8-dimethylallylsteppogenin | 152464-78-3

• 物质功能分类: 天然产物 - 黄酮类化合物
• 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-dimethylallylsteppogenin
• 英文别名: (2S)-(-)-leachianone G；(2S)-leachianone G；8-prenylnaringenin；leachianone G；leachianone；(2S)-2-(2,4-dihydroxyphenyl)-5,7-dihydroxy-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
• CAS: 152464-78-3
• 化学式: C₂₀H₂₀O₆
• 分子量: 356.375
• InChiKey: VBOYLFNGTSLAAZ-SFHVURJKSA-N

物化性质

• 沸点：
  639.6±55.0 °C(Predicted)
• 密度：
  1.384±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 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：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  DMAPP 、 8-dimethylallylsteppogenin 生成 pyrophosphoric acid 、 (2S,4R,6E,8S)-8-[(2S,2'R,4'S,5R,5'R,7S,7'R,9R,10R,10'R)-2'-[(2S,3S,5R,6R)-6-羟基-6-(羟甲基)-3,5-二甲基四氢-2H-吡喃-2-基]-9-{[(2R,5S,6R)-5-甲氧基-6-甲基四氢-2H-吡喃-2-基]氧代}-2,4',10,10'-四甲基-2,7'-联(1,6-二氧杂螺[4.5]d
  参考文献：
  名称：

  Characterization of Leachianone G 2″ -Dimethylallyltransferase, a Novel Prenyl Side-Chain Elongation Enzyme for the Formation of the Lavandulyl Group of Sophoraflavanone G in Sophora flavescens Ait. Cell Suspension Cultures

  摘要：

  在黄檗Sophora flavescens Ait.培养细胞中鉴定出一种新的异戊二烯基侧链延长酶——Leachianone G (LG) 2′′-dimethylallyltransferase。该酶将一个二甲基烯丙基基团转移至LG的8号位附加的另一个二甲基烯丙基基团的2′′位，形成sophoraflavanone G，这是一种特有于该植物的分支单萜基结合的黄烷酮。这种膜结合的二甲基烯丙基转移酶需要Mg2+（最佳浓度为10 mm）参与反应，其最适pH为8.8。它利用二甲基烯丙基二磷酸盐作为唯一的异戊二烯基供体，而LG中的2′-羟基功能对其活性是必不可少的。二甲基烯丙基二磷酸盐和LG的表观Km值分别为59和2.3 μm。利用蔗糖密度梯度离心法还研究了参与薰衣草基团形成的三种酶的亚细胞定位。两种异戊二烯基转移酶——柚皮素8-二甲基烯丙基转移酶和LG 2′′-dimethylallyltransferase定位于质体内，而催化薰衣草基团形成的关键步骤的8-二甲基烯丙基柚皮素2′-羟化酶则与内质网相关。这些结果表明质体和内质网在薰衣草基团形成中密切合作。

  DOI：

  10.1104/pp.103.025213
• 作为产物：
  描述：

  8-异戊烯基柚皮素 在 8-dimethylallylnaringenin 2'-hydroxylase 、 氧气 、 还原型辅酶II(NADPH)四钠盐 作用下， 以 乙醇 为溶剂， 生成 8-dimethylallylsteppogenin
  参考文献：
  名称：

  8-Dimethylallylnaringenin 2′-hydroxylase, the crucial cytochrome P450 mono-oxygenase for lavandulylated flavanone formation in Sophora flavescens cultured cells

  摘要：

  8-Dimethylallylnaringenin (8-DMAN) 2'-hydroxylase, which is indispensable for the formation of a lavandulylated flavanone, sophoraflavanone G, was detected in cell suspension cultures of Sophora flavescens. The enzyme catalyzes the 2'-hydroxylation of 8-DMAN to leachianone G, and is tightly bound to the membrane. It required NADPH and molecular oxygen as cofactors, and was inhibited by several cytochrome P450 inhibitors such as carbon monoxide and cytochrome c, indicating that the reaction is mediated by a cytochrome P450 monooxygenase. The optimum pH of 8-DMAN 2'-hydroxylase was 8.5, and the enzyme hydroxylated only 8-DMAN. Apparent Km values for 8-DMAN and NADPH of the enzyme were 55 and 34 muM, respectively. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(01)00270-9

