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1 Original Article Journal of Apiculture 33(1) : 43~53 (2018) DOI: /apiculture Studies on the Organic Compounds and Mineral Constituents of Acanthopanax (Acanthopanax senticosus) and Acacia (Robinia pseudo-acacia) Honey Produced in Korea Weon Ki Paik*, Ae Kyung Kwak, Keun Hong Kim, Myeong Lyeol Lee 1, Yong Soo Choi 1 and Hye Kyung Kim 1 Division of Life Science & Chemistry, Daejin University 1 Department of Agricultural Biology, National Institute of Agricultural Science, RDA (Received 26 March 2018; Revised 25 April 2018; Accepted 26 April 2018) Abstract In order to use as a new functional food material, we analyzed the chemical components including the organic compounds, minerals and Vitamin C of acanthopanax and acacia honey which were produced in South Korea. The condensed rate of methanol extraction in honey was 85.5% of acanthopanax honey and it was 93.06% of acacia honey. In the case of acanthopanax honey, main organic compounds that extract by organic solvents in GC-MS analysis were trichloromethane, phosphine, superpalite, carbon tetrachloride, methyclolpropane, cyclopentane etc. and main aromatic compounds that extract by organic solvents in SPME analysis were dibutyl phthalate, pelargonaldehyde, cyclopentasiloxane, hexasiloxane, pyrrolidine, lauros tearic acid, vulvic acid etc. Also, in case of acacia honey, main organic compounds were trichloromethan, acetoxyethane, hexanaphthene, acetidin etc. and main aromatic compounds were hydrazomethan, azulene, cyclotrisiloxane, hydrazine etc. Proximate composition was crude protein 0.43%, crude fat 0.36%, crude ash 0.04% in acanthopanax honey and crude protein 0.10%, crude fat 0.29%, crude ash 0.06% in acacia honey. Free sugar that analyze by HPLC was fructose 32.38%, glucose 25.25%, total sugars 57.63% in acanthopanax honey and fructose 48.52%, glucose 24.29%, total sugars 72.81% in acacia honey. Vitamin C was not detected in two sample honeys. Minerals by ICP analysis were detected total 23 kinds in acanthopanax honey, K ppm > Na 6.234ppm > Si 4.206ppm > B 3.461ppm > Ca 2.235ppm > Mg 0.742ppm etc. and total 22 kinds in acacia honey, Na 4.527ppm > Si 3.420ppm > K 3.091ppm > Zn 1.482ppm etc. Key words: Acanthopanax honey, Acacia honey, Organic compounds, Minerals, GC-MS, SPME, ICP *Corresponding author @daejin.ac.kr 43

2 44,. ( ) ( ) (Honey Plants),, (, 2003;, 2007;, 2011),.,,,, (Honey),, (, 2007). (330kcal/100g),, (Ferreres et al., 1991; Sabatier et al., 1992; Chen et al., 2000) (Blaser, 1990; Willix et al., 1992; Molan, 1992, 2001, 2002; Shin and Ustunol, 2005), (, 1994)., hydroxy methyl furfur(hmf), (Kushnir, 1979; White et al., 1962, 1963, 1967, 1979, 1980; Davies, 1975), (1971), (1972) royal jelly, (1984) HMF, diastatic activity,,, (1991), diastase HMF. (2001), (2005), (, 1995;, 2001, 2002;, 2002;, 2003;, 2003;, 2003;, 2008; 2013).,., (Rural Development Administrate RDA, 2015). (Acanthopanax senticosus) (Robinia pseudo-acacia),,,,,, (Leptospermum scoparium)

3 45 Fig. 1. Schematic diagram of solvent extraction of each honey., honeynz (www. honeynz.co.nz) 2013 UMF(Unique Manuka Factor) g 500ml(MeOH 4 : H 2 O 1) 24 Fig. 1 Haxane, Chloroform, Ethyl acetate, Butanol. (SPME) Gas Chromatography SCAN ( : Agilent 6890GC/5973iMSD). ( ). 105 C, Kjeltec 8400 Analyzer unit Foss(Denmark), FOSS Drive unit 2050(Sweden), 500 C. 100g,,,. C Table 1. 5 (fructose, glucose, sucrose, lactose, maltose) (St.Lois, MO, USA) 50% 30 3,590 g 20 (CR-22N, Hitachi, Tokyo, Japan) 0.2µm membrane filter(minisart RC, Sartorious). HPLC(Nanospace SI-2, Shiseido, Tokyo, Japan) (RI-201H, Shodex, Tokyo, Japan). Imtakt Unison UK-Amino( mm, 3µm), 60 C, 10µl,

