3,5,8a-trimethyl-3a,5,6,7,8,8a,9,9a-octahydro-3H-naphtho[2,3-b]furan-2-one | 40285-97-0

• 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
• 英文名称: 3,5,8a-trimethyl-3a,5,6,7,8,8a,9,9a-octahydro-3H-naphtho[2,3-b]furan-2-one
• 英文别名: dihydrohelenine；(3aR,5S,8aR,9aR)-3,5,8a-trimethyl-3,3a,5,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-2-one
• CAS: 40285-97-0
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: UHXFRFWUSTUALX-NUKRYZRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.32
• 重原子数：
  17.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  土木香内酯 在 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以1.91 g的产率得到3,5,8a-trimethyl-3a,5,6,7,8,8a,9,9a-octahydro-3H-naphtho[2,3-b]furan-2-one
  参考文献：
  名称：

  总状土木香倍半萜内酯的分离、化学转化和抗真菌潜力

  摘要：

  本研究报告了两种eudesmanolide 型倍半萜内酯的分离，即。alantolactone 和 isoalantolactone，来自 Inula racemosa Hook L. 的根，并使用各种试剂进行化学转化。使用孢子萌发抑制方法评估了所有分离和合成的化合物对稻瘟病菌、念珠镰刀菌和小麦链格孢的体外抗真菌潜力。为了了解倍半萜内酯的结构与其抗真菌功能的关系，研究了结构活性关系。发现异戊内酯及其衍生物与丙戊内酯及其衍生物相比毒性更大。在不同的合成化合物中，溴仿衍生物的效果最好，而甲氧基衍生物的效果最差。

  DOI：

  10.1007/s10600-020-02989-1

文献信息

• Helenine blocks NLRP3 activation by disrupting the NEK7-NLRP3 interaction and ameliorates inflammatory diseases
  作者：Zhi-E Fang、Yan Wang、Shuyi Bian、Shuanglin Qin、Huanying Zhao、Jincai Wen、Tingting Liu、Lutong Ren、Qiang Li、Wei Shi、Jia Zhao、Huijie Yang、Rui Peng、Qin Wang、Zhaofang Bai、Guang Xu

  DOI：10.1016/j.phymed.2023.155159

  日期：2024.1

  factors in NLRP3 activation, Hel inhibited NLRP3-dependent ASC oligomerization but did not regulating inflammasome priming, K+ efflux, Ca2+ influx, or mitochondrial damage and mtROS. Moreover, Hel effectively interrupted the binding of NEK7-NLRP3, which was dependent on the active double C=C of the α,β-unsaturated carbonyl units in Hel. In mouse models, Hel showed promising therapeutic effects in the treatment

  背景 NLRP3 炎症小体的参与与多种炎症状况的进展相关。然而，目前还没有单一化合物用于临床。从天然产物中寻找NLRP3炎症小体的抑制剂是一个有吸引力的方向。据报道，从Inula helenium L.中提取的化合物 Helenin (Hel)具有抗炎活性。然而，潜在的分子机制和特定的炎症信号通路仍不清楚。 目的 本研究旨在确定 Hel 对 NLRP3 炎症小体的影响及其潜在机制，同时评估其作为治疗干预 NLRP3 过度激活介导的炎症疾病的潜力。 方法 在 BMDM（骨髓源性巨噬细胞）中用 Hel 进行预处理，然后用 NLRP3 触发器刺激并测量活性 caspase-1 和白细胞介素 1β (IL-1β) 的表达。通过测定细胞内K +和Ca 2+、ASC寡聚化和线粒体活性氧(mtROS)产生来探讨Hel对NLRP3激活的初步机制。随后，利用免疫共沉淀研究蛋白质-蛋白质相互作用，并通过Hel
• Structural requirements of sesquiterpene lactones to inhibit LPS-induced nitric oxide synthesis in RAW 264.7 macrophages
  作者：Verena M Dirsch、Hermann Stuppner、Ernst P Ellmerer-Müller、Angelika M Vollmar

  DOI：10.1016/s0968-0896(00)00202-9

  日期：2000.12

  Some sesquiterpene lactones were recently demonstrated to inhibit inducible nitric oxide synthase (iNOS)-dependent nitric oxide (NO) synthesis. The primary objective of the present study was, therefore, to find evidence for structural requirements of sesquiterpene lactones regarding their capability to inhibit iNOS-dependent NO synthesis. Sesquiterpene lactones 1-11 were examined for their influence on nitrite accumulation in cell culture supernatants of LPS-induced RAW 264.7 macrophages. Except the taraxinic acid beta -D-glucopyranosylester 8 all compounds showed a dose-dependent inhibition of nitrite accumulation in cell culture supernatants with IC(50) values ranging from 0.5 to 36.8 muM High activity seemed to be dependent on an alpha -methylene-gamma -lactone functionality. Cytotoxicity and the ability to inhibit activation of transcription factor NF-kappaB are further biological activities of sesquiterpene lactones. The second point of interest was, therefore, whether the structural requirements of sesquiterpene lactones for these activities may differ or be the same for those needed to inhibit iNOS-dependent NO synthesis. Using concentrations of 111 required to inhibit NO synthesis cell viability was determined and NF-kappaB binding activity was measured by gel-shift experiments. Interestingly, compounds almost equally effective in inhibiting nitrite accumulation did not show the same cytotoxic potential, and most sesquiterpene lactones inhibited nitrite accumulation at concentrations where inhibition of NF-kappaB activation was not significant. These results suggest that different biological activities of sesquiterpene lactones have different structural requirements. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis of deuterium-labeled sesquiterpene lactones isolated from Inula helenium L
  作者：Marcel Schaeffer、Jean Luc Stampf、Claude Benezra

  DOI：10.1021/jo00287a024

  日期：1989.12
• SCHAEFFER, MARCEL;STAMPF, JEAN-LUC;BENEZRA, CLAUDE, J. ORG. CHEM., 54,(1989) N6, C. 6106
  作者：SCHAEFFER, MARCEL、STAMPF, JEAN-LUC、BENEZRA, CLAUDE

  DOI：——

  日期：——
• Isolation, Chemical Transformation, and Antifungal Potential of Sesquiterpene Lactones from Inula Racemosa
  作者：Ramandeep Kaur、K. K. Chahal、Urvashi

  DOI：10.1007/s10600-020-02989-1

  日期：2020.3

  The present study reports the isolation of two eudesmanolide type sesquiterpenoid lactones, viz. alantolactone and isoalantolactone, from the roots of Inula racemosa Hook L. and their chemical transformations using various reagents. All the compounds isolated and synthesized were assessed for their in vitro antifungal potential against Dreschlera oryzae, Fusarium moniliforme, and Alternaria triticina

  本研究报告了两种eudesmanolide 型倍半萜内酯的分离，即。alantolactone 和 isoalantolactone，来自 Inula racemosa Hook L. 的根，并使用各种试剂进行化学转化。使用孢子萌发抑制方法评估了所有分离和合成的化合物对稻瘟病菌、念珠镰刀菌和小麦链格孢的体外抗真菌潜力。为了了解倍半萜内酯的结构与其抗真菌功能的关系，研究了结构活性关系。发现异戊内酯及其衍生物与丙戊内酯及其衍生物相比毒性更大。在不同的合成化合物中，溴仿衍生物的效果最好，而甲氧基衍生物的效果最差。