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http://dx.doi.org/10.7783/KJMCS.2018.26.4.317

Enhancement of Solubility and Nanonization of Phenolic Compound in Extrudate from Angelica gigas Nakai by Hot Melt Extrusion using Surfactant  

Azad, Md Obyedul Kalam (Department of Bio-Health Technology, Kangwon National University)
Cho, Hyun Jong (Department of Pharmacy, Kangwon National University)
Go, Eun Ji (Department of Herbal Medicine Resource, Kangwon National University)
Lim, Jung Dae (Department of Herbal Medicine Resource, Kangwon National University)
Park, Cheol Ho (Department of Bio-Health Technology, Kangwon National University)
Kang, Wie Soo (Department of Bio-Health Technology, Kangwon National University)
Publication Information
Korean Journal of Medicinal Crop Science / v.26, no.4, 2018 , pp. 317-327 More about this Journal
Abstract
Background: The root of Angelica gigas Nakai is used as a traditional herbal medicine in Korea for the treatment of many diseases. However, the poor water solubility of the active components in A. gigas Nakai is a major obstacle to its bioavailability. Methods and Results: This work aimed at enhancing the solubility of the active compounds of A. gigas Nakai by a chemical (using a surfactant) and physical (hot melt extrusion, HME) crosslinking method. Fourier transform infrared spectroscopy revealed multiple peaks in the case of the extrudate solids, attributable to new functional groups including carboxylic acid, alkynes, and benzene derivatives. Differential scanning calorimetry analysis showed that the extrudate soilid had a lower glass transition temperature ($T_g$) and enthalpy (${\Delta}H$) ($T_g:43^{\circ}C$, ${\Delta}H$ : < 6 J/g) as compared to the non-extrudate ($T_g:68.5^{\circ}C$, ${\Delta}H:123.2$) formulations. X-ray powder diffraction analysis revealed the amorphization of crystalline materials in the extrudate solid. In addition, enhanced solubility (53%), nanonization (403 nm), and a higher amount of extracted phenolic compounds were achieved in the extrudate solid than in the non-extrudate (solubility : 36%, nanonization : 1,499 nm) formulation. Among the different extrudates, acetic acid and span 80 mediated formulations showed superior extractions efficiency. Conclusions: HME successfully enhanced the production of amorphous nano dispersions of phenolic compound including decursin from extrudate solid formulations.
Keywords
Angelica gigas Nakai; Hot Melt Extrusion; Nano-solid Dispersion; Size Reduction; Solubility;
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1 Yoshioka M, Hancock BC and Zografi G. (1994). Crystallization of indomethacin from the amorphous state below and above its glass transition temperature. Journal of Pharmacology. 83:1700-1705.
2 Zeleznak KJ and Hoseney RC. (1987). The glass transition in starch. Cereal Chemistry. 64:121-124.
3 Wilson M, Williams MA, Jones DS and Andrews GP. (2012). Hot-melt extrusion technology and pharmaceutical application. Therapeutic Delivery. 3:787-797.   DOI
4 Yan JJ, Kim DH, Moon YS, Jung JS, Ahn EM, Baek NI and Song DK. (2004). Protection against $\beta$-amyloid peptide-induced memory impairment with long-term administration of extract of Angelica gigas or decursinol in mice. Progress in Neuro-Psychopharmacology and Biological Psychiatry. 28:25-30.   DOI
5 Repka MA, Battu SK, Upadhye SB, Thumma S, Crowley MM, Zhang F, Martin C and McGinity JW. (2007). Pharmaceutical applications of hot-melt extrusion: Part II. Drug Development and Industrial Pharmacy. 33:1043-1057.   DOI
6 Rosen MJ. (2004). Surfactants and interfacial phenomena (3rd ed.). John Wiley and Sons. Hoboken. NJ, USA. p.52-95.
7 Sebestyen E. (1974). Grain storage: Problems of grains preservation in storage facilities. Journal of Flour Animal Feed Milling. 10:24-25.
8 Sharma S, Kori S and Parmar A. (2015). Surfactant mediated extraction of total phenolic contents(TPC) and antioxidants from fruits juices. Food Chemistry. 185:284-288.   DOI
9 Silverstein RM, Webster FX and Kiemle DJ. (2005). Spectrometric identification of organic compounds (7th ed.). John Wiley and Sons. Hoboken. NM, USA. p.425-456.
10 Singleton VL and Rossi JA. (1965). Colorimetry of total phenolics with phosphomolybdic-phosphotungstic acid reagents. American Journal of Enology and Viticulture. 16:144-458.
11 Ti H, Zhang R, Zhang M, Wei Z, Chi J, Deng Y and Zhang Y. (2015). Effect of extrusion on phytochemical profiles in milled fractions of black rice. Food Chemistry. 178:186-194.   DOI
12 Tita B, Fulias A, Bandur G, Marian E and Tita D. (2011). Compatibility study between ketoprofen and pharmaceutical excipients used in solid dosage forms. Journal of Pharmaceutical and Biomedical Analysis. 56:221-227.   DOI
13 Vichapong J, Sookserm M, Srijesdaruk V and Swatsitang P. (2010). High performance liquid chromatographic analysis of phenolic compounds and their antioxidant activities in rice varieties. LWT-Food Science and Technology. 43:1325-1330.   DOI
14 Williams III RO, Watts AB and Miller DA. (2012). Formulating poorly water soluble drugs. Springer. New York. NY, USA. p.45-300.
