xanthogalenol | 265659-35-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: xanthogalenol
• 英文别名: (E)-1-[2,6-dihydroxy-4-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
• CAS: 265659-35-6
• 化学式: C₂₁H₂₂O₅
• 分子量: 354.403
• InChiKey: ALGFNVZQNNGHPA-YRNVUSSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  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
• 作为产物：
  描述：

  在 盐酸 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以54%的产率得到xanthogalenol
  参考文献：
  名称：

  Natural and non-natural prenylated chalcones: Synthesis, cytotoxicity and anti-oxidative activity

  摘要：

  A general strategy for the synthesis of 30-prenylated chalcones was established and a series of prenylated hydroxychalcones, including the hop (Humulus lupulus L.) secondary metabolites xanthohumol (1), desmethylxanthohumol (2), xanthogalenol (3), and 4-methylxanthohumol (4) were synthesized. The influence of the A-ring hydroxylation pattern on the cytotoxic activity of the prenylated chalcones was investigated in a HeLa cell line and revealed that non-natural prenylated chalcones, like 2',3,4',5-tetrahydroxy-6'-methoxy-3'-prenylchalcone (9, IC50 3.2 +/- 0.4 mu M) as well as the phase 1 metabolite of xanthohumol (1), 3-hydroxyxanthohumol (8, IC50 2.5 +/- 0.5 mu M), were more active in comparison to 1 (IC50 9.4 +/- 1.4 mu M). A comparison of the cytotoxic activity of xanthohumol (1) and 3-hydroxyxanthohumol (8) with the non-prenylated analogs helichrysetin (12, IC50 5.2 +/- 0.8) and 3-hydroxyhelichrysetin (13, IC50 14.8 +/- 2.1) showed that the prenyl side chain at C-3' has an influence on the cytotoxicity against HeLa cells only for the dihydroxylated derivative. This offers interesting synthetic possibilities for the development of more potent compounds. The ORAC activity of the synthesized compounds was also investigated and revealed the highest activity for compounds 12, 4'-methylxanthohumol (4), and desmethylxanthohumol (2), with 4.4 +/- 0.6, 3.8 +/- 0.4, and 3.8 +/- 0.5 Trolox equivalents, respectively. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.02.079

文献信息

• SONG-SAN, SUN;WATANABE, SATORU;SAITO, TAIICHI, PHYTOCHEMISTRY, 28,(1989) N, C. 1776-1777
  作者：SONG-SAN, SUN、WATANABE, SATORU、SAITO, TAIICHI

  DOI：——

  日期：——
• US7326734B2
  申请人：——

  公开号：US7326734B2

  公开（公告）日：2008-02-05
• Natural and non-natural prenylated chalcones: Synthesis, cytotoxicity and anti-oxidative activity
  作者：Susanne Vogel、Susanne Ohmayer、Gabi Brunner、Jörg Heilmann

  DOI：10.1016/j.bmc.2008.02.079

  日期：2008.4

  A general strategy for the synthesis of 30-prenylated chalcones was established and a series of prenylated hydroxychalcones, including the hop (Humulus lupulus L.) secondary metabolites xanthohumol (1), desmethylxanthohumol (2), xanthogalenol (3), and 4-methylxanthohumol (4) were synthesized. The influence of the A-ring hydroxylation pattern on the cytotoxic activity of the prenylated chalcones was investigated in a HeLa cell line and revealed that non-natural prenylated chalcones, like 2',3,4',5-tetrahydroxy-6'-methoxy-3'-prenylchalcone (9, IC50 3.2 +/- 0.4 mu M) as well as the phase 1 metabolite of xanthohumol (1), 3-hydroxyxanthohumol (8, IC50 2.5 +/- 0.5 mu M), were more active in comparison to 1 (IC50 9.4 +/- 1.4 mu M). A comparison of the cytotoxic activity of xanthohumol (1) and 3-hydroxyxanthohumol (8) with the non-prenylated analogs helichrysetin (12, IC50 5.2 +/- 0.8) and 3-hydroxyhelichrysetin (13, IC50 14.8 +/- 2.1) showed that the prenyl side chain at C-3' has an influence on the cytotoxicity against HeLa cells only for the dihydroxylated derivative. This offers interesting synthetic possibilities for the development of more potent compounds. The ORAC activity of the synthesized compounds was also investigated and revealed the highest activity for compounds 12, 4'-methylxanthohumol (4), and desmethylxanthohumol (2), with 4.4 +/- 0.6, 3.8 +/- 0.4, and 3.8 +/- 0.5 Trolox equivalents, respectively. (C) 2008 Elsevier Ltd. All rights reserved.
• 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.