3'-异戊烯基柚皮素 | 119240-82-3

• 物质功能分类: 生物化工 - 提取物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 3'-异戊烯基柚皮素
• 中文别名: 甘草黄酮提取物
• 英文名称: 3’-prenylnaringenin
• 英文别名: 3′-prenylnaringenin；3'-prenylliquiritigenin；3'-prenylnaringenin；licoflavanone；licoflavanon；licoflavone；(S)-5,7-Dihydroxy-2-(4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl)chroman-4-one；(2S)-5,7-dihydroxy-2-[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]-2,3-dihydrochromen-4-one
• CAS: 119240-82-3
• 化学式: C₂₀H₂₀O₅
• 分子量: 340.376
• InChiKey: CGKWSLSAYABZTL-SFHVURJKSA-N

物化性质

• 熔点：
  134-135 °C
• 沸点：
  589.9±50.0 °C(Predicted)
• 密度：
  1.314±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  3'-异戊烯基柚皮素 在 盐酸 、 甲醇 作用下， 反应 5.0h， 以28 mg的产率得到cyclolicoflavanone
  参考文献：
  名称：

  Two antimicrobial flavanones from the leaves of Glycyrrhiza glabra.

  摘要：

  从甘草变种（Glycyrrhiza glabra var. Typica）的叶子中分离出了一种名为甘草黄酮（licoflavanone）的新前基黄烷酮，以及一种抗菌剂--pinocembrin。

  DOI：

  10.1248/cpb.36.4174
• 作为产物：
  描述：

  DMAPP 、 (S)-柚皮素 在 fungal prenyltransferase AnaPT 、 calcium chloride 作用下， 以 二甲基亚砜 、 甘油 为溶剂， 反应 16.0h， 以54.2%的产率得到3'-异戊烯基柚皮素
  参考文献：
  名称：

  Complementary Flavonoid Prenylations by Fungal Indole Prenyltransferases

  摘要：

  Flavonoids are found mainly in plants and exhibit diverse biological and pharmacological activities, which can often be enhanced by prenylations. In plants, such reactions are catalyzed by membrane-bound prenyltransferases. In this study, the prenylation of nine flavonoids from different classes by a soluble fungal prenyltransferase (AnaPT) involved in the biosynthesis of the prenylated indole alkaloid acetylaszonalenin is demonstrated. The behavior of AnaPT toward flavonoids regarding substrate acceptance and prenylation positions clearly differs from that of the indole prenyltransferase 7-DMATS. The two enzymes are therefore complementary in flavonoid prenylations.

  DOI：

  10.1021/acs.jnatprod.5b00422

文献信息

• Prenylated flavonoids in the roots of yellow lupin
  作者：Satoshi Tahara、Yasufumi Katagiri、John L. Ingham、Junya Mizutani

  DOI：10.1016/s0031-9422(00)89648-x

  日期：1994.8

  A further investigation of the methanol-soluble compounds in yellow lupin roots has revealed a new diprenylchromone, a new coumaronochromone (lupinalbin H), a new isoflavone 5,7,4'-trihydroxy-8,3'-di-(3,3-dimethylallyl)isoflavone (isolupalbigenin), and some complex flavanones. The latter compounds have been identified as two known diprenylated flavanones (lonchocarpol A and euchrestaflavanone A), two diasteroisomeric pairs of dihydrofuranoflavanones (lonchocarpols C-1 and C-2, and lonchocarpols D-1 and D-2; the structures formerly proposed for lonchocarpols C and D were also reinvestigated), a new furanoflavanone (lupinenol), and three 8-prenylflavanones with an additional (2RS)-hydroxy-3-methyl-3-butenyl side chain. The structures of the latter flavanones were unambiguously identified by spectroscopic (H-1 NMR) comparison with 6-, 8- and 3'-prenylnaringenins chemically prepared from (2S)-naringenin. The antifungal activity of the prenylated naringenins, and of the various yellow lupin flavanones, was determined by TLC place bioassays using Cladosporium herbarum as the test fungus.
• FUKUI, HIROSHI;GOTO, KATSUMI;TABATA, MAMORU, CHEM. AND PHARM. BULL., 36,(1988) N 10, C. 4174-4176
  作者：FUKUI, HIROSHI、GOTO, KATSUMI、TABATA, MAMORU

  DOI：——

  日期：——
• Complementary Flavonoid Prenylations by Fungal Indole Prenyltransferases
  作者：Kang Zhou、Xia Yu、Xiulan Xie、Shu-Ming Li

  DOI：10.1021/acs.jnatprod.5b00422

  日期：2015.9.25

  Flavonoids are found mainly in plants and exhibit diverse biological and pharmacological activities, which can often be enhanced by prenylations. In plants, such reactions are catalyzed by membrane-bound prenyltransferases. In this study, the prenylation of nine flavonoids from different classes by a soluble fungal prenyltransferase (AnaPT) involved in the biosynthesis of the prenylated indole alkaloid acetylaszonalenin is demonstrated. The behavior of AnaPT toward flavonoids regarding substrate acceptance and prenylation positions clearly differs from that of the indole prenyltransferase 7-DMATS. The two enzymes are therefore complementary in flavonoid prenylations.
• Two antimicrobial flavanones from the leaves of Glycyrrhiza glabra.
  作者：HIROSHI FUKUI、KATSUMI GOTO、MAMORU TABATA

  DOI：10.1248/cpb.36.4174

  日期：——

  A new prenylated flavanone named licoflavanone was isolated, together with pinocembrin, from the leaves of Glycyrrhiza glabra var. Typica as an antimicrobial agent.

  从甘草变种（Glycyrrhiza glabra var. Typica）的叶子中分离出了一种名为甘草黄酮（licoflavanone）的新前基黄烷酮，以及一种抗菌剂--pinocembrin。