7-O-methyl-6-prenylnaringenin

• 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: 7-O-methyl-6-prenylnaringenin
• 英文别名: 5,4'-Dihydroxy-7-methoxy-6-C-prenylflavanone；5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
• 化学式: C₂₁H₂₂O₅
• 分子量: 354.403
• InChiKey: PMQBKFKEJGCJIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  xanthogalenol 以 甲醇 、 水 为溶剂， 生成 7-O-methyl-6-prenylnaringenin 、 5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-8-(3-methylbut-2-enyl)chroman-4-one
  参考文献：
  名称：

  Prenylflavonoid variation in Humulus lupulus: distribution and taxonomic significance of xanthogalenol and 4′-O-methylxanthohumol

  摘要：

  The resins produced by either lupulin or leaf glands of over 120 plants of Humulus lupulus and one plant of H. japonicus (Cannabinaceae) were analyzed for the presence of prenylated flavonoids. The H. lupulus taxa investigated were H. lupulus var. lupulus from Europe, H. lupulus var. cordifolius from Japan, and H. lupulus From North America. Fifty-two of the plants examined were cultivars of European, American, and Japanese origin, Twenty-two flavonoids were detected in the glandular exudates of. H. lupulus by HPLC-MS-MS. Xanthohumol (3'-prenyl-6'-O-methylchalconaringenin) was the principal prenylflavonoid in all H. lupulus plants and was accompanied by 11 structurally similar chalcones. Ten flavonoids were identified as the flavanone isomers of these chalcones. Three other prenylchalcones were isolated from H. lupulus cv. 'Galena', one of which was identified as 3'-prenyl-4'-O-methylchalconaringenin (named 'xanthogalenol'). The distribution of three 4'-O-methylchalcones, i.e, xanthogalenol, 4'-O-methylxanthohumol, and 4',6'-di-O-methylchalconaringenin, was found to be limited to wild American plants from the Missouri-Mississippi river basin, H. lupulus var. cordifolius, and most of their descendents, These 4'-O-methylchalcones were absent from cultivars of European origin; and from wild hops from Europe and southwestern USA, The flavonoid dichotomy (presence versus absence of 4'-O-methylchalcones) indicates that there are at least two evolutionary lineages within H. lupulus (European and Japanese-American). which is in agreement with morphological, molecular, and phytogeographical evidence. Leaf glands of H. japonicus from eastern Asia did not produce the N. lupulus prenylflavonoids. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(00)00005-4

文献信息

• Prenylflavonoid variation in Humulus lupulus: distribution and taxonomic significance of xanthogalenol and 4′-O-methylxanthohumol
  作者：Jan F. Stevens、Alan W. Taylor、Gail B. Nickerson、Monika Ivancic、John Henning、Alfred Haunold、Max L. Deinzer

  DOI：10.1016/s0031-9422(00)00005-4

  日期：2000.4

  The resins produced by either lupulin or leaf glands of over 120 plants of Humulus lupulus and one plant of H. japonicus (Cannabinaceae) were analyzed for the presence of prenylated flavonoids. The H. lupulus taxa investigated were H. lupulus var. lupulus from Europe, H. lupulus var. cordifolius from Japan, and H. lupulus From North America. Fifty-two of the plants examined were cultivars of European, American, and Japanese origin, Twenty-two flavonoids were detected in the glandular exudates of. H. lupulus by HPLC-MS-MS. Xanthohumol (3'-prenyl-6'-O-methylchalconaringenin) was the principal prenylflavonoid in all H. lupulus plants and was accompanied by 11 structurally similar chalcones. Ten flavonoids were identified as the flavanone isomers of these chalcones. Three other prenylchalcones were isolated from H. lupulus cv. 'Galena', one of which was identified as 3'-prenyl-4'-O-methylchalconaringenin (named 'xanthogalenol'). The distribution of three 4'-O-methylchalcones, i.e, xanthogalenol, 4'-O-methylxanthohumol, and 4',6'-di-O-methylchalconaringenin, was found to be limited to wild American plants from the Missouri-Mississippi river basin, H. lupulus var. cordifolius, and most of their descendents, These 4'-O-methylchalcones were absent from cultivars of European origin; and from wild hops from Europe and southwestern USA, The flavonoid dichotomy (presence versus absence of 4'-O-methylchalcones) indicates that there are at least two evolutionary lineages within H. lupulus (European and Japanese-American). which is in agreement with morphological, molecular, and phytogeographical evidence. Leaf glands of H. japonicus from eastern Asia did not produce the N. lupulus prenylflavonoids. (C) 2000 Elsevier Science Ltd. All rights reserved.