刺梨苷 F1 | 95298-47-8

• 物质功能分类: 生物化工 - 提取物
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 刺梨苷 F1
• 中文别名: 刺梨苷；刺梨苷F1
• 英文名称: kajiichigoside F1
• 英文别名: kaji-ichigoside F1；[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1R,2R,4aS,6aR,6aS,6bR,8aR,10S,11R,12aR,14bS)-1,10,11-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• CAS: 95298-47-8
• 化学式: C₃₆H₅₈O₁₀
• 分子量: 650.851
• InChiKey: MLKQAGPAYHTNQQ-FUZXVMJXSA-N

物化性质

• 熔点：
  230-232 °C(Solv: chloroform (67-66-3); methanol (67-56-1))
• 沸点：
  741.5±60.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  46
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  177
• 氢给体数：
  7
• 氢受体数：
  10

制备方法与用途

刺梨苷和黄酮类成分为刺梨的主要活性物质，在增强免疫力、延缓衰老、抗动脉粥样硬化及健胃消食等方面均具有较好的效果。

刺梨苷在治疗急性高原缺氧方面表现出较好疗效。其通过抗氧化作用，能够显著改善脑部组织的损伤，并降低血清丙二醛水平，提升血清超氧化物歧化酶含量，在临床治疗中具有较高的使用价值。

制备方法如下：取约2.5g刺梨药材粉末，精密称定后放入250ml圆底烧瓶中，加入100ml甲醇，在水浴条件下回流。过滤后，残渣用40ml甲醇洗涤四次（每次10ml），合并滤液并浓缩至约10ml。将此溶液置于中性氧化铝柱（100~120目，10g，内径10~15mm）中，以90%甲醇100ml进行洗脱，收集洗脱液，并浓缩至干。最后用甲醇溶解残渣后转移至10ml量瓶中，稀释至刻度并摇匀，通过0.45μm微孔滤膜过滤，取续滤液即得。实验结果表明，提取的最佳方法是采用甲醇作为溶剂，在回流条件下提取1小时，并通过中性氧化铝柱干燥得到刺梨苷。

Kaji-ichigoside F1 是从金樱根中分离得到的一种具有溶血性和体外抗病毒活性的化合物。

化学性质：Kaji-ichigoside F1 为白色结晶，可溶于甲醇、乙醇及DMSO等有机溶剂。

用途：主要用于含量测定、鉴定和药理实验。

反应信息

• 作为反应物：
  描述：

  刺梨苷 F1 在 盐酸 、 水 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以21 mg的产率得到euscaphic acid
  参考文献：
  名称：

  生物活性制导隔离和Antiadipogenic化合物的鉴定石垭茶（叶亮叶杨桐）

  摘要：

  肥胖症是一种全球流行病，导致罹患2型糖尿病，心脏病和癌症等疾病的风险更高。传统的中国茶石ya茶（叶蝉叶）由于其可口的风味和多种治疗作用（例如降低血压和血脂以及消炎等）而被广泛食用。但是，目前尚无相关研究关于Shiya茶的抗肥胖作用的报道。尤其是，什叶茶中除了黄酮类以外，还没有有益健康的化合物的报道。因此，已将3T3-L1前脂肪细胞用作生物活性指导的鉴定模型，以验证Shiya茶对脂肪形成的抑制作用，并鉴定出抗脂肪形成的化合物。四个三萜皂苷（1 –4），已使用NMR（1D和2D NMR）和液相色谱法（1D和2D NMR）鉴定了一种新化合物（2α，3α-二羟基熊果酸28- O - β- d-吡喃葡萄糖基酯，化合物1）和类黄酮（5）。 LC）–MS技术。化合物1是主要的抗脂肪生成成分，IC 50值为27.6μg / mL，已首次在石屋茶中鉴定出来。为了了解结构与活性之间的关系，获得了三种水解化合物

  DOI：

  10.1021/acs.jafc.9b01326
• 作为产物：
  描述：

  potentillanoside A 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以68.2%的产率得到1-O-[(2beta,3alpha,5Xi,9beta,18alpha)-2,3,19-三羟基-28-氧代乌苏-12-烯-28-基]-beta-D-吡喃葡萄糖
  参考文献：
  名称：

  Hepatoprotective triterpenes from traditional Tibetan medicine Potentilla anserina

  摘要：

  A methanol extract from the tuberous roots of Potentilla anserina (Rosaceae) exhibited hepatoprotective effects against D-galactosamine (D-GalN)/lipopolysaccharide-induced liver injuries in mice. Six triterpene 28-O-monoglucopyranosyl esters, potentillanosides A-F, were isolated from the extract along with 32 known compounds, including 15 triterpenes. The structures of potentillanosides A-F were determined on the basis of spectroscopic properties and chemical evidence. Four ursane-type triterpene 28-O-monoglycosyl esters, potentillanoside A (IC50 = 46.7 mu M), 28-O-beta-D-glucopyranosyl pomolic acid (IC50 = 9.5 - mu M), rosamutin (IC50 = 35.5 mu M), and kaji-ichigoside F1 (IC50 = 14.1 mu M), inhibited D-GalN-induced cytotoxicity in primary cultured mouse hepatocytes. Among these four triterpenes, potentillanoside A, rosamutin, and kaji-ichigoside F1 exhibited in vivo hepatoprotective effects at doses of 50-100 mg/kg, p.o. The mode of action was ascribable to the reduction in cytotoxicity caused by D-GalN. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2014.03.002

