eujavanicol A | 952585-38-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: eujavanicol A
• 英文别名: 1-[(1S,2S,4aR,5S,6R,8R,8aS)-2-[(2R)-butan-2-yl]-5,6-dihydroxy-1,8-dimethyl-4a,5,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]-3-hydroxypropan-1-one
• CAS: 952585-38-5
• 化学式: C₁₉H₃₂O₄
• 分子量: 324.461
• InChiKey: KOPHBZXWJSZGMB-HAWFMJENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  eujavanicol A 在 四氧化锇 作用下， 以 吡啶 、 苯 为溶剂， 生成 Acetic acid (1R,2S,3R,4R,4aS,5R,7R,8S,8aR)-7-acetoxy-4-(3-acetoxy-propionyl)-3-((R)-sec-butyl)-1,8-dihydroxy-4,5-dimethyl-decahydro-naphthalen-2-yl ester
  参考文献：
  名称：

  Trichoharzin, a new polyketide produced by the imperfect fungus Trichoderma harzianum separated from the marine sponge Micale cecilia

  摘要：

  Trichoharzin (1) has been isolated from a culture of the imperfect fungus Trichoderma harzianum, which was separated from the marine sponge Micale cecilia, and the absolute stereostructure elucidated. Trichoharzin (1) is a new polyketide constructed with an alkylated decalin skeleton and esterified with 3-methylglutaconic acid, a rare acyl moiety.

  DOI：

  10.1016/s0040-4039(00)61513-7
• 作为产物：
  描述：

  trichoharzin 在 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 生成 eujavanicol A
  参考文献：
  名称：

  Trichoharzin, a new polyketide produced by the imperfect fungus Trichoderma harzianum separated from the marine sponge Micale cecilia

  摘要：

  Trichoharzin (1) has been isolated from a culture of the imperfect fungus Trichoderma harzianum, which was separated from the marine sponge Micale cecilia, and the absolute stereostructure elucidated. Trichoharzin (1) is a new polyketide constructed with an alkylated decalin skeleton and esterified with 3-methylglutaconic acid, a rare acyl moiety.

  DOI：

  10.1016/s0040-4039(00)61513-7

文献信息

• Tandyukisins E and F, novel cytotoxic decalin derivatives isolated from a marine sponge-derived fungus
  作者：Mayo Suzue、Takashi Kikuchi、Reiko Tanaka、Takeshi Yamada

  DOI：10.1016/j.tetlet.2016.10.004

  日期：2016.11

  have been isolated from a strain of Trichoderma harzianum OUPS-111D-4 originally derived from the marine sponge Halichondria okadai, and their structures have been elucidated on the basis of spectroscopic analyses using 1D and 2D NMR techniques. In addition, their chemical structures were established by chemical transformation. In our continuing search for cytotoxic metabolites from this strain, we isolated

  以前报道过的鞣花素A–D是一种新型十氢萘衍生物，是从最初来源于海洋海绵哈里肯氏梭菌（Halichondria okadai）的哈茨木霉OUPS-111D-4菌株中分离得到的，其结构已根据使用1D和2D进行的光谱分析得到了阐明。 NMR技术。另外，它们的化学结构是通过化学转化建立的。在我们继续寻找该菌株的细胞毒性代谢产物的过程中，我们分离了两个新的十氢萘衍生物，称为鞣花素E（1）和F（2）。它们具有独特的化学结构，其侧链与迄今为止获得的丹参素不同。此外，它们对癌细胞系P388，HL-60和L1210表现出明显的细胞毒性。
• Determination of the Chemical Structures of Tandyukisins B–D, Isolated from a Marine Sponge-Derived Fungus
  作者：Takeshi Yamada、Yoshihide Umebayashi、Maiko Kawashima、Yuma Sugiura、Takashi Kikuchi、Reiko Tanaka

  DOI：10.3390/md13053231

  日期：——

  Tandyukisins B–D (1–3), novel decalin derivatives, have been isolated from a strain of Trichoderma harzianum OUPS-111D-4 originally derived from the marine sponge Halichondria okadai, and their structures have been elucidated on the basis of spectroscopic analyses using 1D and 2D NMR techniques. In addition, their chemical structures were established by chemical transformation. They exhibited weak cytotoxicity, but selective growth inhibition on panel screening using 39 human cancer cell lines.

