羽扇烯基棕榈酸酯 | 32214-80-5

• 物质功能分类: 天然产物 - 萜类
• 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: 羽扇烯基棕榈酸酯
• 英文名称: lupeol palmitate
• 英文别名: lupeyl palmitate；[(1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-yl] hexadecanoate
• CAS: 32214-80-5
• 化学式: C₄₆H₈₀O₂
• 分子量: 665.14
• InChiKey: BWXDHBQGBNPJMN-VBHWJLTNSA-N

物化性质

• 熔点：
  110℃
• 沸点：
  659.5±24.0 °C(Predicted)
• 密度：
  0.96±0.1 g/cm3(Predicted)
• LogP：
  19.310 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  17.8
• 重原子数：
  48
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 储存条件：
  室温

制备方法与用途

羽扇豆醇棕榈酸酯是一种具有抗溃疡活性的天然化合物，它还具备胃保护作用[1]。

反应信息

• 作为反应物：
  描述：

  羽扇烯基棕榈酸酯 在 甲醇 、 selenium(IV) oxide 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 (3beta)-3-羟基羽扇-20(30)-烯-29-醛
  参考文献：
  名称：

  五环三萜吡嗪的合成、生物学评价、分子对接研究和计算机 ADMET 评价

  摘要：

  通过在 C-2 / C-3 处引入吡嗪并修饰羽扇豆醇衍生物的相对未开发的 C-30 位置，进行了新的羽扇豆酸棕榈酸酯和 3β-棕榈酰氧基-olean-12-ene 衍生物的半合成，并对其细胞毒性进行了研究。和抗炎活性进行了评价。衍生物7、10和11显着抑制肿瘤细胞系 U251 、 K562、HCT-15、MCF-7 和 SKLU- 1，化合物7和11更具有活性（IC 50 25.4±2.0 µM 和 7.1±0.4 µM，分别）比肿瘤线 PC-3 中的阳性对照（依托泊苷 (IC 50 31.5±2.2 µM)。在化合物1中的 C-2 / C-3 处引入吡嗪和2或化合物1的 C-30 修饰降低了 TPA 诱导的小鼠耳水肿中的抗炎活性。根据对天然化合物及其衍生物潜在生物活性的PASS在线评估结果，研究了对pNF-κB易位至前列腺癌（PC-3 ）细胞核的抑制作用以及化合物7、10的结合方式和11通过分子对接研究探索了人类

  DOI：

  10.1016/j.bioorg.2022.105924
• 作为产物：
  描述：

  羽扇豆醇 、 棕榈酸 在 4-二甲氨基吡啶 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 羽扇烯基棕榈酸酯
  参考文献：
  名称：

  Gastroprotective properties of Lupeol-derived ester: Pre-clinical evidences of Lupeol-stearate as a potent antiulcer agent

  摘要：

  Lupeol (1) was isolated from hexane branch extract of Maytenus salicifolia and the Lupeol stearate (2), Lupeol palmitate (3), Lupeol myristate (4), Lupeol laurate (5) and Lupeol caprylate (6) were obtained reacting 1 with an adequate carboxylic acid. Swiss mice were treated with vehicle, carbenoxolone or Lupeol esters before administration of ethanol/HCl or indomethacin. Additionally, the involvement of nitric oxide (NO), sulfhydryl compounds (NP-SH), alpha-2 adrenergic receptors (alpha 2-AR) and prostaglandins (PGE) in antiulcer effects was investigated using appropriate inhibitors or antagonist. Oxidative and inflammatory parameters were measured after euthanasia and anti-secretory effects was evaluated in pylorus-ligated rats. Ethanol/HCl ulcerated the gastric mucosa by 64.45 +/- 6.58 mm(2), which the oral treatment with 1, 4 and 6 (10 mg/kg), and 3 and 5 (30 mg/kg) reduced the lesion area. Interestingly, 2 reduced the gastric ulcer by oral route in a potent and dosedependent manner (ED50 = 0.40 mg/kg), which was accompanied by the increase in reduced glutathione levels and by the reduction of lipids peroxidation and myeloperoxidase and superoxide dismutase activities. Moreover, 2 (0.1 mg/kg) also prevented the ulcerogenesis by intraperitoneal route. The participation of NO, NP-SH, alpha 2-AR and PGE in 2-mediated gastroprotection was confirmed. In indomethacin-induced ulcer, 2 (1 mg/kg, p.o) also reduced the ulcer area and increased the PGE 2 levels. However, 2 did not alter the gastric acid secretion. Therefore, these findings indicate that the obtention of 2 potentiated the antiulcer activity of 1 and that this compound can elicit gastroprotective action due a diversified mode of action.

