(+)-neo-olivil

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 呋喃类木脂素
• 英文名称: (+)-neo-olivil
• 英文别名: (+)-Neoolivil；4-[(2R,3S,4S,5R)-5-(4-hydroxy-3-methoxyphenyl)-3,4-bis(hydroxymethyl)oxolan-2-yl]-2-methoxyphenol
• 化学式: C₂₀H₂₄O₇
• 分子量: 376.406
• InChiKey: NYDZRKZVFLLTLO-NSMLZSOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  109
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-甲基-N-(三甲基硅烷基)三氟乙酰胺 、 (+)-neo-olivil 反应 8.0h， 生成 (2R,3S,4S,5R)-2,5-Bis-(3-methoxy-4-trimethylsilanyloxy-phenyl)-3,4-bis-trimethylsilanyloxymethyl-tetrahydro-furan
  参考文献：
  名称：

  Lignans from the Roots ofUrtica dioicaand their Metabolites Bind to Human Sex Hormone Binding Globulin (SHBG)

  摘要：

  刺荨麻（Urtica dioica L.）根的极性萃取物中含有木脂素（+）-neoolivil、（-）-secoisolariciresinol、dehydrodiconiferyl alcohol、isariciresinol、pinoresinol 和 3,4-divanillyltetrahydrofuran。这些化合物或从荨麻根中分离出来，或通过半合成方法获得。在体外试验中测试了它们与人类性激素结合球蛋白（SHBG）的亲和力。此外，还检测了植物木酚素在人体肠道中的主要转化产物肠二醇和肠内酯以及肠呋喃的活性。在体外试验中，除 (-)-pinoresinol 外，所有木酚素都与 SHBG 具有结合亲和力。(-)-3,4-divanillyltetrahydrofuran 的亲和力非常高。这些研究结果讨论了植物木酚素对良性前列腺增生症（BPH）的潜在有益作用。

  DOI：

  10.1055/s-2006-957756
• 作为产物：
  描述：

  (7R,7′R,8S,8′S)-4,4′-dibenzyloxy-3,3′-dimethoxy-7,7′-epoxylignane-9,9′-diol 在 5%-palladium/activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 6.0h， 以64%的产率得到(+)-neo-olivil
  参考文献：
  名称：

  Synthesis of All Stereoisomers of 3,3′-Dimethoxy-7,7′-epoxylignane-4,4′-diol and Their Plant Growth Inhibitory Activity

  摘要：

  All stereoisomers of 3,3'-dimethoxy-7,7'-epoxylignane-4,4'-diol were synthesized to examine the effect of stereochemistry on their plant growth inhibitory activity using lettuce and Italian ryegrass. The effect of structural modifications such as dehydroxylation, methoxylation and hydroxylation at the 9- and 9'-positions of the lignans on the activity was also studied. Most of the epoxylignanes showed higher plant growth inhibitory potency against ryegrass than against lettuce, and the inhibitory activity varied depending on the configurations of each position of the tetrahydrofuran ring (7-, 7'-, 8-, and 8'-positions of the epoxylignanes). Among the 9,9'-position-modified derivatives, the dehydroxy derivatives showed the highest potency. These results suggested that the plant growth inhibitory activity should be influenced by the structure of the epoxylignanes.

  DOI：

  10.1021/jf4046396

文献信息

• Four New Lignan Glycosides from Osmanthus fragransLour. var. aurantiacusMakino
  作者：Koichi Machida、Megumi Yamauchi、Eriko Kurashina、Masao Kikuchi

  DOI：10.1002/hlca.201000074

  日期：2010.11

  Four new tetrahydrofuranoid lignan glycosides, (7S,8R,7′R,8′S)‐4,9,4′,7′‐tetrahydroxy‐3,3′‐dimethoxy‐7,9′‐epoxylignan 9‐O‐β‐D‐glucopyranoside (2), (7R,8S,7′S,8′R)‐4,9,4′,7′‐tetrahydroxy‐3,3′‐dimethoxy‐7,9′‐epoxylignan 9‐O‐β‐D‐glucopyranoside (3), (7R,8S,7′R,8′S)‐4,9,4′,9′‐tetrahydroxy‐3,3′‐dimethoxy‐7,7′‐epoxylignan 9‐O‐β‐D‐glucopyranoside (4), and rel‐(7R,8S,7′S,8′R)‐4,9,4′,9′‐tetrahydroxy‐3,3′‐dimethoxy‐7

