(+/-)-isoarctigenin | 119030-66-9

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 呋喃类木脂素
• 英文名称: (+/-)-isoarctigenin
• 英文别名: (±)-buplerol；(3S,4S)-3-[(3,4-dimethoxyphenyl)methyl]-4-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
• CAS: 119030-66-9
• 化学式: C₂₁H₂₄O₆
• 分子量: 372.418
• InChiKey: NWFYESYCEQICQP-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+/-)-isoarctigenin 在 三氟乙酸 ruthenium(IV) oxide 、 三氟化硼乙醚 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以85%的产率得到trans-2-hydroxy-6-(hydroxymethyl)-3,10,11-trimethoxydibenzo[1a,4a:8a,12a]cyclooctadiene-7-carboxylic acid lactone
  参考文献：
  名称：

  使用四（三氟乙酸）钌对顺式和反式-2,3-二苄基丁内酯进行氧化环化

  摘要：

  已经合成了一系列顺式和反式-2,3-二苄基丁内酯，并使用四（三氟乙酸）钌进行氧化环化，得到属于木脂烷和异庚烷系列的二苯并环辛二烯内酯。

  DOI：

  10.1016/s0040-4020(01)00273-3
• 作为产物：
  描述：

  benzyl dihydroferulic acid chloride 在 sodium periodate 、 四氧化锇 、 lithium aluminium tetrahydride 、 titanium(IV) chloride tetrahydrofuran 、 palladium on activated carbon 、 氢气 、 N-甲基吗啉氧化物 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 200.67h， 生成 (+/-)-isoarctigenin
  参考文献：
  名称：

  5-羟甲基二苄基丁内酯及相关木脂素的模块化合成及生物学研究

  摘要：

  二苄基丁内酯木脂素以其优异的生物学特性而闻名，特别是其显着的抗增殖活性。在此，我们报告了一种利用酰基-克莱森重排立体选择性制备关键中间体的二苄基丁内酯木脂素的新型、高效、会聚合成。报道的合成路线能够修饰这些木脂素以产生这些木脂素的 5-羟甲基衍生物。评估了这些类似物的生物活性，其衍生物显示出优异的细胞毒性特征，导致 Jurkat T 白血病细胞程序性细胞死亡，其中不到 2% 的孵育细胞进入坏死细胞死亡途径。

  DOI：

  10.3390/molecules23123057

文献信息

• Oxidative cyclisation of cis- and trans-2,3-dibenzylbutyrolactones using phenyl iodonium bis(trifluoroacetate) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone
  作者：Robert S Ward、David D Hughes

  DOI：10.1016/s0040-4020(01)00472-0

  日期：2001.6

  A series of cis- and trans-2,3-dibenzylbutyrolactones have been subjected to oxidative cyclisation using phenyl iodonium bis(trifluoroacetate) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. The products obtained include two novel spirodienones 6 and 11, which rearrange with acid to give the dibenzocyclo-octadienes 7, and 12 and 13, respectively.

  使用苯基碘双（三氟乙酸酯）和2,3-二氯-5,6-二氰基-1,4-苯醌，对一系列顺式和反式-2,3-二苄基丁内酯进行了氧化环化反应。获得的产品包括两个新的spirodienones 6和11，其与酸重新排列，得到dibenzocyclo-辛二烯7，和12和13，分别。
• Burden, Jonathan K.; Cambie, Richard C.; Craw, Peter A., Australian Journal of Chemistry, 1988, vol. 41, # 6, p. 919 - 933
  作者：Burden, Jonathan K.、Cambie, Richard C.、Craw, Peter A.、Rutledge, Peter S.、Woodgate, Paul D.

  DOI：——

  日期：——
• New Furofuran and Butyrolactone Lignans with Antioxidant Activity from the Stem Bark of <i>Styrax </i><i>j</i><i>aponica</i>
  作者：Byung-Sun Min、Min-Kyun Na、Sei-Ryang Oh、Kyung-Seop Ahn、Gil-Saeng Jeong、Gao Li、Sang-Ku Lee、Hyouk Joung、Hyeong-Kyu Lee

