alkannin isovalerate

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: alkannin isovalerate
• 英文别名: Isovaleryl alkannin；[(1S)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] 3-methylbutanoate
• 化学式: C₂₁H₂₄O₆
• 分子量: 372.418
• InChiKey: UTOUNDHZJFIVPK-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  异戊酸 、 紫草素 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 alkannin isovalerate
  参考文献：
  名称：

  Antimicrobial Activities of Naphthazarins from Arnebia euchroma

  摘要：

  Bioassay-directed fractionation of extract of Arnebia euchroma led to the isolation of alkannin (1), shikonin (2), and their derivatives (3-8) as the active principles against methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant enterococci (VRE). The stereochemistry of alpha-methylbutyryl alkannin (8) is revealed for the first time, and the antimicrobial activity of 8 was compared with its corresponding diastereomer (9). The derivatives 3-9 showed stronger anti-MRSA activity [minimum inhibitory concentrations (MICs) ranged from 1.56 to 3.13 mug/mL] than alkannin or shikonin (MIC = 6.25 mug/mL). Anti-MRSA activity of derivatives was bactericidal with minimum bactericidal concentration (MBC)/ MIC less than or equal to 2. In a time-kill assay, the bactericidal activity against MRSA was achieved as rapidly as 2 h. The derivatives 3-9 were also active against vancomycin-resistant Enterococcus faecium (F935) and vancomycin-resistant Enterococcus faecalis (CKU-17) with MICs similar to those with MRSA. Aromatic ester derivatives were also synthesized for antimicrobial activity comparison. None of these compounds were active against Gram-negative bacteria tested. Their cytotoxicity was also evaluated on selected cancer cell lines, and they expressed their activity in the range 0.6-5.4 mug/mL (CD50). Our results indicate that the ester derivatives of alkannin are potential candidates of anti-MRSA and anti-VRE agents with antitumor activity.

  DOI：

  10.1021/np010599w

文献信息

• [EN] PATCH<br/>[FR] PATCH<br/>[JA] 貼付剤
  申请人：MEDICAL FRONT CO LTD

  公开号：WO2020162629A1

  公开（公告）日：2020-08-13

  【課題】粘着剤層から皮膚へシコニン類が適度に放出され、皮膚から剥脱しにくく、剥がすときに糊残りを生じさせにくい貼付剤を提供する。 【課題を解決するための手段】支持体と粘着剤層を備え、粘着剤層は樹脂組成物と液状組成物を含んで成り樹脂組成物の含有量が２５質量％以上１００質量％未満であり、液状組成物はシコニン類とノニオン界面活性剤を含有し、アクリル系共重合体は、（メタ）アクリル酸アルキルエステル、分子内にヒドロキシ基を有しない（メタ）アクリル酸アルコキシアルキルエステル、及び飽和脂肪酸ビニルエステルから選ばれたモノマーに由来する第１構成単位と、（メタ）アクリル酸ヒドロキシアルキルエステル、及びヒドロキシアルキル（メタ）アクリルアミドから選ばれたモノマーに由来する第２構成単位と、で構成されたアクリル系共重合体が、イソシアネート系架橋剤で架橋された網目構造を有する貼付剤である。
• Antimicrobial Activities of Naphthazarins from <i>Arnebia </i><i>e</i><i>uchroma</i>
  作者：Chien-Chang Shen、Wan-Jr Syu、Shyh-Yuan Li、Chia-Hung Lin、Gum-Hee Lee、Chang-Ming Sun

  DOI：10.1021/np010599w

  日期：2002.12.1

  Bioassay-directed fractionation of extract of Arnebia euchroma led to the isolation of alkannin (1), shikonin (2), and their derivatives (3-8) as the active principles against methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant enterococci (VRE). The stereochemistry of alpha-methylbutyryl alkannin (8) is revealed for the first time, and the antimicrobial activity of 8 was compared with its corresponding diastereomer (9). The derivatives 3-9 showed stronger anti-MRSA activity [minimum inhibitory concentrations (MICs) ranged from 1.56 to 3.13 mug/mL] than alkannin or shikonin (MIC = 6.25 mug/mL). Anti-MRSA activity of derivatives was bactericidal with minimum bactericidal concentration (MBC)/ MIC less than or equal to 2. In a time-kill assay, the bactericidal activity against MRSA was achieved as rapidly as 2 h. The derivatives 3-9 were also active against vancomycin-resistant Enterococcus faecium (F935) and vancomycin-resistant Enterococcus faecalis (CKU-17) with MICs similar to those with MRSA. Aromatic ester derivatives were also synthesized for antimicrobial activity comparison. None of these compounds were active against Gram-negative bacteria tested. Their cytotoxicity was also evaluated on selected cancer cell lines, and they expressed their activity in the range 0.6-5.4 mug/mL (CD50). Our results indicate that the ester derivatives of alkannin are potential candidates of anti-MRSA and anti-VRE agents with antitumor activity.