萘-1,3,8-三醇 | 7124-49-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 萘-1,3,8-三醇
• 英文名称: 1,3,8-Trihydroxynaphthalene
• 英文别名: naphthalene-1,3,8-triol；1,3,8-Trihydroxy-naphthalin；1,3,8-Trihydroxynaphthalin；Naphthalin-1,3,8-triol
• CAS: 7124-49-4
• 化学式: C₁₀H₈O₃
• 分子量: 176.172
• InChiKey: USWUTUCXLQBQCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  萘-1,3,8-三醇 生成 2-羟基胡桃醌
  参考文献：
  名称：

  ASLANOV, X. A.;NAVREZOVA, N. SH.;MUFTAXOV, R. A.;NIGAJ, K. G.;STEPANCHENK+, UZNIINTI, 356-UZ

  摘要：

  DOI：
• 作为产物：
  描述：

  3,5-二苄氧基苯甲醇 在 palladium on activated charcoal barium dihydroxide 、 sodium hydroxide 、 高氯酸 、 苄基三乙基氯化铵 、 氢气 、 sodium methylate 、 溶剂黄146 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 24.74h， 生成 萘-1,3,8-三醇
  参考文献：
  名称：

  仿生还原四羟基萘（黑色素生物合成的关键中间体）的机理研究。

  摘要：

  1,3,6,8-四羟基萘（T4HN）是一种芳香族聚酮化合物，是真菌黑色素的一般前体。黑色素的生物合成涉及T4HN的两个连续脱氧，包括酚碳的还原和脱水。在用硼氢化钠的仿生还原中研究了首次生成双降戟的还原。还原需要强碱性条件，导致T4HN互变异构化成反应性物质，其结构已通过NMR光谱得以阐明。

  DOI：

  10.1248/cpb.49.192

文献信息

• Pentaketide metabolites of verticillium dahliae
  作者：A.A. Bell、R.D. Stipanovic、J.E. Puhalla

  DOI：10.1016/0040-4020(76)85009-0

  日期：1976.1

  of the brown brm-1 mutant of Verticillium dahliae Kleb. restored normal black pigment (melanin) synthesis when added to plate cultures of 10 albino mutants. The active metabolite was isolated and identified as (+)-scytalone [3,4-dihydro-3,6,8-trihydroxy-1(2H)naphthalenone] by physical characteristics (m.p., UV, IR, NMR, MS) and chemical conversions. Related metabolites, flaviolin and cis-hydroxyscytalone

  黄萎病菌的棕色brm -1突变体的培养滤液。当添加到10个白化突变体的平板培养物中时，恢复了正常的黑色素（黑色素）合成。通过物理特性（mp，UV，IR，NMR，MS）和化学性质分离出活性代谢物，并将其鉴定为（+）-辛酮[3,4-dihydro-3,6,8-trihydroxy-1（2H）萘]。转换。还分离并鉴定了相关的代谢物黄素蛋白和顺式羟基cytalone 。黄病毒素及其衍生物有助于brm -1突变体的红棕色。赛蜜可能是真菌中黑色素生物合成的一般中间体。
• FUNGI TRANSFORMANT FOR MELANIN PRODUCTION AND USES THEREOF
  申请人：Tzean Min-Nan

  公开号：US20110158970A1

  公开（公告）日：2011-06-30

  The present invention cloned melanin biosynthesis genes encoding polyketide synthase (PKS), scytalone dehydratase (SCD) and 1.3.8-trihydroxynaphthalene reductase (THN) from the dematiaceous Alternasia alternate into plasmid pCAMBIA1300, followed by transformation of the plasmid into Matarhizium anisopliae via Agrobacterium tumefaciens -mediated transformation. The transformant was able to express the abovementioned genes and synthesize melanin, which then showed enhanced UV tolerance. The transcription and expression of these melanin genes were confirmed in several pathways. The tolerances toward UV radiation, drought and high temperature were increased significantly in these transformants. In addition, the host insects were more susceptible to these transformants under UV radiation.

