helenalin acetate | 10180-86-6

• 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: helenalin acetate
• 英文别名: acetylhelenalin；Angustibalin；[(3aR,5R,5aR,8aR,9S,9aR)-5,8a-dimethyl-1-methylidene-2,8-dioxo-3a,4,5,5a,9,9a-hexahydroazuleno[6,5-b]furan-9-yl] acetate
• CAS: 10180-86-6
• 化学式: C₁₇H₂₀O₅
• 分子量: 304.343
• InChiKey: DCNRYQODUSSOKC-HKHYKUHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  helenalin acetate 在 乙酸乙酯 、 铂 作用下， 生成 tetrahydroacetylhelenalin
  参考文献：
  名称：

  Helenalin. III. Reduction and Dehydrogenation

  摘要：

  DOI：

  10.1021/ja01175a089
• 作为产物：
  描述：

  心菊内酯 、 乙酸酐 在 吡啶 作用下， 反应 6.0h， 以70%的产率得到helenalin acetate
  参考文献：
  名称：

  倍半萜内酯衍生物的制备：细胞毒活性和作用选择性

  摘要：

  癌症是全世界最重要的死亡原因之一。实体瘤代表了绝大多数癌症（> 90%），用于治疗的化疗药物的特点仍然是疗效和毒性各不相同。倍半萜内酯是一组天然存在的化合物，具有多种生物活性，包括细胞毒活性。合成了一系列来自倍半萜内酯小茴香素 (1)、海兰素 (2) 和处女膜素 (3) 的氧化和氧氮化衍生物 (4-15)。发现 Helenalin 的硅烷化衍生物化合物 13 和 14 对肿瘤细胞系的活性最强，GI50 值范围为 0.15 至 0.59 μM。双三唑基香豆素衍生物 (11) 被证明在测试的乳房、子宫颈、肺、和结肠肿瘤细胞系。该化合物对脾细胞的毒性最小 (CC50 = 524.1 µM)，对肿瘤细胞系的选择性最大。该化合物对 WiDr 人结肠肿瘤细胞系的 GI50 为 2.3 µM，SI 为 227.9。因此，化合物11可以考虑用于进一步研究，并且是开发新抗肿瘤剂的候选物。

  DOI：

  10.3390/molecules24061113

文献信息

• Structure-activity relationship in the gastric cytoprotective effect of several sesquiterpene lactones
  作者：Oscar S. Giordano、Mauricio J. Pestchanker、Eduardo Guerreiro、Jose R. Saad、Ricardo D. Enriz、Ana M. Rodriguez、Esteban A. Jauregui、Jorge Guzman、Alejandra O. M. Maria、Graciela H. Wendel

  DOI：10.1021/jm00091a013

  日期：1992.6

  a non sterically hindered Michael acceptor seems to be an essential structural requirement for the cytoprotective activity in this family of compounds. This observation suggests that cytoprotection is mediated through a Michael reaction between the sulfhydryl-containing peptides of the mucosa and Michael acceptors present in the molecules under study. This mechanism of action is in addition to and

  报道了几种倍半萜内酯对胃细胞保护活性的结构要求。对潜在活跃中心进行了理论实验研究。还原类似物的生物学评估以及这些化合物与内源性半胱氨酸残基之间的分子相互作用的模拟表明，非空间阻碍的迈克尔受体的存在似乎是该化合物家族中细胞保护活性的基本结构要求。该观察结果表明，细胞保护作用是通过粘膜中含巯基的肽与研究分子中存在的迈克尔受体之间的迈克尔反应介导的。这种作用机制是对我们先前论文中提出的机制的补充，并且与之不同。
• Stabilized retinol for cosmetic dermatological, and pharmaceutical compositions, and use thereof
  申请人：——

  公开号：US20030232091A1

  公开（公告）日：2003-12-18

  The present invention relates to a controlled release system useful to stabilize retinol, retinol derivatives, and extracts containing retinol in cosmetic, dermatological, and pharmaceutical compositions. More specifically, the present invention pertains to stabilized retinol in a solid hydrophobic particle that sustains the release of retinol during the product shelf life and enables a gradual and prolonged release of effective levels of retinol and other cosmetic, dermatological, and pharmaceutical active ingredients into biological surfaces. The present invention also refers to a process of stabilizing retinol, retinol derivatives, and extracts containing retinol in cosmetic, dermatological, and pharmaceutical compositions. The invention further relates to cosmetic, dermatological, and pharmaceutical products comprising stable retinol in a hydrophobic particle that can deliver effective levels of retinol and other cosmetic, dermatological, and pharmaceutical active ingredients to biological surfaces over an extended period of time.

