oxyphyllol B | 226546-99-2

• 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: oxyphyllol B
• 英文别名: (4R,4aS,6S,8R)-8-hydroxy-4,4a-dimethyl-6-prop-1-en-2-yl-3,4,5,6,7,8-hexahydronaphthalen-2-one
• CAS: 226546-99-2
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: AHROGQKIGMNGTG-FKGLVLAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  oxyphyllol B 在 吡啶 、 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 为溶剂， 反应 11.67h， 生成 4-Bromo-benzoic acid (2S,4R,4aS,6S,8R)-8-hydroxy-6-isopropenyl-4,4a-dimethyl-2,3,4,4a,5,6,7,8-octahydro-naphthalen-2-yl ester
  参考文献：
  名称：

  Absolute Stereostructures of Three New Sesquiterpenes from the Fruit of Alpinia oxyphylla with Inhibitory Effects on Nitric Oxide Production and Degranulation in RBL-2H3 Cells

  摘要：

  The 80% aqueous acetone extract and the ethyl acetate-soluble portion from the dried fruit of Alpinia oxyphylla MIQUEL Were found to show inhibitory effects on nitric oxide production in lipopolysaccharide-activated activated macrophages and antigen-induced degranulation in RBL-2H3 cells. A new eudesmane-type sesquiterpene, oxyphyllol A, and two eremophilane-type sesquiterpenes, oxyphyllols B and C, were isolated from the ethyl acetate-soluble portion, together with 16 known constituents. The absolute stereostructures of oxyphyllols A, B, and C were determined on the basis of chemical and physicochemical evidence. The effects of isolated component on nitric oxide production were examined, and nine constituents including oxyphyllol A and nootkatone were found to show inhibitory activity. On the other hand, five constituents inhibited the release of beta-hexosaminidase from RBL-2H3 cells.

  DOI：

  10.1021/np020078o
• 作为产物：
  描述：

  (+)-香柏酮 在 sodium phosphite 、 monooxygenase cytochrome P₄₅₀ CYP₁₀₂A₁ with Ala substituted by para-acetyl-phenylalanine at 78 position 、 水 、 nicotinamide adenine dinucleotide phosphate 作用下， 以 aq. phosphate buffer 为溶剂， 反应 12.0h， 以54%的产率得到oxyphyllol B
  参考文献：
  名称：

  通过非天然氨基酸诱变提高 P450 氧化催化剂的效率和区域选择性

  摘要：

  非天然选择：在细胞色素 P450 活性位点内的单个位置加入非天然氨基酸显着改变酶的区域选择性（如图所示）或提高其催化效率。该研究表明，非天然氨基酸诱变构成了改进 P450 氧化催化剂的有前途的新策略。

  DOI：

  10.1002/cbic.201400060

文献信息

• Natural Product Diversification by One‐Step Biocatalysis using Human P450 3A4
  作者：Nico D. Fessner、Christopher Grimm、Matic Srdič、Hansjörg Weber、Wolfgang Kroutil、Ulrich Schwaneberg、Anton Glieder

  DOI：10.1002/cctc.202101564

  日期：2022.1.10

  Doing it all: In this study, the synthetic potential of human cytochrome P450 3A4 as a Pichia pastoris-based whole-cell biocatalyst for the diversification of natural products was successfully explored. A total of 31 authentic human metabolites of six selected natural products were isolated at a preparative 100-mg scale, many of them for the first time, revealing an unprecedented degree of diversification

  全力以赴：在这项研究中，成功​​探索了人类细胞色素 P450 3A4 作为基于毕赤酵母的全细胞生物催化剂在天然产物多样化方面的合成潜力。以 100 mg 的制备规模分离了六种选定天然产物的总共 31 种真实人体代谢物，其中许多是第一次，揭示了前所未有的多样化程度。
• Biotransformation of the sesquiterpene (+)-valencene by cytochrome P450cam and P450BM-3
  作者：Rebecca J. Sowden、Samina Yasmin、Nicholas H. Rees、Stephen G. Bell、Luet-Lok Wong