4 46 Table 1. HPLC operation condition for free sugars and vitamin C Free sugars Vitamin C Instrument Nanospace SI-2, Shiseido, Tokyo, Japan Detector RID(RI-201H,Shodex, Tokyo, Japan) PDA(Thermo Fisher, USA) Wave length Refrative Index 254nm Analytical Column Imtakt Unison Uk-Amino Shiseido Capcellpak MG120 (3.0mm 250mm, 3um) (4.6mm 250mm, 5um) Column Oven Temp. 60 C 40 C Flow rate 0.4ml/min 0.5ml/min Injection vol. 10ul 5ul Mobile Phase 90% ACN, M KH 2 PO 4 : ACN, 98 : 2 90% 0.4ml 40. C 1g 5% (Metaphosphoric acid, Wako) 20mL (Ultra- Turrax T25, IKA Labo, Germany) 50mL, refrigerated centrifuge(5804r, Eppendorf, Germany) 12,500 g 10 HPLC(Nanospace SI-2, Shiseido, Tokyo, Japan). Shiseido Capcellpak MG 120( mm, 5um), 0.05 M KH 2 PO 4 acetonitrile 98:2, 254nm, 5µl, 40 C, 0.5ml/min. (, 2003) 100mL ICP(Inductively coupled plasma) Optical Emission Spectrometer(Model Name: Optima 2000DV, PerkinElmer, USA), forward RF power; 1,300W, pump flow rate; 1.5ml/min, plasma flow; 15L/min, auxiliary flow; 0.2L/min, nebulizer flow; 0.65L/min. 100g (MeOH) 85.50%, 93.06%, H 2 O 75.84g, 83.26g, Butanol 5.74g, 5.01g. Hexane Ethyl acetate Chloroform 0.64g, 2.07g, 1.21g, 1.04g, 3.6g. 0.35g. Haxane, Chloroform, Ethyl acetate, Butanol H 2 O % H 2 O 77.63g (, 2014),, (Kim and Rhee, 1996) H 2 O. (MeOH) 91.00%, H 2 O 78.32g Butanol, Hexane, Ethyl acetate Chloroform 7.06g, 0.67g, 4.60g 0.35g (Fig. 2). Fig. 3. GC-MS Chloroform

5 Condensed mass (g) Acanthopanax honey Acacia honey Manuka honey 10 0 Hexane Fraction Chloroform Fraction Ethyl acetate Fraction Butanol Fraction H 2 O Fraction Fig. 2. Condensed mass (g) of solvent extractions of acanthopanax (Acanthopanax senticosus), acacia (Robinia pseudo-acacia) and manuka (Leptospermum scoparium) honey 100 (g). Trichloromethane(peak abundance: 5,800, 000), Formyl trichloride, Methenyl trichloride, Superpalite, Carbon Tetrachloride, Butanol Methyclolpropane(peak : 3,200,000), Acetidin, Acetoxyethane, 2- Propenoic acid, Propylcarbinol, Phosphine, Haxane Cyclopentane(peak : 5,800,000), Trimethylene oxide, 3-Methylpentane, Triptane, Hexyl hydride Ethyl acetate Trichloromethane(peak : 5,800,000), Trimethylene oxide, Propanoic acid, 1-Acetoxypropane, 1-Propyl acetate. SPME Dibutyl phthalate(peak : 4,000,000) Pelargonaldehyde, Cyclopentasiloxane, Hexasiloxane, Cycloheptasiloxane, Pyrrolidine, Dodecanoic acid, Lauros tearic acid, Vulvic acid, Dodecylic acid. Fig. 4. GC-MS Chloroform Trichloromethane(peak abundance: 11,000,000), Hexyl hydride, Gettysolve-B, Butanol Propyl carbinol(peak :5,200,000), Acetoxyethane, Acetidin, Haxane Hexanaphthene(peak : 11,600,000), Cyclohexane Ethyl acetate Methane trichloride(peak : 6,000,000), Propanoic acid. SPME Hexyl hydride(peak :31,0000), Hydrazomethan, Cyclotrisiloxane, Cyclopentasiloxane, Hydrazine, Cyclotrisiloxane, Azulene, Dioctyl adipate. (2014) GC-MS Formyl trichloride, Methenyl trichloride, Cyclopentane, Ethyl ethanoate, Trichloromethan, Butyl hydroxide, Butyraldehyde, Methylolpropan, Propyl carbinol, Propanoic acid, Acetoxyethane, Triptane, SPME 1,2-Benzenedicarboxylic acid, Benzaldehyde, Octacosane, Hexatriacontane, Cyclopentasiloxane, Pentanoic acid, Naphthalene, Nonanaldehyde, Cyclopentasiloxane, Pelargonaldehyde, Aldehyde, 3-Pyridinecarbonitrile, Nicotinonitrile, Pyrobenzol, Cyclotrisiloxane, Cyclohexatriene. 100g 21.22%, 0.43%, 0.36%, 0.04%, 77.95%, 18.75%, 0.10%, 0.44%, 0.06%, 80.65%

