naringenin 7-O-cetyl ether

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: naringenin 7-O-cetyl ether
• 英文别名: 7-(hexadecyloxy)-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one；7-Hexadecoxy-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
• 化学式: C₃₁H₄₄O₅
• 分子量: 496.687
• InChiKey: FARULBRCBBGUFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.5
• 重原子数：
  36
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  柚皮素 、 溴代十六烷 在 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 12.0h， 以72%的产率得到naringenin 7-O-cetyl ether
  参考文献：
  名称：

  补充柚皮苷及其合成衍生物会改变高胆固醇饮食大鼠的红细胞和肝脏的抗氧化酶活性。

  摘要：

  测试了柚皮苷（1）及其合成衍生物柚皮苷7-O-鲸蜡基醚（2）的抗氧化作用。给雄性大鼠喂食1 g / 100 g高胆固醇饮食6周，并补充1或2种营养物（0.073 mmol / 100 g饮食），以研究其对红细胞和肝脏中抗氧化酶活性的影响。补充化合物1或2的组中的红细胞过氧化氢酶（CAT）和超氧化物歧化酶（SOD）的活性显着高于对照组，而补充化合物2的组中的肝SOD和CAT活性则显着降低。高胆固醇饮食的化合物1和2的补品降低或趋于降低血浆TBARS水平，即脂质过氧化物产物，同时增强血浆对氧磷酶的活性。

  DOI：

  10.1016/s0968-0896(02)00059-7

文献信息

• The anti-Zika virus and anti-tumoral activity of the citrus flavanone lipophilic naringenin-based compounds
  作者：Larissa Albuquerque de Oliveira Mendes、Carolina Sousa Ponciano、Allan Henrique Depieri Cataneo、Pryscilla Fanini Wowk、Juliano Bordignon、Heveline Silva、Mauro Vieira de Almeida、Eloah Pereira Ávila

  DOI：10.1016/j.cbi.2020.109218

  日期：2020.11

  antiproliferative activities against melanoma (B16–F10) and breast carcinoma (4T1) cells showed the ether derivatives were actives, with IC50 ranging from 6.76, 18.5 and 22.6 μM to 28.53, 45.1 and 32.3 μM referring to ZIKV, B16–F10 and 4T1 cell lines, respectively. The lipophilic ethers present the ability to inhibit selectively ZIKV-replication in human cells and inhibitions. This class of modifications in flavonoid

  黄酮类化合物是天然产物，因其多种用途而广为人知，例如抗病毒，抗增殖，抗肿瘤活性和抗氧化特性。黄烷酮柚皮苷存在于柑橘类水果中，并已被研究用来对抗仍然缺乏有效治疗方法的复发性疾病。研究小组一直在努力开发新的，安全的和活跃的候选药物来对抗这些病原体或疾病，尽管最近报道了针对寨卡病毒（ZIKV）和肿瘤细胞的良好结果，但由于柑橘柚皮素含量低，其使用受到限制生物利用度。通过官能化进行结构交换，例如，连接亲脂基团而不是羟基，可以进一步增强生物学特性。 在此，证明了区域选择性柚皮素单7-O-醚以及单和双脂肪酸酯（在结构上为亲脂性）的合成和表征。最后，体外抗ZIKV作用和针对黑色素瘤（B16-F10）和乳腺癌（4T1）细胞的抗增殖活性表明，醚衍生物具有活性，IC 50范围为6.76、18.5和22.6μM，至28.53、45.1和32.3μM分别指ZIKV，B16–F10和4T1细胞系。亲脂醚具有选择性抑制人细胞中ZIKV复制和抑制的能力。
• Flavanone derivatives and composition for preventing or treating blood lipid level-related diseases comprising same
  申请人：KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY

  公开号：US20010006978A1

  公开（公告）日：2001-07-05

  A compound of formula (I) treating or preventing an elevated blood lipid level-related disease and inhibiting the activities of acyl-CoA:cholesterol-O-acyltransferase(ACAT) and 3-hydroxy-3-methylglutaryl CoA(HMG-CoA) reductase: 1 wherein, R′ is R 5 R 6 CO group; R 2 is H or R 6 CO group; R 3 is H, CH3, R 5 or R 6 CO group; R 4 is H, OH, OR 5 or R 6 COO group; R 5 is a C 2-5 alkyl group substituted with a phenyl group optionally having one or more substituents selected from the group consisting of C 1-3 alkyl, OH, Cl and NO 2 ; a C 1-5 alkyl group substituted with a naphthyl group optionally having one or more substituents selected from the group consisting of C 1-3 alkyl, OH, Cl and NO 2 ; a C 10-18 alkyl; or a C 10-18 alkenyl group; and R 6 is a C 10-18 alkenyl group; or an aryl group optionally having one or more substituents selected from the group consisting of C 1-3 alkyl, OH, Cl or NO 2 .