15 Merisko-Liversidge EM and Liversidge GG. (2008). Drug nanoparticles: Formulating poorly water-soluble compounds. Toxicologic Pathology. 36:43-48.   DOI
16 Morales JO and McConville JT. (2011). Manufacture and characterization of mucoadhesive buccal films. European Journal of Pharmaceutics and Biopharmaceutics. 77:187-199.   DOI
17 Nam SY, Lee SY, Kim JJ, Kang WS and Yoon IS. (2018). Polydopamine-coated nanocomposites of Angelica gigas Nakai extract and their therapeutic potential for triple-negative breast cancer cells. Colloids and Surfaces B: Biointerfaces. 165:74-82.   DOI
18 Morales P, Cebadera-Miranda L, Caamara RM, Reis FS, Barros L, Berrios JDJ, Ferreira ICFR and Camara M. (2015). Lentil flour formulations to develop new snack-type products by extrusion processing: Phytochemicals and antioxidant capacity. Journal of Functional Foods. 19:537-544.   DOI
19 Morsy SMI. (2014). Role of surfactants in nanotechnology and their applications. International Journal of Current Microbiology and Applied Science. 3:237-260.
20 Murdande SB, Pikal MJ, Shanker RM and Bogner RH. (2010). Solubility advantage of amorphous pharmaceuticals: I.A thermodyanamic analysis. Journal of Pharmaceutical Science. 99:1254-1264.   DOI
21 Obradovic V, Babic J, Subaric D, Ackar D and Jozinovic A. (2014). Improvement of nutritional and functional properties of extruded food products. Journal of Food and Nutrition Research. 53:189-206.
22 Piao J, Lee JY, Weon JB, Ma CJ, Ko HJ, Kim DD and Kang WS and Cho HJ. (2015). Angelica gigas Nakai and soluplusbased solid formulations prepared by hot-melting extrusion: Oral absorption enhancing and memory ameliorating effects. PLoS ONE. 10:e0124447. http://journals.plos.org/plosone/article?id=10.1371/journal.pone.0124447 (cited by Jan 25).   DOI
23 Kim KM, Kim MJ and Kang JS. (2009). Absorption, distribution, metabolism, and excretion of decursin and decursinol angelate from Angelica gigas Nakai. Journal of Microbiology and Biotechnology. 19:1569-1572.   DOI
24 Kralova I and Sjoblom J. (2009). Surfactants used in food industry: A review. Journal of Dispersion Science and Technology. 30:1363-1383.   DOI
25 Lee SY, Nam SY, Choi YH, Kim MJ, Koo JS, Chae BJ, Kang WS and Cho HJ. (2017a). Fabrication and characterizations of hot-melt extruded nanocomposites based on zinc sulfate monohydrate and soluplus. Applied Sciences. 7:902. http://www.mdpi.com/2076-3417/7/9/902/htm (cited by 2018 Jan 6).   DOI
26 Lawrence MJ and Rees GD. (2012). Microemulsion-based media as novel drug delivery system. Advance Drug Delivery Reviews. 64:175-193.   DOI
27 Lee SH, Shin DS, Kim JS, Oh KB and Kang SS. (2003). Antibacterial coumarins from Angelica gigas roots. Archives of Pharmacal Research. 26:449-452.   DOI
28 Lee SY, Lee JJ, Nam SY, Kang WS, Yoon IS and Cho HJ. (2017b). Fabrication of polymer matrix-free nanocomposites based on Angelica gigas Nakai extract and their application to breast cancer therapy. Colloids and Surfaces B: Biointerfaces. 159:781-790.   DOI
29 Ma Y, Jung JY, Jung YJ, Choi JH, Jeong WS, Song YS, Kang JS, Bi K and Kim MJ. (2009). Anti-inflammatory activities of coumarins isolated from Angelica gigas Nakai on LPSstimulated RAW 264.7 cells. Journal of Food Science and Nutrition. 14:179-187.
