(8S,8'S)-bisdihydrosiringenin | 147852-15-1

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 二苄基丁烷木脂素
• 英文名称: (8S,8'S)-bisdihydrosiringenin
• 英文别名: (2S,3S)-2,3-bis[(4-hydroxy-3,5-dimethoxyphenyl)methyl]butane-1,4-diol
• CAS: 147852-15-1
• 化学式: C₂₂H₃₀O₈
• 分子量: 422.475
• InChiKey: XTRARZPRFYUCGZ-HZPDHXFCSA-N

物化性质

• 熔点：
  178 °C
• 沸点：
  660.0±55.0 °C(predicted)
• 密度：
  1.251±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  118
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 (8S,8'S)-bisdihydrosiringenin 以 甲醇 、 乙醚 为溶剂， 反应 12.0h， 以85%的产率得到(2R*,3R*)-2,3-dihydroxymethyl-1,4-bis-(3,4,5-trimethoxyphenyl)butane
  参考文献：
  名称：

  Indonesian Medicinal Plants. IV. On the Constituents of the Bark of Fagara rhetza (Rutaceae). (2). Lignan Glycosides and Two Apioglucosides.

  摘要：

  从印度尼西亚弗洛雷斯岛产药用植物飞龙掌血（芸香科）树皮中分离得到2个新的木脂素苷，命名为hazaleanin A（1）和hazaleanin B（2）；2个新的芹糖葡萄糖苷，命名为异丙基芹糖葡萄糖苷（3）和4-羟基愈创木酚芹糖葡萄糖苷（4）。根据化学和物理化学证据，包括1型的苷元衍生物的不对称合成，阐述了1、2、3、4的化学结构。

  DOI：

  10.1248/cpb.40.2639
• 作为产物：
  描述：

  Ssioriside; (2S,3S)-4-羟基-2,3-双[(4-羟基-3,5-二甲氧基苯基)甲基]丁基 beta-D-吡喃木糖苷 生成 (8S,8'S)-bisdihydrosiringenin
  参考文献：
  名称：

  YOSHINARI;KIYOSHI;SASHIDA, YUTAKA;SHIMOMURA, HIROKO, CHEM. AND PHARM. BULL., 37,(1989) N2, C. 3301-3303

  摘要：

  DOI：

文献信息

• Two new lignan xylosides from the barks of Prunus ssiori and Prunus padus.
  作者：Kiyoshi YOSHINARI、Yutaka SASHIDA、Hiroko SHIMOMURA

  DOI：10.1248/cpb.37.3301

  日期：——

  Phytochemical examinations of the barks of Prunus species have led to the isolation of two new lignan xylosides, ssioriside (9) and prupaside (12). Compound 9 was obtained from Prunus (P.) ssiori and P. padus and 12 from P. padus. The spectroscopic data and chemical evidence allowed assignment of the structures of 9 and 12 as (8S, 8'S)-4, 4'-dihydroxy-3, 5, 3', 5'-tetramethoxy-8-8'-butyrolignan 9-O-β-D xylopyranoside and (8R, 7S, 8'R)-5, 5'-dimethoxylari-ciresinol 9'-O-β-D-xylopyranoside, respectively. Several previously reported compounds were also obtained and identified.

  对Prunus属树皮进行的植物化学研究发现并分离出了两种新的木脂素木糖苷——ssioriside（9）和prupaside（12）。化合物9从Prunus（P.）ssiori和P. padus中获得，12仅从P. padus中获得。根据光谱数据和化学证据，化合物9和12的结构被分别确定为(8S, 8'S)-4, 4'-二羟基-3, 5, 3', 5'-四甲氧基-8-8'-丁基木脂素9-O-β-D-木糖苷和(8R, 7S, 8'R)-5, 5'-二甲氧基芝麻素9'-O-β-D-木糖苷。此外，还获得了并鉴定了之前报道的几种化合物。
• Pinoresinol‐lariciresinol reductase: Substrate versatility, enantiospecificity, and kinetic properties
  作者：Julianne K. Hwang、Syed G.A. Moinuddin、Laurence B. Davin、Norman G. Lewis

