山柰酚-3-O-beta-D-吡喃葡萄糖基-7-O-alpha-L-吡喃鼠李糖苷 | 2392-95-2

• 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: 山柰酚-3-O-beta-D-吡喃葡萄糖基-7-O-alpha-L-吡喃鼠李糖苷
• 中文别名: 2-吡咯烷-1-基乙基{2-[(己氧基)甲基]苯基}氨基甲酸酯乙二酸酯
• 英文名称: kaempferol 3-O-β-D-glucopyranosyl-7-O-α-L-rhamnopyranoside
• 英文别名: Kaempferol 3-O-Glc 7-O-Rha；kaempferol 3-O-β-D-glucopyranoside-7-O-α-L-rhamnopyranoside；kaempferol 3-glucoside-7-rhamnoside；kaempferol 3-O-glucoside-7-O-rhamnoside；camperol-3-O-β-D-glucopyranosyl-7-O-α-L-rhamnopyranoside；kaempferol 3-O-beta-D-glucopyranosyl-7-O-alpha-L-rhamnopyranoside；5-hydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
• CAS: 2392-95-2
• 化学式: C₂₇H₃₀O₁₅
• 分子量: 594.526
• InChiKey: JYXSWDCPHRTYGU-RVCYDTIBSA-N

物化性质

• 熔点：
  245-247 °C
• 沸点：
  957.5±65.0 °C(Predicted)
• 密度：
  1.76±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  42
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  245
• 氢给体数：
  9
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  山柰酚-3-O-beta-D-吡喃葡萄糖基-7-O-alpha-L-吡喃鼠李糖苷 在 盐酸 作用下， 以 水 为溶剂， 反应 3.0h， 生成 L-鼠李糖 、 葡萄糖
  参考文献：
  名称：

  Further acylated flavonol bisdesmosides fromSinocrassula indica

  摘要：

  Further investigation on the whole herbs of Sinocrassula indica (Crassulaceae) led to the isolation of four new acylated flavonol bisdesmosides, sinocrassosides A(13) (1), B-6 (2), B-7 (3), and D-4 (4), together with kaempferol 3-O--d-(6-O-acetyl)glucopyranosyl-7-O--l-rhamnopyranoside (5). Their structures were established by spectral and chemical methods.

  DOI：

  10.1080/10286020.2013.800973
• 作为产物：
  描述：

  kaempferol 3-O-β-D-(2-O-acetyl)glucopyranosyl-7-O-α-L-rhamnopyranoside 在 水 、 potassium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 生成 山柰酚-3-O-beta-D-吡喃葡萄糖基-7-O-alpha-L-吡喃鼠李糖苷
  参考文献：
  名称：

  Further acylated flavonol bisdesmosides fromSinocrassula indica

  摘要：

  Further investigation on the whole herbs of Sinocrassula indica (Crassulaceae) led to the isolation of four new acylated flavonol bisdesmosides, sinocrassosides A(13) (1), B-6 (2), B-7 (3), and D-4 (4), together with kaempferol 3-O--d-(6-O-acetyl)glucopyranosyl-7-O--l-rhamnopyranoside (5). Their structures were established by spectral and chemical methods.

  DOI：

  10.1080/10286020.2013.800973

文献信息

• Flavonoids with hepatoprotective activity from the leaves of <i>Cleome viscosa</i> L.
  作者：Tan Phat Nguyen、Cong Luan Tran、Chi Hung Vuong、Thi Hong Tuoi Do、Tien Dung Le、Dinh Tri Mai、Nhat Minh Phan

  DOI：10.1080/14786419.2017.1283497

  日期：2017.11.17

  kaempferol 7-O-α-l-rhamnopyranoside (6), kaempferitrin (7) and kaempferol 3-O-β-d-glucopyranoside 7-O-α-l-rhamnopyranoside (8) were isolated by various chromatography methods from the leaves of Cleome viscosa L. Their structures were elucidated by IR, UV, HR-ESI-MS and NMR (1D & 2D) experiments. The cytotoxicity and hepatoprotective activities using HepG2 human hepatoma cell line of 1 were measured by

  一个新的黄酮醇苷命名visconoside C（1），具有七个已知黄酮醇苷一起，槲皮素-3-O-β- d吡喃葡萄糖苷7-O-α-升-rhamnopyranoside（2），槲皮素-7-O-α-升-鼠李糖吡喃糖苷（3），黄芪甲素（4），山emp酚3- O-（4- O-乙酰基）-α - l-鼠李糖吡喃糖苷（5），山emp酚7- O - α - l-鼠李糖吡喃糖苷（6），山竹铁素（7）和山奈酚3- ö - β -d吡喃葡萄糖苷7- ö - α -升-rhamnopyranoside（8）通过从所述叶片各种色谱方法分离黄花草其结构经IR，UV，HR-ESI-MS和NMR（1D＆2D）阐明L.实验。通过MTT法测定使用HepG2人肝癌细胞系1的细胞毒性和保肝活性。在25μM和50μM的浓度下，1对HepG2细胞具有细胞毒性活性（与阿霉素对照相比，细胞活力分别降低至22.2和23.0％），而在100μ
• Kaempferol and its glycosides from Equisetum silvaticum L. from the Khanty-Mansi autonomous area
  作者：V. M. Bonacheva、E. Kh. Botirov

