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1 Korean J. Plant Res. 27(2): (2014) Print ISSN Online ISSN Original Research Article 참나리와하늘말나리인경의성분분석 박태영 1, 서경순 1, 최성규 2, 윤경원 2 * 1 장흥군버섯산업연구원, 2 순천대학교한약자원개발학과 Chemical Constituents of Bulb of Lilium lancifolium Thunberg and Lilium tsingtauense Gilg Tae Young Park 1, Kyoung-Sun Seo 1, Seongkyu Choi 2 and Kyeong Won Yun 2 * 1 Jangheung Research Institute for Mushroom Industry, Jangheung , Korea 2 Department of Oriental Medicine Resources, Sunchon National University, Suncheon , Korea Abstract - In this study, the chemical constituents of bulb from Lilium lancifolium and Lilium tsingtauense were investigated. The content of moisture, crude protein and fiber of bulb from L. tsingtauense was higher than that of L. lancifolium, whereas the content of crude ash and nitrogen free extract of bulb from L. lancifolium was higher than that of L. tsingtauense. HPLC analysis revealed that total free sugar and amino acid content of bulb from L. tsingtauense was higher than that of L. lancifolium. There was no remarkable difference in proximate composition between the two species. The content of p-coumaric acid and ferulic acid was 1.93 mg% and 0.25 mg% in ethyl acetate fraction of L. lancifolium, on the other hand, 2.94 mg% and 0.46 mg% in ether fraction of L. tsingtauense. These results suggest that the bulb of L. tsingtauense can be considered as promising oriental medicine resource likewise L. lancifolium. Key words - Lilium lancifolium, Lilium tsingtauense, Free sugar, Amino acid, Proximate composition, Phenolic compound 서언 고령인구가증가함에따라노화억제와건강유지에대한관심이높아지고있으며, 건강한삶을유지하기위한일환으로천연소재들의생리활성물질연구가광범위하게진행되고있다 (Goldberg, 1994). 특히, 식용가능한생약과채소에대한연구들이주를이루어항산화성, 항암성및항진균성등의생리활성및유용성분분석에관한결과들이다수보고되고있다 (Han et al., 1992; Cao et al., 1996; Jansen, 2002; Nanasombat and Teckcheuen, 2009). 백합과 (Liliaceae) 식물은전세계적으로약 220 속 3500종, 우리나라에는 32속 88종이분포하고있다 (Ock, 2004). 한약재로써백합 ( 百合 ) 은참나리 (Lilium lancifolium Thunb.) 및동속근연식물의비늘줄기로 (Lee, 1996) colchicine, ferulic acid, p-coumaric acid, sinapic acid, capsanthin 성분이함유되어있어약용및기능성식품원료로도사용되고있다 (Lee and * 교신저자 ( ) : ykw@sunchon.ac.kr Park, 2002). 백합의한의약적효능은폐를윤택하게하며가래, 기관지염, 진통, 신경통, 거담, 이뇨제등의치료에사용되었으며정력도길러준다고하였다 (Ock, 2004). 과거우리나라에서는백합을약품뿐아니라식품으로도활용하였는데, 조선무쌍신식요리제법에백합떡의요리법이기록되어있으며 (Lee, 1943), 한국, 중국, 일본등동아시아지역에서는백합의구근을이용하여과자, 국수, 탕및전분등의다양한식품으로활용되어왔다 (KPPA, 1994). 한약재백합 ( 百合 ) 으로쓰이는참나리 (Lilium lancifolium) 는우리나라각처의산이나들에나는다년초로초장은약 1.5 m이며비늘줄기는둥근모양으로지름이 5 8 cm 이다. 줄기는기둥모양으로자갈색을띠고, 줄기끝에흰색의털이있다. 잎은호생으로꽃은 7 8 월에개화하며황적색으로줄기끝에 2 10송이가량이붙고, 지름은 7 10 cm이다 (Lee, 1996). 참나리와동속 ( 同屬 ) 식물인하늘말나리 (Lilium tsingtauense) 는우리나라각처의산지에나는다년초로초장은 1 m 이상이고, 비늘줄기는둥근모양으로흰색이며, 비늘조각은성기게붙고줄기는곧게 c 본학회지의저작권은 ( 사 ) 한국자원식물학회지에있으며, 이의무단전재나복제를금합니다. This is an Open-Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License ( which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.

