(7R,8S)-去氢二松柏醇 | 155836-29-6

• 物质功能分类: 有机原料 - 醇、酚、酚醇类化合物及衍生物
• 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)-去氢二松柏醇
• 中文别名: 3-苯并呋喃甲醇,2,3-二氢-2-(4-羟基-3-甲氧苯基)-5-[(1E)-3-羟基-1-丙烯基]-7-甲氧基-,(2R,3S)-
• 英文名称: (2R,3S)-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-5-[(1E)-3-hydroxyprop-1-en-1-yl]-7-methoxybenzofuran-3-methanol
• 英文别名: (2R,3S)-(-)-dehydrodiconiferyl alcohol；(7R,8S)-dehydrodiconiferyl alcohol；(-)-dehydrodiconiferyl alcohol；dehydrodiconiferyl alcohol；(-)-(7R,8S)-dehydrodiconiferyl alcohol；4-[(2R,3S)-3-(hydroxymethyl)-5-[(E)-3-hydroxyprop-1-enyl]-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenol
• CAS: 155836-29-6
• 化学式: C₂₀H₂₂O₆
• 分子量: 358.391
• InChiKey: KUSXBOZNRPQEON-GWKPYITFSA-N

物化性质

• 沸点：
  562.0±50.0 °C(Predicted)
• 密度：
  1.292±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• 储存条件：
  存储于室温环境下，需确保容器密封且环境通风良好。

制备方法与用途

(7R,8S)-脱氢二甘醇是从皂角刺中分离得到的一种天然产物，具有抗肿瘤活性。

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (E)-3-[(2R,3S)-2,3-dihydro-2-(4'-hydroxy-3'-methoxyphenyl)-3-hydroxymethyl-7-methoxy-1-benzo[b]furan-5-yl]-2-propenal 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 1.0h， 以80%的产率得到(7R,8S)-去氢二松柏醇
  参考文献：
  名称：

  On the absolute structure of optically active neolignans containing a dihydrobenzo[b]furan skeleton

  摘要：

  Several optically pure neolignans containing a dihydrobenzo[b]furan skeleton were synthesized. Based on an X-ray crystallographic study and circular dichroism results, the absolute configurations of some naturally occurring neolignans, namely balanophonin (1), PGI(2) inducer (2), dehydrodiconiferyl alcohol-4-beta-D-glucoside (3), dehydroconiferyl alcohol (4) and 3',4-di-O-methyicedrusin (5) have been unambiguously established. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00725-x

文献信息

• The constituents of Cistanche tubulosa (Schrenk) Hook. f. II. Isolation and structures of a new phenylethanoid glycoside and a new neolignan glycoside.
  作者：Fumio YOSHIZAWA、Takeshi DEYAMA、Nobuo TAKIZAWA、Khan USMANGHANI、Mansoor AHMAD

  DOI：10.1248/cpb.38.1927

  日期：——

  A New phenylethanoid glycoside, named tubuloside E (I), and a new neolignan glycoside, dehydrodiconiferyl alcohol γ'-O-β-D-glucopyranoside (II), were isolated from the whole plants of Cistanche tubulosa (SCHRENK)HOOK. f. (Orobanchaceae), together with dehydrodiconiferyl alcohol 4-O-β-D-glucopyranoside (III), syringalide A 3'-α-L-rhamnopyranoside (IV), isosyringalide 3'-α-L-rhamnopyranoside (V), (+)-syringaresinol O-β-D-glucopyranoside (VI), (+)-pinoresinol O-β-D-glucopyranoside (VII), liriodendrin (VIII), 6-deoxycatalpol (IX), 8-epiloganic acid (X), 20-hydroxyecdysone (XI), 8-hydroxygeraniol 1-β-D-glucopyranoside (XII) and syringin (XIII). The structure of tubuloside E (I) was established as 2-(3, 4-dihydroxyphenyl)ethyl O-α-L-rhamnopyranosyl-(1→3)-2-O-acetyl-4-O-p-coumaroyl-β-D-glucopyranoside on the basis of chemical evidence and spectral data.

  一种新的苯乙醇苷，名为管状苷E (I)，和一种新的新木脂酸苷，去氢二香草醇γ'-O-β-D-葡萄糖吡喃苷 (II)，从全株管状肉苷(Cistanche tubulosa (SCHRENK)HOOK. f.，爵床科)中分离出来，此外还分离出了去氢二香草醇4-O-β-D-葡萄糖吡喃苷 (III)、香豆醇A 3'-α-L-鼠李吡喃苷 (IV)、异香豆醇 3'-α-L-鼠李吡喃苷 (V)、（+）-香豆苷 O-β-D-葡萄糖吡喃苷 (VI)、（+）-松脂醇 O-β-D-葡萄糖吡喃苷 (VII)、黄心树苷 (VIII)、6-脱氧卡塔普洛 (IX)、8-表罗甘酸 (X)、20-羟基蜕皮素 (XI)、8-羟基香叶醇1-β-D-葡萄糖吡喃苷 (XII)和香豆醇 (XIII)。根据化学证据和光谱数据，确定管状苷E (I)的结构为2-(3, 4-二羟基苯)乙基 O-α-L-鼠李吡喃糖-(1→3)-2-O-乙酰基-4-O-对香豆酸基-β-D-葡萄糖吡喃苷。
• Asymmetric biomimetic oxidations of phenols using oxazolidines as chiral auxiliaries: the enantioselective synthesis of (+)- and (−)-dehydrodiconiferyl alcohol
  作者：Maurizio Bruschi、Marco Orlandi、Bruno Rindone、Petteri Rummakko、Luca Zoia

