3-甲基鞣花酸 | 51768-38-8

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 中文名称: 3-甲基鞣花酸
• 英文名称: 3-O-methylellagic acid
• 英文别名: ellagic acid-3-methyl ether；ellagic acid methyl ether；3-methyl ellagic acid；methyl ellagic acid；6,7,13-trihydroxy-14-methoxy-2,9-dioxatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione
• CAS: 51768-38-8
• 化学式: C₁₅H₈O₈
• 分子量: 316.224
• InChiKey: FAARLWTXUUQFSN-UHFFFAOYSA-N

物化性质

• 沸点：
  734.3±60.0 °C(Predicted)
• 密度：
  1.840±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  8

制备方法与用途

生物活性

3-O-甲基芹糖酸是一种天然产物，从 Myrciaria cauliflora 中分离得到，具有抗炎活性。此外，它还对葡萄糖转运有抑制作用，并展现出抗菌活性，特别是对于葡萄球菌 ATCC 25923 菌株的最小抑菌浓度（MIC）为 32 μg/mL。

靶点

• MIC: 32 μg/mL (金黄色葡萄球菌 ATCC 25923)

反应信息

• 作为反应物：
  描述：

  3-甲基鞣花酸 生成 tetramethylellagic acid
  参考文献：
  名称：

  TADZHIBAEV, M. M.;BATIROV, EH. X.;VDOVIN, A. D.;MALIKOV, V. M.;LUTFULLIN,+, XIMIYA PRIROD. SOED.,(1987) N 5, 753-755

  摘要：

  DOI：
• 作为产物：
  描述：

  ellagic acid-3-methyl ether-4'sodium sulphate 在 盐酸 作用下， 反应 0.03h， 生成 3-甲基鞣花酸
  参考文献：
  名称：

  Hussein, Pharmazie, 2004, vol. 59, # 6, p. 484 - 487

  摘要：

  DOI：

文献信息

• Bone mineralization enhancing activity of a methoxyellagic acid glucoside from a Feijoa sellowiana leaf extract
  作者：Ayoub、Hussein、Hashim、Hegazi、Linscheid、Harms、Wende、Lindequist、Nawwar, Mahmoud A.M.

  DOI：10.1691/ph.2009.8635

  日期：——

  The capability of an aqueous methanol extract obtained from the leaves of Feijoa sellowiana Berg. on possible prevention and treatment of osteoporosis has been examined by evaluating its stimulating effect on the two human osteoblastic cell lines HOS58 and SaOS-2. The extract was found to increase significantly the mineralization of cultivated human bone cell, whereby a clear increment (15.3 ± 2.7%) in von Kossa positive area was determined when administering 25 μg/ml leaf extract. A phytochemical investigation of the extract has demonstrated the high phenolic content and led to the isolation and identification of twenty three of them, among which the new 3-methoxyellagic acid 4-O-β-glucopyranoside was fully identified. All structures were elucidated on the basis of conventional analytical methods and confirmed by FTMS, 1D- and 2D-NMR data. The new compound was found to cause a significant increase of mineralized area at 20 μg/mL, while at lower concentrations the effect was not significant. However, an increase of the number of mineralized spots (nodules) at all tested concentrations of the compound was observed.

  通过评估从黄花飞燕草（Feijoa sellowiana Berg.）叶片中提取的甲醇水提取物对两种人类成骨细胞系 HOS58 和 SaOS-2 的刺激作用，研究了这种提取物预防和治疗骨质疏松症的能力。研究发现，叶提取物能明显增加培养的人骨细胞的矿化度，当服用 25 μg/ml 的叶提取物时，von Kossa 阳性面积明显增加（15.3 ± 2.7%）。萃取物的植物化学研究表明其含有大量酚类物质，并分离和鉴定出 23 种酚类物质，其中新的 3-甲氧基鞣花酸 4-O-β-吡喃葡萄糖苷已被完全鉴定。所有结构都是根据传统分析方法阐明的，并通过 FTMS、1D- 和 2D-NMR 数据得到证实。研究发现，当浓度为 20 μg/mL 时，新化合物能显著增加矿化面积，而在较低浓度时，其效果并不明显。不过，在所有测试浓度的化合物中，都观察到矿化点（结核）的数量有所增加。
• Ellagic acid glycosides with hepatoprotective activity from traditional Tibetan medicine Potentilla anserina
  作者：Toshio Morikawa、Katsuya Imura、Yoshinori Akagi、Osamu Muraoka、Kiyofumi Ninomiya

  DOI：10.1007/s11418-017-1137-y

  日期：2018.1

  Two new gallic acid glycosides, potentillanosides G (1) and H (2), were newly isolated from the methanol extract of the tuberous roots of Potentilla anserina (Rosaceae), together with a known compound, ellagic acid 3-O-α-l-rhamnopyranoside (3). Their structures were elucidated on the basis of chemical and physicochemical evidence. Among the constituents, potentillanoside H (2, IC50 = 99.5 μM) was found to show hepatoprotective activity.

