8,10-di-O-allyl-bergenin | 1373402-14-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 8,10-di-O-allyl-bergenin
• 英文别名: 8,10-diallyloxybergenin；8,10-bis(allyloxy)-3,4-dihydroxy-2-(hydroxymethyl)-9-methoxy-2,3,4,4a-tetrahydropyrano[3,2-c]isochromen-6(10bH)-one；(2R,3S,4S,4aR,10bS)-3,4-dihydroxy-2-(hydroxymethyl)-9-methoxy-8,10-bis(prop-2-enoxy)-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-6-one
• CAS: 1373402-14-2
• 化学式: C₂₀H₂₄O₉
• 分子量: 408.405
• InChiKey: INGWJXYIPMQJMB-UMILVCPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  8,10-di-O-allyl-bergenin 在 吗啉 、 四(三苯基膦)钯 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 11-O-benzoylbergenin
  参考文献：
  名称：

  作为蘑菇酪氨酸酶抑制剂的香柠檬素类似物的合成和生物学评价

  摘要：

  在这份手稿中，我们合成了一系列 bergenin 类似物，分析了它们对两种生物活性（抗氧化活性 (ORAC) 和蘑菇酪氨酸酶抑制活性）的结构重要性。其中，含有儿茶酚部分的化合物 5 表现出最大的抗氧化活性（3.75 μmol Trolox 当量/μmol 5）。此外，与熊果苷（IC50 值 = 221.8 ± 1.9 μM）和曲酸（IC50 值 = 46.6 ± 3.8 μM）的标准酪氨酸酶抑制剂相比，发现化合物 5 最有效（IC50 值 = 17.5 ± 0.04 μM） . bergenin 衍生物的 bergenin 部分、酯键和苯甲酸部分影响两种生物活性。酪氨酸酶抑制活性受苯甲酸部分取代基的影响。

  DOI：

  10.1007/s12272-012-0903-3
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 8,10-di-O-allyl-bergenin
  参考文献：
  名称：

  Synthesis of new bergenin derivatives as potent inhibitors of inflammatory mediators NO and TNF-α

  摘要：

  Bergenin is an isocoumarin natural product which aides in fat loss, healthy weight maintenance, enhancing the lipolytic effects of norepinephrine, inhibiting the formation of interleukin 1 alpha and cyclooxygenases-2. Here we describe the anti-inflammatory activity of new bergenin derivatives 1-15 in the respiratory burst assay. Bergenin was isolated from the crude extract of Mallotus philippenensis after repeated column chromatography and was then subjected to chemical derivatization. The structures of all compounds were elucidated by NMR and mass spectroscopic techniques. Compound 2 was also studied using single crystal X-ray diffraction. Compounds 4, (54.5 +/- 2.2%) 5 (47.5 +/- 0.5%) 5, and 15 (86.8 +/- 1.9%) showed significant (P <= 0.005) NO inhibitory activities whereas 6, 7, 11, 12 and 13 displayed moderate inhibitory activities that ranges between 16% and 31%. Furthermore compounds 4 and 15, were discovered as significant (P <= 0.005) TNF-alpha inhibitors with 98% and 96% inhibition, respectively, while compounds 3, 5, 7, 8, 11, and 12 showed low level of TNF-alpha inhibition (0.4-28%). Compounds 8, 13 and 15 exhibited moderate anti-inflammatory IC50 activities with 212, 222, and 253 mu M, respectively, compared to the standard anti-inflammatory drug indomethacin as well as the parent bergenin compound. No cytotoxic effects could be detected when the compounds were tested on 3T3 cells up to concentrations of 100 mu M. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.02.096

文献信息

• Structure-activity relationships of bergenin derivatives effect on α-glucosidase inhibition
  作者：Yusei Kashima、Hidehiko Yamaki、Takuya Suzuki、Mitsuo Miyazawa