  四个新木脂素tetrahydrofuranoid苷，（7小号，8 - [R，7' - [R，8'小号）-4,9,4'，7'-四羟基-3,3'-二甲氧基- 7,9'-epoxylignan 9- ö - β - d吡喃葡萄糖苷（2），（7 - [R，8小号，7'小号，8' - [R）-4,9,4'，7'-四羟基-3,3'-二甲氧基- 7,9'- epoxylignan 9- ø - β - d吡喃葡萄糖苷（3），（7 - [R，8小号，7' - [R，8'小号）-4,9,4'，9'-四羟基-3,3'-二甲氧基- 7 ，7'-环氧木脂素9-ø - β - d吡喃葡萄糖苷（4），和rel-（7 - [R，8小号，7'小号，8' - [R）-4,9,4'，9'-四羟基-3,3'-二甲氧基- 7 ，7'- epoxylignan 9- ø - β - d吡喃葡萄糖苷（5），和10木脂素甙，已知1和6
• Lignans from the Roots of<i>Urtica dioica</i>and their Metabolites Bind to Human Sex Hormone Binding Globulin (SHBG)
  作者：Matthias Schöttner、Dietmar Ganßer、Gerhard Spiteller

  DOI：10.1055/s-2006-957756

  日期：1997.12

  Polar extracts of the stinging nettle (Urtica dioica L.) roots contain the lignans (+)-neoolivil, (-)-secoisolariciresinol, dehydrodiconiferyl alcohol, isolariciresinol, pinoresinol, and 3,4-divanillyltetrahydrofuran. These compounds were either isolated from Urtica roots, or obtained semisynthetically. Their affinity to human sex hormone binding globulin (SHBG) was tested in an in vitro assay. In addition, the main intestinal transformation products of plant lignans in humans, enterodiol and entero-lactone, together with enterofuran were checked for their activity. All lignans except (-)-pinoresinol developed a binding affinity to SHBG in the in vitro assay. The affinity of (-)-3,4-divanillyltetrahydrofuran was outstandingly high. These findings are discussed with respect to potential beneficial effects of plant lignans on benign prostatic hyperplasia (BPH).

  刺荨麻（Urtica dioica L.）根的极性萃取物中含有木脂素（+）-neoolivil、（-）-secoisolariciresinol、dehydrodiconiferyl alcohol、isariciresinol、pinoresinol 和 3,4-divanillyltetrahydrofuran。这些化合物或从荨麻根中分离出来，或通过半合成方法获得。在体外试验中测试了它们与人类性激素结合球蛋白（SHBG）的亲和力。此外，还检测了植物木酚素在人体肠道中的主要转化产物肠二醇和肠内酯以及肠呋喃的活性。在体外试验中，除 (-)-pinoresinol 外，所有木酚素都与 SHBG 具有结合亲和力。(-)-3,4-divanillyltetrahydrofuran 的亲和力非常高。这些研究结果讨论了植物木酚素对良性前列腺增生症（BPH）的潜在有益作用。
• Synthesis of All Stereoisomers of 3,3′-Dimethoxy-7,7′-epoxylignane-4,4′-diol and Their Plant Growth Inhibitory Activity
  作者：Hisashi Nishiwaki、Kumiko Nakayama、Yoshihiro Shuto、Satoshi Yamauchi

  DOI：10.1021/jf4046396

  日期：2014.1.22

  All stereoisomers of 3,3'-dimethoxy-7,7'-epoxylignane-4,4'-diol were synthesized to examine the effect of stereochemistry on their plant growth inhibitory activity using lettuce and Italian ryegrass. The effect of structural modifications such as dehydroxylation, methoxylation and hydroxylation at the 9- and 9'-positions of the lignans on the activity was also studied. Most of the epoxylignanes showed higher plant growth inhibitory potency against ryegrass than against lettuce, and the inhibitory activity varied depending on the configurations of each position of the tetrahydrofuran ring (7-, 7'-, 8-, and 8'-positions of the epoxylignanes). Among the 9,9'-position-modified derivatives, the dehydroxy derivatives showed the highest potency. These results suggested that the plant growth inhibitory activity should be influenced by the structure of the epoxylignanes.