  从一株原产于海洋海绵 Halichondria okadai 的毛霉 OUPS-111D-4 中分离出了新型蜕皮素衍生物 Tandyukisins B-D（1-3），并利用一维和二维核磁共振技术对其进行了光谱分析，从而阐明了它们的结构。此外，还通过化学转化建立了它们的化学结构。它们的细胞毒性较弱，但在使用 39 种人类癌细胞株进行的小组筛选中表现出选择性生长抑制作用。
• The Polyketides with Antimicrobial Activities from a Mangrove Endophytic Fungus Trichoderma lentiforme ML-P8-2
  作者：Yihao Yin、Qi Tan、Jianying Wu、Tao Chen、Wencong Yang、Zhigang She、Bo Wang

  DOI：10.3390/md21110566

  日期：——

  Five new polyketides, including two chromones (1–2), two phenyl derivatives (4–5), and a tandyukusin derivative (6), along with five known polyketides (3 and 7–10) were isolated from mangrove endophytic fungus Trichoderma lentiforme ML-P8-2. The planar structures of compounds were elucidated via detailed 1D, 2D NMR, and HR-ESI-MS analysis. ECD spectra, optical rotation values calculation, and alkali

  从红树林内生真菌木霉中分离出五种新的聚酮化合物，包括两种色酮 (1-2)、两种苯基衍生物 (4-5) 和一种 tandyukusin 衍生物 (6)，以及五种已知的聚酮化合物（3 和 7-10） ML-P8-2。通过详细的 1D、2D NMR 和 HR-ESI-MS 分析阐明了化合物的平面结构。应用ECD光谱、旋光值计算和碱水解测定新化合物的绝对构型。在生物测定中，6 和 9 对意大利青霉菌表现出良好的抗真菌活性，两种化合物的 MIC 值为 6.25 μM。此外，3 显示出中等的 AChE 抑制活性，IC50 值为 20.6 ± 0.3 μM。
• Dehydrodecalin derivative from marine isolate of the fungus Wardomyces inflatus
  作者：O. F. Smetanina、A. I. Kalinovskii、A. A. Kicha、A. N. Yurchenko、M. V. Pivkin、T. A. Kuznetsova

  DOI：10.1007/s10600-009-9457-0

  日期：2009.9

  In connection with the program to discover biologically active compounds in extracts of marine isolates of microscopic fungi, we tested 1000 strains of marine fungi isolated from marine sediments of Sakhalin Bay for the presence in their extracts of compounds with antibiotic activity that were active in early embryogenesis of the sea urchin Strongylocentrotus intermedius. One of them, Wardomyces inflatus

  与在微观真菌海洋分离物的提取物中发现生物活性化合物的计划有关，我们测试了从库页岛湾海洋沉积物中分离的 1000 株海洋真菌，以确定它们提取物中是否存在具有抗生素活性的化合物，这些化合物在早期胚胎发生中具有活性海胆 Strongylocentrotus intermedius。其中之一，Wardomyces inflatus (Marchal) Hennebert，合成了这样的化合物。这种真菌通常寄生在陆生植物上 [1, 2] 并且是我们第一次从深 (50 m) 海洋沉积物中分离出来的。用培养基将真菌的菌丝体用EtOAc萃取两次。蒸发萃取液。将固体溶解在EtOH:H 2 O(1:4)中并依次用己烷、CHCl 3 和BuOH萃取(2x)。真空蒸发CHCl 3 萃取液。干燥固体(700mg)在SiO 2 柱(25×2cm)上层析。化合物1(27mg)通过己烷:EtOAc(85:15)洗脱。该化合
• Eujavanicols A–C, Decalin Derivatives from Eupenicillium javanicum
  作者：Shou Nakadate、Koohei Nozawa、Hitoshi Horie、Yuichi Fujii、Masahiro Nagai、Tomoo Hosoe、Ken-ichi Kawai、Takashi Yaguchi、Kazutaka Fukushima

  DOI：10.1021/np078008a

  日期：2007.9.1

  Three new decalin derivatives, eujavanicols A-C (1-3), were isolated from an extract of Eupenicillium javanicum IFM 54704. Their structures were determined by chemical and spectroscopic methods.