苯(甲)醛,2,4-二羟基-6-甲基-3-[(2E,4E)-3-甲基-5-[(1R,2R,6R)-1,2,6-三甲基-3-羰基环己基]-2,4-戊二烯-1-基]- | 165187-16-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 苯(甲)醛,2,4-二羟基-6-甲基-3-[(2E,4E)-3-甲基-5-[(1R,2R,6R)-1,2,6-三甲基-3-羰基环己基]-2,4-戊二烯-1-基]-
• 英文名称: cylindrol B
• 英文别名: 2,4-dihydroxy-6-methyl-3-[(2E,4E)-3-methyl-5-[(1R,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dienyl]benzaldehyde
• CAS: 165187-16-6
• 化学式: C₂₃H₃₀O₄
• 分子量: 370.489
• InChiKey: AQCKKGIVKOHRLM-HBFAXEOFSA-N

物化性质

• 沸点：
  547.7±39.0 °C(Predicted)
• 密度：
  1.137±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 苯(甲)醛,2,4-二羟基-6-甲基-3-[(2E,4E)-3-甲基-5-[(1R,2R,6R)-1,2,6-三甲基-3-羰基环己基]-2,4-戊二烯-1-基]- 在 12,13-dihydrocylindrol B 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 2-Hydroxy-4-methoxy-6-methyl-3-[(2E,4E)-3-methyl-5-((1R,2R,6R)-1,2,6-trimethyl-3-oxo-cyclohexyl)-penta-2,4-dienyl]-benzaldehyde
  参考文献：
  名称：

  Chemistry and Biology of Cylindrols:  Novel Inhibitors of Ras Farnesyl-Protein Transferase from Cylindrocarpon lucidum

  摘要：

  Farnesyl-protein transferase (FPTase) is an enzyme responsible for the farnesylation of Ras protein. Farnesylation is required for cell-transforming activity in several tumor-types, and therefore, inhibition of FPTase activity may be a potential target for anticancer drugs. Our continued search for novel inhibitors led to the isolation of a number of bicyclic resorcinaldehyde cyclohexanone derivatives named here cylindrols A(1) to A(4), cylindrols B and B-1, and a number of known compounds, from Cylindrocarpon Lucidum. The compounds were isolated by bioassay-guided separation using Sephadex LH-20, silica gel, and reverse phase HPLC. Structures were elucidated by extensive application of 2D NMR and X-ray crystallography. The determination of absolute stereochemistry was accomplished by CD measurements. Chemical transformations of the most abundant compound resulted in a number of key derivatives which were critical for the evaluation of structure activity relationship. These compounds are members of ascochlorin family and showed a wide range of inhibitory activity (0.7 mu M to > 140 mu M) against FPTase. The FPTase activity was noncompetitive with respect to both substrates. Isolation, structures, chemical transformations, and FPTase activity are discussed in detail.

  DOI：

  10.1021/jo961074p
• 作为产物：
  描述：

  LL-Z 1272β 在 ascochlorin biosynthetic enzyme E from fungus Fusarium sp. NBRC₁₀₀₈₄₄ 、 ascochlorin biosynthetic enzyme F from fungus Fusarium sp. NBRC₁₀₀₈₄₄ 、 ascochlorin biosynthetic enzyme G from fungus Fusarium sp. NBRC₁₀₀₈₄₄ 作用下， 生成 苯(甲)醛,2,4-二羟基-6-甲基-3-[(2E,4E)-3-甲基-5-[(1R,2R,6R)-1,2,6-三甲基-3-羰基环己基]-2,4-戊二烯-1-基]-
  参考文献：
  名称：

  镰刀菌属Ascochlorin生物合成途径中的多域P450环氧酶和萜烯环化酶。

  摘要：

  抗坏血酸是医学上重要的真菌类萜。其在镰刀菌中的生物合成途径。鉴定，并研究了法呢基通过多结构域，可溶性P450单加氧酶AscE的立体选择性环氧化以及膜结合的环化酶AscF随后形成的独特的甲基环己酮环的过程。前体定向的生物合成产生了新型的溴取代衍生物，其表现出有效的细胞毒性活性。这项研究为医学上重要的类胡萝卜素类药物的未来代谢工程化铺平了道路。

  DOI：

  10.1021/acs.orglett.9b00616
• 作为试剂：
  描述：

  重氮甲烷 、 3-Methyl-butyric acid (E)-(R)-4-(3-chloro-5-formyl-2,6-dihydroxy-4-methyl-phenyl)-2-methyl-1-((1S,2R,6R)-1,2,6-trimethyl-3-oxo-cyclohexylmethyl)-but-2-enyl ester 在 苯(甲)醛,2,4-二羟基-6-甲基-3-[(2E,4E)-3-甲基-5-[(1R,2R,6R)-1,2,6-三甲基-3-羰基环己基]-2,4-戊二烯-1-基]- 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 2-Hydroxy-4-methoxy-6-methyl-3-[(E)-3-methyl-5-((1S,2R,6R)-1,2,6-trimethyl-3-oxo-cyclohexyl)-pent-2-enyl]-benzaldehyde
  参考文献：
  名称：

  Chemistry and Biology of Cylindrols:  Novel Inhibitors of Ras Farnesyl-Protein Transferase from Cylindrocarpon lucidum

