(5S)-1,7-bis(4-hydroxyphenyl)-5-hydroxyheptan-3-one | 41137-85-3

• 物质功能分类: 天然产物 - 酚类
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (5S)-1,7-bis(4-hydroxyphenyl)-5-hydroxyheptan-3-one
• 英文别名: platyphyllone；platyphyllonol；(S)-1,7-Bis(4-hydroxyphenyl)-5-hydroxyheptan-3-one；(5S)-5-hydroxy-1,7-bis(4-hydroxyphenyl)heptan-3-one
• CAS: 41137-85-3
• 化学式: C₁₉H₂₂O₄
• 分子量: 314.381
• InChiKey: ZBFSUZGUYFFWGY-SFHVURJKSA-N

物化性质

• 沸点：
  575.2±50.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2914501900

反应信息

• 作为反应物：
  描述：

  (5S)-1,7-bis(4-hydroxyphenyl)-5-hydroxyheptan-3-one 在 sodium tetrahydroborate 、 对甲苯磺酰肼 作用下， 以 甲醇 为溶剂， 以9 mg的产率得到Centrolobol; (R)-(-)-1,7-双对羟基苯基-3-庚醇
  参考文献：
  名称：

  桔梗苷和 (-)-Centrolobol 的绝对构型

  摘要：

  通过 13C NMR 光谱确定桔梗苷的绝对构型为 S。在此建立的基础上，先前分配给 (-)-centrolobol 的 C-3 处手性的 S-构型被修改为 R-构型。

  DOI：

  10.1246/bcsj.58.2423
• 作为产物：
  描述：

  platyphylloside 在 Taka-diastase 、 水 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以55 mg的产率得到(5S)-1,7-bis(4-hydroxyphenyl)-5-hydroxyheptan-3-one
  参考文献：
  名称：

  桔梗苷和 (-)-Centrolobol 的绝对构型

  摘要：

  通过 13C NMR 光谱确定桔梗苷的绝对构型为 S。在此建立的基础上，先前分配给 (-)-centrolobol 的 C-3 处手性的 S-构型被修改为 R-构型。

  DOI：

  10.1246/bcsj.58.2423

文献信息

• A New Diarylheptanoid Glycoside from the Stem Bark of Alnus hirsuta and Protective Effects of Diarylheptanoid Derivatives in Human HepG2 Cells
  作者：Daae Park、Hyoung Ja Kim、Seo Yun Jung、Chang-Soo Yook、Changbae Jin、Yong Sup Lee

  DOI：10.1248/cpb.58.238

  日期：——

  To search for secondary metabolites of Alnus hirsuta (Betulaceae), various chromatographic separations of the ethyl acetate soluble fraction of the stem bark of A. hirsuta led to the isolation of a new diarylheptanoid glycoside, (3R)-1,7-bis-(4-dihydroxyphenyl)-3-heptanol 3-O-β-D-glucopyranosyl(1→3)-β-D-xylopyranoside (13) and twelve diarylheptanoid derivatives, namely, oregonin (1), rubranoside A (2), hirsutanonol 5-O-β-D-glucopyranoside (3), rubranoside B (4), rubranoside C (5), hirsutanonol (6), hirsutenone (7), (5S)-O-methylhirsutanonol (8), platyphylloside (9), platyphyllonol 5-O-β-D-xylopyranoside (10), aceroside VII (11) and platyphyllenone (12). Isolates were assessed for their hepatoprotective effects against tert-butylhydroperoxide (t-BHP)-induced toxicity in HepG2 cells. Of these isolates, compounds 1—8 showed significant hepatoprotective effects on t-BHP-induced damage to HepG2 cells, with 8 exhibiting the greatest protective effect (50.7±3.7% at a concentration of 10 μM).

