urs-12-ene-28-carboxy-3β-octadecanoate

• 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
• 英文名称: urs-12-ene-28-carboxy-3β-octadecanoate
• 英文别名: 3β-(octadecanoyloxy)urs-12-en-28-oic acid；Urs-12-ene-28-carboxy-3beta-octadecanoate；(1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-1,2,6a,6b,9,9,12a-heptamethyl-10-octadecanoyloxy-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
• 化学式: C₄₈H₈₂O₄
• 分子量: 723.177
• InChiKey: WCVGGGIAUJJJKG-DGUJLNNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.3
• 重原子数：
  52
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  熊果酸 、 硬脂酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以38 mg的产率得到urs-12-ene-28-carboxy-3β-octadecanoate
  参考文献：
  名称：

  Antileishmanial Activity of the Hydroalcoholic Extract of Miconia langsdorffii, Isolated Compounds, and Semi-Synthetic Derivatives

  摘要：

  Miconia langsdorffii Cogn 地上部分的粗水醇提取物的体外活性。针对亚马逊利什曼病的前鞭毛体形式进行了评估，亚马逊利什曼病是人类皮肤利什曼病的病原体。对该提取物进行生物测定引导的分馏，结果鉴定出三萜熊果酸和齐墩果酸是该馏分中表现出最高活性的主要化合物。制备了几种熊果酸半合成衍生物，以探讨是否可以获得活性更高的化合物。在这些熊果酸衍生物质中，C-28甲酯衍生物表现出最好的抗利什曼尼活性。

  DOI：

  10.3390/molecules16021825

文献信息

• Antileishmanial Activity of the Hydroalcoholic Extract of Miconia langsdorffii, Isolated Compounds, and Semi-Synthetic Derivatives
  作者：Juliana A. Peixoto、Márcio Luis Andrade e Silva、Antônio E. M. Crotti、Rodrigo Cassio Sola Veneziani、Valéria M. M. Gimenez、Ana H. Januário、Milton Groppo、Lizandra G. Magalhães、Fransérgio F. Dos Santos、Sérgio Albuquerque、Ademar A. Da Silva Filho、Wilson R. Cunha

  DOI：10.3390/molecules16021825

  日期：——

  The in vitro activity of the crude hydroalcoholic extract of the aerial parts of Miconia langsdorffii Cogn. was evaluated against the promastigote forms of L. amazonensis, the causative agent of cutaneous leishmaniasis in humans. The bioassay-guided fractionation of this extract led to identification of the triterpenes ursolic acid and oleanolic acid as the major compounds in the fraction that displayed the highest activity. Several ursolic acid semi-synthetic derivatives were prepared, to find out whether more active compounds could be obtained. Among these ursolic acid-derived substances, the C-28 methyl ester derivative exhibited the best antileishmanial activity.

  Miconia langsdorffii Cogn 地上部分的粗水醇提取物的体外活性。针对亚马逊利什曼病的前鞭毛体形式进行了评估，亚马逊利什曼病是人类皮肤利什曼病的病原体。对该提取物进行生物测定引导的分馏，结果鉴定出三萜熊果酸和齐墩果酸是该馏分中表现出最高活性的主要化合物。制备了几种熊果酸半合成衍生物，以探讨是否可以获得活性更高的化合物。在这些熊果酸衍生物质中，C-28甲酯衍生物表现出最好的抗利什曼尼活性。
• Antifeedant Activity of Some Pentacyclic Triterpene Acids and Their Fatty Acid Ester Analogues
  作者：Uppuluri V. Mallavadhani、Anita Mahapatra、S. Sabitha Raja、C. Manjula

  DOI：10.1021/jf020691d

  日期：2003.3.1

  The 3-O-fatty acid ester derivatives (C(12)-C(18)) of two pentacyclic triterpenic acids, ursolic acid and oleanolic acid, were synthesized under mild esterification conditions in excellent yields (80-85%) and screened for their antifeedant activity, together with the parent acids, against the agricultural pest tobacco caterpillar larvae (Spodoptera litura F) in a no-choice laboratory study. The Ur

  在温和的酯化条件下以极佳的收率（80-85％）合成了两种五环三萜酸，熊果酸和齐墩果酸的3-O-脂肪酸酯衍生物（C（12）-C（18））在一项非选择的实验室研究中，它们与母体酸一起对农用烟草毛虫幼虫（Spodoptera litura F）的拒食活性。发现Urs-12-ene-28-羧基-3β-十八碳酸酯和olean-12-ene-28-羧基-3β-十六碳酸酯即使在48 h后仍显示出在50 microg / cm（2）浓度下异常有效的拒食活性。
• Antimicrobial Activity of Some Pentacyclic Triterpenes and Their Synthesized 3-O-Lipophilic Chains
  作者：Uppuluri Venkata Mallavadhani、Anita Mahapatra、Kaiser Jamil、Peddi Srinivasa Reddy

