Citation: Mian Dou, Xi-Hui He, Yan Sun, Fang Peng, Jiang-Yun Liu, Li-Li Hao, Shi-Lin Yang. Controlled acid hydrolysis and kinetics of flavone C-glycosides from trollflowers[J]. Chinese Chemical Letters, ;2015, 26(2): 255-258. doi: 10.1016/j.cclet.2014.11.021 shu

Controlled acid hydrolysis and kinetics of flavone C-glycosides from trollflowers

Mian Dou ^a,b ,
Xi-Hui He ^b ,
Yan Sun ^a ,
Fang Peng ^a ,
Jiang-Yun Liu ^a,, ,
Li-Li Hao ^a ,
Shi-Lin Yang ^a

1.
a College of Pharmaceutical Sciences, Soochow University, Suzhou 215123, China;
2.
b School of Pharmaceutical Sciences, Peking University Health Science Center, Beijing 100191, China

Corresponding author: Jiang-Yun Liu,
Received Date: 14 June 2014
Available Online: 29 September 2014
Fund Project: This work was supported by National Natural Science Foundation of China (No. 81274190) (No. 81274190) and Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD). (No. BE2012649)

Acid hydrolysis mechanisms of orientin-2″-O-galactopyranoside (OGA), orientin and other flavone C-glycosides in the trollflowers (Trollius chinensis Bunge) were studied in this report for the first time. Hydrolysis parameters including temperature, acidity, solvent and reaction time were comprehensively investigated. OGA could be hydrolyzed to orientin, followed by an isomerization to isoorientin to isoorientin via a reversible Wessely-Moser rearrangement reaction under stronger acidic conditions. A first-order kinetic model fitted the hydrolysis process of OGA well. Under the optimal hydrolysis conditions of 80℃, 1.0 mol/L H⁺ and 7 h reaction time, about 77% OGA was transformed to orientin with no detectable isoorientin. These results could be helpful for better understanding of the acid hydrolysis kinetics of flavone C-glycosides, as well as the preparation of these valuable components under controlled acid hydrolysis conditions.
- Flavone C-glycoside,
- Orientin,
- Trollius chinensis,
- Acid hydrolysis,
- Kinetic
1. [1]
  [1] Chinese Pharmacopeia Committee, Chinese Pharmacopeia (Part I), China Medical Science and Technology Press, Beijing, 2010, p. 372 (Hawthorn leave extract); 828 (Trollflower throat lozenge).
2. [2]
  [2] Y. Zhang, B. Bao, B. Lu, et al., Determination of flavone C-glucosides in antioxidant of bamboo leaves (AOB) fortified foods by reversed phase high-performance liquid chromatography with ultraviolet diode arraydetection, J. Chromatogr. A 1065 (2005) 177-185.
3. [3]
  [3] R.F. Wang, X.W. Yang, C.M. Ma, Trolliside, a new compound from the flowers of Trollius chinensis, J. Asian Nat. Prod. Res. 6 (2004) 139-144.
4. [4]
  [4] (a) J.H. Zou, J.S. Yang, L. Zhou, Acylated flavone C-glycosides from Trollius Ledebouri, J. Nat. Prod. 67 (2004) 664-666; (b) J.H. Zou, J.S. Yang, Y.S. Dong, L. Zhou, G. Lin, Flavone C-glycosides from flowers of Trollius ledebouri, Phytochemistry 66 (2005) 1121-1125.
5. [5]
  [5] S.Q. Cai, R. Wang, X. Yang, et al., Antiviral flavonoid-type C-glycosides from the flowers of Trollius chinensis, Chem. Biodivers. 3 (2006) 343-348.
6. [6]
  [6] X.Q. Li, Z.L. Xiong, X.X. Ying, et al., A rapid ultra-performance liquid chromatography-electrospray ionization tandem mass spectrometric method for the qualitative and quantitative analysis of the constituents of the flower of Trollius ledibouri Reichb, Anal. Chim. Acta 580 (2006) 170-180.
7. [7]
  [7] Y. Zhang, X. Tie, B. Bao, X. Wu, Y. Zhang, Metabolism of flavone C-glucosides and pcoumaric acid from antioxidant of bamboo leaves (AOB) in rats, Br. J. Nutr. 97 (2007) 484-494.