文献信息

• β-glucosyl esters of 19α-hydroxyursolic acid derivatives in leaves of Rubus species
  作者：Takashi Seto、Takashi Tanaka、Osamu Tanaka、Naohiro Naruhashi

  DOI：10.1016/0031-9422(84)83023-x

  日期：1984.1
• Biotransformation of oleanolic acid by<i>Alternaria longipes</i>and<i>Penicillium adametzi</i>
  作者：Dai-Lin Liu、Ying Liu、Feng Qiu、Ying Gao、Jing-Ze Zhang

  DOI：10.1080/10286020.2010.547028

  日期：2011.2

  Microbial transformation of oleanolic acid (1) was carried out. Six transformed products (2-7) from 1 by Alternaria longipes and three transformed products (8-10) from 1 by Penicillium adametzi were isolated. Their structures were elucidated as 2,3,19-trihydroxy-ursolic acid-28-O--d-glucopyranoside (2), 2,3,19-trihydroxy-ursolic acid-28-O--d-glucopyranoside (3), oleanolic acid 28-O--d-glucopyranosyl ester (4), oleanolic acid-3-O--d-glucopyranoside (5), 3-O-(-d-glucopyranosyl)-oleanolic acid-28-O--d-glucopyranoside (6), 2,3,19a-trihydroxy-oleanolic acid-28-O--d-glucopyranoside (7), 21-hydroxyl oleanolic acid-28-O--d-glucopyranoside (8), 21-hydroxyl oleanolic acid (9), and 7,21-dihydroxyl oleanolic acid (10) based on the extensive NMR studies. Among them, 10 was a new compound and compounds 5 and 8-10 had stronger cytotoxic activities against Hela cell lines than the substrate. At the same time, it was reported for the first time in this paper that the skeletons of compounds 2 and 3 were changed from oleanane to uranane and seven glycosidation products were obtained by biotransformation.
• Hepatoprotective triterpenes from traditional Tibetan medicine Potentilla anserina
  作者：Toshio Morikawa、Kiyofumi Ninomiya、Katsuya Imura、Takahiro Yamaguchi、Yoshinori Akagi、Masayuki Yoshikawa、Takao Hayakawa、Osamu Muraoka

  DOI：10.1016/j.phytochem.2014.03.002

  日期：2014.6

  A methanol extract from the tuberous roots of Potentilla anserina (Rosaceae) exhibited hepatoprotective effects against D-galactosamine (D-GalN)/lipopolysaccharide-induced liver injuries in mice. Six triterpene 28-O-monoglucopyranosyl esters, potentillanosides A-F, were isolated from the extract along with 32 known compounds, including 15 triterpenes. The structures of potentillanosides A-F were determined on the basis of spectroscopic properties and chemical evidence. Four ursane-type triterpene 28-O-monoglycosyl esters, potentillanoside A (IC50 = 46.7 mu M), 28-O-beta-D-glucopyranosyl pomolic acid (IC50 = 9.5 - mu M), rosamutin (IC50 = 35.5 mu M), and kaji-ichigoside F1 (IC50 = 14.1 mu M), inhibited D-GalN-induced cytotoxicity in primary cultured mouse hepatocytes. Among these four triterpenes, potentillanoside A, rosamutin, and kaji-ichigoside F1 exhibited in vivo hepatoprotective effects at doses of 50-100 mg/kg, p.o. The mode of action was ascribable to the reduction in cytotoxicity caused by D-GalN. (C) 2014 Elsevier Ltd. All rights reserved.
• Bioactivity-Guided Isolation and Identification of Antiadipogenic Compounds in Shiya Tea (Leaves of <i>Adinandra nitida</i>)
  作者：Chunmao Yuan、Linhua Huang、Joon Hyuk Suh、Yu Wang

  DOI：10.1021/acs.jafc.9b01326

  日期：2019.6.19

  antiadipogenic constituent with an IC50 value of 27.6 μg/mL, has been identified for the first time in Shiya tea. To understand the structure–activity relationship, three hydrolytic compounds (1s, 2s, and 5s) were obtained to provide an inhibitory effect on lipid accumulation during 3T3-L1 adipocyte differentiation. The inhibitory effect of the triterpenoid (1s) possessing no sugar group decreased

  肥胖症是一种全球流行病，导致罹患2型糖尿病，心脏病和癌症等疾病的风险更高。传统的中国茶石ya茶（叶蝉叶）由于其可口的风味和多种治疗作用（例如降低血压和血脂以及消炎等）而被广泛食用。但是，目前尚无相关研究关于Shiya茶的抗肥胖作用的报道。尤其是，什叶茶中除了黄酮类以外，还没有有益健康的化合物的报道。因此，已将3T3-L1前脂肪细胞用作生物活性指导的鉴定模型，以验证Shiya茶对脂肪形成的抑制作用，并鉴定出抗脂肪形成的化合物。四个三萜皂苷（1 –4），已使用NMR（1D和2D NMR）和液相色谱法（1D和2D NMR）鉴定了一种新化合物（2α，3α-二羟基熊果酸28- O - β- d-吡喃葡萄糖基酯，化合物1）和类黄酮（5）。 LC）–MS技术。化合物1是主要的抗脂肪生成成分，IC 50值为27.6μg / mL，已首次在石屋茶中鉴定出来。为了了解结构与活性之间的关系，获得了三种水解化合物