  本发明涉及一种控释系统，用于稳定化妆品、皮肤病学和药物组合物中的视黄醇、视黄醇衍生物和含有视黄醇的提取物。更具体地说，本发明涉及在固体疏水性颗粒中稳定视黄醇，该颗粒可在产品保质期内维持视黄醇的释放，并使有效水平的视黄醇和其他化妆品、皮肤病学和药物活性成分逐渐并长时间地释放到生物表面。本发明还涉及一种稳定化妆品、皮肤病学和药物组合物中的视黄醇、视黄醇衍生物和含有视黄醇的提取物的工艺。本发明还涉及在疏水性颗粒中含有稳定视黄醇的化妆品、皮肤病学和药物产品，该疏水性颗粒可在较长时间内将有效水平的视黄醇和其他化妆品、皮肤病学和药物活性成分输送到生物表面。
• Multi component controlled delivery system for soap bars
  申请人：——

  公开号：US20030207776A1

  公开（公告）日：2003-11-06

  The present invention relates to an improved controlled delivery system that can be incorporated in soap bars to enhance deposition of active ingredients and sensory markers onto skin. The carrier system also provides controlled release or prolonged release of these actives from the skin over an extended period of time. The controlled delivery system of the present invention comprises substantially free-flowing, powder formed of solid hydrophobic, positively charged, nanospheres of encapsulated active ingredients, that are encapsulated in moisture sensitive microspheres. The high cationic charge density of the nanosphere improves deposition of active ingredients onto skin. The high cationic charge density on the nanosphere surface is created by incorporating a cationic conditioning agent into the solid hydrophobic matrix of the nanospheres, by incorporating a cationic charge “booster” in the moisture sensitive microsphere matrix, or by using a cationic conditioning agent in the nanosphere matrix in conjunction with a cationic charge “booster” in the microsphere matrix. The invention also pertains to soap products comprising the controlled release system of the present invention.

  本发明涉及一种改进的可控给药系统，可将其加入肥皂条中，以增强活性成分和感官标记在皮肤上的沉积。该载体系统还能使这些活性成分在较长时间内从皮肤中控制释放或延长释放时间。本发明的控释系统包括基本自由流动的粉末，由固态疏水性、带正电荷、封装活性成分的纳米球组成，这些纳米球封装在湿敏微球中。纳米球的高阳离子电荷密度提高了活性成分在皮肤上的沉积效果。纳米球表面的高阳离子电荷密度是通过在纳米球的固态疏水基质中加入阳离子调节剂，在湿敏微球基质中加入阳离子电荷 "增效剂"，或在纳米球基质中使用阳离子调节剂的同时在微球基质中使用阳离子电荷 "增效剂 "而产生的。本发明还涉及包含本发明控释系统的肥皂产品。
• Personal care article and method for inhibiting attachment of yeast to skin
  申请人：——

  公开号：US20030224034A1

  公开（公告）日：2003-12-04

  A personal care article including an isoprenoid compound, and a method of inhibiting attachment of pathogenic fungi to skin using an isoprenoid compound in combination with a personal care article. The isopreniod compound may be farnesol, which is particularly effective against the pathogenic yeast Candida albicans.

  一种包括异戊二烯化合物的个人护理用品，以及一种使用异戊二烯化合物与个人护理用品相结合抑制致病真菌附着皮肤的方法。异戊二烯化合物可以是法尼醇，它对致病性酵母菌 白色念珠菌。
• Skin care compositions including hexapeptide complexes and methods of their manufacture
  申请人：Dilallo Natalie

  公开号：US20060198800A1

  公开（公告）日：2006-09-07

  Skin care compositions disclosed herein include, at a minimum, safe and effective amounts of at least one wrinkle reduction agent, which is a hexapeptide, and a natural exfoliating complex. The skin care compositions provide natural skin exfoliation, reduce fine lines and wrinkles, and improve skin elasticity and firmness.

  本文公开的护肤组合物至少包括安全有效量的至少一种除皱剂（六胜肽）和天然去角质复合物。护肤组合物能天然去除皮肤角质，减少细纹和皱纹，改善皮肤弹性和紧致度。