Eugenol and isoeugenol, characteristic aromatic constituents of spices, are biosynthesized via reduction of a coniferyl alcohol ester
Eugenol and isoeugenol, characteristic aromatic constituents of spices, are biosynthesized via reduction of a coniferyl alcohol ester
复制标题
DOI：
10.1073/pnas.0603732103
复制
发表时间：
2006-06-27
影响因子：
11.1
通讯作者：
Pichersky, Eran
中科院分区：
文献类型：
--
作者：
Koeduka, Takao;Fridman, Eyal;Pichersky, Eran
苯丙烯类化合物，如chavicol、t-anol、丁香酚和异丁香酚，由植物产生，作为对抗动物和微生物的防御化合物以及作为传粉者的花引诱剂。此外，人类自古以来就将苯丙烯用于食品防腐和调味以及用作药剂。先前的研究表明，植物中的苯丙烯是由取代的苯丙烯醇合成的，尽管这种转化所涉及的酶的身份和反应机制的性质仍然不清楚。我们在这里表明，腺毛的甜罗勒（罗勒），合成和积累苯丙烯，具有一种酶，可以使用乙酸松柏酯和NADPH形成丁香酚。矮牵牛（Petonia hybrida cv. Mitchell）的花，其释放大量的异丁香酚，具有与罗勒丁香酚形成酶同源的酶，其也使用乙酸松柏酯和NADPH作为底物，但催化异丁香酚的形成。罗勒和矮牵牛苯丙酮酸形成酶属于NADPH依赖性还原酶的结构家族，其还包括松醇-落叶松树脂醇还原酶、α-还原酶和苯基香豆烷苄醚还原酶。
Phenylpropenes such as chavicol, t-anol, eugenol, and isoeugenol are produced by plants as defense compounds against animals and microorganisms and as floral attractants of pollinators. Moreover, humans have used phenylpropenes since antiquity for food preservation and flavoring and as medicinal agents. Previous research suggested that the phenylpropenes are synthesized in plants from substituted phenylpropenols, although the identity of the enzymes and the nature of the reaction mechanism involved in this transformation have remained obscure. We show here that glandular trichomes of sweet basil (Ocimum basilicum), which synthesize and accumulate phenylpropenes, possess an enzyme that can use coniferyl acetate and NADPH to form eugenol. Petunia (Petunia hybrida cv. Mitchell) flowers, which emit large amounts of isoeugenol, possess an enzyme homologous to the basil eugenol-forming enzyme that also uses coniferyl acetate and NADPH as substrates but catalyzes the formation of isoeugenol. The basil and petunia phenylpropene-forming enzymes belong to a structural family of NADPH-dependent reductases that also includes pinoresinol-lariciresinol reductase, isoflavone reductase, and phenylcoumaran benzylic ether reductase.