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shikimic acid accelerates phase change and flowering in Chinese jujube

Horticultural Plant Journal 2024年第2期10卷 413-424页

作者： Xianwei Meng Zhiguo Liu Li Dai Weiqiang Zhao Jiurui Wang Lili Wang Yuanpei Cui Ying Li Yinshan Cui Yao Zhang Luyao Wang Fengjiao Yu Jin Zhao Mengjun Liu Research Center of Chinese Jujube Hebei Agricultural UniversityBaodingHebei 071000China College of Horticulture Hebei Agricultural UniversityBaodingHebei 071000China College of Life Science Hebei Agricultural UniversityBaodingHebei 071000China College of Forestry Hebei Agricultural UniversityBaodingHebei 071000China eCollege of Economics and ManagementHebei Agricultural UniversityBaodingHebei 071000China College of Economics and Management Hebei Agricultural University

The juvenile-to-adult phase change with first flowering as the indicator plays a crucial role in the lifecycle of fruit trees. However, the molecular mechanisms underlying phase change in fruit trees remain largely unknown. shikimic acid (ShA) pathway is a main metabolic pathway closely related to the synthesis of hormones and many important secondary metabolites participating in plant phase change. So,whether ShA regulates phase change in plants is worth clarifying. Here, the distinct morphological characteristics and the underlying mechanisms of phase change in jujube (Ziziphus jujuba Mill.), an important fruit tree native to China with nutritious fruit and outstanding tolerance abiotic stresses, were clarified. A combined transcriptome and metabolome analysis found that ShA is positively involved in jujube(Yuhong’×Xing 16’) phase change. The genes in the upstream of ShA synthesis pathway (ZjDAHPS, ZjDHQS and ZjSDH), the contents of ShA and the downstream secondary metabolites like phenols were significantly upregulated in the phase change period. Further, the treatment of spraying exogenous ShA verified that ShA at a very low concentration (60 mg·L^(-1)) can substantially speed up the phase change and flowering of jujube and other tested plants including Arabidopsis, tomato and wheat. The exogenous ShA (60 mg·L^(-1)) treatment in jujube seedlings could increase the accumulation of endogenous ShA, enhance leaf photosynthesis and the synthesis of phenols especially flavonoids and phenolic acids, and promote the expression of genes (ZjCOs, ZjNFYs and ZjPHYs) involved in flowering pathway. Basing on above results, we put forward a propose for the underlying mechanism of ShA regulating phase change, and a hypothesis that ShA could be considered a phytohormone-like substance because it is endogenous, ubiquitous, movable and highly efficient at very low concentrations. This study highlights the critical role of ShA in plant phase change and its phytohormone-like propert

关键词： Ziziphus jujuba Mill. Phase change Flowering shikimic acid Transcriptome Metabolome

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Enhanced production of shikimic acid using a multi-gene co-expression system in Escherichia coli

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Chinese Journal of Natural Medicines 2016年第4期14卷 286-293页

作者： LIU Xiang-Lei LIN Jun HU Hai-Feng ZHOU Bin ZHU Bao-Quan State Key Laboratory of New Drug and Pharmaceutical Process Shanghai Institute of Pharmaceutical IndustryChina State Institute of Pharmaceutical IndustryShanghai 201203China

shikimic acid(SA) is the key synthetic material for the chemical synthesis of Oseltamivir, which is prescribed as the front-line treatment for serious cases of influenza. Multi-gene expression vector can be used for expressing the plurality of the genes in one plasmid, so it is widely applied to increase the yield of metabolites. In the present study, on the basis of a shikimate kinase genetic defect strain Escherichia coli BL21(?aro L/aro K, DE3), the key enzyme genes aro G, aro B, tkt A and aro E of SA pathway were co-expressed and compared systematically by constructing a series of multi-gene expression vectors. The results showed that different gene co-expression combinations(two, three or four genes) or gene orders had different effects on the production of SA. SA production of the recombinant BL21-GBAE reached to 886.38 mg·L^(-1), which was 17-fold(P < 0.05) of the parent strain BL21(?aro L/aro K, DE3).

关键词： shikimic acid Escherichia coli Multi-gene co-expression

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Improved Stereoselective Syntheses of （-t-）-Valiolamine and （-I-）-Valienamine Starting from （-）-shikimic acid

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Chinese Journal of Chemistry 2017年第4期35卷 457-464页

作者： Fenglei Li Wei Ding Na Quan Jiajia Wu Yungang He Xingliang Zhu Xiaoxin Shi Jianhong Zhao Shanghai Key Laboratory of Chemical Biology School of Pharmacy East China University of Science and Technology Shanghai 200237 China

Improved stereoselective syntheses of the targeted compounds （＋）-valiolamine 1 and （＋）-valienamine 2 starting from naturally abundant （–）-shikimic acid are described. A common key intermediate compound 7 was first synthesized from （–）-shikimic acid in 9 steps. The compound 7 was then converted to （＋）-valiolamine 1 in 3 steps, and was also converted to （＋）-valienamine 2 in 4 steps. In summary, （＋）-valiolamine 1 and （＋）-valienamine 2 were synthesized from （–）-shikimic acid in 12 （or 13） steps in 40% and 39% overall yields, respectively.

