8-hydroxyhyperforin 8,1-hemiacetal | 59014-02-7

• 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: 8-hydroxyhyperforin 8,1-hemiacetal
• 英文别名: 3-hydroxyhyperforin-3,9-hemiketal；Hydroxyhyperforin；(1R,3R,4R,5S,7R,8S)-8-hydroxy-4-methyl-1,5,7-tris(3-methylbut-2-enyl)-4-(4-methylpent-3-enyl)-3-(2-methylpropanoyl)-9-oxatricyclo[5.2.1.03,8]decane-2,10-dione
• CAS: 59014-02-7
• 化学式: C₃₅H₅₂O₅
• 分子量: 552.795
• InChiKey: IFUPNXPBDBNEAO-GAONCQJMSA-N

物化性质

• 沸点：
  624.2±55.0 °C(Predicted)
• 密度：
  1.060±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  8-hydroxyhyperforin 8,1-hemiacetal 在 哌啶 、 水 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以40%的产率得到hyphenrone A
  参考文献：
  名称：

  Polycyclic Polyprenylated Acylphloroglucinol Congeners Possessing Diverse Structures from Hypericum henryi

  摘要：

  Polycyclic polyprenylated acylphloroglucinols (PPAPs) are a class of hybrid natural products sharing the mevalonate/methylerythritol phosphate and polyketide biosynthetic pathways and showing considerable structural and bioactive diversity. In a systematic phytochemical investigation of Hypericum henryi, 40 PPAP-type derivatives, including the new compounds hyphenrones G-Q, were obtained. These compounds represent 12 different structural types, including four unusual skeletons exemplified by 5, 8, 10, and 17. The 12 different core structures found are explicable in terms of their biosynthetic origin. The structure of a known PPAP, perforatumone, was revised to hyphenrone A (5) by NMR spectroscopic and biomimetic synthesis methods. Several compounds exhibited inhibitory activities against acetylcholinesterase and human tumor cell lines. This study deals with the structural diversity, function, and biogenesis of natural PPAPs.

  DOI：

  10.1021/acs.jnatprod.5b00057
• 作为产物：
  描述：

  hyperforin dicyclohexylammonium salt 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以100%的产率得到8-hydroxyhyperforin 8,1-hemiacetal
  参考文献：
  名称：

  Hyperforin类似物的合成和生物学评估。第一部分：烯醇化的环己二酮部分的改性。

  摘要：

  通过酰化，烷基化和氧化修饰圣约翰草的酰基间苯三酚成分hyperforin（1）对抑制5-羟色胺的突触体积聚产生不利影响，在此体外测试中显示存在确定的构效关系并突出了烯醇化的环己二酮部分对神经递质再摄取活性的作用。

  DOI：

  10.1021/np0105681

文献信息

• Oxidative Fragmentation of the Bridgedβ-Triketone Core of Hyperforin
  作者：Luisella Verotta、Erminio Lovaglio、Olov Sterner、Giovanni Appendino、Ezio Bombardelli

  DOI：10.1002/ejoc.200300568

  日期：2004.3

  The beta-triketone core of the antidepressant phloroglucinol hyperforin (1) undergoes a series of peroxide-induced oxidative rearrangements leading to compound 5, which is formed by opening of ring A, and compound 6, which is formed by removal of the C-1 carbonyl bridge. A mechanistic rationale for this process is proposed. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).

  抗抑郁药间苯三酚 hyperforin (1) 的 β-三酮核心经历了一系列过氧化物诱导的氧化重排，导致通过打开环 A 形成化合物 5 和通过去除 C-1 形成的化合物 6羰基桥。提出了该过程的机械原理。((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)。
• Modulation of Chemoselectivity by Protein Additives. Remarkable Effects in the Oxidation of Hyperforin
  作者：Luisella Verotta、Erminio Lovaglio、Olov Sterner、Giovanni Appendino、Ezio Bombardelli

  DOI：10.1021/jo048857s

  日期：2004.11.1

  Protein additives have a dramatic effect on the H2O2 oxidation of hyperforin, either protecting the enolized phloroglucinol core from oxidation (human albumin) or promoting (HRP and ovalbumin) reaction pathways derived from the intermediacy of the enollactone 4, a minor component of the oxidation mixture in the absence of protein additives. To rationalize the exquisite specificity of several steps

  蛋白质添加剂对Hyperforin的H 2 O 2氧化具有显著作用，可以保护烯醇化的间苯三酚核心免受氧化（人白蛋白）或促进（HRP和卵清蛋白）中间烯醇内酯4的中间成分衍生的反应途径（HRP和卵清蛋白）。在没有蛋白质添加剂的情况下氧化混合物。为了合理化几个步骤的精巧特异性及其机理，提出了有机催化作用。蛋白质添加剂的使用可实现烯醇内酯6的简单直接制备，这是一种有趣的用于生物活性诱导和/或调节的多功能支架。
• Synthesis and Biological Evaluation of Hyperforin Analogues. Part I. Modification of the Enolized Cyclohexanedione Moiety
  作者：Luisella Verotta、Giovanni Appendino、Emanuela Belloro、Federica Bianchi、Olov Sterner、Marco Lovati、Ezio Bombardelli

  DOI：10.1021/np0105681

  日期：2002.4.1

  Modification of the St. John's wort acylphloroglucinol constituent, hyperforin (1), by acylation, alkylation, and oxidation resulted in detrimental effects on the inhibition of the synaptosomal accumulation of serotonin, showing the existence of definite structure-activity relationships in this in vitro test system and highlighting the role of the enolized cyclohexanedione moiety for activity on neurotransmitter

  通过酰化，烷基化和氧化修饰圣约翰草的酰基间苯三酚成分hyperforin（1）对抑制5-羟色胺的突触体积聚产生不利影响，在此体外测试中显示存在确定的构效关系并突出了烯醇化的环己二酮部分对神经递质再摄取活性的作用。
• Polycyclic Polyprenylated Acylphloroglucinol Congeners Possessing Diverse Structures from <i>Hypericum henryi</i>
  作者：Xing-Wei Yang、Ming-Ming Li、Xia Liu、Daneel Ferreira、Yuanqing Ding、Jing-Jing Zhang、Yang Liao、Hong-Bo Qin、Gang Xu

  DOI：10.1021/acs.jnatprod.5b00057

  日期：2015.4.24

  Polycyclic polyprenylated acylphloroglucinols (PPAPs) are a class of hybrid natural products sharing the mevalonate/methylerythritol phosphate and polyketide biosynthetic pathways and showing considerable structural and bioactive diversity. In a systematic phytochemical investigation of Hypericum henryi, 40 PPAP-type derivatives, including the new compounds hyphenrones G-Q, were obtained. These compounds represent 12 different structural types, including four unusual skeletons exemplified by 5, 8, 10, and 17. The 12 different core structures found are explicable in terms of their biosynthetic origin. The structure of a known PPAP, perforatumone, was revised to hyphenrone A (5) by NMR spectroscopic and biomimetic synthesis methods. Several compounds exhibited inhibitory activities against acetylcholinesterase and human tumor cell lines. This study deals with the structural diversity, function, and biogenesis of natural PPAPs.