2-Phytyl-1,4-dihydroxynaphthalene

• 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: 2-Phytyl-1,4-dihydroxynaphthalene
• 英文别名: 2-[(E,7R,11R)-3,7,11,15-tetramethylhexadec-2-enyl]naphthalene-1,4-diol
• 化学式: C₃₀H₄₆O₂
• 分子量: 438.7
• InChiKey: AEFNZGGBWOQYID-KQPZCCJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.5
• 重原子数：
  32
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Phytyl-1,4-dihydroxynaphthalene 、 S-腺苷蛋氨酸 生成 氢(+1)阳离子 、 二氢维他命 K1 、 S-(5'-腺苷)-L-高半胱氨酸
  参考文献：
  名称：

  专用的II型NADPH脱氢酶在拟南芥和拟南芥中维生素K1的生物合成中执行倒数第二步。

  摘要：

  拟南芥NAD（P）H脱氢酶C1（NDC1; At5g08740）的突变导致去甲基叶醌的积累，后者是维生素K1的晚期生物合成中间体。基因共表达和系统发育组学分析表明，在整个原核和真核世系中，维生素K生物合成与NDC1同源物之间存在保守的功能关联。编码一种这样的同源物的集胞藻ndbB的缺失导致与在蓝细菌脱甲基萘醌甲基转移酶敲除中观察到的那些缺陷相同的缺陷。纯化的脱甲基萘醌甲基转移酶的化学模型和分析表明，凭借S-腺苷-1-甲硫氨酸的强亲电性质，维生素K脱甲基前体的甲基化反应严格取决于其萘醌环的还原形式。NDC1被证明可以催化这种先决条件的降低，方法是使用NADPH和去甲基叶绿体醌作为底物，黄酮腺嘌呤二核苷酸作为辅因子。NDC1表现出Michaelis-Menten动力学，并被敌萘醌（一种竞争性的萘醌氧化还原酶抑制剂）显着抑制。这些数据表明，去甲基萘醌环的还原代表了维生素K生物合成途径中的一个真实

  DOI：

  10.1105/tpc.15.00103
• 作为产物：
  描述：

  2-((7R:11R)-trans-phytyl)-naphthoquinone-(1.4) 、 氢(+1)阳离子 、 NADPH(4-) 生成 2-Phytyl-1,4-dihydroxynaphthalene 、 NADP⁺
  参考文献：
  名称：

  叶绿体脂滴 II 型 NAD(P)H 醌氧化还原酶对于异戊二烯醌代谢和维生素 K1 积累至关重要。

  摘要：

  脂滴是真核生物中普遍存在的细胞结构，是脂质代谢所必需的。目前对除油体以外的植物脂滴知之甚少。在这里，我们定义了叶绿体脂滴（质体球）在能量和异戊二烯醌代谢中的双重作用。异戊二烯醌--plastoquinone、plastochromanol-8、phylloquinone（维生素K(1)）和生育酚（维生素E）-部分存储在plastoglobules 中。这项工作表明 NAD(P)H 脱氢酶 C1 (NDC1) (At5g08740)，一种 II 型 NAD(P)H 醌氧化还原酶，与质体球结合。NDC1 在体外减少质体醌类似物，并通过减少质体球的质体醌储库影响体内总质体醌库的整体氧化还原状态。最后，

  DOI：

  10.1073/pnas.1104790108

文献信息

• Deficiency in Phylloquinone (Vitamin K1) Methylation Affects Prenyl Quinone Distribution, Photosystem I Abundance, and Anthocyanin Accumulation in the Arabidopsis AtmenG Mutant
  作者：Antje Lohmann、Mark Aurel Schöttler、Claire Bréhélin、Felix Kessler、Ralph Bock、Edgar B. Cahoon、Peter Dörmann