关键词： valiolamine valienamine shikimic acid practical synthesis

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Facile Synthesis of Dipeptidomimetics of shikimic acid

Facile Synthesis of Dipeptidomimetics of Shikimic Acid

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有机合成创新—产业化的新动力——中国化学会全国第三届有机合成化学与过程学术讨论会

作者：杨大成汪林发 School of Chemistry and Chemical Engineering Southwest University

A series of new amino acid derivatives of shikimic acid(dipeptidomimetics of shikimic acid) were synthesized by coupling of shikimic acid derivatives modified by 4-nitrobenzaldehyde with seven amino acid methyl *** st... 详细信息

关键词： shikimic acid shikimic acid derivatives amino acid derivatives dipeptidomimetics

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Extraction and Content Determination of shikimic acid in Pinus elliottii Engelm

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Agricultural Science & Technology 2010年第3期11卷 177-181页

作者：谢济运陈小鹏李志荣陈芳粟本超广西大学化学化工学院广西南宁530004 柳州师范高等专科学校广西柳州545004

[Objective] The aim was to provide scientific basis for development and utilization of Pinus elliottii Engelm resources.[Method] The extraction process of shikimic acid in Pinus elliottii Engelm was studied,and the content of shikimic acid was determined by *** HPLC conditions were as follows;Alltima NH2 （5 μm,4.6 mm × 150 mm） column separation;the mobile phase was acetonitrile-2%H3PO4 （90：10）;the flowing velocity was 1 ml/min;test wavelength was 213 nm,the width of belt was 16 nm;reference wavelength was 300 nm,the width of belt was 80 nm.[Result] By the single factor and orthogonal tests,the optimum conditions were found as follows：ethanol concentration 60%,extraction temperature 75 ℃,solid-liquid ratio 1：25,extraction time 2.5 *** extraction rate of shikimic acid was 1.49%.[Conclusion] shikimic acid in Pinus elliottii Engelm could be used as a new resource to develop and utilize.

关键词： Pinus elliottii Engelm shikimic acid Ethanol extraction Orthogonal test

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Facile Syntheses of (6S)-6-Fluoroshikimic acid and (6R)-6-Hydroxyshikimic acid

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Chemical Research in Chinese Universities 2002年第2期18卷 146-152页

作者： Chuanjun Song Shende Jiang Gurdial Singh Department of Chemistry University of SunderlandSunderlandSR13SDUK Department of Applied Chemistry Tianjin UniversityTianjin 300072P.R.China

(6S)-6-Fluoroshikimic acid 2 and (6 R ) 6 hydroxyshikimic acid 3 have been synthesized via an OsO 4 catalysed dihydroxylation of diene 7, which was derived from (-) shikimic acid 1.

关键词： Shikimate pathway shikimic acid Fluoroshikimic acid Dihydroxylation Fluorination

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Novel and Efficient Syntheses of Four Useful Shikimate- derived Epoxy Chiral Building Blocks via Cyclic Sulfite Intermediates

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Chinese Journal of Chemistry 2012年第12期30卷 2759-2766页

作者： Quan Na Nie Liangdeng Shi Xiaoxin Zhu Ruiheng Lu Xian Department of Pharmaceutical Engineering School of Pharmacy East China University of Science and Technology Shanghai 200237 China

All of the four stereoisomers of methyl 4,5-epoxy-3-hydroxy-cyclohex-l-ene-carboxylate （la--ld） are useful chiral building blocks. Novel and efficient syntheses of these four epoxy chiral building blocks from naturally abun- dant （--）-shikimic acid （2） via cyclic sulfite intermediates are described in this article. The targeted compound （3R,4R,5S）-la was synthesized via four steps from （--）-shikimic acid in 79% overall yield. The other three targeted compounds （3S,4R,5S）-lb, （3S,4S,5R）-1c and （3R,4S,5R）-ld were synthesized via seven steps from （--）-shikimic acid in 56%, 64% and 65% overall yields, respectively.

