8-Isopentylnaringenin | 936573-99-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 8-Isopentylnaringenin
• 英文别名: (+/-)-8-(3-Methylbutyl)naringenin；5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbutyl)-3,4-dihydro-2H-1-benzopyran-4-one；5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbutyl)-2,3-dihydrochromen-4-one
• CAS: 936573-99-8
• 化学式: C₂₀H₂₂O₅
• 分子量: 342.392
• InChiKey: UKBYGNGSGOXLFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  硫酸二甲酯 、 8-Isopentylnaringenin 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 8-Isopentyl-5,7,4-trimethoxynaringenin
  参考文献：
  名称：

  A new flavanone with antifungal activity isolated from hops.

  摘要：

  6-异戊烯基柚皮素1（之前由其他研究人员合成）与黄腐醇2和异黄腐醇3一起从啤酒花（Humulus lupulus L.）的硬树脂中分离出来。研究人员对1和槐黄酮B的结构进行了研究；后者之前被报道为6-异戊烯基柚皮素，现已修订为8-异戊烯基柚皮素。1、2和3被发现具有抗真菌活性。

  DOI：

  10.1271/bbb1961.48.2771
• 作为产物：
  描述：

  4',7-二羟基-5-甲氧基-8-(3-甲基-2-丁烯基)黄烷酮 在 platinum(IV) oxide 三氯化铝 、 氢气 作用下， 以 甲醇 、 硝基苯 为溶剂， 反应 1.5h， 生成 8-Isopentylnaringenin
  参考文献：
  名称：

  A new flavanone with antifungal activity isolated from hops.

  摘要：

  6-异戊烯基柚皮素1（之前由其他研究人员合成）与黄腐醇2和异黄腐醇3一起从啤酒花（Humulus lupulus L.）的硬树脂中分离出来。研究人员对1和槐黄酮B的结构进行了研究；后者之前被报道为6-异戊烯基柚皮素，现已修订为8-异戊烯基柚皮素。1、2和3被发现具有抗真菌活性。

  DOI：

  10.1271/bbb1961.48.2771

文献信息

• Production of hop extracts having oestrogenic and antiproliferative bioactivity
  申请人：Biodynamics

  公开号：EP1543834A1

  公开（公告）日：2005-06-22

  The invention relates to a method for the production of a hop extract enriched in prenylated flavonoids or derivatives thereof, whereby the method comprises the steps of subjecting a hop product to an isomerisation reaction in the presence of an amount of a base and to at least one extraction.

  这项发明涉及一种生产富含前缀化黄酮类化合物或其衍生物的啤酒花提取物的方法，其中该方法包括以下步骤：在碱的存在下对啤酒花产品进行异构化反应，并至少进行一次提取。
• Subtle Side-Chain Modifications of the Hop Phytoestrogen 8-Prenylnaringenin Result in Distinct Agonist/Antagonist Activity Profiles for Estrogen Receptors α and β
  作者：Frederik Roelens、Nina Heldring、Willem Dhooge、Martin Bengtsson、Frank Comhaire、Jan-Åke Gustafsson、Eckardt Treuter、Denis De Keukeleire

  DOI：10.1021/jm060692n

  日期：2006.12.1

  In search of therapeutic agents for estrogen-related pathologies, phytoestrogens are being extensively explored. In contrast to naringenin, 8-prenylnaringenin is a potent hop-derived estrogenic compound, highlighting the importance of the prenyl group for hormonal activity. We investigated the effects of substituting the prenyl group at C(8) with alkyl chains of varying lengths and branching patterns on estrogen receptor (ER) subtype ER alpha- and ER beta-binding affinities and transcriptional activities. In addition, features of the ligand-induced receptor conformations were explored using a set of specific ER-binding peptides. The new 8-alkylnaringenins were found to span an activity spectrum ranging from full agonism to partial agonism to antagonism. Most strikingly, 8-(2,2-dimethylpropyl) naringenin exhibited full agonist character on ERR, but pronounced antagonist character on ER beta. Knowledge on how ER-subtype-selective activities can be designed provides valuable information for future drug or tool compound discovery.
• PRODUCTION OF HOP EXTRACTS HAVING OESTROGENIC AND ANTIPROLIFERATIVE BIOACTIVITY
  申请人：Biodynamics

  公开号：EP1727555A1

  公开（公告）日：2006-12-06
• Method for the production of enriched hop extracts having combined oestrogenic and antiproliferative bioactivity
  申请人：Maes Francis

  公开号：US20070110835A1

  公开（公告）日：2007-05-17

  The present invention relates to a method for the production of a hop extract which is enriched in 8-prenylnaringenin with respect to 6-prenylnaringenin, which method comprises the steps of subjecting a hop product to (1) an isomerisation reaction in the presence of water as a solvent and in the presence of an amount of a base and (2) to at least one extraction. In that way a hop extract may be extract is obtained which contains 6-prenylnaringenin and 8-prenylinaringening in a ratio (8-prenylnaringenin ×100%)/(8-prenylnaringenin+6-prenylnaringenin) of at least 50%. The extract preferably also contains xanthohumol, the weight ratio of xanthohumol to 8-prenylnaringenin being at least 10.
• [EN] PRODUCTION OF HOP EXTRACTS HAVING OESTROGENIC AND ANTIPROLIFERATIVE BIOACTIVITY<br/>[FR] PRODUCTION D'EXTRAITS DE HOUBLON PRESENTANT UNE ACTIVITE ESTROGENIQUE ET ANTI-PROLIFERANTE
  申请人：BIODYNAMICS

  公开号：WO2005058336A1

  公开（公告）日：2005-06-30

  The present invention relates to a method for the production of a hop extract which is enriched in 8-prenylnaringenin with respect to 6-prenylnaringenin, which method comprises the steps of subjecting a hop product to (1) an isomerisation reaction in the presence of water as a solvent and in the presence of an amount of a base and (2) to at least one extraction. In that way a hop extract may be extract is obtained which contains 6-prenylnaringenin and 8-­prenyinaringening in a ratio (8-prenylnaringenin x 100%)/(8-prenylnaringenin + 6­prenyInaringenin) of at least 50%. The extract preferably also contains xanthohumol, the weight ratio of xanthohumol to 8-prenylnaringenin being at least 10.