2-(3,4-二羟基苯基)-2,3-二氢色烯-4-酮 | 6563-37-7

• 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: 2-(3,4-二羟基苯基)-2,3-二氢色烯-4-酮
• 英文名称: 3',4'-dihydroxyflavanone
• 英文别名: 2-(3,4-Dihydroxyphenyl)chroman-4-one；2-(3,4-dihydroxyphenyl)-2,3-dihydrochromen-4-one
• CAS: 6563-37-7
• 化学式: C₁₅H₁₂O₄
• 分子量: 256.258
• InChiKey: LHARPARLCDEZDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,4,2'-trihydroxy-trans-chalcone 在 硫酸 作用下， 生成 2-(3,4-二羟基苯基)-2,3-二氢色烯-4-酮
  参考文献：
  名称：

  The Preparation of the Polyhydroxychalcones

  摘要：

  DOI：

  10.1021/ja01873a023

文献信息

• Production of Hydroxlated Flavonoids with Cytochrome P450 BM3 Variant F87V and Their Antioxidative Activities
  作者：Emi KITAMURA、Toshihiko OTOMATSU、Chiemi MAEDA、Yoko AOKI、Chihiro OTA、Norihiko MISAWA、Kazutoshi SHINDO

  DOI：10.1271/bbb.130148

  日期：2013.6.23

  A variant of P450 BM3 with an F87V substitution [P450 BM3 (F87V)] is a substrate-promiscuous cytochrome P450 monooxygenase. We investigated the bioconversion of various flavonoids (favanones, chalcone, and isoflavone) by using recombinant Escherichia coli cells, which expressed the gene coding for P450 BM3 (F87V), to give their corresponding hydroxylated products. Potent antioxidative activities were observed in some of the products.

  具有 F87V 取代的 P450 BM3 变体[P450 BM3 (F87V)]是一种底物易混的细胞色素 P450 单加氧酶。我们利用表达了 P450 BM3 (F87V) 编码基因的重组大肠杆菌细胞，研究了多种黄酮类化合物（蚕豆酮、查尔酮和异黄酮）的生物转化，以得到相应的羟化产物。在一些产物中观察到了强效的抗氧化活性。
• Microbial Metabolism. Part 12.
  作者：Julie Rakel Mikell、Wimal Herath、Ikhlas Ahmad Khan

  DOI：10.1248/cpb.59.692

  日期：——

  Fermentation of 4′-hydroxyflavanone (1) with fungal cultures, Beauveria bassiana (ATCC 13144 and ATCC 7159) yielded 6,3′,4′-trihydroxyflavanone (2), 3′,4′-dihydroxyflavanone 6-O-β-D-4-methoxyglucopyranoside (3), 4′-hydroxyflavanone 3′-sulfate (4), 6,4′-dihydroxyflavanone 3′-sulfate (5) and 4′-hydroxyflavanone 6-O-β-D-4-methoxyglucopyranoside (7). B. bassiana (ATCC 13144) and B. bassiana (ATCC 7159) in addition, gave one more metabolite each, namely, flavanone 4′-O-β-D-4-methoxyglucopyranoside (6) and 6,4′-dihydroxyflavanone (8) respectively. Cunninghamella echinulata (ATCC 9244) transformed 1 to 6,4′-dihydroxyflavanone (8), flavanone-4′-O-β-D-glucopyranoside (9), 3′-hydroxyflavanone 4′-sulfate (10), 3′,4′-dihydroxyflavanone (11) and 4′-hydroxyflavanone-3′-O-β-D-glucopyranoside (12). Mucor ramannianus (ATCC 9628) metabolized 1 to 2,4-trans-4′-hydroxyflavan-4-ol (13), 2,4-cis-4′-hydroxyflavan-4-ol (14), 2,4-trans-3′,4′-dihydroxyflavan-4-ol (15), 2,4-cis-3′,4′-dihydroxyflavan-4-ol (16), 2,4-trans-3′-hydroxy-4′-methoxyflavan-4-ol (17), flavanone 4′-O-α-D-6-deoxyallopyranoside (18) and 2,4-cis-4-hydroxyflavanone 4′-O-α-D-6-deoxyallopyranoside (19). Metabolites 13 and 14 were also produced by Ramichloridium anceps (ATCC 15672). The former was also produced by C. echinulata. Structures of the metabolic products were elucidated by means of spectroscopic data. None of the metabolites tested showed antibacterial, antifungal and antiprotozoal activities against selected organisms.