  DOI：

  10.1016/j.cbi.2020.108964

文献信息

• Terpenoids in four Inula species from Bulgaria
  作者：Antoaneta Trendafilova、Victoria Ivanova、Milka Todorova、Plamena Staleva、Ina Aneva

  DOI：10.2298/jsc210730087t

  日期：——

  Phytochemical study of the chloroform extract of the aerial parts of Inula germanica L., I. ensifolia L., I. conyza (Griess.) DC. and I. salicina L. led to the identification of 33 terpenoids. ?- and ?-amyrin, lupeol, taraxasterol, ?-taraxasterol and their 3-O-acetates and 3-O-palmitates were identified by GC/MS. In addition, the structures of 3-O-palmitates of mainaladiol, arnidiol, faradiol and 16-hydroxylupeol were confirmed by NMR. ent-Kaur-16-en-19- -oic acid and its 15?-(3-methylpentanoyloxy) and 15?-(3-methylbutanoyloxy) derivatives were isolated from I. conyza. Ten closely related sesquiterpene lactones (germacranolides and melampolides) were found in I. germanica and their structural identification was performed by spectral analyses. I. ensifolia and I. salicina were free of sesquiterpene lactones and diterpenoids. All triterpenoids and diterpenoids, grazielia acid, desacetylovatifolin and 8-(2-methylbutanoyloxy)- 1(10),4,11(13)-germacrutrien-6,12-olide-14-oic acid are described for the first time in the studied species. The principal component analysis was used to find a relationship between th? investigated up to now Inula species, growing in Bulgaria.

  通过对 Inula germanica L.、I. ensifolia L.、I. conyza (Griess.) DC.和 I. salicina L.气生部分的氯仿提取物进行植物化学研究，鉴定出 33 种萜类化合物。通过气相色谱/质谱（GC/MS）鉴定了"-"和"-"阿米林"、"羽扇豆醇"、"蒲公英甾醇"、"蒲公英甾醇 "及其 3-O-乙酸酯和 3-O-棕榈酸酯。此外，还通过核磁共振确认了mainaladiol、arnidiol、faradiol 和 16-hydroxylupeol 的 3-O-棕榈酸酯的结构。从 I. conyza 中分离出 ent-Kaur-16-en-19-oic acid 及其 15?-（3-甲基戊酰氧基）和 15?-（3-甲基丁酰氧基）衍生物。在 I. germanica 中发现了 10 种密切相关的倍半萜内酯（germacranolides 和 melampolides），并通过光谱分析进行了结构鉴定。I. ensifolia 和 I. salicina 不含倍半萜内酯和二萜。所有三萜类和二萜类化合物、grazielia 酸、去乙酰vatifolin 和 8-（2-甲基丁酰氧基）- 1(10),4,11(13)-germacrutrien-6,12-olide-14-oic acid 都是首次在所研究的物种中发现。研究人员利用主成分分析法找到了生长在保加利亚的茵陈物种之间的关系。
• Unusual homologous long-chain alkanoic acid esters of lupeol from Koelpinia linearis
  作者：T.K. Razdan、P.K. Kachroo、M.A. Qurishi、A.K. Kalla、E.S. Waight

  DOI：10.1016/0031-9422(95)00687-7

  日期：1996.3

  Abstract An unusual series of five long-chain alkanoic acid (C 14 C 18 ) esters of lupeol was isolated from the methanol extract of koelpinia linearis and characterized by chemical and spectroscopic methods, including 13 C NMR. The spectral assignments were achieved by APT and DEPT techniques.

  摘要 5 个不同寻常的羽扇豆醇长链链烷酸(C 14 C 18 ) 酯是从koelpinia linearis 的甲醇提取物中分离出来的，并通过化学和光谱方法，包括13 C NMR 进行表征。光谱分配是通过 APT 和 DEPT 技术实现的。
• A PLANT EXTRACT AND ITS PHARMACEUTICAL AND COSMETIC USE
  申请人：Cognis France, S.A.S.

  公开号：EP1711194A1

  公开（公告）日：2006-10-18
• Composition Containing a Plant Extract and Process for Producing Same
  申请人：Henry Florence

  公开号：US20070281047A1

  公开（公告）日：2007-12-06

  A composition which includes a pulp extract from the fruit of Argania spinosa and at least one dermopharmaceutical or cosmetic auxiliary and/or additive is provided. A process for producing an extract from the fruit of Argania spinosa , and a triterpene fraction of an extract of the pulp of the fruit of Argania spinosa including lupeol, α-amyrine, β-amyrine, taraxasterol, and psi-taraxasterol are also provided.
• BIO-AVAILABILITY/BIO-EFFICACY ENHANCING ACTIVITY OF STEVIA REBAUDIANA AND EXTRACTS AND FRACTIONS AND COMPOUNDS THEREOF
  申请人：Gokaraju Ganga Raju

  公开号：US20100112101A1

  公开（公告）日：2010-05-06

  The present invention discloses bio-efficacy and bio-availability enhancing composition comprising, an effective amount of stevia compound selected from raw powder or extract, or fraction(s) or compound(s) or combinations thereof derived from the whole plant or plant parts of genus Stevia , preferably leaves of Stevia rebaudiana for enhancing the bio-availability and bio-efficacy of therapeutic agents, cosmetic agents, supplements, food ingredients and beverages selected from but not limited to pharmaceutical drugs, nutrients (micro and macro nutrients), vitamins, minerals, Proteins, amino acids, enzymes, nutraceuticals, herbal drugs/products and antioxidants.