2 韓資植誌 Korean J. Plant Res. 27(2) : 125~132(2014) 선다. 잎은줄기중간부분에 6 12장씩윤생하며, 줄기윗부분의작은잎은호생한다. 꽃은황적색으로줄기끝에 1 3 송이가붙고, 꽃자루가있다 (Lee, 1996). 참나리와하늘말나리에대한연구로는계통분류학적인연구 (Sim et al., 2007; Kim et al., 2006) 가많이이루어져있으며, 그외에도생육특성 (Kim, 2007; Song, 2007) 및유전육종 (Kwon, 2006; Joung, 2008) 으로많이진행되어져왔다. 그러나한약재백합 ( 百合 ) 으로쓰이는참나리와유사한식물의이화학적성분및생리활성연구는부족한실정이다. 따라서본연구는한약재백합 ( 百合 ) 으로쓰이는백합과 (Liliaceae) 동속식물인참나리와하늘말나리의이화학적성분을분석하여약용자원으로의활용및식품개발을위한기초자료로제공하고자일반성분, 유리당및총아미노산과기능성성분으로 ρ-coumaric acid 와 ferulic acid 의함량을분석한것이다. 재료및방법실험재료본실험에서사용된참나리 (Lilium lancifolium) 와하늘말나리 (L. tsingtauense) 의인경은전남고흥군나로도 ( 위도 , 경도 ) 에서 2011 년 7월에채취하여 45 드라이오븐 (C-DO drying oven, Vision scientific Co. Ltd, Korea) 에서 24시간건조한후분쇄하여분말로만들어서 100 mesh 체로걸러본실험에사용하였다. 시약본실험에서사용된분석및추출, chromatography 용용매와시약은일급또는특급시약을구입하여사용하였다. 일반성분일반성분은 AOAC방법 (Association of official analytical chemist, 1990) 방법에따라분석하였다. 수분은시료 1 g을각각칭량병에담고 105 dry oven 에서항량이될때까지건조시켜무게를측정하여구하였다. 조회분은시료 2 g을 250 에서예비회화한후 600 에서직접회화법으로, 조단백질의함량은 Kjeldahl 법 (Sin, 1987) 으로측정된질소량에질소계수 6.25 를곱하여산출하였으며, 조지방의함량은 Soxhlet 추출법 (Lee et al., 2008) 으로, 조섬유는 Henneberg Stohmann 개량법 (Kim et al., 2007) 으로구하였다. 그리고가용성무질소물의함량은총량에서조회분, 조단백질, 조지방및조섬유의함량을 Table 1. HPLC conditions for analysis of free sugars Items Instrument Detector Conditions 1200 Series, Agilent Technologies, USA ELSD detector Column ZORBAX Carbohydrate (4.6 mm I.D. 150 mm L.) Solvent 75% Acetonitrile Column temp. 30 Flow rate 1.4 ml/min Injection volume 5 μl Table 2. HPLC conditions for analysis of total amino acid Items Instrument Detector Conditions 1200 Series, Agilent Technologies, USA Agilent Technologies 1200 Series FLD Column AccQ-Tag (3.9 mm I.D. 150 mm L.) Column temp 37 Buffer solution Flow rate Injection volume 뺀값으로산출하였다. 유리당 A : AccQ-Tag eluent A (acetate-phosphate buffer) B : AccQ-Tag eluent B (100% acetonitrile) C : water 1.0 ml/min 5 μl 유리당성분은 Wilson et al. (1981) 의방법에따라분석하였다. 즉시료 1 g에증류수 30 ml 를가하고 homogenizer 로마쇄하여교반한후침출시켜 50 ml 로정용하여원심분리 (1,500 rpm 30 min) 한후상징액을취하여 0.45 µm membrane filter(millipore Co., USA) 로여과한여액으로 HPLC (1200 Series, Agilent Technologies, USA) 를이용하여분석하였으며함량은적분계에의한외부표준법으로계산하였다. HPLC 조건은 Table 1과같다. 구성아미노산구성아미노산분석은시료분쇄시료 0.5 g을시험관에넣고 -126-

