1-sinapoyl-β-D-glucopyranoside | 78185-48-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 1-sinapoyl-β-D-glucopyranoside
• 英文别名: sinapoylglucose；1-O-sinapoyl-β-D-glucose；1-O-sinapoyl β-D-glucopyranoside；1-O-Sinapoyl-beta-D-glucose；[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate
• CAS: 78185-48-5
• 化学式: C₁₇H₂₂O₁₀
• 分子量: 386.356
• InChiKey: XRKBRPFTFKKHEF-DGDBGZAXSA-N

物化性质

• 沸点：
  630.0±55.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  155
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-sinapoyl-β-D-glucopyranoside 在 1-O-sinapoyl-β-glucose:L-malate sinapoyltransferase 作用下， 以 二甲基亚砜 为溶剂， 生成 3,5-二甲氧基-4-羟基肉桂酸 、 1(E),2(E)-di-O-sinapoyl β-D-glucopyranoside
  参考文献：
  名称：

  拟南芥 sinapoylglucose:malate sinapoyltransferase 的活性揭示丝氨酸羧肽酶样酰基转移酶的功能多样化

  摘要：

  对来自拟南芥的丝氨酸羧肽酶样 (SCPL) 1-O-sinapoyl-beta-glucose:l-malate sinapoyltransferase (SMT) 的催化特性的分析表明，该酶除了主要的 l-苹果酸sinapoylation 外，还具有少量水解和歧化活性，分别产生游离芥子酸和 1,2-二-O-芥子酰-β-葡萄糖。该酶从供体分子 1-O-sinapoyl-β-葡萄糖中释放芥子酸的能力表明在所提出的随机顺序双双催化机制中存在短寿命的酰基酶中间体。SMT 催化的 disinapoylglucose 形成已通过对接研究得到证实，已建立的同源结构模型说明了活性位点中两个 1-O-sinapoyl-β-葡萄糖分子的可能结合以及两种葡萄糖酯的分子间反应。SMT 基因嵌入五个 SCPL 芥子酰转移酶基因的串联簇中，这些基因编码具有高氨基酸序列同一性和部分重叠底物特异性的酶。我们假设在编码 SCPL

  DOI：

  10.1016/j.phytochem.2008.03.021
• 作为产物：
  描述：

  3,5-二甲氧基-4-羟基肉桂酸 、 4-硝基苯-Β-D-吡喃葡萄糖苷 在 Os₉BGlu₃₁ 作用下， 生成 1-sinapoyl-β-D-glucopyranoside
  参考文献：
  名称：

  酶法合成酚酸葡萄糖酯以测试对胆管癌细胞的活性。

  摘要：

  糖苷水解酶家族 1 (GH1) 酶主要催化水解反应，而水稻 Os9BGlu31 优先催化转糖基化，将一个葡萄糖基部分转移到另一个糖苷配基部分，通过保留机制形成新的糖基化化合物。在本研究中，Os9BGlu31 用于合成八种酚酸葡萄糖酯，并评估其在胆管癌细胞中的活性。对Os9BGlu31野生型及其突变体的转糖基化产物进行了检测、毫克级生产和纯化，并通过核磁共振波谱表征了它们的结构。通过抗氧化剂和抗增殖测定评估转糖基化产物，然后对选定的酚酸葡萄糖酯进行抗迁移测定。 Os9BGlu31 突变体比野生型酶对酚酸产生更高的产量和活性，以产生酚酸葡萄糖酯。其中，没食子酸葡萄糖酯（β-glucogallin）在胆管癌细胞中具有最高的抗氧化活性和抗增殖活性。它还抑制胆管癌细胞的迁移。我们的研究表明，水稻 Os9BGlu31 转葡萄糖苷酶是一种有前景的一步反应中生物活性化合物糖基化酶，并提供了 β-葡萄糖没食

  DOI：

  10.1007/s00253-023-12895-5

文献信息

• Molecular regulation of sinapate ester metabolism in <i>Brassica napus</i>: expression of genes, properties of the encoded proteins and correlation of enzyme activities with metabolite accumulation
  作者：Carsten Milkowski、Alfred Baumert、Diana Schmidt、Lilian Nehlin、Dieter Strack

