ent-beyer-15-en-18-ol | 77064-10-9

• 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: ent-beyer-15-en-18-ol
• 英文别名: [(1R,4S,5S,9S,10S,13S)-5,9,13-trimethyl-5-tetracyclo[11.2.1.01,10.04,9]hexadec-14-enyl]methanol
• CAS: 77064-10-9
• 化学式: C₂₀H₃₂O
• 分子量: 288.473
• InChiKey: CIGQQQTZOIDQQR-BGSOWLKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  ent-beyer-15-en-18-ol 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 1,4-二氧六环 为溶剂， 反应 108.0h， 生成 (+)-hibaene
  参考文献：
  名称：

  Diterpenoids from Baccharis tola

  摘要：

  DOI：

  10.1016/0031-9422(80)83018-4
• 作为产物：
  描述：

  ent-beyer-15-en-18-O-succinate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 ent-beyer-15-en-18-ol
  参考文献：
  名称：

  Antibacterial Diterpenoids from Fabiana densa var. ramulosa

  摘要：

  对密叶香茶菜（Fabiana densa Remy var. ramulosa Wedd.）树脂渗出物的生物监测分馏，分离出两种新的二萜：ent-beyer-15-en-18-O-琥珀酸酯和ent-beyer-15-en-18-O-草酸酯，这两种化合物是这种提取物所具有的抗菌活性的唯一来源。通过一维和二维核磁共振光谱确定了它们的结构。

  DOI：

  10.1055/s-2002-26746

文献信息

• Gastroprotective activity of ent-beyerene derivatives in mice: Effects on gastric secretion, endogenous prostaglandins and non-protein sulfhydryls
  作者：Teresa Parra、Julio Benites、Lina M. Ruiz、Beatriz Sepulveda、Mario Simirgiotis、Carlos Areche

  DOI：10.1016/j.bmcl.2015.04.095

  日期：2015.7

  Seventeen compounds (2–18) synthetized from the diterpenoid ent-beyer-15-en-18-ol (1) isolated from aerial part of Baccharis tola were tested for their gastroprotective activity on the model of HCl/EtOH-induced gastric lesions in mice. Furthermore cytotoxicity test toward fibroblasts and AGS cells were performed. The results showed that compound 1 (ED50 = 50 mg/kg), 2, 6 and 13 were the most active

  十七化合物（2 - 18）从所述二萜synthetized ENT -beyer-15-SC-18醇（1）从地上部分分离Baccharis托拉对盐酸/模型的胃保护活性进行了测试EtOH中诱导的胃损伤在老鼠。此外，对成纤维细胞和AGS细胞进行了细胞毒性测试。结果表明，化合物1（ED 50  = 50毫克/千克），2，6和13是最活跃关于胃保护活性。化合物8 – 10和17 – 18对成纤维细胞和AGS细胞显示出最低的细胞毒性。关于到胃保护作用方式，其效果由诱发6（50毫克/千克）经吲哚美辛逆转，但不是由Ñ乙基马来，Ñ ģ硝基-升-精氨酸甲基酯或钌红，这表明前列腺素参与6的胃保护作用模式。
• The microbiological transformation of some ent-beyerene diterpenoids by Gibberella fujikuroi to beyergibberellins and beyerenolides
  作者：Carmen E. Diaz、Braulio M. Fraga、Antonio G. Gonzalez、James R. Hanson、Melchor G. Hernandez、Aurelio San Martin

  DOI：10.1016/s0031-9422(00)81050-x

  日期：1985.1

  Abstract The microbiological transformation by Gibberelia fujikuroi of ent -beyer-15-ene into the beyergibberellins A 9 and A 13 , 7β-hydroxy- and 7β,18-dihydroxybeyerenolides, and of ent -beyer-15-en-19-ol into beyergibberellins A 4 , A 7 , A 9 , A 13 and A 25 ,and 7β-hydroxy-and 7β,18-dihydroxybeyerenolides is described. In contrast, ent -beyer-15-en-18-ol gave ent -7α, 18,19-trihydroxybeyer-15-ene

