Journal of Pharmaceutical and Biomedical Sciences

The Extraction and Isolation of Flavonoid from Astragali Radix and Their Enzymatic Acylation Derivatives with Fatty Acid Vinyl Esters by Novozym435

Qingxia Peng, Rian Yan, Haimei Li

Abstract


This study aimed at developing a strategy to gain access to more Astragalus flavonoids and then enzymatically acylated through transesterification with fatty acid vinyl esters by Novozym435. The extraction of total flavonoids was optimized by considering the concentration of ethanol, ultrasonic extraction temperature, liquid to material ratio and ultrasonic power. The optimized conditions were as follows: 20:1(mL/g) of the liquid to the material, 70% ethanol ultrasonic temperature of 80 celcius with the aid of ultrasonic waves in 300 W. Calycosin-7-O-Beta-D-glucoside (C7G) and formononetin-7-O-Beta-D-glucoside (F7G) were separated from total flavonoids by column chromatography and then identified by mass spectrometry (MS) and nuclear magnetic resonance (NMR). Furthermore, the absorption peak at approximate 1700 cm-1 in IR analysis indicated acylation did actually take place.


Keywords


extraction, isolation, Astragali Radix, enzymatic acylation, vinyl eaters.

Full Text:

References


Zheng QH, Findlay JA. Constituents of Astragalus Membranceus. J Nat Prod. 1991; 54: 810-815. doi.org/10.1021/np50075a009.

Bratkov VM, Shkondrov AM, Zdraveva PK, Krasteva IN. Flavonoids from the Genus Astragalus: Phytochemistry and Biological Activity. Pharmacogn Rev. 2016;10(19):11-32. doi:10.4103/0973-7847.176550.

Hertog MGL, Hollman PCH, Katan MB. Content of potentially anticarcinogenic flavonoids of 28 vegetables and 9 fruits commonly consumed in The Netherlands. Journal of Agricultural and Food Chemistry. 1992 Dec;40(12):2379-2383. doi: 10.1021/jf00024a011.

Yang LP, Shen JG, Xu WC, Li J, Jiang JQ. Secondary metabolites of the genus Astragalus: structure and biological-activity update. Chem Biodivers. 2013 Jun;10(6):1004-54. doi: 10.1002/cbdv.201100444.

Harborne JB, Williams CA. Advances in flavonoid research since 1992. Phytochemistry. 2000 Nov;55(6):481-504. doi: 10.1016/s0031-9422(00)00235-1.

Dugas AJ Jr, Castañeda-Acosta J, Bonin GC, Price KL, Fischer NH, Winston GW. Evaluation of the total peroxyl radical-scavenging capacity of flavonoids: structure-activity relationships. J Nat Prod. 2000 Mar;63(3):327-31. doi: 10.1021/np990352n.

Cho WC, Leung KN. In vitro and in vivo immunomodulating and immunorestorative effects of Astragalus membranaceus. J Ethnopharmacol. 2007 Aug 15;113(1):132-41. doi: 10.1016/j.jep.2007.05.020.

Ionkova I, Shkondrov A, Krasteva I, Ionkov T. Recent progress in phytochemistry, pharmacology and biotechnology of Astragalus saponins. Phytochem Rev. 2014, 13 (2): 343-374. doi: 10.1007/s11101-014-9347-3.

Zhang, Zhang D, Wang D. Progressive studies on biological activity of total flavonoids of Astragalus. China Journal of Chinese Materia Medica. 2010 Jan;35(2):253-256. doi: 10.4268/cjcmm20100230.

Hu Y, Min J, Qu Y, Zhang X, Zhang J, Yu X, Dai L. Biocatalytic Synthesis of Calycosin-7-O-?-D-Glucoside with Uridine Diphosphate–Glucose Regeneration System. Catalysts. 2020; 10(2):258. https://doi.org/10.3390/catal10020258.

Fu J, Wang Z, Huang L, Zheng S, Wang D, Chen S, Zhang H, Yang S. Review of the botanical characteristics, phytochemistry, and pharmacology of Astragalus membranaceus (Huangqi). Phytother Res. 2014 Sep;28(9):1275-83. doi: 10.1002/ptr.5188.

Promden W, Monthakantirat O, Umehara K, Noguchi H, De-Eknamkul W. Structure and antioxidant activity relationships of isoflavonoids from Dalbergia parviflora. Molecules. 2014 Feb 20;19(2):2226-37. doi: 10.3390/molecules19022226.

Yerramsetty V, Mathias K, Bunzel M, Ismail B. Detection and structural characterization of thermally generated isoflavone malonylglucoside derivatives. J Agric Food Chem. 2011 Jan 12;59(1):174-83. doi: 10.1021/jf103564y.

Huang Z, Fang F, Wang J, Wong CW. Structural activity relationship of flavonoids with estrogen-related receptor gamma. FEBS Lett. 2010 Jan 4;584(1):22-6. doi: 10.1016/j.febslet.2009.11.026.

Zhang P, Liu S, Zhao Z, You L, Harrison MD, Zhang Z. Enzymatic acylation of cyanidin-3-glucoside with fatty acid methyl esters improves stability and antioxidant activity. Food Chem. 2021 May 1;343:128482. doi: 10.1016/j.foodchem.2020.128482.

Yang W, Kortesniemi M, Yang B, Zheng J. Enzymatic Acylation of Anthocyanins Isolated from Alpine Bearberry ( Arctostaphylos alpina) and Lipophilic Properties, Thermostability, and Antioxidant Capacity of the Derivatives. J Agric Food Chem. 2018 Mar 21;66(11):2909-2916. doi: 10.1021/acs.jafc.7b05924.

Yang RF, Geng LL, Lu HQ, Fan XD. Ultrasound-synergized electrostatic field extraction of total flavonoids from Hemerocallis citrina baroni. Ultrasonics Sonochemistry. 2017, 34: 571-579. doi: 10.1016/j.ultsonch.2016.06.037.

González-Sabín J, Morán-Ramallal R, Rebolledo F. Regioselective enzymatic acylation of complex natural products: expanding molecular diversity. Chem Soc Rev. 2011 Nov;40(11):5321-35. doi: 10.1039/c1cs15081b.


Refbacks

  • There are currently no refbacks.


Copyright (c) 2021 Journal of Pharmaceutical and Biomedical Sciences

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.