文献信息

• Regio- and Stereospecific Prenylation of Flavonoids by<i>Sophora flavescens</i>Prenyltransferase
  作者：Ridao Chen、Xiao Liu、Jianhua Zou、Yunze Yin、Bin Ou、Jianhua Li、Ruishan Wang、Dan Xie、Peicheng Zhang、Jungui Dai

  DOI：10.1002/adsc.201300196

  日期：2013.6.17

  activities. The reaction catalyzed by prenyltransferases represents a Friedel–Crafts alkylation of the flavonoid skeleton in the biosynthesis of natural prenylflavonoids and often contributes to the structural diversity and biological activity of these compounds. However, only a few plant flavonoid prenyltransferases have been identified thus far, and these prenyltransferases exhibit strict substrate

  异戊二烯类黄酮是有价值的天然产物，广泛分布在植物中。它们通常具有不同的生物学特性，包括植物雌激素，抗菌，抗肿瘤和抗糖尿病活性。异戊二烯基转移酶催化的反应代表天然异戊二烯类黄酮生物合成中黄酮类骨架的弗里德-克来夫特烷基化，通常有助于这些化合物的结构多样性和生物活性。然而，到目前为止，仅鉴定出几种植物类黄酮异戊二烯基转移酶，并且这些异戊二烯基转移酶表现出严格的底物特异性和低催化效率。在本文中，苦参中的类黄酮异戊二烯基转移酶，SfFPT，已被证明对结构不同类型的类黄酮（即黄烷酮，黄酮，黄烷醇和二氢查耳酮等）的C-8表现出高催化效率和高区域特异性。此外，SfPFT对左旋黄烷酮产生（2 S）-异戊烯基黄烷酮具有严格的立体特异性。这项研究是第一个证明体外植物黄酮类异戊二烯基转移酶的底物混杂性和立体特异性。鉴于其底物的混杂性和高催化效率，SfFPT可以用作一种环境友好且高效的生物催化剂，用于类黄酮的区域
• T-TYPE CALCIUM CHANNEL INHIBITOR
  申请人：KINKI UNIVERSITY

  公开号：US20200308132A1

  公开（公告）日：2020-10-01

  A new analgesic has been developed for T-type calcium channels as therapeutic targets. The present invention provides a T-type calcium channel inhibitor which is a compound represented by formula (1): wherein each of R 1 and R 2 independently represents —H or —OH; R 3 represents —OH; R 4 represents —OH or —H; R 5 represents a straight or branched alkyl or cycloalkyl-alkyl group having one to ten carbon atoms or a straight or branched alkenyl or cycloalkyl-alkenyl group having two to ten carbon atoms, or a pharmaceutically acceptable salt or solvate thereof. The present invention also provides this T-type calcium channel inhibitor, a medicament containing the T-type calcium channel inhibitor, and a therapeutic or prophylactic agent for a disease having an effective T-type calcium channel inhibitory action.

  已经开发出一种新的镇痛剂，用于T型钙通道作为治疗靶点。本发明提供了一种T型钙通道抑制剂，其化学式表示为（1）：其中R1和R2分别独立表示—H或—OH；R3表示—OH；R4表示—OH或—H；R5表示具有一到十个碳原子的直链或支链烷基或环烷基烷基，或具有两到十个碳原子的直链或支链烯基或环烷基烯基，或其药学上可接受的盐或溶剂。本发明还提供了这种T型钙通道抑制剂，含有T型钙通道抑制剂的药物，以及用于具有有效T型钙通道抑制作用的疾病的治疗或预防剂。
• T-type calcium channel inhibitor
  申请人：KINKI UNIVERSITY