关键词： chiron cyclic sulfite epoxide shikimic acid synthesis

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Enantioselective Total Synthesis of the (+) Antipode of Zeylenone

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Chinese Chemical Letters 2004年第12期15卷 1433-1436页

作者： AnLIU ZhanZhuLIU ZhongMeiZOU ShiZhiCHEN LiZhenXU ShiLinYANG InstituteofMedicinalPlantDevelopment ChineseAcademyofMedicalSciencesandPekingUnionMedicalCollegeBeijing100094 InstituteofMateriaMedica ChineseAcademyofMedicalSciencesandPekingUnionMedicalCollegeBeijing100050

Starting from shikimic acid, the total synthesis of zeylenone was studied. The productwas proved to be the (+)antipode of zeylenone through analysis and comparison of their respectivespectra (including NMR, MS, IR and... 详细信息

关键词： Zeylenone absolute configurtion shikimic acid total synthesis enantiomer.

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Occurrence of Glyphosate-Resistant Horseweed (Conyza canadensis) Population in China

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Agricultural Sciences in China 2011年第7期10卷 1049-1055页

作者： SONG Xiao-ling WU Jia-jun ZHANG Hong-jun QIANG Sheng Weed Research Laboratory Nanjing Agricultural University Nanjing 210095 P.R.China Institute for the Control of Agrochemicals Ministry of Agriculture （CAMA） Beijing 100026 P.R.China

Horseweed （Conyza canadensis）, an invasive alien weed, is one of the main weeds in orchards in China. Although glyphosate has been used for control of horseweed and many other weeds in orchards for more than 25 years in China, a case of glyphosate-resistant horseweed has not been identified in orchard in China so far despite glyphosate-resistant horseweed cases have been reported in some other countries. Seeds of 25 horseweed populations were collected from different orchards with different glyphosate application history. Potted seedlings with 11-13-leaf growth stage were treated with glyphosate at 0.035, 0.07, 0.14, 0.28, 0.56, 1.12, 2.24, 4.48, and 8.96 kg a.i. ha-1. The dosage dependence response curve of each population was constructed with Log-logistic dose response regression equations. The ED50 value of each population was calculated and compared with the susceptible population from China. Different populations had different relative glyphosate-resistant levels which increased with the number of years of glyphosate application. Two populations with the highest resistance levels, 8.28 and 7.95 times, were found in Ningbo, Zhejiang Province, China, where glyphosate was used for weed control in orchards twice each year for 15 yr. The two resistant populations accumulated approximately two to four times less shikimic acid than the two susceptible populations 48 h after glyphosate application.

关键词： horseweed [Conyza canadensis (L.) Cronq.] glyphosate resistance shikimic acid

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Glyphosate Effects on Sugarcane Metabolism and Growth

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American Journal of Plant Sciences 2014年第24期5卷 3585-3593页

作者： Caio Antonio Carbonari Giovanna Larissa Gimenes Cotrick Gomes Edivaldo Domingues Velini Renato Fernandes Machado Plinio Saulo Simoes Gabrielle de Castro Macedo Department of Crop Science College of Agricultural SciencesSao Paulo State University(UNESP)BotucatuBrazil

Glyphosate is the most widely used herbicide in the world. In sugarcane, it is used as a herbicide when applied at its field rate, but it is also used as ripener when applied as low doses. However, the effects of glyphosate on plant metabolism and sugarcane growth are not fully understood. This study aimed to evaluate the metabolic changes and the effects on sugarcane plant growth caused by the application of different doses of glyphosate. Sugarcane plants were grown in a greenhouse and subjected to glyphosate applications at doses of 7.2;18;36;72;180;360 and 720 g a.e. ha-1. Plants grown without an herbicide application were used as a control. Plants from each treatment were collected at 2, 7, 14, and 21 days after treatment (DAT) application to quantify the levels of shikimic acid, quinic acid, shikimate-3-phosphate, glyphosate, α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA), phenylalanine, tyrosine, and tryptophan. Visual evaluations of plant intoxication were performed at the same time as the collection of plants, and the quantification of their shoot dry biomass was performed at 21 DAT. At doses of glyphosate greater than 72 g a.e. ha-1, increases in the levels of shikimic acid, quinic acid, and shikimate-3-phosphate occurred and AMPA was detected in the plants. Initially, glyphosate caused increases in the plant levels of phenylalanine and tyrosine at doses of 72 and 180 g a.e. ha-1, although a decrease in the levels of aromatic amino acids subsequently occurred at and above the doses of 72 or 180 g a.e. ha-1. The doses ranging from 7.2 to 36 g a.e. ha-1 promoted an increase in plant shoot biomass, and doses greater than 72 g a.e. ha-1 caused significant reductions in dry mass.

关键词： EPSPS AMPA shikimic acid Herbicide Sugarcane Ripener

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