  DOI：10.1002/chir.23218

  日期：2020.6

  Two western red cedar pinoresinol‐lariciresinol reductase (PLR) homologues were studied to determine their enantioselective, substrate versatility, and kinetic properties. PLRs are downstream of dirigent protein engendered, coniferyl alcohol derived, stereoselective coupling to afford entry into the 8‐ and 8′‐linked furofuran lignan, pinoresinol. Our investigations showed that each PLR homolog can

  研究了两个西部红柏松脂松香醇-larresresinol还原酶（PLR）的同系物，以确定它们的对映选择性，底物通用性和动力学性质。PLR位于产生的稀疏蛋白质，针叶树醇衍生的立体选择性偶联的下游，以使其进入8和8'连接的呋喃呋喃木脂体木脂松酚。我们的研究表明，每个PLR同源物都可以通过修饰的芳环取代基对映异构地代谢不同的呋喃呋喃木脂素，但是其中C4 / C4'上的酚基对于催化是必不可少的。这些结果与PLR活性部位中醌甲基化物中间体的形成是一致的。定点诱变和动力学测量提供了对影响对映选择性和动力学性质的因素的进一步了解。根据这些数据，
• Lignan Glycosides from the Twigs of <i>Chaenomeles sinensis</i> and Their Biological Activities
  作者：Chung Sub Kim、Lalita Subedi、Sun Yeou Kim、Sang Un Choi、Ki Hyun Kim、Kang Ro Lee

  DOI：10.1021/acs.jnatprod.5b00090

  日期：2015.5.22

  Phytochemical investigation of the twigs of Chaenomeles sinensis led to the isolation and identification of six new lignan glycosides, chaenomiside A-F (1-6), along with five known ones (7-11). Their chemical structures were determined by spectroscopic methods, including NMR, MS, ECD, and GC/MS analyses. All the isolated compounds (1-11) were tested for their inhibitory effects on nitric oxide (NO) production in lipopolysaccharide-activated murine microglial cells and the secretion of nerve growth factor (NGF) in a C6 rat glioma cell line. Compound 6 significantly reduced NO levels in the murine microglia BV2 cells with an IC50 value of 21.3 mu M, and compounds 1, 3, and 6 were potent stimulants of NGF release with stimulation levels of 151.74 +/- 6.77%, 144.31 +/- 7.49%, and 167.61 +/- 18.5%, respectively.
• Weinges,K., Chemische Berichte, 1961, vol. 94, p. 2522 - 2533
  作者：Weinges,K.

  DOI：——

  日期：——
• Indonesian Medicinal Plants. IV. On the Constituents of the Bark of Fagara rhetza (Rutaceae). (2). Lignan Glycosides and Two Apioglucosides.
  作者：Hirotaka SHIBUYA、Yasuyuki TAKEDA、Ru-song ZHANG、Akihiko TANITAME、Yen-Li TSAI、Isao KITAGAWA

  DOI：10.1248/cpb.40.2639

  日期：——

  Two new lignan glycosides, named hazaleanin A (1) and hazaleanin B (2), and two new apioglucosides, named isopropyl apioglucoside (3) and 4-hydroxyguaiacol apioglucoside (4), were isolated from the bark of Fagara rhetza (Rutaceae), an Indonesian medicinal plant from Flores Island, Indonesia. The chemical structures of 1, 2, 3, and 4 have been elucidated on the basis of chemical and physicochemical evidence, including a chiral synthesis of an aglycone derivative of 1.

  从印度尼西亚弗洛雷斯岛产药用植物飞龙掌血（芸香科）树皮中分离得到2个新的木脂素苷，命名为hazaleanin A（1）和hazaleanin B（2）；2个新的芹糖葡萄糖苷，命名为异丙基芹糖葡萄糖苷（3）和4-羟基愈创木酚芹糖葡萄糖苷（4）。根据化学和物理化学证据，包括1型的苷元衍生物的不对称合成，阐述了1、2、3、4的化学结构。