guttiferone A

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: guttiferone A
• 化学式: C₃₈H₅₀O₆
• 分子量: 602.811
• InChiKey: UPSZSDCJPYYIEO-GHCWVHGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.06
• 重原子数：
  44.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  111.9
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  guttiferone A 在 culture biomass of Rhodotorula buffonii 作用下， 以 aq. phosphate buffer 为溶剂， 反应 168.0h， 以48%的产率得到3,16-oxy-guttiferone A
  参考文献：
  名称：

  Yeast-Mediated Xanthone Synthesis through Oxidative Intramolecular Cyclization

  摘要：

  Benzoylphloroglucinol derivatives are natural products showing diverse biological activities that could be modulated by structural modifications. For this purpose, we studied the biotransformation of guttiferone A and of maclurin using a combinatorial approach for screening active microorganism strains. We found a novel and unexpected yeast-catalyzed oxidation that has selectively given a new oxy-guttiferone A and norathyriol.

  DOI：

  10.1021/ol302283p

文献信息

• Semisynthesis and antimicrobial activity of novel guttiferone-A derivatives
  作者：Kris S.T. Dias、Jaqueline P. Januário、Jéssica Lopes D’ Dego、Amanda L.T. Dias、Marcelo H. dos Santos、Ihosvany Camps、Luiz Felipe L. Coelho、Claudio Viegas

  DOI：10.1016/j.bmc.2012.02.023

  日期：2012.4

  Six derivatives of guttiferone-A (LFQM-79, 80, 81, 82, 113 and 114) were synthesized and evaluated for their antimicrobial activity against the opportunistic or pathogenic fungi Candida albicans (ATCC 09548), Candida glabrata (ATCC 90030), Candida krusei (ATCC 6258), Candida parapsilosis (ATCC 69548), Candida tropicalis (ATCC 750), Cryptococcus neoformans (ATCC 90012), Trichophyton tonsurans, Microsporum

  合成了六种古蒂胶酮A衍生物（LFQM-79、80、81、82、113和114）并评估了其对机会性或致病性真菌白色念珠菌（ATCC 09548），光滑念珠菌（ATCC 90030），念珠菌的抗菌活性克鲁斯（ATCC 6258），副念珠菌（ATCC 69548），热带念珠菌（ATCC 750），新隐球菌（ATCC 90012），扁毛癣菌，小孢子石膏以及针对机会性和致病性革兰氏阳性细菌金黄色葡萄球菌（ATCC 6）表皮葡萄球菌（ATCC 12228），蜡状芽孢杆菌（ATCC 11778）和革兰氏阴性大肠杆菌（ATCC 25922），铜绿假单胞菌（ATCC 9027），鼠伤寒沙门氏菌（ATCC 14028），变形杆菌（ATCC 25933）。将衍生物的抗微生物活性与Guttiferone-A进行了比较，结果显示它们比原始分子更有效，有时甚至比治疗药物中建立的标准药物强。目前的研究表明，Guttif
• Biotransformation of guttiferones, <i>Symphonia globulifera</i> metabolites, by <i>Bipolaris cactivora</i>, an endophytic fungus isolated from its leaves
  作者：Pauline Menelle、Jérôme Quintin、Kevin Cottet、Yann Fromentin、Joëlle Dupont、Marie-Christine Lallemand、Didier Buisson

  DOI：10.1039/d0ob02443k

  日期：——

  Biotransformations by endophytes of host-plant metabolites allow to produce molecular diversity and obtain molecules that are little present in the plant.

  内生菌对寄主植物代谢物的生物转化能够产生分子多样性，获得植物中少量存在的分子。
• Progress on PPAPs cyclization: Guttiferone A as a case study
  作者：Pauline Menelle、Kévin Cottet、Yann Fromentin、Thomas Gaslonde、François-Hugues Porée、Didier Buisson、Marie-Christine Lallemand

  DOI：10.1016/j.tetlet.2017.11.041

  日期：2017.12

  Guttiferone A and cyclized analogs are naturally occurring polycyclic polyprenylated acyl phloroglucinols possessing antiparasitic activities. Naturally occurring xanthones possess increased activity, but are either rare or difficult to synthesize. In this paper, three optimized methodologies to access natural, hydroxylated and non-natural xanthonic skeletons from guttiferone A are described. These

  Guttiferone A和环化类似物是具有抗寄生虫活性的天然存在的多环多亚丙基化酰基间苯三酚。天然存在的氧杂蒽酮具有增强的活性，但是很少或难以合成。在本文中，描述了从guttiferone A访问天然，羟基化和非天然黄嘌呤骨架的三种优化方法。这些化合物将用作进一步SAR研究的起始材料。
• Yeast-Mediated Xanthone Synthesis through Oxidative Intramolecular Cyclization
  作者：Yann Fromentin、Philippe Grellier、Jean Duplex Wansi、Marie-Christine Lallemand、Didier Buisson

  DOI：10.1021/ol302283p

  日期：2012.10.5

  Benzoylphloroglucinol derivatives are natural products showing diverse biological activities that could be modulated by structural modifications. For this purpose, we studied the biotransformation of guttiferone A and of maclurin using a combinatorial approach for screening active microorganism strains. We found a novel and unexpected yeast-catalyzed oxidation that has selectively given a new oxy-guttiferone A and norathyriol.