(Z)-2-甲基-2-丁烯酸(3aR,4R,6R,10Z,11aR)-2,3,3a,4,5,6,7,11alpha-八氢-10-羟基甲基-6-甲基-3-亚甲基-2,7-二氧代-6,9-环氧环癸并[b]呋喃-4-基酯 | 59481-48-0

• 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: (Z)-2-甲基-2-丁烯酸(3aR,4R,6R,10Z,11aR)-2,3,3a,4,5,6,7,11alpha-八氢-10-羟基甲基-6-甲基-3-亚甲基-2,7-二氧代-6,9-环氧环癸并[b]呋喃-4-基酯
• 英文名称: budlein A
• 英文别名: [(2Z,4R,8R,9R,11R)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.04,8]tetradeca-1(13),2-dien-9-yl] (Z)-2-methylbut-2-enoate
• CAS: 59481-48-0
• 化学式: C₂₀H₂₂O₇
• 分子量: 374.39
• InChiKey: BMVJFNLJSZHNNS-ZXRHVTAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  99.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (Z)-2-甲基-2-丁烯酸(3aR,4R,6R,10Z,11aR)-2,3,3a,4,5,6,7,11alpha-八氢-10-羟基甲基-6-甲基-3-亚甲基-2,7-二氧代-6,9-环氧环癸并[b]呋喃-4-基酯 在 Stryker's reagent 作用下， 反应 5.0h， 以33%的产率得到(3aS,4R,6R,10S,11aR)-10-(hydroxymethyl)-6-methyl-3-methylene-2,7-dioxo-2,3,3a,4,5,6,7,10,11,11a-decahydro-6,9-epoxycyclodeca[b]furan-4-yl (2Z)-2-methylbut-2-enoate
  参考文献：
  名称：

  Structurally modified natural sesquiterpene lactones constitute effective and less toxic schistosomicidal compounds

  摘要：

  倍半萜内酯具有活性，但同时也具有高细胞毒性。在本研究中，我们对结构上的微小改变如何影响倍半萜内酯的细胞毒性和杀血吸虫活性进行了评估。具体而言，我们评估了倍半萜内酯类化合物budlein-A及其四个衍生物的活性。本研究中提出的budlein-A的结构修饰降低了细胞毒性并改变了分子的抗寄生虫行为。这些研究结果还为更好地理解倍半萜内酯的细胞毒性提供了数据。此外，本文还根据核磁共振和HRESIMS数据，建立了三种合成倍半萜内酯的结构。首次完整、详细地提供了五种倍半萜内酯的1H和13C 1D和2D核磁共振数据，并阐明了所有J值和所有多重性的测量结果。

  DOI：

  10.1039/c4ob00426d

文献信息

• Terpenoids and a flavan-3-ol from viguiera quinqueradiata
  作者：Guillermo Delgado、Laura Alvarez、Alfonso Romo de Vivar

  DOI：10.1016/s0031-9422(00)80405-7

  日期：1984.1

  Abstract The isolation is reported of the new natural products from Viguiera quinqueradiata, acetylleptocarpin and (2R,3S-4′-hydroxy-3′,5,7-tri-O-methyl-flavan-3-ol. The diterpenes 15α-angeloyloxy-ent-kaur-16-en-19-oic acid, 15α-tigloyloxy-ent-kaur-16-en-19-oic acid and the sesquiterpene lactones leptocarpin and budlein A were also found.

  摘要 报道了从紫荆树中分离出新的天然产物，乙酰leptocarpin 和 (2R,3S-4'-hydroxy-3',5,7-tri-O-methyl-flavan-3-ol。二萜 15α-angeloyloxy -ent-kaur-16-en-19-oic酸、15α-tigloyloxy-ent-kaur-16-en-19-oic酸和倍半萜内酯leptocarpin和budlein A也被发现。
• Unusual biotransformation products of the sesquiterpene lactone budlein A by Aspergillus species
  作者：Nilton Syogo Arakawa、Leonardo Gobbo-Neto、Sérgio Ricardo Ambrosio、Gilmara Ausech Antonucci、Suely Vilela Sampaio、Mônica Tallarico Pupo、Suraia Said、Thomas J. Schmidt、Fernando Batista Da Costa

  DOI：10.1016/j.phytochem.2013.09.022

  日期：2013.12

  Biotransformation of chemicals by microorganisms can be effective in increasing chemical diversity. Some fungi have been described to be useful for the biotransformation of sesquiterpene lactones. Nevertheless, in most cases, only minor or simple transformations of functional groups have been observed. Budlein A is a sesquiterpene lactone found in high amounts in American sunflower-like species of the genus Viguiera (Asteraceae). It shows important biological effects like in vitro and in vivo anti-inflammatory activity, as well as cytotoxicity against cancer cell lines. With the aim to obtain potentially bioactive derivatives of budlein A and taking into account that obtaining semi-synthetic analogues is a very complex task, the capability of soil fungi to promote biotransformation was investigated. In this work, the biotransformation of budlein A by the soil fungi Aspergillus terreus and A. niger affording three unusual sesquiterpenoid derivatives with carbon skeletons is reported. The chemical structures of the compounds were elucidated by 1D and 2D NMR spectrometry and HR-ESI-MS. The stereochemistry and molecular conformation of one derivative was assessed by molecular modeling techniques. The fungal metabolites displayed a reduced cytotoxicity against HL-60 cells when compared to the original natural product. The results show the versatility of microbial-catalyzed biotransformations leading to unusual derivatives. (C) 2013 Elsevier Ltd. All rights reserved.