7R,8S-二氢去氢双松柏醇 | 126253-41-6

• 物质功能分类: 天然产物 - 木脂素
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 中文名称: 7R,8S-二氢去氢双松柏醇
• 英文名称: 4-[(2R,3S)-3-Hydroxymethyl-5-(3-hydroxy-propyl)-7-methoxy-2,3-dihydro-benzofuran-2-yl]-2-methoxy-phenol
• 英文别名: (7R,8S)-4-hydroxy-3,5′-dimethoxy-4′,7-epoxy-8,3′-neoligna-9,9′-ole；(7R,8S)-4,9,9'-trihydroxyl-3,3'-dimethoxyl-7,8-dihydrobenzofuran-1'-propylneolignan；(-)-(2R,3S)-dihydrodehydrodiconiferyl alcohol；(7'S,8'R)-dihydrodehydrodiconiferyl alcohol；(2R,3S)-dihydrodehydrodiconiferyl alcohol；(7R,8S)-dihydrodehydrodiconifenyl alcohol；Dihydrodehydroconiferyl alcohol, (7R,8S)-(-)-；4-[(2R,3S)-3-(hydroxymethyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenol
• CAS: 126253-41-6
• 化学式: C₂₀H₂₄O₆
• 分子量: 360.407
• InChiKey: SBLZVJIHPWRSQQ-BEFAXECRSA-N

物化性质

• 沸点：
  540.9±50.0 °C(Predicted)
• 密度：
  1.261±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7R,8S-二氢去氢双松柏醇 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以57%的产率得到5-(3-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)-3-benzo[b]furan-carbaldehyde
  参考文献：
  名称：

  揭示木质素氧化反应过程中苯基香豆素键的命运†

  摘要：

  在选择性氧化条件下，除β-O-4以外，大多数木质素键的命运是未知的。在这项工作中，我们使用先进的β-5木质素模型化合物来确定DDQ氧化过程中软木木质素中苯香豆素单元的命运。通过使用模型化合物以及使用HSQC和HMBC NMR对氧化木质素聚合物进行详细表征的方法，我们表明苯基香豆酮是一种主要产物，因此构成了氧化木质素中的新型非天然β-5键。此外，这些单元在木质素中的反应性使我们进一步研究了它们在木质素中的连接性，表明它们同时被发现是酚和醚化单元。此处开发的发现和方法将有助于提高选择性氧化木质素解聚工艺的效率，

  DOI：

  10.1039/c7ob03087h
• 作为产物：
  描述：

  (7R,8S)-去氢二松柏醇 在 1,4-二巯基-2,3-丁二醇 作用下， 以 phosphate buffer 为溶剂， 反应 24.0h， 生成 7R,8S-二氢去氢双松柏醇
  参考文献：
  名称：

  Pinus taeda phenylpropenal double-bond reductase: Purification, cDNA cloning, heterologous expression in Escherichia coli, and subcellular localization in P. taeda

  摘要：

  A phenylpropenal double-bond reductase (PPDBR) was obtained from cell suspension cultures of loblolly pine (Pinus taeda L.). Following trypsin digestion and amino acid sequencing, the cDNA encoding this protein was subsequently cloned, with the functional recombinant protein expressed in Escherichia coli and characterized. PPDBR readily converted both dehydrodiconiferyl and coniferyl aldehydes into dihydrodehydrodiconiferyl and dihydroconiferyl aldehydes, when NADPH was added as cofactor. However, it was unable to reduce directly either the double bond of dehydrodiconiferyl or coniferyl alcohols in the presence of NADPH. During this reductive step, the corresponding 4-proR hydrogen was abstracted from [4R-H-3]-NADPH during hydride transfer. This is thus the first report of a double-bond reductase involved in phenylpropanoid metabolism, and which is presumed to be involved in plant defense. In situ mRNA hybridization indicated that the PPDBR transcripts in P. taeda stem sections were localized to the vascular cambium, as well as to radial and axial parenchyma cell types.Additionally, using P. taeda cell suspension culture crude protein extracts, dehydrodiconiferyl and coniferyl alcohols could be dehydrogenated to afford dehydrodiconiferyl and coniferyl aldehydes. Furthermore, these same extracts were able to convert dihydrodehydrodiconiferyl and dihydroconiferyl aldehydes into the corresponding alcohols. Taken together, these results indicate that in the crude extracts dehydrodiconiferyl and coniferyl alcohols can be converted to dihydrodehydrodiconiferyl and dihydroconiferyl alcohols through a three-step process, i.e. by initial phenylpropenol oxidation, then sequential PPDBR and phenylpropanal reductions, respectively. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2006.07.001