  DOI：10.1111/j.1365-313x.2004.02036.x

  日期：2004.4

  Members of the Brassicaceae family accumulate specific sinapate esters, i.e. sinapoylcholine (sinapine), which is considered as a major antinutritive compound in seeds of important crop plants like Brassica napus, and sinapoylmalate, which is implicated in UV‐B tolerance in leaves. We have studied the molecular regulation of the sinapate ester metabolism in B. napus, and we describe expression of genes, some properties of the encoded proteins and profiles of the metabolites and enzyme activities. The cloned cDNAs encoding the key enzymes of sinapine biosynthesis, UDP‐glucose (UDP‐Glc):B. napus sinapate glucosyltransferase (BnSGT1) and sinapoylglucose:B. napus choline sinapoyltransferase (BnSCT), were functionally expressed. BnSGT1 belongs to a subgroup of plant GTs catalysing the formation of 1‐O‐hydroxycinnamoyl‐β‐d‐glucoses. BnSCT is another member of serine carboxypeptidase‐like (SCPL) family of acyltransferases. The B. napus genome contains at least two SGT and SCT genes, each derived from its progenitors B. oleracea and B. rapa. BnSGT1 and BnSCT activities are subjected to pronounced transcriptional regulation. BnSGT1 transcript level increases throughout early stages of seed development until the early cotyledonary stage, and stays constant in later stages. The highest level of BnSGT1 transcripts is reached in 2‐day‐old seedlings followed by a dramatic decrease. In contrast, expression of BnSCT is restricted to developing seeds. Regulation of gene expression at the transcript level seems to be responsible for changes of BnSGT1 and BnSCT activities during seed and seedling development of B. napus. Together with sinapine esterase (SCE) and sinapoylglucose:malate sinapoyltransferase (SMT), activities of BnSGT1 and BnSCT show a close correlation with the accumulation kinetics of the corresponding metabolites.

  摘要十字花科（Brassicaceae）植物积累特定的莽草酸酯，即莽草酰胆碱（sinapoylcholine，sinapine）和莽草酰基丙二酸酯（sinapoylmalate），前者被认为是十字花科（Brassica）等重要作物种子中的主要抗营养性化合物，后者则与叶片的紫外线-B耐受性有关。我们研究了油菜中芒硝酯代谢的分子调控，描述了基因的表达、编码蛋白的一些特性以及代谢产物和酶活性的概况。克隆的cDNA编码了油菜碱生物合成的关键酶--UDP-葡萄糖（UDP-Glc）：油菜碱式糖基转移酶（BnSGT1）和油菜碱式酰葡萄糖：油菜胆碱酰基转移酶（BnSCT）。BnSGT1 属于催化 1-O-hydroxycinnamoyl-β-d-glucose 形成的植物 GTs 亚群。BnSCT 是丝氨酸羧肽酶（SCPL）酰基转移酶家族的另一个成员。油菜基因组中至少含有两个 SGT 和 SCT 基因，分别来自其祖先 B. oleracea 和 B. rapa。BnSGT1 和 BnSCT 的活性受到明显的转录调控。BnSGT1 的转录水平在种子发育的整个早期阶段都在增加，直到子叶早期阶段，并在后期阶段保持不变。BnSGT1 转录本的最高水平在 2 天大的幼苗期达到，随后急剧下降。相比之下，BnSCT 的表达仅限于发育中的种子。转录本水平的基因表达调控似乎是导致 BnSGT1 和 BnSCT 活性在油菜种子和幼苗发育过程中发生变化的原因。BnSGT1 和 BnSCT 的活性与西奈平酯酶（SCE）和西奈平葡萄糖：苹果酸西奈平基转移酶（SMT）一起，显示出与相应代谢物的积累动力学密切相关。
• Biochemical Characterization of Sinapoylglucose:Choline Sinapoyltransferase, a Serine Carboxypeptidase-like Protein That Functions as an Acyltransferase in Plant Secondary Metabolism
  作者：Amber M. Shirley、Clint Chapple

  DOI：10.1074/jbc.m302362200

  日期：2003.5

  employed for catalysis by classical serine carboxypeptidases, although the importance of these residues and the mechanism by which this class of SCPL proteins catalyze acyltransferase reactions is unknown. To characterize further SCT and its catalytic mechanism, we have employed the Saccharomyces cerevisiae vacuolar protein localization 1 mutant, which secretes the serine carboxypeptidase, carboxypeptidase