  摘要：

  Farnesyl-protein transferase (FPTase) is an enzyme responsible for the farnesylation of Ras protein. Farnesylation is required for cell-transforming activity in several tumor-types, and therefore, inhibition of FPTase activity may be a potential target for anticancer drugs. Our continued search for novel inhibitors led to the isolation of a number of bicyclic resorcinaldehyde cyclohexanone derivatives named here cylindrols A(1) to A(4), cylindrols B and B-1, and a number of known compounds, from Cylindrocarpon Lucidum. The compounds were isolated by bioassay-guided separation using Sephadex LH-20, silica gel, and reverse phase HPLC. Structures were elucidated by extensive application of 2D NMR and X-ray crystallography. The determination of absolute stereochemistry was accomplished by CD measurements. Chemical transformations of the most abundant compound resulted in a number of key derivatives which were critical for the evaluation of structure activity relationship. These compounds are members of ascochlorin family and showed a wide range of inhibitory activity (0.7 mu M to > 140 mu M) against FPTase. The FPTase activity was noncompetitive with respect to both substrates. Isolation, structures, chemical transformations, and FPTase activity are discussed in detail.

  DOI：

  10.1021/jo961074p

文献信息

• Bacterial strain having anti-fungal properties and uses thereof
  申请人：Kontzamanis Graumann Smith MacMillan Inc.

  公开号：US11470793B2

  公开（公告）日：2022-10-18

  Described herein is the evaluation of the antifungal properties of bacterial strain KGS-3 against Fusarium Head Blight (FHB)) white mold, blackleg and a number of potato fungal diseases and the plant growth effect attained. KGS-3 is a novel strain of Paenibacillus polymyxa that can suppress bacterial and fungal plant diseases. KGS-3 is predicted to produce antifungal metabolites polymyxin, fusaricidin, and paenilarvin and has been demonstrated to produce cylindrol B. KGS-3 is a plant growth promoting bacteria demonstrated to increase protein content of plants and/or plant products.

  本文描述了细菌菌株 KGS-3 对镰刀菌头枯病（FHB）、白霉病、黑腿病和多种马铃薯真菌病害的抗真菌特性评估以及所取得的植物生长效果。KGS-3 是多肉芽孢杆菌（Paenibacillus polymyxa）的一种新型菌株，可抑制细菌和真菌植物病害。据预测，KGS-3 能产生抗真菌代谢物多粘菌素、镰刀菌素和保尼拉菌素，并已证明能产生圆柱醇 B。
• MEROTERPENOID COMPOUNDS FOR USE IN THE PREVENTION AND TREATMENT OF A NEUROLOGICAL DISORDER
  申请人：Société des Produits Nestlé S.A.

  公开号：EP3681488A1

  公开（公告）日：2020-07-22
• Bacterial Strain having Anti-Fungal Properties and Uses Thereof
  申请人：Kontzamanis Graumann Smith MacMillan Inc.

  公开号：US20210360890A1

  公开（公告）日：2021-11-25

  Described herein is the evaluation of the antifungal properties of bacterial strain KGS-3 against Fusarium Head Blight (FHB)) white mold, blackleg and a number of potato fungal diseases and the plant growth effect attained. KGS-3 is a novel strain of Paenibacillus polymyxa that can suppress bacterial and fungal plant diseases. KGS-3 is predicted to produce antifungal metabolites polymyxin, fusaricidin, and paenilarvin and has been demonstrated to produce cylindrol B. KGS-3 is a plant growth promoting bacteria demonstrated to increase protein content of plants and/or plant products.
• [EN] MEROTERPENOID COMPOUNDS FOR USE IN THE PREVENTION AND TREATMENT OF A NEUROLOGICAL DISORDER<br/>[FR] COMPOSÉS MÉROTERPÉNOÏDES DESTINÉS À ÊTRE UTILISÉS DANS LA PRÉVENTION ET LE TRAITEMENT D'UN TROUBLE NEUROLOGIQUE
  申请人：NESTEC SA

  公开号：WO2019053159A1

  公开（公告）日：2019-03-21

  The present invention relates to a compound, in particular a meroterpenoid compound, or salt thereof, for use in the prevention and/or treatment of a neurological disorder in an individual. The compound of the invention can promote lactate secretion. A composition comprising the compound of the invention, and a food or food extract enriched with said compound or composition is also provided.
• [EN] BACTERIAL STRAIN HAVING ANTI-FUNGAL PROPERTIES AND USES THEREOF<br/>[FR] SOUCHE BACTÉRIENNE POSSÉDANT DES PROPRIÉTÉS ANTIFONGIQUES ET UTILISATIONS CORRESPONDANTES
  申请人：KONTZAMANIS GRAUMANN SMITH MACMILLAN INC

  公开号：WO2020154813A1

  公开（公告）日：2020-08-06

  Described herein is the evaluation of the antifungal properties of bacterial strain KGS- 3 against Fusarium Head Blight (FHB)) white mold, blackleg and a number of potato fungal diseases and the plant growth effect attained. KGS-3 is a novel strain of Paenibacillus polymyxa that can suppress bacterial and fungal plant diseases. KGS-3 is predicted to produce antifungal metabolites polymyxin, fusaricidin, and paenilarvin and has been demonstrated to produce cylindrol B. KGS-3 is a plant growth promoting bacteria demonstrated to increase protein content of plants and/or plant products.