  DOI：10.1248/bpb.27.1576

  日期：——

  The major metabolites of Diopsyros melanoxylon viz. amyrins and ursolic acid and their lipophilic 3-O-fatty acid ester chains (C12—C18), which are synthesized now under mild esterification conditions in excellent yields (80—95%), were evaluated for their antimicrobial activity against a series of Gram positive and Gram negative bacteria. Significantly these compounds were found to exhibit potent activity against Gram negative bacteria Pseudomonas syringae (ATCC #13457) and fairly good activity against Gram positive bacteria, Bacillus sphaericus (ATCC #14577) and Bacillus subtilis (ATCC #6051).

  Diopsyros melanoxylon 即 Diopsyros melanoxylon 的主要代谢物。香树脂素和熊果酸及其亲脂性 3-O-脂肪酸酯链 (C12-C18) 现在在温和的酯化条件下以优异的产率 (80-95%) 合成，并评估了它们对一系列革兰氏菌的抗菌活性。阳性和革兰氏阴性细菌。值得注意的是，这些化合物被发现对革兰氏阴性菌丁香假单胞菌 (ATCC #13457) 表现出强大的活性，对革兰氏阳性菌、球形芽孢杆菌 (ATCC #14577) 和枯草芽孢杆菌 (ATCC #6051) 表现出相当好的活性。
• [EN] COMPOSITION FOR PREVENTING HAIR LOSS AND ACCELERATING HAIR GROWTH<br/>[FR] COMPOSITION POUR LA PRÉVENTION DE LA CHUTE DES CHEVEUX ET L'ACCÉLÉRATION DE LA CROISSANCE DES CHEVEUX
  申请人：RNS CO LTD

  公开号：WO2014077621A1

  公开（公告）日：2014-05-22

  본 발명은 탈모방지 및 모발성장 촉진제 조성물로써, 화학식 1으로 표시되고 A는 다원환 고리화합물(polycyclic compound)로부터 유래되고, R은 히드록시 또는 탄소수 1 내지 20개로 구성된 포화 혹은 불포화된 직쇄 또는 분지쇄의 알킬옥시기 또는 아실옥시기이다.
• Synthesis and Antimicrobial Activity of Ursolic Acid Ester Derivatives
  作者：Vinicius Viana Pereira、Nara Rúbia Pereira、Rafael César Gonçalves Pereira、Lucienir Pains Duarte、Jacqueline Aparecida Takahashi、Roqueline Rodrigues Silva

  DOI：10.1002/cbdv.202100566

  日期：2022.1

  antimicrobial agents. Ursolic acid is a triterpene with known antibacterial action, being naturally found in plants, such as Jaracanda oxyphylla and Jacaranda caroba (Bignoniaceae). Ursolic acid derivative esters have revealed potential biological activities, such as antitumor, antiviral, and antibacterial activity. In this study, sixteen esters (1-16) were synthesized from ursolic acid using DIC/DMAP and characterized

  微生物引起的感染是全世界发病和死亡的主要原因，天然产物仍然是发现新抗菌剂的重要来源。熊果酸是一种具有已知抗菌作用的三萜，天然存在于植物中，例如Jaracanda oxyphylla和Jacaranda caroba （紫葳科）。熊果酸衍生物酯已显示出潜在的生物活性，例如抗肿瘤、抗病毒和抗菌活性。在本研究中，使用 DIC/DMAP 从熊果酸合成了 16 种酯 ( 1 - 16 )，并通过红外 (IR)、核磁共振 ( 1 H- 和13 C-NMR) 和质谱进行了表征。所有熊果酸酯均针对蜡样芽孢杆菌、金黄色葡萄球菌、大肠杆菌、鼠伤寒沙门氏菌和白色念珠菌进行了评估。 6种化合物（ 3、9、11、13、14和16 ）为首次描述，收率高达91.6 %。化合物11 （ 3β- （3,4-二甲氧基苯甲酰基）熊果酸）和15 （ 3β-烟酰熊果酸）显示出良好的抗真菌活性，对白色念珠菌生长的抑制率分别为93.1%和95