ramalin

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ramalin
• 英文别名: 2-amino-5-(2-(2-hydroxyphenyl) hydrazinyl)-5-oxopentanoic acid；2-Amino-5-[2-(2-hydroxyphenyl)hydrazinyl]-5-oxopentanoic acid
• 化学式: C₁₁H₁₅N₃O₄
• 分子量: 253.258
• InChiKey: CRSVHQICRXRCEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  125
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  烟酰氯 、 ramalin 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以0.57 g的产率得到
  参考文献：
  名称：

  글루타민 유도체와 이들의 합성방법

  摘要：

  这是一项关于新型谷氨酰胺衍生物及其合成方法的发明。更具体地说，它涉及使用醛基氯甲酸酯制备的谷氨酸衍生物，以及通过反应保护羟基的保护氢化吡咯烷盐化合物制备的谷氨酰胺衍生物，并去除保护基的方法。

  公开号：

  KR20210148530A
• 作为产物：
  描述：

  Benzyl 5-[2-(2-hydroxyphenyl)hydrazinyl]-5-oxo-2-(phenylmethoxycarbonylamino)pentanoate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以92%的产率得到ramalin
  参考文献：
  名称：

  중금속 주석을 사용하지 않는 라말린의 합성방법

  摘要：

  该发明涉及拉马林的合成方法，更详细地说，涉及利用烷基氯甲酰胺制备的谷氨酸衍生物和利用羟基保护的羟基苯胺制备的羟肼盐化合物进行反应制备拉马林的合成方法。

  公开号：

  KR20190049980A

文献信息

• "METHOD FOR PREPARING RAMALIN"
  申请人：Yim Joung Han

  公开号：US20130211133A1

  公开（公告）日：2013-08-15

  The present invention relates to a method for synthesizing ramalin, and more particularly to a method for synthesizing ramalin, which comprises allowing 2-hydrazinylphenol to react with L-glutamic acid having a protected carboxyl group at C-1 and a protected amino group at C-2, and a method for preventing decomposition of the ramalin. According to the present invention, ramalin having excellent antioxidant and anti-inflammatory activities can be synthesized in high yield, and thus can be produced in large amounts. In addition, ramalin can be stably maintained for a long period of time, and thus can be easily used for industrial purposes.

  本发明涉及一种合成拉马林的方法，更具体地涉及一种合成拉马林的方法，包括使2-联苯酚与具有在C-1处保护羧基和在C-2处保护氨基的L-谷氨酸发生反应，并且一种防止拉马林分解的方法。根据本发明，可以高产率地合成具有优异抗氧化和抗炎活性的拉马林，因此可以大量生产。此外，拉马林可以长时间稳定保存，因此可以轻松用于工业用途。
• METHOD FOR SYNTHESIZING RAMALIN BY USING A GLUTAMIC ACID DERIVATIVE AND HYDROXY ANILINE OR HYDROXY ANILINE HAVING PROTECTED HYDROXY GROUP
  申请人：Korea Institute of Ocean Science and Technology

  公开号：EP2816028B1

  公开（公告）日：2019-11-27
• Ramalin inhibits differentiation of 3T3-L1 preadipocytes and suppresses adiposity and body weight in a high-fat diet-fed C57BL/6J mice
  作者：Seo-Young Kim、Yeon Jeong Jang、Bongkyun Park、Joung-Han Yim、Hong-Kum Lee、Dong-Kwon Rhee、Suhkneung Pyo

  DOI：10.1016/j.cbi.2016.07.034

  日期：2016.9

  Obesity is a serious global health problem. Natural substances that could be effective remedies for treatment of obesity, and which are relatively safe, are desired. The aim of this study was to examine the anti-obesity effect and the mechanism of ramalin in 3T3-L1 preadipocytes and high fat diet (HFD)-induced obese mice. In this study, 3T3-L1 cells were treated with various concentrations of ramalin (1,5, and 10 mu g/ml). Ramalin reduced the accumulation of intracellular lipid droplets in 3T3-L1 cells. In addition, ramalin inhibited 3T3-L1 adipocyte differentiation by blocking adipogenic gene expression including CCAAT enhancer binding proteins (C/EBPs), peroxisome proliferator-activated receptors gamma (PPAR gamma), adipocyte fatty acid-binding protein (aP2), and leptin. The suppression of adipogenesis by ramalin was mediated through the inhibition of MAPK pathways. Ramalin also reduced the secretion of INF-alpha and IL-6 in 3T3-L1 adipocytes. Oral administration of ramalin (50 and 100 mg/kg) to HFD-fed mice reduced body weight gain and abdominal fat accumulation without changes in food intake. Ramalin also attenuated organ weight and basal serum level by inhibiting liver X receptors (LXRs), sterol regulatory element-binding protein-1c (SREBP-1c), and lipoprotein lipase (LPL) mRNA expression in HFD-fed mice. Taken together, these results indicate that ramalin inhibits adipogenesis in 3T3-L1 preadipocytes and prevents HFD-induced obesity. The present study also provides insight into the mechanisms underlying the anti-obesity activity of ramalin and suggests that ramalin has the potential to prevent obesity. (C) 2016 Elsevier Ireland Ltd. All rights reserved.
• NOVEL COMPOUND RAMALIN AND USE THEREOF
  申请人：Yim Joung Han

  公开号：US20110262374A1

  公开（公告）日：2011-10-27

  The present invention relates to a novel compound having excellent antioxidant activity, isolated from Ramalina terebrata , and more particularly to a novel compound, Ramalin, having excellent antioxidant activity, isolated from the Antarctic lichen Ramalina terebrata , a method for preparing the Ramalin, and a pharmaceutical composition, a functional food and a functional cosmetic composition, which contain the Ramalin as an active ingredient. The Ramalin according to the invention has significantly excellent antioxidant effects compared to commercially available antioxidants, and thus can be widely used in agents for treating oxidation-related diseases, anti-aging functional foods, functional cosmetic products for skin whitening and wrinkle reduction, etc.
• PHARMACEUTICAL COMPOSITION FOR THE PREVENTION OR TREATMENT OF INFLAMMATORY DISEASES OR IMMUNE DISEASES CONTAINING RAMALIN
  申请人：Yim Joung Han

  公开号：US20130116324A1

  公开（公告）日：2013-05-09

  The present invention relates to the novel use (anti-inflammatory activity) of Ramalin isolated from the Antarctic lichen Ramalina terebrata , and more specifically to a pharmaceutical composition containing Ramalin as an active ingredient. Ramalin of the invention is a compound derived from natural material, has no toxicity or side effects, and inhibits the expression of inducible nitric oxide synthase (iNOS) in the transcription stage to significantly inhibit the production of nitric oxide (NO) that is a key mediator of inflammatory responses. In addition, it inhibits the activation of the inflammatory mediator NF-κB, inhibits p38 MAPK, ERK1/2 and JNK signaling pathways, and inhibits the expression of the LPS receptor TLR4, suggesting that Ramalin has an excellent anti-inflammatory effect. Thus, the composition containing Ramalin can be effectively used to fundamentally treat or prevent inflammatory diseases or immune diseases and to relieve or alleviate the symptoms of the diseases.