11-O-acetyl-alkannin

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 11-O-acetyl-alkannin
• 英文别名: alkannin-1'-acetate；alkannin acetate；acetyl alkannin；acetylalkannin；(S)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-enyl acetate；[(1S)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] acetate
• 化学式: C₁₈H₁₈O₆
• 分子量: 330.337
• InChiKey: WNFXUXZJJKTDOZ-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  11-O-acetyl-alkannin 生成 紫草素
  参考文献：
  名称：

  Shikonin derivatives. Part VI. Chemical investigations of Arnebia decumbens.

  摘要：

  DOI：

  10.1271/bbb1961.50.1651
• 作为产物：
  描述：

  紫草素 、 溶剂黄146 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 11-O-acetyl-alkannin
  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

• NAPHTHALENEDIONE COMPOUNDS
  申请人：Sunten Phytotech Co., Ltd.

  公开号：EP2004174A2

  公开（公告）日：2008-12-24
• Naphthalenedione Compounds
  申请人：Chien Du-Shieng

  公开号：US20070238782A1

  公开（公告）日：2007-10-11

  This invention relates to compositions containing a compound of formula (I) shown below: Each variable is defined in the specification. Also disclosed are methods of using these compositions to treat acne, psoriasis, and infective skin ulcer.
• COMPOSITIONS OF LITHOSPERMUM ERYTHRORHIZON (GROMWELL ROOT) AND METHODS OF MAKING AND USING THE COMPOSITIONS
  申请人：Access Business Group International LLC

  公开号：US20180110722A1

  公开（公告）日：2018-04-26

  Compositions for suppressing sebum production in skin (e.g., seborrheic skin), and minimizing glycation in skin (e.g., mature skin) with enhanced UV absorptive properties are described. In particular, the present invention relates to a composition containing a skin benefit agent that includes Lithospermum erythrorhizon . Also, methods of suppressing sebum production in skin (e.g., seborrheic skin) and minimizing glycation in skin (e.g., mature skin) by applying a composition to the skin, wherein the composition comprises an effective amount of a derivative of Lithospermum erythrorhizon are also described.
• US7622506B2
  申请人：——

  公开号：US7622506B2

  公开（公告）日：2009-11-24
• [EN] NAPHTHALENEDIONE COMPOUNDS<br/>[FR] COMPOSÉS DE NAPHTALÈNEDIONE
  申请人：SUNTEN PHYTOTECH CO LTD

  公开号：WO2007118227A2

  公开（公告）日：2007-10-18

  [EN] This invention relates to compositions containing a compound of formula (I). Each variable is defined in the specification. Also disclosed are methods of using these compositions to treat acne, psoriasis, and infective skin ulcer.
  [FR] L'invention concerne des compositions contenant un composé représenté par la formule (I). Chaque variable est définie dans le descriptif. L'invention concerne aussi des procédés d'utilisation de ces compositions pour traiter l'acné, le psoriasis et un ulcère cutané infectieux.