  为了寻找桤木属植物糙皮桤木的次生代谢产物，对糙皮桤木树皮乙酸乙酯可溶部分的多种色谱分离法导致了新二芳基庚烷糖苷（3R）-1，7-双（4-二羟基苯基）-3-庚醇3-O-β-D-吡喃葡糖基（1→3）-β-D-吡喃木糖苷（13）和十二个二芳基庚烷衍生物的分离，其中，分别为oregin（1）、rubranoside A（2）、hirsutanonol 5-O-β-D-吡喃葡糖苷（3）、rubranoside B（4）、rubranoside C（5）、hirsutanonol（6）、hirsutenone（7）、（5S）-O-甲基hirsutanonol（8）、platyphylloside（9）、platyphyllonol 5-O-β-D-吡喃木糖苷（10）、aceroside VII（11）和platyphyllenone（12）。分离的化合物通过评估 HepG2 细胞中对抗叔丁基过氧化氢（t-BHP）诱导的毒性来测试其肝保护作用。在这些分离的化合物中，化合物1—8对t-BHP诱导的HepG2细胞损伤有显著的保护作用，其中8的保护效果最好，在10 μM浓度下的保护效果为50.7±3.7%。
• Platyphylloside: Metabolism and digestibility reductionin vitro
  作者：Kerstin Sunnerheim-Sjöberg、Per-Göran Knutsson

  DOI：10.1007/bf02027566

  日期：1995.9

  The metabolism of platyphylloside [(5S)-5-hydroxy-1,7-bis-(4-hydroxyphenyl)-3-heptanone-5-O-beta-D-glucopyranoside]-known to reduce digestibility-was studied in vitro in sheep rumen liquor. Platyphylloside is hydrolyzed to 5-hydroxy-3-platyphyllone [(5S)-5-hydroxy-1,7-bis-(4-hydroxyphenyl)-3-heptanone], which is reduced to centrolobol [1,7-bis-(4-hydroxyphenyl)-3-heptanol], via 3-platyphyllone [7-bis-(4-hydroxyphenyl)-3-heptanone]. The digestibility-reducing effect was shown to be correlated with the concentration of centrolobol.
• Minor diarylheptanoid glycosides of Alnus rubra bark
  作者：Jie Chen、Ruben F. Gonzalez-Laredo、Joseph J. Karchesy

  DOI：10.1016/s0031-9422(99)00523-3

  日期：2000.4

  The diarylheptanoid (S)-1,7-bis-(4-hydroxyphenyl)-heptan-3-one-5-O-beta-D-xylopyranoside and two known compounds. 1,7-bis(3,4-dihydroxyphenyl)-heptan-3-one-5-O-beta-D-glucopyranoside and platyphylloside were isolated from Alnus rubra bark. Structures were establishes by application of spectrometric techniques. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Anticancer diarylheptanoid glycosides from the inner bark of Betula papyrifera
  作者：Vakhtang Mshvildadze、Jean Legault、Serge Lavoie、Charles Gauthier、André Pichette

  DOI：10.1016/j.phytochem.2007.05.018

  日期：2007.10

  Phytochemical investigations of the MeOH extract of Betula papyrifera inner bark led to the isolation of ten phenolic compounds of the following types: diarylheptanoid glycosides (1-4), a diarylheptanoid (5), a lignan (6), flavonoids (7-8) and chavicol glycosides (9-10). Among them, the diarylheptanoid glycoside, (S)-1,7-bis-(4-hydroxyphenyl)-heptan-3-one-5-O-alpha-L-arabinofuranosyl-(1 -> 6)-beta-D-gluco-pyranoside, papyriferoside A (1), was isolated and its structure was determined on the basis of 1D and 2D NMR, HPLC-MS, as well as high resolution mass spectroscopic data. Platyphylloside (4) exerted the strongest cytotoxic activity of all isolated compounds with IC50 values ranging from 10.3 to 13.8 mu M. (C) 2007 Elsevier Ltd. All rights reserved.
• DIARYL HEPATONOID-BASED COMPOUNDS USEFUL AS VIRUS INHIBITORS
  申请人：Ra Jeong Chan

  公开号：US20110105738A1

  公开（公告）日：2011-05-05

  The present invention relates to the use of diaryl hepatonoid-based compounds of formula (1) for inhibiting viral activity. The diaryl hepatonoid-based compounds have an excellent effect of inhibiting viral activity, and thus will be useful as therapeutic agents against virus-related diseases.