  DOI：10.1039/b413068e

  日期：——

  The sesquiterpenoids are a large class of naturally occurring compounds with biological functions and desirable properties. Oxidation of the sesquiterpene (+)-valencene by wild type and mutants of P450cam from Pseudomonas putida, and of P450BM-3 from Bacillus megaterium, have been investigated as a potential route to (+)-nootkatone, a fine fragrance. Wild type P450cam did not oxidise (+)-valencene

  倍半萜是一大类具有生物学功能和所需特性的天然存在的化合物。已经研究了野生型和恶臭假单胞菌P450cam突变体以及巨大芽孢杆菌P450BM-3突变体对倍半萜烯（+）-瓦伦烯的氧化作用，将其作为制备（+）-Nootkatone（一种精美香料）的潜在途径。野生型P450cam不会氧化（+）-瓦伦烯，但突变体显示的活性高达9.8 nmol（nmol P450）（-1）min（-1），其中（+）-反式-NOTOKATOL和（+）-NOOTKATONE构成>产品的85％。野生型P450BM-3和突变体比P450cam具有更高的活性（长达43 min（-1）），但选择性低得多。在许多产品中，顺式和反式-（+）-Nootkatol，（+）-Nootkatone，顺式-（+）-Valencene-1,10-环氧，反式-（+）-Nootkaton-9-ol和（ +）-nootkatone-13S，从全细胞反应
• Arantes, Simone F.; Farooq, Afgan; Hanson, James R., Journal of Chemical Research, Miniprint, 1999, # 3, p. 801 - 812
  作者：Arantes, Simone F.、Farooq, Afgan、Hanson, James R.

  DOI：——

  日期：——
• Enhancing the Efficiency and Regioselectivity of P450 Oxidation Catalysts by Unnatural Amino Acid Mutagenesis
  作者：Joshua N. Kolev、Jacqueline M. Zaengle、Rajesh Ravikumar、Rudi Fasan

  DOI：10.1002/cbic.201400060

  日期：2014.5.5

  Unnatural choice: Incorporating unnatural amino acids at single positions within the active site of a cytochrome P450 significantly changes the regioselectivity (shown) of the enzyme or enhances its catalytic efficiency. This study demonstrates that unnatural amino acid mutagenesis constitutes a promising new strategy for improving P450 oxidation catalysts.

  非天然选择：在细胞色素 P450 活性位点内的单个位置加入非天然氨基酸显着改变酶的区域选择性（如图所示）或提高其催化效率。该研究表明，非天然氨基酸诱变构成了改进 P450 氧化催化剂的有前途的新策略。
• Absolute Stereostructures of Three New Sesquiterpenes from the Fruit of <i>Alpinia </i><i>o</i><i>xyphylla</i> with Inhibitory Effects on Nitric Oxide Production and Degranulation in RBL-2H3 Cells
  作者：Toshio Morikawa、Hisashi Matsuda、Iwao Toguchida、Kazuho Ueda、Masayuki Yoshikawa

  DOI：10.1021/np020078o

  日期：2002.10.1

  The 80% aqueous acetone extract and the ethyl acetate-soluble portion from the dried fruit of Alpinia oxyphylla MIQUEL Were found to show inhibitory effects on nitric oxide production in lipopolysaccharide-activated activated macrophages and antigen-induced degranulation in RBL-2H3 cells. A new eudesmane-type sesquiterpene, oxyphyllol A, and two eremophilane-type sesquiterpenes, oxyphyllols B and C, were isolated from the ethyl acetate-soluble portion, together with 16 known constituents. The absolute stereostructures of oxyphyllols A, B, and C were determined on the basis of chemical and physicochemical evidence. The effects of isolated component on nitric oxide production were examined, and nine constituents including oxyphyllol A and nootkatone were found to show inhibitory activity. On the other hand, five constituents inhibited the release of beta-hexosaminidase from RBL-2H3 cells.