文献信息

• Lignans in cell cultures of Picea glehnii
  作者：Kensuke Nabeta、Megumi Hirata、Yuriko Ohki、S.W.Ananda Samaraweera、Hiroshi Okuyama

  DOI：10.1016/0031-9422(94)85069-0

  日期：1994.1

  Abstract A suspension culture derived from the seedling leaves of Picea glehnii accumulated two lignans, pinoresinol and trans -dihydrodehydrodiconiferyl alcohol. The enantiometric compositions of pinoresinol [(+)-isomer/(−)-isomer: 0.57] and dihydrodehydrodiconiferyl alcohol [(+)-2 R , 3 S -isomer/(−)-2 S , 3 R -isomer: 0.21] from the cells were determined by HPLC analysis using a chiral column. Peroxidase

  摘要 来自云杉幼苗叶的悬浮培养物积累了两种木脂素，松脂醇和反式二氢脱氢二松果醇。松脂醇[(+)-异构体/(-)-异构体：0.57]和二氢脱氢二松果醇[(+)-2R, 3 S-异构体/(-)-2 S, 3 R-异构体：0.21]的对映组成来自细胞的 HPLC 分析使用手性柱进行测定。在 28 天龄细胞（K-Pi 缓​​冲液，pH 7.39）的无细胞提取物中检测到了催化松柏醇氧化偶联的过氧化物酶活性。无细胞提取物形成木脂素的外消旋形式。
• Kinetic resolution of a dihydrobenzofuran-type neolignan by lipase-catalysed acetylation
  作者：Stefaan M.O. Van Dyck、Guy L.F. Lemière、Tim H.M. Jonckers、Roger Dommisse、Luc Pieters、Volker Buss

  DOI：10.1016/s0957-4166(01)00135-5

  日期：2001.4

  The kinetic resolution of 3,5′-dimethoxy-4′,7-epoxy-8,3′-neolignane-4,9,9′-triol 1 by lipase-catalysed acetylation in an organic solvent was investigated. Ten different lipases were screened for enantioselectivity in the reaction. The enantiomeric excess (e.e.) of the products was strongly dependent on the type of lipase used. After optimisation of the reaction conditions for Candida cylindracea lipase

  研究了在有机溶剂中通过脂肪酶催化的乙酰化反应3,5'-二甲氧基-4'，7-环氧-8,3'-新戊烷-4,9,9'-三醇1的动力学拆分。筛选了十种不同的脂肪酶以进行反应中的对映选择性。产品的对映体过量（ee）在很大程度上取决于所用脂肪酶的类型。优化了念珠菌脂肪酶的反应条件后，反应的ee和收率大大提高，在某些情况下，尽管对映体纯度很低，但仍可以分离出对映体纯的起始原料1（主要是乙酰化（2 R，3 S）-1和（2 S，3 R）-酯。
• Phenolic constituents from the core of Kenaf (Hibiscus cannabinus)
  作者：Ana M.L Seca、Artur M.S Silva、Armando J.D Silvestre、José A.S Cavaleiro、Fernando M.J Domingues、Carlos Pascoal-Neto

  DOI：10.1016/s0031-9422(00)00473-8

  日期：2001.4

  several other lignans, aldehydes and a tyramine derivative were isolated from the acetone extract of core of kenaf (Hibiscus cannabinus). All the structures were established by spectroscopic methods. The hitherto unreported 13C NMR spectra of some compounds are also presented and discussed. 2D NMR techniques have allowed the revision of certain previously reported 13C NMR assignments of some scarce naturally