30 Maniruzzaman M. Rana MM. Boateng JS, Mitchell JC and Douroumis D. (2013). Dissolution enhancement of poorly water-soluble APIs processed by hot-melt extrusion using hydrophilic polymers. Drug Development and Industrial Pharmacy. 39:218-227.   DOI
31 McClements DJ and Xiao H. (2012). Potential biological fate of ingested nanoemulsions: Influence of particle characteristics. Food and function. 3:202-220.   DOI
32 Hosseinzadeh R, Khorsandi and Hemmaty S. (2013). Study of the effect of surfactants on extraction and determination of polyphenolic compounds and antioxidant capacity of fruits extracts. PLoS one. 8:E57353. http://journals.plos.org/plosone/article?id=10.1371/journal.pone.0057353 (cited by 2018 Feb 7).   DOI
33 Kang TC, Hwang IK, Park SK, An SJ, Yoon DK, Moon SM, Lee YB, Sohn HS, Cho SS and Won MH. (2001). Chronological changes of N-methyl-D-aspartate receptors and excitatory amino acid carrier 1 immunoreactivities in CA1 area and subiculum after transient forebrain ischemia. Journal of Neurocytology. 30:945-955.   DOI
34 Hu J, Johnston KP and Williams RO. (2004). Nanoparticle engineering processes for enhancing the dissolution rates of poorly water soluble drugs. Drug Development and Industrial Pharmacy. 30:233-245.   DOI
35 Hulsmann S, Backensfeld T, Keitel S and Bodmeier R. (2000). Melt extrusion-an alternative method for enhancing the dissolution rate of $17{\beta}$-estradiol hemihydrate. European Journal of Pharmaceutics and Biopharmaceutics. 49:237-242.   DOI
36 Jurisic V, Julson JL, Kricka T, Curic D. Voca N and Karunanithy C. (2015). Effect of extrusion pretreatment on enzymatic hydrolysis of Miscanthus for the purpose of ethanol production. Journal of Agricultural Science. 7:132-142.
37 Khoddami A, Wilkes MA and Robert TH. (2013). Techniques for analysis of plant phenolic compounds. Molecules. 18:2328-2375.   DOI
38 Cocchi M, Foca G, Lucisano M, Marchetti A, Pegani MA, Tassi L and Ulrici A. (2004). Classification of cereal flours by chemometric analysis of MIR spectra. Journal of Agricultural and Food Chemistry. 52:1062-1067.   DOI
39 Correia LP, Procopio JVV, de Santana CP, Santos AFO, Cavalcante HMM and Macedo RO. (2013). Characterization of herbal medicine with different particle sizes using pyrolysis GC/MS, SEM, and thermal techniques. Journal of Thermal Analysis and Calorimetry. 111:1691-1698.   DOI
40 Davidov-Pardo G, Arozarena I and Marin-Arroyo MR. (2011). Stability of polyphenolic extracts from grape seeds after thermal treatments. European Food Research and Technology. 232:211-220.   DOI
41 Harper JM. (1992). A Comparative analysis of single and twinscrew extruders. In Kokini JL et al. (ed.). Food extrusion science and technology. Marcel Dekker. New York. NY, USA. p.139-149.
42 Fox SC. (2014). Remington education pharmaceutics. Published by Pharmaceutical Press. London, England. p.28-53.
43 Ghimeray AK, Sharma P, Phoutaxay P, Salitxay T, Woo SH, Park SU and Park CH. (2014). Far infrared irradiation alters total polyphenol, total flavonoid, antioxidant property and quercetin production in tartary buckwheat sprout powder. Journal of Cereal Science. 59:167-172.   DOI
44 Hagi G and Hatami A. (2010). Simultaneous quantification of flavonoids and phenolic acids in plant materials by a newly developed isocratic high-perfomance liquid chromatography approach. Journal of Agricultural and Food Chemistry. 58:10812-10816.   DOI
45 Hasenhuettl GL and Harel RW. (2008). Food emulsifiers and their applications (2nd ed.). Springer Science. New York. NY, USA. p.11-37.
46 Holmberg K, Jonsson B, Kronberg B and Lindman B. (2003). Surfactants and polymers in aqueous solution, John Wiley and Sons. Chichester, England. p.16-99.
47 Agrawal S, Ashokraj Y, Bharatam PV, Pillai O and Panchagnula R. (2004). Solid-state characterization of rifampicin samples and its biopharmaceutic relevance. European Journal of Pharmaceutical Science. 22:127-144.   DOI
48 Ansel HC. (1985). Introduction to pharmaceutical dosage forms. Lea and Febiger. Philadelphia. PA, USA. p.147-149.
49 Bae IY, Lee JY, Kwak BY and Lee HG. (2011). Estrogenic effects of various extracts from Chamdanggui(Angelica gigas Nakai) and Sogdan(Phlomis umbrosa Turcz). Food Science and Biotechnology. 20:1113-1118.   DOI
50 Baird JA and Taylor LS. (2012). Evaluation of amorphous solid dispersion properties using thermal analysis techniques. Advance Drug Delivery Reviews. 64:396-421.   DOI
51 Braca A, Fico G, Morelli I, de Simone F, Tomè F and de Tommasi N. (2003). Antioxidant and free radical scavenging activity of flavonol glycosides from different Aconitum species. Journal of Ethnopharmacology. 86:63-67.   DOI
52 Chalermchaiwat P, Jangchud K, Jangchud A, Charunuch C and Prinyawiwatkul W. (2015). Antioxidant activity, free gamma-aminobutyric acid content, selected physical properties and consumer acceptance of germinated brown rice extrudates as affected by extrusion process. LWT-Food Science and Technology. 64:490-496.   DOI
53 Choi KO, Lee I, Paik SYR, Kim DE, Lim JD, Kang WS and Ko S. (2012). Ultrafine Angelica gigas powder normalizes ovarian hormone levels and has antiosteoporosis properties in ovariectomized rats: Particle size effect. Journal of Medicinal Food. 15:863-872.   DOI