8. [8]
  [8] N. Krafczyk, M.A. Glomb, Characterization of phenolic compounds in rooibos tea, J. Agric. Food Chem. 56 (2008) 3368-3376.
9. [9]
  [9] A.K. Verma, R. Pratap, Chemistry of biologically important flavones, Tetrahedron 68 (2012) 8523-8538.
10. [10]
  [10] J.Y. Liu, J.Y. Feng, S.Y. Li, et al., Flavone C-glycosides from the flowers of Trollius chinensis and their anti-complementary activity, J. Asian Nat. Prod. Res. 15 (2013) 325-331.
11. [11]
  [11] Y. Sun, H.Y. Yuan, L.L. Hao, et al., Enrichment and antioxidant properties of flavone C-glycosides from trollflowers using macroporous resin, Food Chem. 141 (2013) 533-541.
12. [12]
  [12] Y.L. Li, S.C. Ma, Y.T. Yang, S.M. Ye, P.P. But, Antiviral activities of flavonoids and organic acid from Trollius chinensis Bunge, J. Ethnopharmacol. 79 (2002) 365-368.
13. [13]
  [13] X.A. Wu, Y.M. Zhao, N.J. Yu, Flavone C-glycosides from Trollius ledebouri reichb, J. Asian Nat. Prod. Res. 7 (2005) 1-4.
14. [14]
  [14] C.N. Sun, M.M. Shen, L.L. Deng, J.Q. Mo, B.W. Zhou, Kinetics of ring-opening polymerization of octamethylcyclotetrasiloxane in microemulsion, Chin. Chem. Lett. 25 (2014) 621-626.
1. [1]
  Dan-Ying Xing , Xiao-Dan Zhao , Chuan-Shu He , Bo Lai . Kinetic study and DFT calculation on the tetracycline abatement by peracetic acid. Chinese Chemical Letters, 2024, 35(9): 109436-. doi: 10.1016/j.cclet.2023.109436
2. [2]
  Yongheng Ren , Yang Chen , Hongwei Chen , Lu Zhang , Jiangfeng Yang , Qi Shi , Lin-Bing Sun , Jinping Li , Libo Li . Electrostatically driven kinetic Inverse CO2/C2H2 separation in LTA-type zeolites. Chinese Journal of Structural Chemistry, 2024, 43(10): 100394-100394. doi: 10.1016/j.cjsc.2024.100394
3. [3]
  Yuexiang Liu , Xiangqiao Yang , Tong Lin , Guantian Yang , Xiaoyong Xu , Bubing Zeng , Zhong Li , Weiping Zhu , Xuhong Qian . Efficient continuous synthesis of 2-[3-(trifluoromethyl)phenyl]malonic acid, a key intermediate of Triflumezopyrim, coupling with esterification-condensation-hydrolysis. Chinese Chemical Letters, 2025, 36(1): 109747-. doi: 10.1016/j.cclet.2024.109747
4. [4]
  Ruilong Geng , Lingzi Peng , Chang Guo . Dynamic kinetic stereodivergent transformations of propargylic ammonium salts via dual nickel and copper catalysis. Chinese Chemical Letters, 2024, 35(8): 109433-. doi: 10.1016/j.cclet.2023.109433
5. [5]
  Ling Tang , Yan Wan , Yangming Lin . Lowering the kinetic barrier via enhancing electrophilicity of surface oxygen to boost acidic oxygen evolution reaction. Chinese Journal of Structural Chemistry, 2024, 43(11): 100345-100345. doi: 10.1016/j.cjsc.2024.100345
6. [6]
  Meng Shan , Yongmei Yu , Mengli Sun , Shuping Yang , Mengqi Wang , Bo Zhu , Junbiao Chang . Bifunctional organocatalyst-catalyzed dynamic kinetic resolution of hemiketals for synthesis of chiral ketals via hydrogen bonding control. Chinese Chemical Letters, 2025, 36(1): 109781-. doi: 10.1016/j.cclet.2024.109781
7. [7]
  Ruixue Liu , Xiaobing Ding , Qiwei Lang , Gen-Qiang Chen , Xumu Zhang . Enantioselective and divergent construction of chiral amino alcohols and oxazolidin-2-ones via Ir-f-phamidol-catalyzed dynamic kinetic asymmetric hydrogenation. Chinese Chemical Letters, 2025, 36(3): 110037-. doi: 10.1016/j.cclet.2024.110037
8. [8]
  Zhen Liu , Zhi-Yuan Ren , Chen Yang , Xiangyi Shao , Li Chen , Xin Li . Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C₆F₅)₃/chiral phosphoric acid. Chinese Chemical Letters, 2024, 35(5): 108939-. doi: 10.1016/j.cclet.2023.108939
9. [9]
