疫诱导促进剂。该组合物能有效诱导受试者产生抗癌细胞免疫。
• Wt1 peptide cancer vaccine composition for mucosal administration
  申请人：NITTO DENKO CORPORATION

  公开号：EP2762160A1

  公开（公告）日：2014-08-06

  The present invention provides a cancer vaccine composition for mucosal administration for inducing cellular immunity, comprising (i) a WT1 peptide and/or a modified WT1 peptide; and (ii) a cellular immunity induction promoter. The composition efficiently induces cellular immunity against a cancer in a subject.

  本发明提供了一种用于粘膜给药以诱导细胞免疫的癌症疫苗组合物，该组合物包含(i)WT1 肽和/或修饰的 WT1 肽；以及(ii)细胞免疫诱导促进剂。该组合物能有效诱导受试者产生抗癌细胞免疫。