  近来，已经从野生番茄和拟南芥中鉴定出了在植物次生代谢中催化转酰基反应的丝氨酸羧肽酶样（SCPL）蛋白。这些包括芥子碱葡萄糖：胆碱芥子碱转移酶（SCT），一种在拟南芥芥子酸酯合成中起作用的酶。SCT和其他已知的SCPL酰基转移酶均共享保守的丝氨酸，天冬氨酸和组氨酸残基，用于经典丝氨酸羧肽酶催化，尽管这些残基的重要性以及这类SCPL蛋白质催化酰基转移酶反应的机制尚不清楚。为了进一步表征SCT及其催化机制，我们使用了酿酒酵母液泡蛋白定位1突变体，该突变体分泌丝氨酸羧肽酶，羧肽酶Y，和其他通常靶向液泡的蛋白质。当在该菌株中表达时，SCT被类似地分泌。已从酵母培养基中纯化出SCT，并将其用于蛋白质的动力学表征。SCT的免疫学分析表明，预期的50 kDa成熟蛋白在酵母和植物中经过蛋白水解处理，最有可能导致衍生自30 kDa和17 kDa多肽的异二聚体的产生。
• Sinapate esters in brassicaceous plants: biochemistry, molecular biology, evolution and metabolic engineering
  作者：Carsten Milkowski、Dieter Strack

  DOI：10.1007/s00425-010-1168-z

  日期：2010.6

  antinutritive character of sinapine and related sinapate esters hamper the use of the valuable seed protein of the oilseed crop B. napus for animal feed and human nutrition. Due to limited variation in seed sinapine content within the assortment of B. napus cultivars, low sinapine lines cannot be generated by conventional breeding giving rise to genetic engineering of sinapate ester metabolism as a promising

  芸苔属植物的特征是通过莽草酸/苯丙烷途径产生明显的朝向芥子酸的代谢通量，该途径被转化为广谱的O-酯缀合物。甘蓝型油菜和拟南芥中丰富的芥子酸酯反映了一个众所周知的代谢网络，包括 UDP-葡萄糖：芥子酸葡萄糖基转移酶 (SGT)、芥子酰葡萄糖:胆碱芥子酸转移酶 (SCT)、芥子酰葡萄糖:l-苹果酸芥子酸转移酶 (SCT) ) 酯酶 (SCE)。1-O-Sinapoylglucose 在种子发育过程中由 SGT 产生，通过 SCT 转化为芥子碱并在发芽种子中被 SCE 水解。释放的芥子酸通过芥子酰葡萄糖进入 SMT 催化的幼苗中芥子酸的生物合成。Sinapoylmalate 参与保护叶子免受 UV-B 辐射的有害影响。Sinapine 可作为储存载体，随时为幼苗中的磷脂酰胆碱生物合成提供胆碱。芥子碱和相关芥子酸酯的抗营养特性阻碍了油料作物欧洲油菜的宝贵种子蛋白质用于动物饲料和人类营养的用途。由于
• Related Arabidopsis Serine Carboxypeptidase-Like Sinapoylglucose Acyltransferases Display Distinct But Overlapping Substrate Specificities
  作者：Christopher M. Fraser、Michael G. Thompson、Amber M. Shirley、John Ralph、Jessica A. Schoenherr、Taksina Sinlapadech、Mark C. Hall、Clint Chapple

