5-prenyldihydrovariecolorin F

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-prenyldihydrovariecolorin F
• 英文别名: (3R,6R)-3-((7-((S)-3-chloro-2-hydroxy-3-methylbutyl)-5-(3-methylbut-2-enyl)-2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl)methyl)-6-methylpiperazine-2,5-dione；5-prenyl-dihydrovariecolorin F；(3R,6R)-3-[[7-[(2S)-3-chloro-2-hydroxy-3-methylbutyl]-2-(2-methylbut-3-en-2-yl)-5-(3-methylbut-2-enyl)-1H-indol-3-yl]methyl]-6-methylpiperazine-2,5-dione
• 化学式: C₂₉H₄₀ClN₃O₃
• 分子量: 514.108
• InChiKey: KORJXHWEJZNGQF-ZQMYSKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  94.2
• 氢给体数：
  4
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-prenyldihydrovariecolorin F 在 盐酸 作用下， 以 水 为溶剂， 反应 2.0h， 生成 D-丙氨酸
  参考文献：
  名称：

  Chemical constituents isolated from Antarctic marine-derived Aspergillus sp. SF-5976 and their anti-inflammatory effects in LPS-stimulated RAW 264.7 and BV2 cells

  摘要：

  Three new benzaldehydes (1-3) and two new dioxopiperazine alkaloids (4 and 5), along with 23 known constituents, were isolated from Antarctic marine-derived Aspergillus sp. SF-5976. Their structures were determined by spectroscopic and chemical methods. Among them, 20 compounds showed inhibitory effects toward lipopolysaccharide (LPS)-induced, nitric oxide (NO) production in RAW 264.7 macrophages with IC50 values of 7.3-77.4 mu M, while 22 compounds did in BV2 microglia with those of 4.6-72.3 mu M. Furthermore, the effects of the newly isolated compounds on LPS-stimulated inducible NO synthase (iNOS) expression were investigated, and 1-3, and 5 inhibited iNOS in RAW 264.7 cells, while 1-5 did in BV2 cells. Also, 1-3 and 5 inhibited LPS-induced prostaglandin E-2 production with IC50 values of 9.1 -66.8 mu M in RAW 264.7 macrophages by suppressing cyclooxygenase-2 (COX-2), while in BV2 microglia, 1-5 showed activities with those of 2.8-49.4 mu M. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2017.05.060

文献信息

• 신규 화합물 및 이를 유효성분으로 함유하는 염증질환 예방 또는 치료용 약학 조성물
  申请人：Korea Institute of Ocean Science ＆ Technology 한국해양과학기술원(120120344616) Corp. No ▼ 131471-0018173BRN ▼134-82-01458

  公开号：KR101742239B1

  公开（公告）日：2017-05-31

  본 발명은 신규 화합물, 및 이를 유효성분으로 함유하는 염증질환 예방 또는 치료용 조성물에 관한 것으로, 보다 상세하게는 해양 진균 Aspergillus sp. SF-5976에서 분리된 항염증 효과를 갖는 아스페라닌 A, 아스페라닌 B, 아스페라닌 C, 5-프레닐-디히드로바리에콜로린 F 및 5-프레닐-디히드로우브루마진 A, 및 이를 함유하는 염증질환 예방 또는 치료용 조성물에 관한 것이다. 본 발명에 따른 아스페라닌 A, 아스페라닌 B, 아스페라닌 C, 5-프레닐-디히드로바리에콜로린 F 또는 5-프레닐-디히드로우브루마진 A를 유효성분으로 함유하는 염증성 질환 예방 또는 치료용 조성물은, 염증반응과 관련하여 RAW264.7 대식세포와 BV2 미세아교세포에서 전염증성 사이토카인 및 매개체 생성을 억제하므로, 염증성 질환의 예방 또는 치료용도로 유용하게 사용될 수 있다.

  这项发明涉及一种新的化合物以及包含其作为有效成分的预防或治疗炎症性疾病的组合物。更详细地说，它涉及具有抗炎作用的Aspergillus sp. SF-5976海洋真菌分离出的Asperalin A、Asperalin B、Asperalin C、5-Phenyl-dihydrovariecolin F和5-Phenyl-dihydroubremagen A，并包含它们的预防或治疗炎症性疾病的组合物。根据本发明，含有Asperalin A、Asperalin B、Asperalin C、5-Phenyl-dihydrovariecolin F或5-Phenyl-dihydroubremagen A作为有效成分的预防或治疗炎症性疾病的组合物，能够抑制RAW264.7巨噬细胞和BV2微型神经胶质细胞中的炎症细胞因子和介质生成与炎症反应相关，因此可用于预防或治疗炎症性疾病。
• KR101742238
  申请人：——

  公开号：——

  公开（公告）日：——
• Chemical constituents isolated from Antarctic marine-derived Aspergillus sp. SF-5976 and their anti-inflammatory effects in LPS-stimulated RAW 264.7 and BV2 cells
  作者：Jaeyoung Kwon、Hyaemin Lee、Wonmin Ko、Dong-Cheol Kim、Kwan-Woo Kim、Hak Cheol Kwon、Yuanqiang Guo、Jae Hak Sohn、Joung Han Yim、Youn-Chul Kim、Hyuncheol Oh、Dongho Lee

  DOI：10.1016/j.tet.2017.05.060

  日期：2017.7

  Three new benzaldehydes (1-3) and two new dioxopiperazine alkaloids (4 and 5), along with 23 known constituents, were isolated from Antarctic marine-derived Aspergillus sp. SF-5976. Their structures were determined by spectroscopic and chemical methods. Among them, 20 compounds showed inhibitory effects toward lipopolysaccharide (LPS)-induced, nitric oxide (NO) production in RAW 264.7 macrophages with IC50 values of 7.3-77.4 mu M, while 22 compounds did in BV2 microglia with those of 4.6-72.3 mu M. Furthermore, the effects of the newly isolated compounds on LPS-stimulated inducible NO synthase (iNOS) expression were investigated, and 1-3, and 5 inhibited iNOS in RAW 264.7 cells, while 1-5 did in BV2 cells. Also, 1-3 and 5 inhibited LPS-induced prostaglandin E-2 production with IC50 values of 9.1 -66.8 mu M in RAW 264.7 macrophages by suppressing cyclooxygenase-2 (COX-2), while in BV2 microglia, 1-5 showed activities with those of 2.8-49.4 mu M. (C) 2017 Elsevier Ltd. All rights reserved.