3 참나리와하늘말나리인경의성분분석 6 N HCl 10 ml 을넣은후시험관끝을불로녹여앰플로만들어밀봉한후 110 에서 24시간가수분해시킨후여과지로여과한다음 methanol 50 ml 로정용하여감압농축하여 20 mm HCl 5 ml로정용하였다 µm membrane filter 로여과하여얻은여액일정량을취하여 Cohen and Michaud (1993) 의방법으로 AccQ-Tag 시약을사용하여유도체화시킨후 HPLC 로분석하였다. 이동상은 AccQ-Tag eluent(a), 100% acetonitrile(b), water(c) 를 gradient 조건으로 A:B:C 를초기 100:0:0(%, v/v) 에서 0.5분에 99:1:0(%, v/v), 18분에 95:5:0(%, v/v), 19분에 91:0:0(%, v/v), 26분에 86.7:13.3:0(%, v/v), 30 분에 84:16:0 (%, v/v), 32분에 83:17:0(%, v/v), 36 분에 83:17:0(%, v/v), 36 분에 0:60:40(%, v/v), 39 분에 100:0:0(%, v/v) 로설정하였다. 유속은 1.0 ml/min 으로하였고, 주입량은 5 µl로설정하여, FLD (1200 Series, Agilent Technologies, USA) 로검출하였으며 AccQ-Tag TM column (Water Co., 3.9 mm I.D. 150 mm L.) 을이용하였다. 함량은적분계에의한외부표준법으로계산하였다. 분석조건은 Table 2와같다. ρ-coumaric acid 와 ferulic acid 함량 ρ-coumaric acid 와 ferulic acid 는백합과에들어있는천연 phenol 성분으로분획물별함량을확인하고자하였다. ρ-coumaric acid 와 ferulic acid 의정량분석은용매별로분획한추출물을건조시킨후 HPLC 용 methanol 에용해한다음 0.45 μm syringe filter (Millipore, Billerica, MA, USA) 로여과하여 HPLC (1200 series, Aglient Technologies, USA.) 를이용하여분석하였다. 이동상은 2% acetic acid 가포함된 45% Table 3. HPLC condition for analysis of ρ-coumaric acid and ferulic acid Items Instrument Detector Column Solvent Column temp. Flow rate Injection volume Conditions 1200 Series, Agilent Technologies, USA Agilent Technologies 1200 Series DAD ZORBAX SB-C 18 (4.6 mm I.D. 150 mm L.) A : 2% acetic acid in 45% acetonitrile B : 2% acetic acid in water 35 l.0 ml/min 5 μl acetonitrile (A 용액 ) 과 2% acetic acid (B 용액 ) 를 gradient 조건으로 A용액 :B용액을초기 50:50(%, v/v) 에서 18분 20분에 100:0, 20 분부터는 50:50 로설정하였다. 유속은 1.0 ml/min 으로하였고, 주입량은 5 µl로설정하였으며, UV 360 nm에서검출하였고 ZORBAX SB-C 18 column (3.5 µm, 4.6 mm I.D. 150 mm L., Agilent Technologies, USA.) 을이용하였다. 함량은적분계에의한외부표준법으로계산하였다. 분석조건은 Table 3 과같다. 통계분석모든실험은 3회반복하였으며, 실험결과를 SPSS 통계프로그램 (ver. 12.0, SPSS Inc., USA) 을이용하여평균값과표준편차를산출하였으며 Duncan s multiple test 를통해그유의성 (p < 0.05) 을확인하였다. 결과및고찰 일반성분참나리 (Lilium lancifolium) 와하늘말나리 (Lilium tsingtauense) 인경의일반성분분석결과는 Table 4와같다. 수분함량은참나리인경은 11.29%, 하늘말나리인경은 13.78% 로하늘말나리인경에서조금높게나타났다. 그리고회분함량은참나리인경은 3.63%, 하늘말나리인경은 2.14% 로나타났고, 조단백은참나리인경은 7.11%, 하늘말나리인경은 9.41% 로하늘말나리인경에서조금높은함량을나타냈다. 조지방함량은참나리인경과하늘말나리인경에서 1.81% 1.82% 로큰차이가없었고, 조섬유함량은참나리인경은 0.71%, 하늘말나리인경은 1.39% 로하늘 Table 4. Proximate composition of bulb from Lilium lancifolium and Lilium tsingtauense Compositions Contents (%) L. lancifolium L. tsingtauense Moisture ± 0.03 z ± 0.00 Crude ash 3.63 ± ± 0.08 Crude protein 7.11 ± ± 0.21 Crude fat 1.81 ± ± 0.09 Crude fiber 0.71 ± ± 0.19 Nitrogen free extract z Values are presented mean ± SD (n=3)