  DOI：10.1021/np040113m

  日期：2004.12.1

  A new furofuran lignan, styraxlignolide B (1), and four new dibenzyl-gamma-butyrolactone lignans, styraxlignolides C-F (2-5), were isolated from the EtOAc-soluble fraction of stem bark of Styrax japonica. Known compounds, taraxerol (6), syringin (7), and (-)-pinoresinol glucoside (8), were also obtained. The structures of styraxligonolides B-F were determined as 2alpha-(4'-hydroxy-3'-methoxyphenyl)-6alpha-(3",4"-methylene-dioxyphenyl)-8-oxo-3,7-dioxabicyclo [3.3.0]octane 4'-O-(beta-D-glucopyranoside) (1), (2S,3S)-2alpha-(3"-hydroxy-4"-methoxybenzyl)-3 -(4'-hydroxy-3'-methoxybenzyl)-gamma-butyrolactone 4'-O-(beta-D-glucopyranoside) (2), (2S,3S)2(alpha-(4"-hydroxy-3"-methoxybenzyl)-3beta-(4'-hydroxy-3'-methoxybenzyl)-gamma-butyrolactone 4'-O-(fi-Dglucopyranoside) (3), (2S,3S)-2(alpha-(4"-hydroxy-3"-methoxybenzyl)-3beta-(4'-hydroxy-3'-methoxybenzyl)-gamma-butyrolactone 4"-O-(beta-D-glucopyranoside) (4), and (2S,3S)-2alpha-(3",4"-dimethoxybenzyl)-3 -(4'-hydroxy-3'-methoxybenzyl)-gamma-butyrolactone 4'-beta4-D-glucopyranoside) (5) by spectroscopic means including 2D NMR. Compounds 1-8 were tested in vitro for antioxidant activity against 1,1-diphenyl-2-pierylhydrazyl (DPPH) radicals. Styraxlignolide C (2), styraxlignolide D (3), styraxlignolide E (4), and (-)-pinoresinol glucoside (8) exhibited weak radical-scavenging activity in the DPPH assay, with IC50 values of 380, 278, 194, and 260 muM, respectively.
• Formation of (−)-arctigenin in Forsythia intermedia
  作者：Shuji Ozawa、Laurence B. Davin、Norman G. Lewis

  DOI：10.1016/s0031-9422(00)95149-5

  日期：1993.2

  Forsythia intermedia cell-free extracts were examined for their ability to catalyse the enantioselective and regiospecific O-methylation of matairesinol. In contrast to the enzymatic steps defined from (+)-pinoresinol to (-)-matairesinol, the conversion of matairesinol into arctigenin was not highly enantioselective; both (+)- and (-)- antipodes of matairesinol served as substrates for methylation, with the naturally occurring (-)-enantiomer slightly preferred. But the cell-free extracts also catalysed the synthesis of (+)- and (-)-isoarctigenins, with (-)-matairesinol again the preferred substrate. Thus the O-methylation of matairesinol, catalysed by F. intermedia cell-free extracts, is neither highly enantioselective nor regiospecific. No evidence that subsequent methylation of either arctigenin or isoarctigenin occurred to afford dimethyl matairesinol was obtained, i.e. the O-methyltransferase(s) only catalysed monomethylation. Taken together, it is proposed that post-coupling methylation does not proceed via regiospecific methylation of matairesinol to give arctigenin directly. Instead, regiospecific glucosylation first occurs to afford matairesinoside; subsequent methylation affords arctiin, which is then converted into arctigenin via action of a beta-glucosidase.
• Modular Synthesis and Biological Investigation of 5-Hydroxymethyl Dibenzyl Butyrolactones and Related Lignans
  作者：Samuel J. Davidson、Lisa I. Pilkington、Nina C. Dempsey-Hibbert、Mohamed El-Mohtadi、Shiying Tang、Thomas Wainwright、Kathryn A. Whitehead、David Barker

  DOI：10.3390/molecules23123057

  日期：——

  Dibenzyl butyrolactone lignans are well known for their excellent biological properties, particularly for their notable anti-proliferative activities. Herein we report a novel, efficient, convergent synthesis of dibenzyl butyrolactone lignans utilizing the acyl-Claisen rearrangement to stereoselectively prepare a key intermediate. The reported synthetic route enables the modification of these lignans to

  二苄基丁内酯木脂素以其优异的生物学特性而闻名，特别是其显着的抗增殖活性。在此，我们报告了一种利用酰基-克莱森重排立体选择性制备关键中间体的二苄基丁内酯木脂素的新型、高效、会聚合成。报道的合成路线能够修饰这些木脂素以产生这些木脂素的 5-羟甲基衍生物。评估了这些类似物的生物活性，其衍生物显示出优异的细胞毒性特征，导致 Jurkat T 白血病细胞程序性细胞死亡，其中不到 2% 的孵育细胞进入坏死细胞死亡途径。