  四种木脂素，勃姆林H [2-(4-羟基-3-甲氧基苯基)-5-[3-(4-羟基-3-甲氧基肉桂酰氧基)丙基]-3-羟甲基-7-甲氧基苯并二氢呋喃]，勃姆林K [2-( 4-羟基-3-甲氧基苯基)-5-[3-(4-羟基肉桂酰氧基)-1-丙烯基]-3-(4-羟基-3-甲氧基肉桂酰氧基甲基)-7-甲氧基苯并二氢呋喃]，苏式-卡罗林聚糖H [threo-1 -(4-羟基-3-甲氧基苯基)-2-[4-[3-(4-羟基-3-甲氧基肉桂酰氧基)丙基]-2-甲氧基苯氧基]-1,3-丙二醇]和苏式-卡罗林聚糖K[苏式-1-(4-羟基-3-甲氧基苯基)-3-(4-羟基-3-甲氧基肉桂酰氧基)-2-[4-[3-(4-羟基肉桂酰氧基)-1-丙烯基]-2-甲氧基苯氧基]-1 -丙醇]以及其他几种木脂素、醛和酪胺衍生物是从洋麻（Hibiscus cannabinus）核心的丙酮提取物中分离出来的。所有结构均通过光谱方法建立。一些化合物的迄今为止未报道的
• Ionone and lignan glycosides from Epimedium diphyllum
  作者：Toshio Miyase、Akira Ueno、Nobuo Takizawa、Hiromi Kobayashi、Hiroko Oguchi

  DOI：10.1016/0031-9422(89)80369-3

  日期：1989.1

  Abstract From the aerial parts of Epimedium diphyllum, a new ionone derivative glucoside, icariside B8, two new lignan glycosides, icarisides E4 and E5 and a new phenylethanoid glucoside, icariside D2, have been isolated together with 20 known compounds. The structures of four new compounds were established by spectral and chemical evidence.

  摘要 从淫羊藿地上部分分离出一种新的紫罗兰酮衍生物苷类淫羊藿苷B8、两种新的木脂素苷类淫羊藿苷E4和E5以及一种新的苯乙醇苷类淫羊藿苷D2以及20种已知化合物。通过光谱和化学证据确定了四种新化合物的结构。
• Evolution of Plant Defense Mechanisms
  作者：David R. Gang、Hiroyuki Kasahara、Zhi-Qiang Xia、Kristine Vander Mijnsbrugge、Guy Bauw、Wout Boerjan、Marc Van Montagu、Laurence B. Davin、Norman G. Lewis

  DOI：10.1074/jbc.274.11.7516

  日期：1999.3

  Pinoresinol-lariciresinol and isoflavone reductase classes are phylogenetically related, as is a third, the so-called "isoflavone reductase homologs," This study establishes the first known catalytic function for the latter, as being able to engender the NADPH-dependent reduction of phenylcoumaran benzylic ethers, Accordingly, all three reductase classes are involved in the biosynthesis of important and related phenylpropanoid-derived plant defense compounds. In this investigation, the phenylcoumaran benzylic ether reductase from the gymnosperm, Pinus taeda, was cloned, with the recombinant protein heterologously expressed in Escherichia coli, The purified enzyme reduces the benzylic ether functionalities of both dehydrodiconiferyl alcohol and dihydrodehydrodiconiferyl alcohol, with a higher affinity for the former, as measured by apparent K-m and V-max values and observed kinetic H-3-isotope effects. It abstracts the 4R-hydride of the required NADPH cofactor in a manner analogous to that of the pinoresinol-lariciresinol reductases and isoflavone reductases. A similar catalytic function was observed for the corresponding recombinant reductase whose gene was cloned from the angiosperm, Populus trichocarpa. Interestingly, both pinoresinol-lariciresinol reductases and isoflavone reductases catalyze enantiospecific conversions, whereas the phenylcoumaran benzylic ether reductase only shows regiospecific discrimination. A possible evolutionary relationship among the three reductase classes is proposed, based on the supposition that phenylcoumaran benzylic ether reductases represent the progenitors of pinoresinol-lariciresinol and isoflavone reductases.