4 韓資植誌 Korean J. Plant Res. 27(2) : 125~132(2014) Table 5. The contents of free sugars in bulb from Lilium lancifolium and Lilium tsingtauense Species Free sugars contents (%) Fructose Glucose Sucrose Total free sugars L. lancifolium 1.25 ± 0.06 z 1.82 ± ± L. tsingtauense 0.45 ± ± ± z Values are presented mean ± SD (n=3). Table 6. The contents of amino acids in bulb from Lilium lancifolium and Lilium tsingtauense Total amino Contents (mean ± SD, mg%) acids L. lancifolium L. lancifolium Aspartic acid ± ± Serine ± ± Glutamic acid ± ± Glycine ± ± Histidine ± ± Arginine ± ± Threonine ± ± Alanine ± ± Proline ± ± Tyrosine ± ± 3.12 Valine ± ± Methionine ± ± 3.88 Lysine ± ± Isoleucine ± ± Leucine ± ± Phenylalanine ± ± TAA z EAA y EAA/TAA(%) z Total amino acid. y Total essential amino acid (Thr.+Val.+Met.+Ile.+Leu.+Phe.+ His.+Lys.). 말나리인경에서함량이높게나타났다. L. davidii 인경의조단백질의함량이 4.17%, 조지방의함량이 0.14% 라는연구 (Joung, 2006) 보다는참나리와하늘말나리인경에서높은함량을나타냈다. 그리고농촌진흥청의연구에서는조단백질의함량이하늘말나리인경에서 5.48% 의함량을나타낸것과달리본연구에서의하늘말나리인경의조단백질함량이 9.41% 로나타났다 (RDA, 2008). 일반성분중단백질함량은총아미노산함량과밀접한관계가있으며 (McMurry, 2008), 가용성무질소물함량은당성분으로변환되는탄수화물의함량과관련된다 (Choi, 2009). 참나리와하늘말나리인경의일반성분분석결과가용성무질소물함량이다른일반성분요소들에비하여월등히높게나타난점은두식물의주요구성성분이탄수화물임을간접적으로보여준결과로사료된다. 유리당참나리와하늘말나리인경에서의유리당함량을 Table 5와같이 fructose, glucose, sucrose 가검출되었다. 참나리와하늘말나리인경에서의총유리당함량은각각 6.29%, 9.74% 로하늘말나리인경에서높게나타났으며, 검출된유리당중에 sucrose의함량이가장높았다. 참나리인경에서는 sucrose 의함량이 3.22% 로가장높았으며, glucose, fructose 순으로나타났다. 하늘말나리인경에서도 sucrose의함량이 6.86% 로가장높았으며, glucose, fructose 순으로높게나타났다. 유리당종류별함량을살펴보면 fructose 의함량이참나리인경에서하늘말나리인경에서보다약간높게나타났으며, glucose, sucrose 의함량은하늘말나리인경에서더높게나타남을확인할수있었다. Joung (2006) 의연구에서참나리인경에서의총유리당함량은 12.35% 로나타난것에비하여낮게나타났지만하늘말나리인경에서는참나리인경에서보다높게나타남을확인하였다. 그리고같은백합과 (Liliaceae) 의둥굴레는 8.91% 로참나리인경에서보다는높지만하늘말나리인경에서보다는낮은함량을나타냈다 (Park et al., 2000). 구성아미노산참나리와하늘말나리인경에서의구성아미노산의함량은 Table 6과같다. 참나리와하늘말나리인경에서의구성아미노산함량은각각 mg %, mg % 로하늘말나리인경에서더높게나타났으나성분비율에서는큰차이가없었다. 그 -128-

5 참나리와하늘말나리인경의성분분석 중에서도모든세포에서사용되는염기성비필수아미노산으로단백질합성에관여하고, 종양세포의억제작용, 면역기능향상등의기능을가지고있는 arginine의함량이가장높았으며참나리인경에서는 mg %, 하늘말나리인경에서는 mg % 로참나리인경에서보다하늘말나리인경에서높은함량을나타냈다. 백합과 Polygonatum odoratum 에들어있는 arginine의함량이 7.38 mg % 으로나타난연구결과 (Jang et al., 2002) 보다는높게나타났다. 또한 histidine, threonine, valine, methionine, lysine, isoleucine, leucine 및 phenylalanine 으로구성된필수아미노산은참나리와하늘말나리인경에서각각 mg %, mg % 로하늘말나리인경에서더높게 Table 7. The contents of p-coumaric acid and ferulic acid in solvent fraction of bulb from Lilium lancifolium and Lilium tsingtauense Contents ( mg %) Solvent Species p-coumaric fraction Ferulic acid acid L. lancifolium Hexane 0.32 ± 0.20 bz 0.02 ± 