6 48 Chloroform Butanol Hexane Ethyl acetate SPME Fig. 3. Organic compound composition spectra of acanthopanax honey by each solvent (Analyzed by Agilent 6890GC/5973iMSD model).

7 49 Chloroform Butanol Hexane Ethyl acetate SPME Fig. 4. Organic compound composition spectra of acacia honey by each solvent (Analyzed by Agilent 6890GC/5973iMSD model).

8 50 Table 2. Proximate chemical composition of acanthopanax, acacia and manuka honey (unit: %) Sample Components Moisture Crude protein Crude fat Crude ash Carbohydrate Acanthopanax honey Acacia honey Manuka honey Results are expressed as Mean S.D. Table 3. Contents of free sugars and vitamin C on acanthopanax, acacia and manuka honey Contents Sample Acanthopanax honey Acacia honey Manuka honey Vitamin C (mg/100g) Total sugars Fructose Free sugars (%) Results are expressed as Mean S.D. Glucose Sucrose Lactose Maltose (Table 2). (2013) (0.28%), (0.57%). (2013)., (1994) 0.26%. (2003) ( 2.71%, 1.06%, 86.41%) %, 0.23%, 0.34%, 0.24%, 79.30%.,. (1984) 0.02%, 0.57%, 0.10%, 0.12%, 0.0%.. HPLC Table 3. fructose, glucose sucrose, lactose, maltose, 57.63% fructose 32.38%, glucose 25.25%. (2013) (62.27), (35.31%) (26.96%) % fructose 48.52%, glucose 24.29%, 70.23% fructose 39.07%, glucose 31.16%., C 3. (2003) sucrose 152mg%, glucose 114mg%, fructose 6mg%, Kim Rhee(1996),.

9 51 Table 4. Mineral contents of acanthopanax, acacia and manuka honey Minerals (ppm) Kind of honey Acanthopanax Acacia Manuka Minerals (ppm) Kind of honey Acanthopanax Acacia Manuka Macrominarals K Na Ca Mg Microminarals Other microminarals B Si Fe Sb Se Ti Co Al Cr As Zn Cd Cu Sr V Ba Mo Li Ni Pb Mn Be Results are expressed as Mean S.D. ICP 23 K ppm > Na 6.234ppm > Si 4.206ppm > B 3.461ppm > Ca 2.235ppm > Mg 0.742ppm, 22 Na 4.527ppm > Si 3.420ppm > K 3.091ppm > Zn 1.482ppm (Table 4). (macrominerals) Mg, Ca, Na, K, (microminerals) Mo, Zn, Cu. K ppm > Na 5.573ppm > Si 4.487ppm > Ca 2.223ppm. K 4.60, 3.84 Na. (2011) K. Ca 7.60, 7.56 Mg 1.50, WHO, Cd (0.041ppm), (0.058ppm), (0.040ppm) (WHO : 0.3ppm ). (Rashed and Soltan, 2004).