  公开号：US10633358B2

  公开（公告）日：2020-04-28

  The present invention provides a T-type calcium channel inhibitor which is a compound represented by formula (1), a pharmaceutically acceptable salt of this compound or a solvate of this compound. The present invention also provides: this T-type calcium channel inhibitor; a pharmaceutical product containing this T-type calcium channel inhibitor; and a therapeutic agent or prophylactic agent for diseases, the effective action of which is a T-type calcium channel inhibitory action. (In formula (1), each of R1 and R2 independently represents H, —OH or —OR11 wherein R11 represents a C1-3 alkyl group; each of R3 and R4 independently represents H, —OH or —OR12, wherein R12 represents a C1-3 alkyl group; and each of R5 and R6 independently represents H, a halogen atom, a C1-10 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a phenyl group (which may be substituted by a C1-6 alkoxy group or a halogen atom), a —C1-3 alkyl-phenyl group (which may be substituted by a C1-6 alkyloxy group or a halogen atom) or a C10-50 prenyl group.)

  本发明提供了一种 T 型钙通道抑制剂，它是由式（1）代表的化合物、该化合物的药学上可接受的盐或该化合物的溶液。本发明还提供：这种 T 型钙通道抑制剂；含有这种 T 型钙通道抑制剂的药品；以及一种治疗剂或疾病预防剂，其有效作用为 T 型钙通道抑制作用。式（1）中，R1 和 R2 各自独立地代表 H、-OH 或-OR11，其中 R11 代表 C1-3 烷基；R3 和 R4 各自独立地代表 H、-OH 或-OR12，其中 R12 代表 C1-3 烷基；R5和R6各自独立地代表H、卤素原子、C1-10烷基、C2-6烯基、C2-6炔基、苯基（可被C1-6烷氧基或卤素原子取代）、-C1-3烷基苯基（可被C1-6烷氧基或卤素原子取代）或C10-50链烯基。)
• US11517556B2
  申请人：GWANGJU INSTITUTE OF SCIENCE AND TECHNOLOGY

  公开号：US11517556B2

  公开（公告）日：2022-12-06

  The present invention relates to novel compounds capable of activating BKCa channels. The use of a composition of the present invention can effectively activate the BKCa channels, and can be used for prevention or treatment of various diseases caused by the deactivation of BKCa channels or the degradation of BKCa channel activity.

  本发明涉及能够激活 BKCa 通道的新型化合物。使用本发明的组合物可以有效激活 BKCa 通道，并可用于预防或治疗因 BKCa 通道失活或 BKCa 通道活性降低而引起的各种疾病。
• Flavanone 8-dimethylallyltransferase in Sophora flavescens cell suspension cultures
  作者：Hirobumi Yamamoto、Masayuki Senda、Kenichiro Inoue

  DOI：10.1016/s0031-9422(00)00198-9

  日期：2000.8

  Dimethylallyl diphosphate: naringenin 8-dimethylallyltransferase (EC 2.5.1) was characterized. The enzyme was enantiospecific for (-)-(2S)-naringenin and utilized 3,3-dimethylallyl diphosphate as sole prenyl donor. It required Mg2+ (optimum concentration, 10 mM), and has an optimum pH of 9-10. The apparent K-m values for 3,3-dimethylallyl diphosphate and naringenin were 120 and 36 mu M, respectively. The microsomal fraction prenylated several other flavanones at the C-8 position less effectively as compared with naringenin. Interestingly, when 2'-hydroxynaringenin was used as a prenyl acceptor, the 8-lavandulyl (sophoraflavanone G) and the 6-dimethylallyl derivatives were formed, together with the 8-dimethylallyl derivative, leachianone G. These results suggest that the 2'-hydroxy group of naringenin plays an important role for the formation of a lavandulyl group. (C) 2000 Elsevier Science Ltd. All rights reserved.