  摘要 Gibberelia fujikuroi 将 ent -beyer-15-ene 转化为 beyergibberellins A 9 和 A 13 、7β-羟基-和 7β,18-dihydroxy beyerenolides，以及 ent -beyer-15-en-19-ol 转化为 beyergibberellins描述了A 4 、A 7 、A 9 、A 13 和A 25 以及7β-羟基-和7β,18-二羟基拜尔烯内酯。相比之下，ent -beyer-15-en-18-ol 得到 ent -7α, 18,19-trihydroxybeyer-15-ene, 7β,18-dihydroxybeyerenolide 和 ent -7α,18-dihydroxybeyer-15-en-19-oic酸再次揭示了 18-羟基对藤黑赤霉在 C-6β 处的氧化转化的抑制作用。
• The chemical and microbiological synthesis of 14-hydroxy-gibberellins
  作者：Braulio M. Fraga、Fernando García-Tellado、Pedro González、Melchor G. Hernández、James R. Hanson

  DOI：10.1016/s0040-4020(01)86597-2

  日期：1992.9

  transformed into 14β-hydroxy-gibberellin A7 methyl ester via the rearrangement of an epoxy-beyergibberellin intermediate using a titanium-amide complex. The diterpene ent-beyer-15-en-19-ol has been transformed by chemical methods into ent-14α,19-dihydroxy-kaur-16-ene. The biotransformation of this compound with the fungus Gibberella fujikuroi gave 14β-hydroxy-gibberellin A7, ent-7α,14α,19-trihydroxy-kaur-16-ene

  赤霉素已通过使用钛-酰胺络合物对环氧-啤酒赤霉素中间体进行重排而转化为14β-羟基-赤霉素A 7甲酯。二萜ENT -beyer-15-SC-19醇已经通过化学方法转化成耳鼻喉科-14α，19二羟基考尔-16-烯。该化合物与藤霉赤霉菌的生物转化产生了14β-羟基赤霉素A 7，ent - 7α，14α，19-三羟基kaur -16-ene和ent - 6α，7α，14α-trihydroxy-kaur-16-en -19-油酸。通过GC-MS鉴定了次要的赤霉素14β-羟基-GA 14。
• <i>ent</i>-Beyerane Diterpenes as a Key Platform for the Development of ArnT-Mediated Colistin Resistance Inhibitors
  作者：Deborah Quaglio、Maria Luisa Mangoni、Roberta Stefanelli、Silvia Corradi、Bruno Casciaro、Valeria Vergine、Federica Lucantoni、Luca Cavinato、Silvia Cammarone、Maria Rosa Loffredo、Floriana Cappiello、Andrea Calcaterra、Silvia Erazo、Francesca Ghirga、Mattia Mori、Francesco Imperi、Fiorentina Ascenzioni、Bruno Botta

  DOI：10.1021/acs.joc.0c01459

  日期：2020.8.21

  Colistin is a last-resort antibiotic for the treatment of multidrug resistant Gram-negative bacterial infections. Recently, a natural ent-beyerene diterpene was identified as a promising inhibitor of the enzyme responsible for colistin resistance mediated by lipid A aminoarabinosylation in Gram-negative bacteria, namely, ArnT (undecaprenyl phosphate-alpha-4-amino-4-deoxy-L-arabinose arabinosyl transferase). Here, semisynthetic analogues of hit were designed, synthetized, and tested against colistin-resistant Pseudomonas aeruginosa strains including clinical isolates to exploit the versatility of the diterpene scaffold. Microbiological assays coupled with molecular modeling indicated that for a more efficient colistin adjuvant activity, likely resulting from inhibition of the ArnT activity by the selected compounds and therefore from their interaction with the catalytic site of ArnT, an ent-beyerane scaffold is required along with an oxalate-like group at C-18/C-19 or a sugar residue at C-19 to resemble L-Ara4N. The ent-beyerane skeleton is identified for the first time as a privileged scaffold for further cost-effective development of valuable colistin resistance inhibitors.
• Diterpenoids from Baccharis tola
  作者：Aurelio San Martín、Juana Rovirosa、Rodolfo Becker、Mariano Castillo

  DOI：10.1016/0031-9422(80)83018-4

  日期：1980.1