Biosynthesis of sesquiterpenes in grape berry exocarp of Vitis vinifera L.: evidence for a transport of farnesyl diphosphate precursors from plastids to the cytosol.
Biosynthesis of sesquiterpenes in grape berry exocarp of Vitis vinifera L.: evidence for a transport of farnesyl diphosphate precursors from plastids to the cytosol.
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DOI：
10.1016/j.phytochem.2013.07.021
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发表时间：
2013-11
期刊：
影响因子：
3.8
通讯作者：
Wüst M
中科院分区：
文献类型：
--
作者：
May B;Lange BM;Wüst M
研究了甲羟戊酸（MVA）和1-脱氧-D-木酮糖5-磷酸/2-C-甲基-D-β-4-磷酸（DOXP/MEP）途径在葡萄果实倍半萜合成中的作用。人们对这类萜类化合物的兴趣越来越大，因为氧化的倍半萜罗通酮被鉴定为澳大利亚设拉子葡萄酒中的胡椒香气影响化合物。为了研究前体供应途径利用，用氘标记的途径特异性前体[5，5 - 2 H2]-1-脱氧-D-木酮糖和[5，5 - 2 H2]-甲羟戊酸内酯进行体内喂养实验。顶空固相微萃取-气相色谱-质谱（HS-SPME-GC-MS）分析所产生的挥发性代谢产物表明，从头倍半萜的生物合成主要位于葡萄浆果外果皮（皮肤），与Lemberger品种的中果皮（果肉）中没有检测到的活性。有趣的是，来自（主要是）细胞质MVA和质体DOXP/MEP途径的前体都被整合到Lemberger、Gewürztraminer和Syrah品种的葡萄倍半萜中。我们的标记数据提供了证据，一个同质的，胞质池的前体倍半萜的生物合成，表明运输的前体主要发生从质体到胞质。倍半萜大根香叶烯D的标记模式与先前从加拿大一枝黄花中克隆的对映选择性（R）-大根香叶烯D合酶的环化机制类似。随后通过对映选择性GC-MS分析证实了这一观察结果，证明葡萄浆果中仅存在（R）-大根香叶烯D，而不是（S）-对映异构体。
The participation of the mevalonic acid (MVA) and 1-deoxy-D-xylulose 5-phosphate/2-C-methyl-D-erythritol-4-phosphate (DOXP/MEP) pathways in sesquiterpene biosynthesis of grape berries was investigated. There is an increasing interest in this class of terpenoids, since the oxygenated sesquiterpene rotundone was identified as the peppery aroma impact compound in Australian Shiraz wines. To investigate precursor supply pathway utilization, in vivo feeding experiments were performed with the deuterium labeled, pathway specific, precursors [5,5-2H2]-1-deoxy-D-xylulose and [5,5-2H2]-mevalonic acid lactone. Head Space-Solid Phase Micro Extraction-Gas Chromatography-Mass Spectrometry (HS-SPME-GC-MS) analysis of the generated volatile metabolites demonstrated that de novo sesquiterpene biosynthesis is mainly located in the grape berry exocarp (skin), with no detectable activity in the mesocarp (flesh) of the Lemberger variety. Interestingly, precursors from both the (primarily) cytosolic MVA and plastidial DOXP/MEP pathways were incorporated into grape sesquiterpenes in the varieties Lemberger, Gewürztraminer and Syrah. Our labeling data provide evidence for a homogenous, cytosolic pool of precursors for sesquiterpene biosynthesis, indicating that a transport of precursors occurs mostly from plastids to the cytosol. The labeling patterns of the sesquiterpene germacrene D were in agreement with a cyclization mechanism analogous to that of a previously cloned enantioselective (R)-germacrene D synthase from Solidago canadensis. This observation was subsequently confirmed by enantioselective GC-MS analysis demonstrating the exclusive presence of (R)-germacrene D, and not the (S)-enantiomer, in grape berries.
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影响因子：
11.6
作者：
Jasinski, M;Stukkens, Y;Boutry, M
通讯作者：
Boutry, M
影响因子：
6.2
作者：
Baumes, R;Wirth, J;Razungles, A
通讯作者：
Razungles, A
DOI：
10.1007/bf01192941
发表时间：
1994-07-01
期刊：
ZEITSCHRIFT FUR LEBENSMITTEL-UNTERSUCHUNG UND-FORSCHUNG
影响因子：
--
作者：
BUCHBAUER, G;JIROVETZ, L;NIKIFOROV, A
通讯作者：
NIKIFOROV, A
影响因子：
6.1
作者：
HARING, HG;BOELENS, H;RIJKENS, F
通讯作者：
RIJKENS, F
影响因子：
6.1
作者：
Kjeldsen, F;Christensen, LP;Edelenbos, M
通讯作者：
Edelenbos, M