  DOI：10.1134/s1068162014070048

  日期：2014.12

  Three flavonoids were isolated from the aerial part of the wood horsetail (Equisetum silvaticum L.); two of them were found for the first time. The compounds were identified as kaempferol, kaempferol 3-O-beta-D-galactopyranosyl-7-O-alpha-L-rhamnopyranoside and kaempferol 3-O-rutinosyl-7-O-L-rhamnopyranoside on the basis of the chemical transformations and IR, UV, H-1-NMR and mass spectra.
• Purification and characterization of a flavonol 3-O-β-heterodisaccharidase from the dried herb of Fagopyrum esculentum Moench
  作者：Andreas Baumgertel、Rudi Grimm、Wilhelm Eisenbeiß、Wolfgang Kreis

  DOI：10.1016/s0031-9422(03)00418-7

  日期：2003.9

  A flavonol-3-O-beta-heterodisaccharide glycosidase (FHG I) was isolated from dried aerial tissues of Fagopyrum esculentum Moench (Fagopyri herba). It has a specific enzyme activity of ca. 3.5 nkat mg(-1) protein in buffered extracts when rutin (quercetin-3-O-rutinoside) was used as substrate and an optimal enzyme activity was seen at around pH 4.8 and 30 degreesC. FHG I was purified about 156-fold to apparent homogeneity by hydrophobic interaction, anion exchange and size exclusion chromatographic steps. The apparent molecular mass of FHG I was 74.5 +/- 2 kDa as determined by SDS-PAGE and it is a monomeric glycoprotein with a carbohydrate content of 23%. The isoelectric point as determined by isoelectric focusing was 5.7 and the energy of activation was 32 kJ mol(-1). FHG I exhibits a high substrate specificity, preferring flavonol 3-O-glycosides comprising the disaccharide rutinose. The K-m and V-max values for the natural substrate rutin were calculated to be 0.561 muM and 745 nkat mg(-1) protein, respectively. Two oligopeptide fragments obtained after enzymatic digestion of FHG I were sequenced and showed similarities to sequences of beta-glucohydrolases from other plant species. Polyclonal antibodies were raised and their specificities determined. Another flavonol 3-O-beta-hcterodisaccharide glycosidase (FHG II) could also be detected in buckwheat herb, having a molecular irlass of 85.3 +/- 2 kDa and an isoelectric point between pH 6.0 and 6.5. (C) 2003 Elsevier Ltd. All rights reserved.
• Evolvosides C–E, flavonol-4-O-triglycosides from Evolvulus alsinoides and their anti-stress activity
  作者：Prasoon Gupta、Upasana Sharma、Praveen Gupta、Kiran Babu Siripurapu、Rakesh Maurya

  DOI：10.1016/j.bmc.2012.12.040

  日期：2013.3

  Phytochemical investigation of the n-butanol fraction of Evolvulus alsinoides (Linn.) led to the isolation of three new phenolic glycosides, evolvosides C, D and E (1-3) along with six known compounds (4-9). The structures of the compounds were elucidated on the basis of spectroscopic analysis, viz. 1D and 2D NMR experiments, chemical study, and comparison with literature data. Evolvoside C (1) was characterized as kaempferol 4'-O-beta-D-glucopyranosyl-(1 -> 2)-alpha-L-rhamnopyranosyl-(1 -> 6)-beta-D-glucopyranoside, whereas evolvosides D and E (2-3) were found to be mono and di-O-methyl derivatives of 1. The new compounds (1-3) represent rare triglycoside derivatives of flavonol at C-4'. The isolated compounds (1-6) were screened for acute stress-induced biochemical changes in male Sprague-Dawley rats at a dose of 40 mg/kg body weight. Compounds 1 and 2 displayed anti-stress effects by normalizing hyperglycemia, plasma corticosterone, plasma creatine kinase, and adrenal hypertrophy. Compounds 3 and 6 were also found to be effective in normalizing most of these stress parameters, whereas compounds 4 and 5 were ineffective in normalizing most of these effects. (C) 2013 Elsevier Ltd. All rights reserved.
• COMPOSITIONS FOR PROLIFERATION OF CELLS AND RELATED METHODS
  申请人：Miller Freda

  公开号：US20110301105A1

  公开（公告）日：2011-12-08

  We have discovered that p63 inhibition results in increased cellular proliferation. We have also performed a screen for agents capable of increasing cellular proliferation, (e.g., of stem cells such as skin-derived precursors (SKPs)). The invention therefore invention provides compositions, methods, and kits for increasing proliferation of cells, using compounds that decrease p63 expression or activity or using the compounds described herein. The invention also features methods of using these compounds for increasing hair growth, improving skin health, or promoting skin repair in a subject.