  Jing LIANG , Qian WANG , Junfeng BAI . Synthesis and structures of cdq-topological quaternary and (4, 4, 8)-c topological quinary Zn-MOFs with both oxalic acid and triazole ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2186-2192. doi: 10.11862/CJIC.20240177
10. [10]
  Bin Dong , Ning Yu , Qiu-Yue Wang , Jing-Ke Ren , Xin-Yu Zhang , Zhi-Jie Zhang , Ruo-Yao Fan , Da-Peng Liu , Yong-Ming Chai . Double active sites promoting hydrogen evolution activity and stability of CoRuOH/Co₂P by rapid hydrolysis. Chinese Chemical Letters, 2024, 35(7): 109221-. doi: 10.1016/j.cclet.2023.109221
11. [11]
  Xian-Fa Jiang , Chongyun Shao , Zhongwen Ouyang , Zhao-Bo Hu , Zhenxing Wang , You Song . Generating electron spin qubit in metal-organic frameworks via spontaneous hydrolysis. Chinese Chemical Letters, 2024, 35(7): 109011-. doi: 10.1016/j.cclet.2023.109011
12. [12]
  Ao Sun , Zipeng Li , Shuchun Li , Xiangbao Meng , Zhongtang Li , Zhongjun Li . Stereoselective synthesis of α-3-deoxy-D-manno-oct-2-ulosonic acid (α-Kdo) derivatives using a C3-p-tolylthio-substituted Kdo fluoride donor. Chinese Chemical Letters, 2025, 36(3): 109972-. doi: 10.1016/j.cclet.2024.109972
13. [13]
  Jing Guo , Zhi-Guo Lu , Rui-Chen Zhao , Bao-Ku Li , Xin Zhang . Nucleic acid therapy for metabolic-related diseases. Chinese Chemical Letters, 2025, 36(3): 109875-. doi: 10.1016/j.cclet.2024.109875
14. [14]
  Wenyi Mei , Lijuan Xie , Xiaodong Zhang , Cunjian Shi , Fengzhi Wang , Qiqi Fu , Zhenjiang Zhao , Honglin Li , Yufang Xu , Zhuo Chen . Design, synthesis and biological evaluation of fluorescent derivatives of ursolic acid in living cells. Chinese Chemical Letters, 2024, 35(5): 108825-. doi: 10.1016/j.cclet.2023.108825
15. [15]
  Huipeng Zhao , Xiaoqiang Du . Polyoxometalates as the redox anolyte for efficient conversion of biomass to formic acid. Chinese Journal of Structural Chemistry, 2024, 43(2): 100246-100246. doi: 10.1016/j.cjsc.2024.100246
16. [16]
  Lihang Wang , Mary Li Javier , Chunshan Luo , Tingsheng Lu , Shudan Yao , Bing Qiu , Yun Wang , Yunfeng Lin . Research advances of tetrahedral framework nucleic acid-based systems in biomedicine. Chinese Chemical Letters, 2024, 35(11): 109591-. doi: 10.1016/j.cclet.2024.109591
17. [17]
  Hanqing Zhang , Xiaoxia Wang , Chen Chen , Xianfeng Yang , Chungli Dong , Yucheng Huang , Xiaoliang Zhao , Dongjiang Yang . Selective CO2-to-formic acid electrochemical conversion by modulating electronic environment of copper phthalocyanine with defective graphene. Chinese Journal of Structural Chemistry, 2023, 42(10): 100089-100089. doi: 10.1016/j.cjsc.2023.100089
18. [18]
  Linshan Peng , Qihang Peng , Tianxiang Jin , Zhirong Liu , Yong Qian . Highly efficient capture of thorium ion by citric acid-modified chitosan gels from aqueous solution. Chinese Chemical Letters, 2024, 35(5): 108891-. doi: 10.1016/j.cclet.2023.108891
19. [19]
  Yingying Yan , Wanhe Jia , Rui Cai , Chun Liu . An AIPE-active fluorinated cationic Pt(Ⅱ) complex for efficient detection of picric acid in aqueous media. Chinese Chemical Letters, 2024, 35(5): 108819-. doi: 10.1016/j.cclet.2023.108819
20. [20]
  Fengyun Li , Zerong Pei , Shuting Chen , Gen li , Mengyang Liu , Liqin Ding , Jingbo Liu , Feng Qiu . Multifunctional nano-herb based on tumor microenvironment for enhanced tumor therapy of gambogic acid. Chinese Chemical Letters, 2024, 35(5): 108752-. doi: 10.1016/j.cclet.2023.108752

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(812)
HTML views(113)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142