  一种化合物，其化学式为(I)，用于治疗或预防与高血脂相关的疾病，并抑制酰基辅酶A：胆固醇-O-酰基转移酶（ACAT）和3-羟基-3-甲基戊二酰辅酶A（HMG-CoA）还原酶的活性。其中，R′为R5R6CO基团；R2为H或R6CO基团；R3为H，CH3，R5或R6CO基团；R4为H，OH，OR5或R6COO基团；R5为一个C2-5烷基基团，其被取代为一个苯基团，该苯基团可以有一个或多个从C1-3烷基，OH，Cl和NO2组成的取代基；一个被取代为一个萘基团的C1-5烷基基团，该萘基团可以有一个或多个从C1-3烷基，OH，Cl和 组成的取代基；一个C10-18烷基；或一个C10-18烯基基团；而R6为一个C10-18烯基基团；或一个芳基基团，该芳基基团可以有一个或多个从C1-3烷基，OH，Cl或 组成的取代基。
• Naringenin 7-O-cetyl ether as inhibitor of HMG-CoA reductase and modulator of plasma and hepatic lipids in high cholesterol-fed rats
  作者：Mi-Kyung Lee、Surk-Sik Moon、Seung-Eun Lee、Song-Hae Bok、Tae-Sook Jeong、Yong Bok Park、Myung-Sook Choi

  DOI：10.1016/s0968-0896(02)00441-8

  日期：2003.2

  Numerous studies in vitro have shown a close relationship between the chemical structure and biologic activity of flavonoids, whereby their basic structure is modified to increase or decrease their biologic activity. The effects of naringenin (1) and its synthetic derivative, naringenin 7-O-cetyl ether (2), on the lipid profile, the cholesterol-regulating enzyme activity and the excretion of sterol were compared in rats fed a high-cholesterol (1% wt/wt) diet. Either 1 or 2 was supplemented with a high-cholesterol diet for 6 weeks at a dose of 0.073 mmol/100 g diet. The supplementation of 1 or 2 significantly lowered the levels (mean SE) of the plasma total cholesterol (4.93 +/- 0.19 and 4.75 +/- 0.16 mmol/L vs 5.87 +/- 0.36 mmol/L, p < 0.05) and hepatic triglyceride (0.12 +/- 0.01 and 0.11 +/- 0.01 mmol/g vs 0.18 +/- 0.01 mmol/g, p < 0.05) and cholesterol (0.23 +/- 0.01 and 0.21 +/- 0.01 mmol/g vs 0.31 +/- 0.01 mmol/g, p < 0.05) compared to those of the control. The compound 1 or 2 supplementation appeared to decrease the excretion of neutral sterols. The plasma HDL-cholesterol concentration and ratio of HDL to total cholesterol were significantly higher in 1 and 2 groups than in control group. Although the biological effect of 2 on inhibiting hepatic HMG-CoA reductase and ACAT activities was only significant compared to the control group, both compounds exhibited a significant hypocholesterolemic effect in rats fed a high-cholesterol diet. The results suggest that cholesterol biosynthesis and esterification were concomitantly reduced by 2, as indicated by the decreased HMG-CoA reductase and ACAT activities. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Naringenin derivatives as anti-atherogenic agents
  作者：Sangku Lee、Chul-Ho Lee、Surk-Sik Moon、Eungsoo Kim、Chul-Tae Kim、Bang-Hyun Kim、Song-Hae Bok、Tae-Sook Jeong

  DOI：10.1016/j.bmcl.2003.09.009

  日期：2003.11

  Two classes of naringenin derivatives were evaluated for anti-atherogenic activity. Naringenin 7-O-oleic ester (2) and naringenin 7-O-cetyl ether (3) inhibited the formation of aortic atherosclerotic lesions in high cholesterol-fed rabbits. (C) 2003 Elsevier Ltd. All rights reserved.
• US6455577B2
  申请人：——

  公开号：US6455577B2

  公开（公告）日：2002-09-24