  用真菌培养物白僵菌（ATCC 13144 和 ATCC 7159）发酵 4'-羟基黄烷酮 (1)，产生 6,3',4'-三羟基黄烷酮 (2)、3',4'-二羟基黄烷酮 6-O-β-<小>D-4-甲氧基吡喃葡萄糖苷 (3), 4′-羟基黄烷酮3'-硫酸酯 (4)、6,4'-二羟基黄烷酮 3'-硫酸酯 (5) 和 4'-羟基黄烷酮 6-O-β-<小>D-4-甲氧基吡喃葡萄糖苷 (7)。此外，B. bassiana (ATCC 13144) 和 B. bassiana (ATCC 7159) 各产生一种代谢物，即黄烷酮 4'-O-β-D-4-methoxyglucopyranoside (6) 和分别为 6,4'-二羟基黄烷酮 (8)。 Cunninghamella echinulata (ATCC 9244) 将 1 转化为 6,4'-二羟基黄烷酮 (8)、flavanone-4'-O-β-D-吡喃葡萄糖苷 (9)、3'-羟基黄烷酮 4'-硫酸盐(10)、3',4'-二羟基黄烷酮 (11) 和4'-羟基黄烷酮-3'-O-β-<小>D-吡喃葡萄糖苷 (12)。拉曼毛霉 (ATCC 9628) 将 1 代谢为 2,4-反式-4'-羟基黄烷-4-醇 (13)、2,4-顺式-4'-羟基黄烷-4-醇 (14)、2,4-反式-3′,4′-二羟基黄烷-4-醇 (15), 2,4-顺式-3′,4′-二羟基黄烷-4-醇(16)、2,4-反式-3′-羟基-4′-甲氧基黄烷-4-醇(17)、黄烷酮4′-O-α-<小>D-6-脱氧吡喃糖苷(18)和 2,4-顺-4-羟基黄烷酮 4'-O-α-<小>D-6-脱氧吡喃糖苷 (19)。代谢物 13 和 14 也由雷米氯铵 (ATCC 15672) 产生。前者也是由 C. echinulata 产生的。通过光谱数据阐明代谢产物的结构。测试的代谢物均未表现出针对选定生物体的抗菌、抗真菌和抗原虫活性。
• Aspergillus niger catalyzes the synthesis of flavonoids from chalcones
  作者：Julio Alarcón、Joel Alderete、Carlos Escobar、Ramiro Araya、Carlos L. Cespedes

  DOI：10.3109/10242422.2013.813489

  日期：2013.8

  Flavonoids, which have many biological activities and have been widely used in nature, can be artificially synthesized. However, regioselective cyclization of chalcones is difficult by chemical methods. In this study, we demonstrated that Aspergillus niger is capable of cyclizing chalcones to flavanones, affording a mimic of plant biosynthetic processes. Chalcones 1-6 were biotransformated to the modified chalcones 8-14 and to the flavanones 15-27. The biotransformation showed that enzymatic cyclization and demethylation occurred during the first days of biotransformation; in contrast, hydroxylation is a later process. With a longer culturing time, it is possible to obtain more hydroxylated flavanones with excellent yields.
• IBRAHIM, ABDEL-RAHIM;ABUL-HAJJ, YUSUF J., J. NATUR. PROD., 53,(1990) N, C. 644-656
  作者：IBRAHIM, ABDEL-RAHIM、ABUL-HAJJ, YUSUF J.

  DOI：——

  日期：——
• OXIDATIONS- UND BLEICHSYSTEM MIT ENZYMATISCH HERGESTELLTEN OXIDATIONSMITTELN
  申请人：Blume, Hildegard

  公开号：EP1012376A2

  公开（公告）日：2000-06-28