10 %, 93.06%, GC-MS Trichloromethane, Phosphine, Superpalite, Carbon Tetrachloride, Methyclolpropane, Cyclopentane Trichloromethan, Hexyl hydride, Propyl carbinol, Acetoxyethane, Acetidin, Hexanaphthene, Methane trichloride. SPME Dibutyl phthalate, Pelargonaldehyde, Cyclopentasiloxane, Hexasiloxane, Pyrrolidine, Dodecanoic acid, Lauros tearic acid, Vulvic acid Hexyl hydride, Hydrazomethan, Azulene, Cyclotrisiloxane, Hydrazine %, 0.43%, 0.36%, 0.04%, 77.95% 18.75%, 0.10%, 0.44%, 0.06%, 80.65%, (0.23%) (0.34%). HPLC 57.63%, fructose 32.38%, glucose 25.25% 72.81%, fructose 48.52%, glucose 24.29%, 70.23%, fructose 39.07%, glucose 31.16% C 3. ICP 23 K ppm > Na 6.234ppm > Si 4.206ppm > B 3.461ppm > Ca 2.235ppm > Mg 0.742ppm, 22 Na 4.527ppm > Si 3.420ppm > K 3.091ppm > Zn 1.482ppm. K ppm > Na 5.573ppm > Si 4.487ppm > Ca 2.223ppm, K 4.6, 3.84 K Na. ( : PJ009378).,, , HMF. 23: ,, : ,,, : , free amino acid. 6: 7.,,,, ( ). 28: ,,, : J. Fd Hyg. Safety 18: ,,,,, pp , p.,,,,,, : ,,,, : 168.,, : ,, : ,,,,,, : ,,,, , Hydroxy Methyl Furfural. 31: :

11 53,,, : 17.,,, : ,,,,, : ,,, diastase hydroxymethylfurfural. 17: 155. Blaser, M. J Helicobacter pylori and the pathogenesis of gastroduodenal inflammation. J. Infect. Dis. 161: Chen, L, A. Mehta, M. Berenbaum. A. R. Zangerl and N J. Engeseth Honeys from different floral sources as inhibitors of enzymatic browning in fruit and vegetable homogenates. J. Agric. Food Chem. 48: Davies, A. M. C Amino acid analysis of from Eleun Countries. J. Apicultural Res. 4: 29. Ferreres, F. A., Tomas-Barberan, B. I. Gil and F. Tomas-Lorents An HPLC technique for flavonoid analysis in honey. J. Sci. Food Afric. 56: Kim, E. S. and Rhee, C. O Comparison of quality attributes of Korean native bee honey and foreign bee by K/Na ratio. J. Kor. Sic. Food Nutr. 25: Kushnir, I Sugar and sugar products; Sensitive thin layer chromatographic detection of high fructose corn syrup and other adulterants in honey. J. Assoc. Anal. Chem. 62: 917. Molan, P. C The antibacterial activity of honey. Bee world 73: Molan, P Why honey is effective as a medicine. Bee world 82: Molan, P Not all honeys are the same for wound healing Bull. Eur. Tissue Rep. Soc. 9: 5-6. Rashed, M. N. and Soltan, M. E Major and trace elements in different types of Egyptian mono-floral and non-floral bee honeys. J. Food. Comp. Anal. 17: Rural Development Administration Agricultural Technology Report accessed on 30, Sabatier S., M. J. Amiot, M. Tacchini and S. Aubert Identification of falvonoids in sunflower honey. J. Food Sci. 57: Shin, H. and Z. Ustunol Carbohydrate composition of honey from different floral sources and their influence on growth of selected intestina bacteria. Food Res. Int. 38: White, J. W. Jr., Riethof, M. L., Subers, M. H. and Kushnir, I Composition of American honey. 1261p. Technical Bull., U.S. Dept. Agr., Washington, D.C. White, J. W. Jr Determination of acidity, nitrogen and ash in honey. J. Assoc. Anal. Chem. 45: 548. White, J. W. Jr. and Kushnir, I Composition of American honey; Protein. J. Apicultural Res. 4: 29. White, J. W. Jr Methods for determining carbohydrates, hydroxyfurfural and proline in honey; Collaborative study. J. Assoc. Ana. Chem. 62: 515. White, J. W. Jr Detection of honey adultration by carbohydrate anylysis. J. Assoc. Anal. Chem. 63: 11. Wilix, D. J., P. C. Molan and C. G. Harfoot A comparison of the sensitivity of wound-infecting species of bacteria to the antibacterial activity of manuka honey and other honeys. J. Appl. Bacteriol. 73:

DBPIA-NURIMEDIA

DBPIA-NURIMEDIA Studies on the Chemical Characteristics of Hovenia (Hovenia dulcis) Honey Produced in Korea Weon Ki Paik*, Ae Kyung Kwak, Myeong Lyeol Lee 1 and Ha Sik Sim 1 Division of Life Science & Chemistry, Daejin