  DOI：10.1104/pp.107.098970

  日期：2007.8

  The Arabidopsis (Arabidopsis thaliana) genome encodes 51 proteins annotated as serine carboxypeptidase-like (SCPL) enzymes. Nineteen of these SCPL proteins are highly similar to one another, and represent a clade that appears to be unique to plants. Two of the most divergent proteins within this group have been characterized to date, sinapoyl-glucose (Glc):malate sinapoyltransferase and sinapoyl-Glc:choline sinapoyltransferase. The fact that two of the least related proteins within this clade are acyltransferases rather than true serine carboxypeptidases suggests that some or all of the remaining members of this group may have similar activities. The gene that encodes sinapoyl-Glc:malate sinapoyltransferase (sinapoyl-Glc accumulator1 [SNG1]: At2g22990) is one of five SCPL genes arranged in a cluster on chromosome 2. In this study, an analysis of deletion mutant lines lacking one or more genes in this SCPL gene cluster reveals that three of these genes also encode sinapoyl-Glc-dependent acyltransferases. At2g23000 encodes sinapoyl-Glc:anthocyanin acyltransferase, an enzyme that is required for the synthesis of the sinapoylated anthocyanins in Arabidopsis. At2g23010 encodes an enzyme capable of synthesizing 1,2-disinapoyl-Glc from two molecules of sinapoyl-Glc, an activity shared by SNG1 and At2g22980. Sequence analysis of these SCPL proteins reveals pairwise percent identities that range from 71% to 78%, suggesting that their differing specificities for acyl acceptor substrates are due to changes in a relatively small subset of amino acids. The study of these SCPL proteins provides an opportunity to examine enzyme structure-function relationships and may shed light on the role of evolution of hydroxycinnamate ester metabolism and the SCPL gene family in Arabidopsis and other flowering plants.

  酶。
• A Novel Glucosylation Reaction on Anthocyanins Catalyzed by Acyl-Glucose–Dependent Glucosyltransferase in the Petals of Carnation and Delphinium  
  作者：Yuki Matsuba、Nobuhiro Sasaki、Masayuki Tera、Masachika Okamura、Yutaka Abe、Emi Okamoto、Haruka Nakamura、Hisakage Funabashi、Makoto Takatsu、Mikako Saito、Hideaki Matsuoka、Kazuo Nagasawa、Yoshihiro Ozeki

  DOI：10.1105/tpc.110.077487

  日期：2010.11.24

  Glucosylation of anthocyanin in carnations (Dianthus caryophyllus) and delphiniums (Delphinium grandiflorum) involves novel sugar donors, aromatic acyl-glucoses, in a reaction catalyzed by the enzymes acyl-glucose–dependent anthocyanin 5(7)-O-glucosyltransferase (AA5GT and AA7GT). The AA5GT enzyme was purified from carnation petals, and cDNAs encoding carnation Dc AA5GT and the delphinium homolog Dg AA7GT were isolated. Recombinant Dc AA5GT and Dg AA7GT proteins showed AA5GT and AA7GT activities in vitro. Although expression of Dc AA5GT in developing carnation petals was highest at early stages, AA5GT activity and anthocyanin accumulation continued to increase during later stages. Neither Dc AA5GT expression nor AA5GT activity was observed in the petals of mutant carnations; these petals accumulated anthocyanin lacking the glucosyl moiety at the 5 position. Transient expression of Dc AA5GT in petal cells of mutant carnations is expected to result in the transfer of a glucose moiety to the 5 position of anthocyanin. The amino acid sequences of Dc AA5GT and Dg AA7GT showed high similarity to glycoside hydrolase family 1 proteins, which typically act as β-glycosidases. A phylogenetic analysis of the amino acid sequences suggested that other plant species are likely to have similar acyl-glucose–dependent glucosyltransferases.

  石竹（Dianthus caryophyllus）和翠雀花（Delphinium grandiflorum）中花青素的葡萄糖化涉及新型糖基供体，芳香基酰基葡萄糖，由酰基葡萄糖依赖的花青素5（7）-O-葡萄糖基转移酶（AA5GT和AA7GT）催化反应。从石竹花瓣中纯化了AA5GT酶，并分离了编码石竹Dc AA5GT和翠雀花同源物Dg AA7GT的cDNA。重组的Dc AA5GT和Dg AA7GT蛋白在体外表现出AA5GT和AA7GT活性。虽然Dc AA5GT在石竹花瓣的发育早期表达最高，但AA5GT活性和花青素积累在后期仍然持续增加。在突变石竹花瓣中，既没有观察到Dc AA5GT表达，也没有AA5GT活性；这些花瓣积累了缺乏5位葡萄糖基的花青素。预计在突变石竹花瓣细胞中短暂表达Dc AA5GT将导致将葡萄糖基转移至花青素的5位。Dc AA5GT和Dg AA7GT的氨基酸序列与糖苷水解酶家族1蛋白的高度相似，这些蛋白通常作为β-葡萄糖苷酶。氨基酸序列的系统发育分析表明，其他植物物种可能具有类似的酰基葡萄糖依赖性葡萄糖转移酶。