Sandalwood Fragrance Biosynthesis Involves Sesquiterpene Synthases of Both the Terpene Synthase (TPS)-a and TPS-b Subfamilies, including Santalene Synthases
Sandalwood Fragrance Biosynthesis Involves Sesquiterpene Synthases of Both the Terpene Synthase (TPS)-a and TPS-b Subfamilies, including Santalene Synthases
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DOI：
10.1074/jbc.m111.231787
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发表时间：
2011-05-20
影响因子：
4.8
通讯作者：
Bohlmann, Joerg
中科院分区：
文献类型：
--
作者：
Jones, Christopher G.;Moniodis, Jessie;Bohlmann, Joerg
檀香油是世界上最珍贵的香水之一。为了鉴定负责檀香烯生物合成的基因和编码酶，我们从三个不同的檀香树种中克隆并表征了三个直系同源萜烯合酶（TPS）基因SaSSy、SauSSy和SspiSSy；分别是檀香 (Santalum album)、南喀里多 (S. austrocaledonicum) 和穗香 (S. spicatum)。编码的酶催化 (E,E)-法尼基二磷酸 (E,E-FPP) 形成 α-、β-、表-β-檀香烯和 α-外香柠檬烯。重组 SaSSy 还用 (Z,Z)-法呢基二磷酸 (Z,Z-FPP) 进行了测试，值得注意的是，发现产生了 α-内-香柠檬烯、α-檀香烯、(Z)-β-法尼烯、表-β-檀香烯和 β-檀香烯的混合物。还从这三个物种中克隆了编码红没药烯/红没药醇合酶的其他 cDNA，并进行了功能表征。檀香烯合酶和红没药烯/红没药醇合酶都属于 TPS-b 系统发育进化枝，该进化枝通常与被子植物单萜合酶相关。对负责形成大环和双环倍半萜的一组直系同源 TPS-a 合酶进行了表征。檀香烯和红没药烯合酶中严格的功能和有限的序列差异与 TPS-a 合酶相反，表明这些化合物在檀香属的进化中发挥了重要作用。
Sandalwood oil is one of the worlds most highly prized fragrances. To identify the genes and encoded enzymes responsible for santalene biosynthesis, we cloned and characterized three orthologous terpene synthase (TPS) genes SaSSy, SauSSy, and SspiSSy from three divergent sandalwood species; Santalum album, S. austrocaledonicum, and S. spicatum, respectively. The encoded enzymes catalyze the formation of alpha-, beta-, epi-beta-santalene, and alpha-exo-bergamotene from (E,E)-farnesyl diphosphate (E,E-FPP). Recombinant SaSSy was additionally tested with (Z,Z)-farnesyl diphosphate (Z,Z-FPP) and remarkably, found to produce a mixture of alpha-endo-bergamotene, alpha-santalene, (Z)-beta-farnesene, epi-beta-santalene, and beta-santalene. Additional cDNAs that encode bisabolene/bisabolol synthases were also cloned and functionally characterized from these three species. Both the santalene synthases and the bisabolene/bisabolol synthases reside in the TPS-b phylogenetic clade, which is more commonly associated with angiosperm monoterpene synthases. An orthologous set of TPS-a synthases responsible for formation of macrocyclic and bicyclic sesquiterpenes were characterized. Strict functionality and limited sequence divergence in the santalene and bisabolene synthases are in contrast to the TPS-a synthases, suggesting these compounds have played a significant role in the evolution of the Santalum genus.