6,9-dihydroxy-2,2-dimethyl-3,4-dihydro-2H-benzo[g]chromene-5,10-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 6,9-dihydroxy-2,2-dimethyl-3,4-dihydro-2H-benzo[g]chromene-5,10-dione
• 英文别名: 6,9-Dihydroxy-2,2-dimethyl-3,4-dihydrobenzo[g]chromene-5,10-dione；6,9-dihydroxy-2,2-dimethyl-3,4-dihydrobenzo[g]chromene-5,10-dione
• 化学式: C₁₅H₁₄O₅
• 分子量: 274.273
• InChiKey: JUXWUGIDXFYILM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  Hydroxysesamone 在 甲酸 作用下， 反应 2.0h， 以15 mg的产率得到6,9-dihydroxy-2,2-dimethyl-3,4-dihydro-2H-benzo[g]chromene-5,10-dione
  参考文献：
  名称：

  Antiplasmodial anthraquinones and hemisynthetic derivatives from the leaves of Tectona grandis (Verbenaceae)

  摘要：

  Chemical investigation of the methanol extract of the leaves of Tectona grandis led to the isolation of one new anthraquinone derivative, grandiquinone A (3-acetoxy-8-hydroxy-2-methylanthraquinone) (1), along with nine known compounds: 5,8-dihydroxy-2-methylanthraquinone (2), hydroxysesamone (3), 3-hydroxy-2-methylanthraquinone (4), quinizarine (5), betulinic acid (6), ursolic acid (7), tectograndone (8), corosolic acid (9) and sitosterol 3-O-b-D-glucopyranoside (10). Compounds 2 and 3 were isolated for the first time from the leaves of this plant, while 5 has never been reported from the genus Tectona. Hydroxysesamone (3) and tectograndone (8) were subjected to cyclisation and acetylation reactions to afford two hemisynthetic derivatives, 6,9-dihydroxy-2,2-(dimethyldihydropyrano)-3,4-dihydro-2Hbenzo[g] chromene-5,10-dione (11) and acetyltectograndone (12) respectively, which are reported here for the first time. The ethyl acetate-soluble portion, some of the isolated compounds and hemisynthetic derivatives were evaluated for their antiplasmodial activity against the multidrug-resistant Dd2 strain of Plasmodium falciparum. Compound 3 showed a prominent activity, while 2, 8, 9, 11 and 12 showed significant in vitro anti-malarial activity. Compound 1 was weakly active in this test. The structures of the compounds were elucidated by spectroscopic methods and comparison of the data with the literature. (C) 2014 Phytochemical Society of Europe. Published by Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.phytol.2014.01.010

文献信息

• Antiplasmodial anthraquinones and hemisynthetic derivatives from the leaves of Tectona grandis (Verbenaceae)
  作者：Theodora K. Kopa、Alembert T. Tchinda、Michel F. Tala、Denis Zofou、Ransom Jumbam、Hippolyte K. Wabo、Vincent P.K. Titanji、Michel Frédérich、Ning-Hua Tan、Pierre Tane

  DOI：10.1016/j.phytol.2014.01.010

  日期：2014.5

  Chemical investigation of the methanol extract of the leaves of Tectona grandis led to the isolation of one new anthraquinone derivative, grandiquinone A (3-acetoxy-8-hydroxy-2-methylanthraquinone) (1), along with nine known compounds: 5,8-dihydroxy-2-methylanthraquinone (2), hydroxysesamone (3), 3-hydroxy-2-methylanthraquinone (4), quinizarine (5), betulinic acid (6), ursolic acid (7), tectograndone (8), corosolic acid (9) and sitosterol 3-O-b-D-glucopyranoside (10). Compounds 2 and 3 were isolated for the first time from the leaves of this plant, while 5 has never been reported from the genus Tectona. Hydroxysesamone (3) and tectograndone (8) were subjected to cyclisation and acetylation reactions to afford two hemisynthetic derivatives, 6,9-dihydroxy-2,2-(dimethyldihydropyrano)-3,4-dihydro-2Hbenzo[g] chromene-5,10-dione (11) and acetyltectograndone (12) respectively, which are reported here for the first time. The ethyl acetate-soluble portion, some of the isolated compounds and hemisynthetic derivatives were evaluated for their antiplasmodial activity against the multidrug-resistant Dd2 strain of Plasmodium falciparum. Compound 3 showed a prominent activity, while 2, 8, 9, 11 and 12 showed significant in vitro anti-malarial activity. Compound 1 was weakly active in this test. The structures of the compounds were elucidated by spectroscopic methods and comparison of the data with the literature. (C) 2014 Phytochemical Society of Europe. Published by Elsevier B. V. All rights reserved.