(+)-3-acetylaltholactone | 65409-11-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡喃类
• 英文名称: (+)-3-acetylaltholactone
• 英文别名: 3-Acetylaltholactone；[(2R,3R,3aR,7aS)-5-oxo-2-phenyl-2,3,3a,7a-tetrahydrofuro[3,2-b]pyran-3-yl] acetate
• CAS: 65409-11-2
• 化学式: C₁₅H₁₄O₅
• 分子量: 274.273
• InChiKey: PQTDQVRTMJEDLP-ZGKBOVNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+)-3-acetylaltholactone 在 四氧化锇 、 N-甲基吲哚酮 、 水 作用下， 以 丙酮 为溶剂， 反应 1.5h， 以75%的产率得到[(2R,3R,3aR,6S,7R,7aS)-6,7-dihydroxy-5-oxo-2-phenyl-2,3,3a,6,7,7a-hexahydrofuro[3,2-b]pyran-3-yl] acetate
  参考文献：
  名称：

  Semisynthesis and Cytotoxicity of Styryl-Lactone Derivatives

  摘要：

  The cytotoxicity and the cell-cycle action of altholactone (1), goniofufurone (2), and eight altholactone derivatives. (5-12), were determined in vitro on L-1210 cells. Semisyntheses and structure-activity relationships of these compounds are described. The results of this study suggest that the cytotoxicity of altholactone (1), 11-nitro-altholactone (8), and 7-chloro-6,7-dihydroaltholactone (10) is due to the accumulation of the cells in the G2 + M phase of the cell cycle.

  DOI：

  10.1021/np990089q
• 作为产物：
  描述：

  (5S,6R,7R,8S)-6-<8-acetoxy-7,8-dihydro-7-(methoxymethoxy)styryl>-5-(methoxymethoxy)-5,6-dihydro-2H-pyran-2-one 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以93%的产率得到(+)-3-acetylaltholactone
  参考文献：
  名称：

  立体控制合成新型苯乙烯基内酯，（+）-goniodiol，（+）-goniotriol，（+）-8-乙酰基goniotriol，（+）-goniofufurone，（+）-9-deoxygoniopypyrone，（+）-goniopypyrone和（+ ）-内酯的常见中间体及其同系物的细胞毒性

  摘要：

  简捷合成（+）-goniodiol，（+）-goniotriol，（+）-8-乙酰基goniotriol，（+）-goniofufurone，（+）-9-脱氧goniopypyrone，（+）-goniopypyrone和（+）-邻甲内酯描述了它们来自手性内酯醛27和36的同类物，作为常见的中间体。合成中的关键特征是基于原位生成不稳定的醛27和36，然后它们与三异丙氧基苯基钛发生化学选择性反应，从而在C-8位提供非对映异构体28、29和37、38。检查了苯乙烯基内酯同源物对P388鼠白血病细胞的细胞毒性。

  DOI：

  10.1016/s0040-4020(99)00023-x

文献信息

• Halogenated benzoate derivatives of altholactone with improved anti-fungal activity
  作者：Jirayut Euanorasetr、Mayura Junhom、Srisurang Tantimavanich、Onanong Vorasin、Bamroong Munyoo、Patoomratana Tuchinda、Watanalai Panbangred

  DOI：10.1080/10286020.2015.1133611

  日期：2016.5.3

  activity with a high MIC value of 128 μg ml−1 against Cryptococcus neoformans and Saccharomyces cerevisiae. Fifteen ester derivatives of altholactone 1–15 were modified by esterification and their structures were confirmed by spectroscopic methods. Most of the ester derivatives exhibited stronger anti-fungal activities than that of the precursor altholactone. 3-Bromo- and 2,4-dichlorobenzoates (7 and

  Altholactone表现出抗真菌活性与128微克ml的高MIC值-1对新型隐球菌和酿酒酵母。altholactone十五酯衍生物1 - 15被酯化改性其结构分别通过光谱方法证实。大多数酯衍生物显示出比前驱体内酯更强的抗真菌活性。3-溴和2,4-二氯苯甲酸酯（7和15）对C的最低抑菌浓度（MIC）最低。新型隐球菌在16微克毫升-1 ，而4-溴，4-碘，和1-溴-3- chlorobenzoates（11 - 13）中显示的有效活性针对酿酒酵母用1μg毫升的MIC值-1。总之，该分析表明，通过向3-OH基团中添加卤代苯甲酰基，可以增强甲内酯的抗真菌活性。
• (+)-Altholactone exhibits broad spectrum immune modulating activity by inhibiting the activation of pro-inflammatory cytokines in RAW 264.7 cell lines
  作者：Tyler A. Johnson、Johann Sohn、Aidan E. Ward、Tanya L. Cohen、Nicholas D. Lorig-Roach、Haixia Chen、Ronaldo A. Pilli、Elizabeth A. Widjaja、Muhammad Hanafi、Leonardus B.S. Kardono、Puspa D. Lotulung、Kyria Boundy-Mills、Leonard F. Bjeldanes