  从荠菜（蔷薇科）块根的甲醇提取物中分离出两种新的没食子酸苷，即荠菜苷 G (1) 和 H (2)，以及一种已知的化合物鞣花酸 3-O-α-L-吡喃鼠李糖苷 (3)。根据化学和物理化学证据阐明了它们的结构。在成分中，荠菜苷 H (2，IC50 = 99.5 μM) 具有保肝活性。
• Ericifolin: An eugenol 5-O-galloylglucoside and other phenolics from Melaleuca ericifolia
  作者：S.A.M. Hussein、A.N.M. Hashim、R.T. El-Sharawy、M.A. Seliem、M. Linscheid、U. Lindequist、M.A.M. Nawwar

  DOI：10.1016/j.phytochem.2007.03.010

  日期：2007.5

  Ericifolin, an eugenol 5-O-beta-(6'-O-galloylglucopyranoside) possessing the naturally unknown phenolic moiety, 5-hydroxyeugenol, together with the two new phenolics, 2-O-p-hydroxybenzoyl-6-O-galloyl-(alpha/beta)-C-4(1)-glucopyranose and 3-methoxyellagic acid 4-O-rhamnopyranoside have been isolated from the antibacterial leaves extract of Melaleuca ericifolia. In addition, 19 known phenolics were also separated and characterized. All structures were elucidated on the basis of analysis of H-1, C-13 NMR, HMQC, HMBC and FTMS spectral data. (C) 2007 Elsevier Ltd. All rights reserved.
• Active Compounds from <i>Lagerstroemia speciosa</i>, Insulin-like Glucose Uptake-Stimulatory/Inhibitory and Adipocyte Differentiation-Inhibitory Activities in 3T3-L1 Cells
  作者：Naisheng Bai、Kan He、Marc Roller、Bolin Zheng、Xiaozhuo Chen、Zhongguang Shao、Tangsheng Peng、Qunyi Zheng

  DOI：10.1021/jf802152z

  日期：2008.12.24

  Seven ellagitannins, lagerstroemin (1), flosin B (2), stachyurin (3), casuarinin (4), casuariin (5), epipunicacortein A (6), and 2, 3-(S)-hexahydroxydiphenoyl-alpha/beta-D-glucose (7), together with one ellagic acid sulfate, 3-O-methyl-ellagic acid 4'-sulfate (8), ellagic acid (9), and four methyl ellagic acid derivatives, 3-O-methylellagic acid (10), 3,3'-di-O-methylellagic acid (11), 3,4,3'-tri-O-methylellagic acid (12), and 3,4,8,9,10-pentahydroxydibenzo[b,d]pyran-6-one (13), were identified by the bioassay-directed isolation from the leaves of Lagerstroemia speciosa (L.) Pers. The chemical structures of these components were established on the basis of one- and two-dimensional NMR and high-resolution mass spectroscopic analyses. Other known compounds, including corosolic acid, gallic acid, 4-hydroxybenzoic acid, 3-O-methylprotocatechuic acid, caffeic acid, p-coumaric acid, kaempferol, quercetin, and isoquercitrin, were also isolated from the same plant. The obtained ellagitannins exhibited strong activities in both stimulating insulin-like glucose uptake (1-5 and 7) and inhibiting adipocyte differentiation (1 and 4) in 3T3-L1 cells. Meanwhile, ellagic acid derivatives (10-13) showed an inhibitory effect on glucose transport assay. This study is the first to report an inhibitory effect for methyl ellagic acid derivatives.
• Ellagic acid derivatives fromEuphorbia ferganensis
  作者：M. M. Tadzhibav、É. Kh. Batirov、A. D. Vdovin、V. M. Malikov、K. L. Lutfullin、M. R. Yagudaev

  DOI：10.1007/bf00598694

  日期：1987.9