Demonstration that menthofuran synthase of mint (Mentha) is a cytochrome P450 monooxygenase:: Cloning, functional expression, and characterization of the responsible gene
Demonstration that menthofuran synthase of mint (Mentha) is a cytochrome P450 monooxygenase:: Cloning, functional expression, and characterization of the responsible gene
复制标题
DOI：
10.1006/abbi.2001.2378
复制
发表时间：
2001-06-15
影响因子：
3.9
通讯作者：
Croteau, R
中科院分区：
文献类型：
--
作者：
Bertea, CM;Schalk, M;Croteau, R
(+)-薄荷呋喃是薄荷精油中一种不受欢迎的单萜类成分，它是从α，β-不饱和酮(+)-普利酮中提取的。从高(+)-薄荷呋喃产生型化学型薄荷的油腺分泌细胞中制备微体制剂，在NADPH和分子氧的存在下将(+)-普鲁酮转化为(+)-薄荷呋喃，这意味着薄荷呋喃的合成机制与哺乳动物肝细胞色素P450类似，涉及(+)-普鲁酮的甲基化、半缩醛的自发环化和呋喃的脱水。从薄荷油腺细胞文库中获得了丰富的细胞色素P450克隆，并在酵母菌和大肠杆菌中进行了功能性表达，编码了(+)-薄荷呋喃合成酶(即(+)-普利酮-9-羟基酶)。该基因全长1479个核苷酸，编码一个493个氨基酸残基的蛋白质，相对分子质量为55,360，具有细胞色素P450的所有预期一级结构元素，并与来自同一来源的细胞色素P450单萜羟基酶(+)-柠檬烯-3-羟基酶最为相似(同源性为35%)，该基因的存在使转基因操作薄荷精油可以提高精油的质量。(C)2001年学术出版社。
(+)-Menthofuran is an undesirable monoterpenoid component of peppermint (Mentha x piperita) essential oil that is derived from the alpha,beta -unsaturated ketone (+)-pulegone. Microsomal preparations, from the oil gland secretory cells of a high (+)-menthofuran-producing chemotype of Mentha pulegium, transform (+)-pulegone to (+)-menthofuran in the presence of NADPH and molecular oxygen, implying that menthofuran is synthesized by a mechanism analogous to that of mammalian liver cytochrome P450s involving the hydroxylation of the syn-methyl group of (+)-pulegone, spontaneous intramolecular cyclization to the hemiketal, and dehydration to the furan, An abundant cytochrome P450 clone from a peppermint oil gland cell cDNA library was functionally expressed in Saccharomyces cerevisiae and Escherichia coli and shown to encode the (+)-menthofuran synthase (i.e., (+)-pulegone-9-hydroxylase). The full-length cDNA contains 1479 nucleotides, and encodes a protein of 493 amino acid residues of molecular weight 55,360, which bears all of the anticipated primary structural elements of a cytochrome P450 and most closely resembles (35% identity) a cytochrome P450 monoterpene hydroxylase, (+)-limonene-3-hydroxylase, from the same source, The availability of this gene permits transgenic manipulation of peppermint to improve the quality of the derived essential oil. (C) 2001 Academic Press.