  DOI：10.3109/14756366.2012.719503

  日期：2013.12.1

  The alpha-glucosidase inhibitory activities of bergenin derivatives were evaluated. Bergenin derivatives were synthesized from bergenin which is a characteristic compound of B. ligulata. A new bergenin derivative, 11-O-(3',4'-dimethoxybenzoyl)-bergenin showed the highest potent inhibitory activity among those of bergenin derivatives. The presence of substituents at 3',4'-position in bergenin derivatives altered the alpha-glucosidase inhibitory activity. 11-O-(3', 4'-dimethoxybenzoyl)-bergenin was noncompetitive inhibitor for alpha-glucosidase. The present study reveals that bergenin derivatives could be classified as a new group of alpha-glucosidase inhibitors.
• Synthesis and biological evaluation of bergenin analogues as mushroom tyrosinase inhibitors
  作者：Yusei Kashima、Mitsuo Miyazawa

  DOI：10.1007/s12272-012-0903-3

  日期：2012.9

  the standard tyrosinase inhibitors of arbutin (IC50 value = 221.8 ± 1.9 μM) and kojic acid (IC50 value = 46.6 ± 3.8 μM). The bergenin moiety, the ester linkage, and benzoic acid moiety of bergenin derivatives affected two biologic activities. Tyrosinase inhibitory activity was affected by substituents of benzoic acid moiety. This manuscript provides a good foundation for the design and development of

  在这份手稿中，我们合成了一系列 bergenin 类似物，分析了它们对两种生物活性（抗氧化活性 (ORAC) 和蘑菇酪氨酸酶抑制活性）的结构重要性。其中，含有儿茶酚部分的化合物 5 表现出最大的抗氧化活性（3.75 μmol Trolox 当量/μmol 5）。此外，与熊果苷（IC50 值 = 221.8 ± 1.9 μM）和曲酸（IC50 值 = 46.6 ± 3.8 μM）的标准酪氨酸酶抑制剂相比，发现化合物 5 最有效（IC50 值 = 17.5 ± 0.04 μM） . bergenin 衍生物的 bergenin 部分、酯键和苯甲酸部分影响两种生物活性。酪氨酸酶抑制活性受苯甲酸部分取代基的影响。
• Synthesis of new bergenin derivatives as potent inhibitors of inflammatory mediators NO and TNF-α
  作者：Muhammad Raza Shah、Mohammad Arfan、Hazrat Amin、Zahid Hussain、Muhammad Irfan Qadir、M. Iqbal Choudhary、Donald VanDerveer、M. Ahmed Mesaik、Samreen Soomro、Almas Jabeen、Inam Ullah Khan

  DOI：10.1016/j.bmcl.2012.02.096

  日期：2012.4

  Bergenin is an isocoumarin natural product which aides in fat loss, healthy weight maintenance, enhancing the lipolytic effects of norepinephrine, inhibiting the formation of interleukin 1 alpha and cyclooxygenases-2. Here we describe the anti-inflammatory activity of new bergenin derivatives 1-15 in the respiratory burst assay. Bergenin was isolated from the crude extract of Mallotus philippenensis after repeated column chromatography and was then subjected to chemical derivatization. The structures of all compounds were elucidated by NMR and mass spectroscopic techniques. Compound 2 was also studied using single crystal X-ray diffraction. Compounds 4, (54.5 +/- 2.2%) 5 (47.5 +/- 0.5%) 5, and 15 (86.8 +/- 1.9%) showed significant (P <= 0.005) NO inhibitory activities whereas 6, 7, 11, 12 and 13 displayed moderate inhibitory activities that ranges between 16% and 31%. Furthermore compounds 4 and 15, were discovered as significant (P <= 0.005) TNF-alpha inhibitors with 98% and 96% inhibition, respectively, while compounds 3, 5, 7, 8, 11, and 12 showed low level of TNF-alpha inhibition (0.4-28%). Compounds 8, 13 and 15 exhibited moderate anti-inflammatory IC50 activities with 212, 222, and 253 mu M, respectively, compared to the standard anti-inflammatory drug indomethacin as well as the parent bergenin compound. No cytotoxic effects could be detected when the compounds were tested on 3T3 cells up to concentrations of 100 mu M. (C) 2012 Elsevier Ltd. All rights reserved.