  DOI：10.1002/poc.1089

  日期：2006.8

  Stereoselective bimolecular radical coupling reactions of phenylpropenoid phenols are described. Evans's 2-oxazolidinone 11a–d derivatives of ferulic acid were prepared and oxidized to give dimeric benzofuran neolignan structures 12–13a–d in 40–50% overall yields. The chiral phenols were dimerized either enzymatically with hydrogen peroxide and horseradish peroxidase (HRP) or with silver oxide. The

  描述了苯基丙烯醛酚的立体选择性双分子自由基偶联反应。制备并氧化了埃文斯的阿魏酸的2-恶唑烷酮11a-d衍生物，并进行了氧化，从而以40-50％的总收率得到了二聚苯并呋喃的新木脂体结构12-13a-d。手性酚用过氧化氢和辣根过氧化物酶（HRP）或氧化银酶促二聚。手性助剂经还原性裂解得到脱氢二癸二烯醇后的对映选择性为对映体过量的18％至62％。构象分析和使用半经验PM3计算的中间喹啉类化合物的活化能用于解释观察到的立体选择性。版权所有©2006 John Wiley＆Sons，Ltd.
• NF-κB Inhibitory Activities of Glycosides and Alkaloids from <i>Zanthoxylum schinifolium</i> Stems
  作者：Wei Li、Seo Young Yang、Xi Tao Yan、Ya Nan Sun、Seok Bean Song、Hee Kyoung Kang、Young Ho Kim

  DOI：10.1248/cpb.c13-00759

  日期：——

  Zanthoxylum schinifolium is an aromatic shrub, the pericarp and leaves of which are widely used in culinary applications in East Asian countries. In the present study, one new neolignan glycoside, zanthoxyloside A (1) together with 16 known glycosides (2–12) and alkaloids (13–17), were isolated from methanol extract of the stems of Z. schinifolium. The absolute configuration of one known monoterpenoid glycoside (2) was determined. The structures of the isolated compounds were established by one dimensional (1D), 2D NMR and mass spectrometry. The nuclear factor-κB (NF-κB) inhibitory activities of the isolated compounds stimulated with tumor necrosis factor alpha (TNFα) were measured using a luciferase reporter system. Compounds 1, 5, 16, and 17 exhibited significant inhibition of NF-κB activation in a dose-dependent manner. Furthermore, compounds 1, 5, 16, and 17 inhibited TNFα-induced expression of inducible nitric oxide synthase (iNOS) and intercellular adhesion molecule-1 (ICAM-1) mRNA and dose-dependent inhibition of iNOS promoter activity.

  Zanthoxylum schinifolium 是一种芳香灌木，其果皮和叶子在东亚国家被广泛用于烹饪。本研究从五味子茎的甲醇提取物中分离出了一种新的新木质素苷--五味子苷 A（1），以及 16 种已知的苷类化合物（2-12）和生物碱（13-17）。确定了一种已知单萜苷（2）的绝对构型。通过一维（1D）、二维核磁共振和质谱分析确定了分离化合物的结构。利用荧光素酶报告系统测定了分离化合物在肿瘤坏死因子α（TNFα）刺激下的核因子κB（NF-κB）抑制活性。化合物 1、5、16 和 17 对 NF-κB 的活化具有显著的抑制作用，其抑制作用呈剂量依赖性。此外，化合物 1、5、16 和 17 还能抑制 TNFα 诱导的诱导型一氧化氮合酶（iNOS）和细胞间粘附分子-1（ICAM-1）mRNA 的表达，并能剂量依赖性地抑制 iNOS 启动子的活性。
• Greca, Marina Della; Molinaro, Antonio; Monaco, Pietro, Heterocycles, 1994, vol. 38, # 5, p. 1099 - 1102
  作者：Greca, Marina Della、Molinaro, Antonio、Monaco, Pietro、Previtera, Lucio

  DOI：——

  日期：——
• Hirai, Nobuhiro; Okamoto, Masahiko; Udagawa, Hiroake, Bioscience, Biotechnology and Biochemistry, 1994, vol. 58, # 9, p. 1679 - 1684
  作者：Hirai, Nobuhiro、Okamoto, Masahiko、Udagawa, Hiroake、Yamamuro, Munehiro、Kato, Masayoshi、Koshimizu, Koichi

  DOI：——

  日期：——