  DOI：10.1074/jbc.m609412200

  日期：2006.12

  Phylloquinone ( vitamin K1) is synthesized in cyanobacteria and in chloroplasts of plants, where it serves as electron carrier of photosystem I. The last step of phylloquinone synthesis in cyanobacteria is the methylation of 2-phytyl-1,4- naphthoquinone by the menG gene product. Here, we report that the uncharacterized Arabidopsis gene At1g23360, which shows sequence similarity to menG, functionally complements the Synechocystis menG mutant. An Arabidopsis mutant, AtmenG, carrying a T-DNA insertion in the gene At1g23360 is devoid of phylloquinone, but contains an increased amount of 2-phytyl-1,4- naphthoquinone. Phylloquinone and 2- phytyl- 1,4- naphthoquinone in thylakoid membranes of wild type and AtmenG, respectively, predominantly localize to photosystem I, whereas excess amounts of prenyl quinones are stored in plastoglobules. Photosystem I reaction centers are decreased in AtmenG plants under high light, as revealed by immunoblot and spectroscopic measurements. Anthocyanin accumulation and chalcone synthase (CHS1) transcription are affected during high light exposure, indicating that alterations in photosynthesis in AtmenG affect gene expression in the nucleus. Photosystem II quantum yield is decreased under high light. Therefore, the loss of phylloquinone methylation affects photosystem I stability or turnover, and the limitation in functional photosystem I complexes results in overreduction of photosystem II under high light.
• Insertional Inactivation of the <i>menG</i> Gene, Encoding 2-Phytyl-1,4-Naphthoquinone Methyltransferase of <i>Synechocystis</i> sp. PCC 6803, Results in the Incorporation of 2-Phytyl-1,4-Naphthoquinone into the A₁ Site and Alteration of the Equilibrium Constant between A₁ and F_X in Photosystem I
  作者：Yumiko Sakuragi、Boris Zybailov、Gaozhong Shen、A. Daniel Jones、Parag R. Chitnis、Art van der Est、Robert Bittl、Stephan Zech、Dietmar Stehlik、John H. Golbeck、Donald A. Bryant

  DOI：10.1021/bi011297w

  日期：2002.1.1

  A gene encoding a methyltransferase (menG) was identified in Syneehocystis sp. PCC 6803 as responsible for transferring the methyl group to 2-phytyl-1,4-naphthoquinone in the biosynthetic pathway of phylloquinone, the secondary electron acceptor in photosystem I (PS I). Mass spectrometric measurements showed that targeted inactivation of the menG gene prevented the methylation step in the synthesis of phylloquinone and led to the accumulation of 2-phytyl-1,4-naphthoquinone in PS I. Growth rates of the wild-type and the menG mutant strains under photoautotrophic and photomixotrophic conditions were virtually identical. The chlorophyll a content of the menG mutant strain was similar to that of wild type when the cells were grown at a light intensity of 50 muE m(-2) s(-1) but was slightly lower when grown at 300 muE m(-2) s(-1). Chlorophyll fluorescence emission measurements at 77 K showed a larger increase in the ratio of PS II to PS I in the menG mutant strain relative to the wild type its the light intensity was elevated from 50 to 300 muE m(-2) s(-1). CW EPR studies at 34 GHz and transient EPR Studies at multiple frequencies showed that the quinone radical in the menG mutant has a similar overall line width as that for the wild type, but consistent with the presence of an aromatic proton at ring position 2, the pattern of hyperfine splittings showed two lines in the low-field region. The spin polarization pattern indicated that 2-phytyl-1,4-naphthoquinone is in the same orientation as phylloquinone, and out-of-phase, spin-echo modulation spectroscopy shows the same P700(+) to Q(-) center-to-center distance as in wild-type PS I. Transient EPR studies indicated that the lifetime for forward electron transfer from Q to F-x is slowed from 290 ns in the wild type to 600 ns in the menG mutant. The redox potential of 2-phytyl-1.4-naphthoquinone is estimated to be 50 to 60 mV more oxidizing than phylloquinone in the A(l) site, which translates to a lowering of the equilibrium constant between Q(-)/Q and F-x /F-x by a factor of ca. 10. The lifetime of the P700(+) [F-A/F-B](-) backreaction decreased from 80 ms in the wild type to 20 ms in the menG mutant strain and is evidence for a thermally activated, uphill electron transfer through the quinone rather than a direct charge recombination between [F-A/F-B](-) and P700(+).
• A Dedicated Type II NADPH Dehydrogenase Performs the Penultimate Step in the Biosynthesis of Vitamin K1 in S<i>ynechocystis</i> and Arabidopsis
  作者：Abdelhak Fatihi、Scott Latimer、Stefan Schmollinger、Anna Block、Patrick H. Dussault、Wim F.J. Vermaas、Sabeeha S. Merchant、Gilles J. Basset

