12-hydroxyfarnesol | 66472-02-4

• 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: 12-hydroxyfarnesol
• 英文别名: 2,6,10-trimethyl-dodeca-2,6,10-triene-1,12-diol；Hydroxyfarnesol；2,6,10-trimethyldodeca-2,6,10-triene-1,12-diol
• CAS: 66472-02-4
• 化学式: C₁₅H₂₆O₂
• 分子量: 238.37
• InChiKey: FLIKBVTXNBEPQQ-UHFFFAOYSA-N

物化性质

• 沸点：
  368.9±37.0 °C(Predicted)
• 密度：
  0.948±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• 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

• 作为产物：
  描述：

  金合欢醇 在 nicotinamide adenine dinucleotide phosphate 、 CsCPR I 、 CYP₇₆F₄₅ 作用下， 以 aq. buffer 为溶剂， 反应 18.0h， 生成 12-hydroxyfarnesol
  参考文献：
  名称：

  Functional expression of a putative geraniol 8-hydroxylase by reconstitution of bacterially expressed plant CYP76F45 and NADPH-cytochrome P450 reductase CPR I from Croton stellatopilosus Ohba

  摘要：

  While attempting to isolate the enzyme geranylgeraniol 18-hydroxylase, which is involved in plaunotol biosynthesis in Croton stellatopilosus (Cs), the cDNAs for a cytochrome P450 monooxygenase (designated as CYP76F45) and an NADPH-cytochrome P450 reductase (designated as CPR I based on its classification) were isolated from the leaf. The CYP76F45 and CsCPR I genes have open reading frames (ORFs) encoding 507- and 711-amino acid proteins with predicted relative molecular weights of 56.7 and 79.0 kDa, respectively. Amino acid sequence comparison showed that both CYP76F45 (63-73%) and CsCPR I (79-83%) share relatively high sequence identities with homologous proteins in other plant species. Phylogenetic tree analysis confirmed that CYP76F45 belongs to the CYP76 family and that CsCPR I belongs to Class I of dicotyledonous CPRs, with both being closely related to Ricinus communis genes. Functional characterization of both enzymes, each expressed separately in Escherichia coli as recombinant proteins, showed that only simultaneous incubation of the membrane-bound proteins with the substrate geraniol (GOH) and the coenzyme NADPH could form 8-hydroxygeraniol. The enzyme mixture could also utilize acyclic sesquiterpene farnesol (FOH) with a comparable substrate preference ratio (GOH:FOH) of 54:46. The levels of the CYP76F45 and CsCPR I transcripts in the shoots, leaves and twigs of C. stellatopilosus were correlated with the levels of a major monoterpenoid indole alkaloid, identified tentatively as 19-E-vallesamine, that accumulated in these plant parts. These results suggested that CYP97C27 and CPR I function as the enzyme geranioI-8-hydroxylase (G8H), which is likely to be involved in the biosynthesis of the indole alkaloid in C. stellatopilosus. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2015.08.005

文献信息

• Neue farnesolderivate aus Tanacetum odessanum
  作者：Ferdinand Bohlmann、Knoll Karl-Heinz

  DOI：10.1016/s0031-9422(00)94177-3

  日期：1978.1
• Functional expression of a putative geraniol 8-hydroxylase by reconstitution of bacterially expressed plant CYP76F45 and NADPH-cytochrome P450 reductase CPR I from Croton stellatopilosus Ohba
  作者：Siriluk Sintupachee、Worrawat Promden、Nattaya Ngamrojanavanich、Worapan Sitthithaworn、Wanchai De-Eknamkul

  DOI：10.1016/j.phytochem.2015.08.005

  日期：2015.10

  While attempting to isolate the enzyme geranylgeraniol 18-hydroxylase, which is involved in plaunotol biosynthesis in Croton stellatopilosus (Cs), the cDNAs for a cytochrome P450 monooxygenase (designated as CYP76F45) and an NADPH-cytochrome P450 reductase (designated as CPR I based on its classification) were isolated from the leaf. The CYP76F45 and CsCPR I genes have open reading frames (ORFs) encoding 507- and 711-amino acid proteins with predicted relative molecular weights of 56.7 and 79.0 kDa, respectively. Amino acid sequence comparison showed that both CYP76F45 (63-73%) and CsCPR I (79-83%) share relatively high sequence identities with homologous proteins in other plant species. Phylogenetic tree analysis confirmed that CYP76F45 belongs to the CYP76 family and that CsCPR I belongs to Class I of dicotyledonous CPRs, with both being closely related to Ricinus communis genes. Functional characterization of both enzymes, each expressed separately in Escherichia coli as recombinant proteins, showed that only simultaneous incubation of the membrane-bound proteins with the substrate geraniol (GOH) and the coenzyme NADPH could form 8-hydroxygeraniol. The enzyme mixture could also utilize acyclic sesquiterpene farnesol (FOH) with a comparable substrate preference ratio (GOH:FOH) of 54:46. The levels of the CYP76F45 and CsCPR I transcripts in the shoots, leaves and twigs of C. stellatopilosus were correlated with the levels of a major monoterpenoid indole alkaloid, identified tentatively as 19-E-vallesamine, that accumulated in these plant parts. These results suggested that CYP97C27 and CPR I function as the enzyme geranioI-8-hydroxylase (G8H), which is likely to be involved in the biosynthesis of the indole alkaloid in C. stellatopilosus. (C) 2015 Elsevier Ltd. All rights reserved.