  DOI：10.1016/j.bmc.2013.04.055

  日期：2013.7

  An evaluation of Indonesian plants to identify compounds with immune modulating activity revealed that the methanolic extract of an Alphonsea javanica Scheff specimen possessed selective anti-inflammatory activity in a nuclear factor-kappa B (NF-kappa B) luciferase and MTT assay using transfected macrophage immune (Raw264.7) cells. A high-throughput LC/MS-ELSD based library approach of the extract in combination with the NF-kappa B and MTT assays revealed the styryl lactone (+)-altholactone (2) was responsible for the activity. Compound 2, its acetylated derivate (+)-3-O-acetylaltholactone (3), and the major compound of this class, (+)-goniothalmin (1), were further evaluated to determine their anti-inflammatory potential in the NF-kappa B assay. Concentration-response studies of 1-3 indicated that only 2 possessed NF-kappa B based anti-inflammatory activity. Compound 2 reduced the LPS-induced NO production, phosphorylation of I kappa B alpha, and the expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) using Western blot analysis. Further studies using qPCR indicated 2 reduced the expression of eight pro-inflammatory cytokines/enzymes (0.8-5.0 mu M) which included: COX-2, iNOS, IP-10, IL-1 beta, MCP-1, GCS-F, IL-6 and IFN-beta. These results indicated that 2 displays broad spectrum immune modulating activity by functioning as an anti-inflammatory agent against LPS-induced NF-kappa B signaling. Conversely the selective cytotoxicity and in vivo anti-tumor and anti-inflammatory activity previously reported for 1 do not appear to arise from a mechanism that is linked to the NF-kappa B immune mediated pathway. (C) 2013 Published by Elsevier Ltd.
• 3-Acetylaltholactone and related styryl-lactones, mitochondrial respiratory chain inhibitors
  作者：Eva Peris、Ernesto Estornell、Nuria Cabedo、Diego Cortes、Almudena Bermejo

  DOI：10.1016/s0031-9422(00)00104-7

  日期：2000.6

  A novel furano-pyrone, 3-acetylaltholactone, and two other known styryl-lactones, altholactone and 5-acetoxyisogoniothalamin oxide, have been isolated from Goniothalamus arvensis (Annonaceae) stem bark. We report here the isolation and structural elucidation of these compounds with furane-pyrone and styryl-pyrone skeletons. postulating also for the first time their mechanism of cytotoxicity based on inhibition on mammalian mitochondrial respiratory chain. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Semisynthesis and Cytotoxicity of Styryl-Lactone Derivatives
  作者：Almudena Bermejo、Stéphane Léonce、Nuria Cabedo、Inmaculada Andreu、Daniel H. Caignard、Ghanem Atassi、Diego Cortes

  DOI：10.1021/np990089q

  日期：1999.8.1

  The cytotoxicity and the cell-cycle action of altholactone (1), goniofufurone (2), and eight altholactone derivatives. (5-12), were determined in vitro on L-1210 cells. Semisyntheses and structure-activity relationships of these compounds are described. The results of this study suggest that the cytotoxicity of altholactone (1), 11-nitro-altholactone (8), and 7-chloro-6,7-dihydroaltholactone (10) is due to the accumulation of the cells in the G2 + M phase of the cell cycle.
• Stereocontrolled syntheses of novel styryl lactones, (+)-goniodiol, (+)-goniotriol, (+)-8-acetylgoniotriol, (+)-goniofufurone, (+)-9-deoxygoniopypyrone, (+)-goniopypyrone, and (+)-altholactone from common intermediates and cytotoxicity of their congeners
  作者：Masayoshi Tsubuki、Kazuo Kanai、Hiromasa Nagase、Toshio Honda

  DOI：10.1016/s0040-4020(99)00023-x

  日期：1999.2

  Concise syntheses of (+)-goniodiol, (+)-goniotriol, (+)-8-acetylgoniotriol, (+)-goniofufurone, (+)-9-deoxygoniopypyrone, (+)-goniopypyrone, and (+)-altholactone and their congeners from chiral lactonic aldehydes 27 and 36 as common intermediates are described. The key features in the syntheses are based on the in situ generation of unstable aldehydes 27 and 36 followed by their chemoselective reaction

  简捷合成（+）-goniodiol，（+）-goniotriol，（+）-8-乙酰基goniotriol，（+）-goniofufurone，（+）-9-脱氧goniopypyrone，（+）-goniopypyrone和（+）-邻甲内酯描述了它们来自手性内酯醛27和36的同类物，作为常见的中间体。合成中的关键特征是基于原位生成不稳定的醛27和36，然后它们与三异丙氧基苯基钛发生化学选择性反应，从而在C-8位提供非对映异构体28、29和37、38。检查了苯乙烯基内酯同源物对P388鼠白血病细胞的细胞毒性。