  DOI：10.1105/tpc.15.00103

  日期：2015.7.8

  demethylated precursor of vitamin K is strictly dependent on the reduced form of its naphthoquinone ring. NDC1 was shown to catalyze such a prerequisite reduction by using NADPH and demethylphylloquinone as substrates and flavine adenine dinucleotide as a cofactor. NDC1 displayed Michaelis-Menten kinetics and was markedly inhibited by dicumarol, a competitive inhibitor of naphthoquinone oxidoreductases. These

  拟南芥NAD（P）H脱氢酶C1（NDC1; At5g08740）的突变导致去甲基叶醌的积累，后者是维生素K1的晚期生物合成中间体。基因共表达和系统发育组学分析表明，在整个原核和真核世系中，维生素K生物合成与NDC1同源物之间存在保守的功能关联。编码一种这样的同源物的集胞藻ndbB的缺失导致与在蓝细菌脱甲基萘醌甲基转移酶敲除中观察到的那些缺陷相同的缺陷。纯化的脱甲基萘醌甲基转移酶的化学模型和分析表明，凭借S-腺苷-1-甲硫氨酸的强亲电性质，维生素K脱甲基前体的甲基化反应严格取决于其萘醌环的还原形式。NDC1被证明可以催化这种先决条件的降低，方法是使用NADPH和去甲基叶绿体醌作为底物，黄酮腺嘌呤二核苷酸作为辅因子。NDC1表现出Michaelis-Menten动力学，并被敌萘醌（一种竞争性的萘醌氧化还原酶抑制剂）显着抑制。这些数据表明，去甲基萘醌环的还原代表了维生素K生物合成途径中的一个真实
• Chloroplast lipid droplet type II NAD(P)H quinone oxidoreductase is essential for prenylquinone metabolism and vitamin K ₁ accumulation
  作者：Lucia Eugeni Piller、Céline Besagni、Brigitte Ksas、Dominique Rumeau、Claire Bréhélin、Gaétan Glauser、Felix Kessler、Michel Havaux

  DOI：10.1073/pnas.1104790108

  日期：2011.8.23

  ubiquitous cellular structures in eukaryotes and are required for lipid metabolism. Little is currently known about plant lipid droplets other than oil bodies. Here, we define dual roles for chloroplast lipid droplets (plastoglobules) in energy and prenylquinone metabolism. The prenylquinones--plastoquinone, plastochromanol-8, phylloquinone (vitamin K(1)), and tocopherol (vitamin E)--are partly stored

  脂滴是真核生物中普遍存在的细胞结构，是脂质代谢所必需的。目前对除油体以外的植物脂滴知之甚少。在这里，我们定义了叶绿体脂滴（质体球）在能量和异戊二烯醌代谢中的双重作用。异戊二烯醌--plastoquinone、plastochromanol-8、phylloquinone（维生素K(1)）和生育酚（维生素E）-部分存储在plastoglobules 中。这项工作表明 NAD(P)H 脱氢酶 C1 (NDC1) (At5g08740)，一种 II 型 NAD(P)H 醌氧化还原酶，与质体球结合。NDC1 在体外减少质体醌类似物，并通过减少质体球的质体醌储库影响体内总质体醌库的整体氧化还原状态。最后，