  本发明将黑色素合成基因聚酮合酶（PKS）、赤霉烷醇脱水酶（SCD）和1.3.8-三羟基萘醌还原酶（THN）从黑色素菌Alternaria alternate中克隆到质粒pCAMBIA1300中，然后通过农杆菌介导转化将质粒转化到拟革菌Matarhizium anisopliae中。转化体能够表达上述基因并合成黑色素，进而表现出增强的紫外线耐受性。这些黑色素基因的转录和表达在多个途径中得到了确认。这些转化体对紫外线辐射、干旱和高温的耐受性显著提高。此外，在紫外线辐射下，寄主昆虫更容易受到这些转化体的影响。
• Fungi transformant for melanin production and uses thereof
  申请人：Tseng Min-Nan

  公开号：US08518393B2

  公开（公告）日：2013-08-27

  The present invention cloned melanin biosynthesis genes encoding polyketide synthase (PKS), scytalone dehydratase (SCD) and 1.3.8-trihydroxynaphthalene reductase (THN) from the dematiaceous Alternasia alternate into plasmid pCAMBIA1300, followed by transformation of the plasmid into Matarhizium anisopliae via Agrobacterium tumefaciens-mediated transformation. The transformant was able to express the abovementioned genes and synthesize melanin, which then showed enhanced UV tolerance. The transcription and expression of these melanin genes were confirmed in several pathways. The tolerances toward UV radiation, drought and high temperature were increased significantly in these transformants. In addition, the host insects were more susceptible to these transformants under UV radiation.

  本发明从黑色素生物合成中克隆了聚酮合酶（PKS）、赤藓烯脱水酶（SCD）和1.3.8-三羟基萘还原酶（THN）编码基因，并将其导入质粒pCAMBIA1300中，随后通过农杆菌介导转化将质粒转化到拟南芥茵蝇霉中。转化体能够表达上述基因并合成黑色素，从而表现出增强的紫外线耐受性。这些黑色素基因的转录和表达在多个途径中得到了确认。这些转化体对紫外线辐射、干旱和高温的耐受性显著提高。此外，在紫外线辐射下，寄主昆虫更容易受到这些转化体的影响。
• Post-Aromatic Deoxygenation in Polyketide Biosynthesis: Reduction of Aromatic Rings in the Biosyntheses of Fungal Melanin and Anthraquinone.
  作者：Koji ICHINOSE、Junko KIYONO、Yutaka EBIZUKA、Ushio SANKAWA

  DOI：10.1248/cpb.41.2015

  日期：——

  Two enzyme reactions involved in the post-aromatic deoxygenation process of fungal melanin and pigments were studied from the viewpoint of enzymic reduction of aromatic rings. Hydroxynaphthalene reductase that catalyzes reduction of the aromatic rings of 1,3,6,8-tetrahydroxynaphthalene and 1,3,8-trihydroxynapthalene was partially purified from Phialophora lagerbergii and characterized. Emodin deoxygenase

  从芳香环酶促还原的角度出发，研究了真菌黑色素和色素在芳香族脱氧后的两种酶反应。从紫菜（Phialophora lagerbergii）中部分纯化并催化了催化1,3,6,8-四羟基萘和1,3,8-三羟基萘的芳环还原的羟基萘还原酶。发现用大黄素的大黄素的大黄素脱氧酶催化大黄素的脱氧以提供chsophophanol，用DEAE-纤维素柱分离成两个蛋白质级分。关于大黄素脱氧酶活性，这两个蛋白质部分协同作用。
• Enzymatic Characterization of Scytalone Dehydratase Val75Met Variant Found in Melanin Biosynthesis Dehydratase Inhibitor (MBI-D) Resistant Strains of the Rice Blast Fungus
  作者：Naoki YAMADA、Takayuki MOTOYAMA、Masayoshi NAKASAKO、Shinzo KAGABU、Toshiaki KUDO、Isamu YAMAGUCHI

  DOI：10.1271/bbb.68.615

  日期：2004.1

  2-dichloro-N-[(R)-1-(4-chlorophenyl)ethyl]-1-ethyl-3-methylcyclopropanecarboxamide) is a potent chemical against the rice blast fungus, Pyricularia oryzae. In 2001, isolates of the fungus with reduced sensitivity to this fungicide appeared in Saga Prefecture of Japan and were regarded as a potential threat to rice protection by carpropamid. The cause of the resistance has been identified genetically as a point mutation

  杀虫ami（（1RS，3SR）-2,2-二氯-N-[（R）-1-（4-氯苯基）乙基] -1-乙基-3-甲基环丙烷甲酰胺）是一种有效的化学物质，可抵御稻瘟病真菌Pyricularia水稻 2001年，对这种杀真菌剂的敏感性降低的真菌分离株出现在日本佐贺县，被认为是对杀虫剂保护稻米的潜在威胁。从基因上已经确定了抗药性的原因是点突变，该突变导致断枝冬酰胺脱水酶中的Val75Met发生变化，这是杀菌剂的主要靶标。我们构建了变体酶的过表达系统，并表征了在催化过程中的动力学以及对甲酰胺异构体的抑制作用。变体酶保留了显着水平的酶活性。与野生型相比，丙酰胺对变异酶的抑制作用降低了200倍以上。基于这些结果，在这里我们提出了变异酶在保持正常酶活性方面的抗丙胺的可能机制。