sesaminol 2'-O-β-D-glucopyranosyl(1->2)-O-[β-D-glucopyranosyl(1->6)]-β-D-glucopyranoside | 157469-83-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: sesaminol 2'-O-β-D-glucopyranosyl(1->2)-O-[β-D-glucopyranosyl(1->6)]-β-D-glucopyranoside
• 英文别名: (+)-sesaminol 2-O-beta-D-glucosyl (1->2)-O-[beta-D-glucosyl (1->6)]-beta-D-glucoside；(2R,3R,4S,5S,6R)-2-[[(2R,3S,4S,5R,6S)-6-[[6-[(3S,3aR,6S,6aR)-3-(1,3-benzodioxol-5-yl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-1,3-benzodioxol-5-yl]oxy]-3,4-dihydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 157469-83-5
• 化学式: C₃₈H₄₈O₂₂
• 分子量: 856.786
• InChiKey: IJZGFTCXUSMUHI-CMBLSTHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  60
• 可旋转键数：
  11
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  313
• 氢给体数：
  10
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  sesaminol 2'-O-β-D-glucopyranosyl(1->2)-O-[β-D-glucopyranosyl(1->6)]-β-D-glucopyranoside 在 Aspergillus usami mut. shirousamii RIB₂₅₀₃ 、 Potato Dextrose Broth 、 sodium chloride 作用下， 以4.6%的产率得到sesaminol 6-catechol
  参考文献：
  名称：

  Antioxidative Catechol Lignans Converted from Sesamin and Sesaminol Triglucoside by Culturing with Aspergillus

  摘要：

  Sesamin and sesaminol triglucoside in sesame seeds are major lignans that display an abundance of biological activities. Although their antioxidative activity in vitro is weak, they have been reported to suppress oxidative stress in vivo. We investigated the production of new antioxidative lignans from sesame lignans by culturing with the genus Aspergillus to enhance the function of food materials. Media containing sesamin or sesaminol triglucoside increased antioxidative activity for DPPH radical scavenging by culturing with Aspergillus usamii mut. shirousamii RIB2503. The antioxidative lignans in sesamin medium were identified as sesamin 2,6-dicatechol and episesamin 2,6-dicatechol. Those in sesaminol triglucoside medium were identified as sesaminol 6-catechol and episesaminol 6-catechol, which are novel antioxidative lignans. It is suggested that they may exhibit higher antioxidative activity than sesamin and sesaminol triglucoside because they have the catechol functional moiety.

  DOI：

  10.1021/jf048743h

文献信息

• Antioxidative Catechol Lignans Converted from Sesamin and Sesaminol Triglucoside by Culturing with <i>Aspergillus</i>
  作者：Yoshiaki Miyake、Syuichi Fukumoto、Miki Okada、Kazuhiro Sakaida、Yoshimasa Nakamura、Toshihiko Osawa

  DOI：10.1021/jf048743h

  日期：2005.1.1

  Sesamin and sesaminol triglucoside in sesame seeds are major lignans that display an abundance of biological activities. Although their antioxidative activity in vitro is weak, they have been reported to suppress oxidative stress in vivo. We investigated the production of new antioxidative lignans from sesame lignans by culturing with the genus Aspergillus to enhance the function of food materials. Media containing sesamin or sesaminol triglucoside increased antioxidative activity for DPPH radical scavenging by culturing with Aspergillus usamii mut. shirousamii RIB2503. The antioxidative lignans in sesamin medium were identified as sesamin 2,6-dicatechol and episesamin 2,6-dicatechol. Those in sesaminol triglucoside medium were identified as sesaminol 6-catechol and episesaminol 6-catechol, which are novel antioxidative lignans. It is suggested that they may exhibit higher antioxidative activity than sesamin and sesaminol triglucoside because they have the catechol functional moiety.