0.01 a Ether Ethyl acetate 1.93 ± 0.87 a Water 0.46 ± 0.19 b 0.15 ± 0.03 a 0.25 ± 0.05 a 0.25 ± 0.05 b 0.10 ± 0.04 a L. tsingtauense Hexane 0.11 ± 0.05 b 0.01 ± 0.00 b Ether 2.94 ± 0.47 a 0.46 ± 0.04 a Ethyl acetate 0.45 ± 0.18 b 0.11 ± 0.05 b Water 0.30 ± 0.12 b 0.08 ± 0.02 b z Values with different letters in the same column were significantly different (p < 0.05). Duncan s test should be compared within each species. 나타났다. 그중에서도사료및식품첨가제로서널리사용되며의약용으로수액체및의약품의합성원료로도사용되고있는 threonine 의함량은참나리인경에서 mg %, 하늘말나리인경에서 mg % 로하늘말나리인경에서더높은함량을나타냈다 (Ikeda, 2003). 백합과에속하는마늘의구성아미노산함량은 6091 mg % 로나타난연구결과 (Kim et al., 2005) 보다는참나리와하늘말나리인경의구성아미노산함량이더높게나타났다. p-coumaric acid와 ferulic acid 함량 p-coumaric acid 와 ferulic acid 는백합과에들어있는천연 phenol성분으로 ferulic acid 는정상세포에는무독한반면, 암세포에는강한독성을보이는것으로보고되어있고 (Han et al., 2003), p-coumaric acid 는항균효과와항산화효과가있는것으로보고되어있다 (Park and Park, 1994; Ferguson et al., 2005). 참나리와하늘말나리인경의분획물별 p-coumaric acid와 ferulic acid 의함량을측정하였다 (Table 7, Fig. 1, 2 and 3). 참나리인경의 ethyl aceate 분획물에서 ferulic acid, p-coumaric acid 의함량이각각 0.25 mg %, 1.93 mg % 로가장높게검출되었으며하늘말나리인경의 ether 분획물에서각각 0.46 mg %, 2.94 mg % 로높게검출되었다. 백삼으로부터유리형, 에스테르형, 결합형 phenolic acids을분류, 정량하였을때 p-coumaric acid 의함량은 27.5 mg /100 g, 27.2 mg /100 g, mg /100 g으로나타났으며, ferulic acid 함량은 38.8 mg /100 g, mg /100 g, mg /100g으로나타난결과 (Choi et al., 2006) 와비교했을때, 본실험결과의 ferulic acid 함량이낮게나타났다. 그러나조와수수에서의 ferulic acid 함량이각각 9.85 μg/g, μg/g 로나타난연구결과 (Seo et al., 2011) Fig. 1. The chromatogram of HPLC of ρ-coumaric acid and ferulic acid standard (A: ρ-coumaric acid, B: Ferulic acid)

$韓資植誌 Korean J. Plant Res. 27(2) : 125~132(2014) Fig. 2. The chromatogram of HPLC of ρ-coumaric acid and ferulic acid in ether fraction of bulb from Lilium lancifolium (A: ρ -Coumaric acid, B: Ferulic acid).$

6 韓資植誌 Korean J. Plant Res. 27(2) : 125~132(2014) Fig. 2. The chromatogram of HPLC of ρ-coumaric acid and ferulic acid in ether fraction of bulb from Lilium lancifolium (A: ρ -Coumaric acid, B: Ferulic acid). Fig. 3. The chromatogram of HPLC of ρ-coumaric acid and ferulic acid in ether fraction of bulb from Lilium tsingtauense (A: ρ -Coumaric acid, B: Ferulic acid). 보다는높은함량을나타났다. 적요백합과 (Liliaceae) 에속하는참나리와하늘말나리인경의일반성분에서조단백질함량은참나리와하늘말나리인경에서비슷하게나타난반면, 수분함량, 조단백질함량및조섬유의함량은하늘말나리인경에서높게나타났으며, 회분함량, 조지방및가용성무질소물함량은참나리인경에서높게나타났다. 유리당분석에서총유리당함량은참나리인경에서보다하늘말나리인경에서높게나타났으며, fructose 를제외하고 glucose 와 sucrose의함량역시하늘말나리인경에서높게나타났다. 구성아미노산분석에서총구성아미노산함량은참나리인경에서보다하늘말나리인경에서높게나타났으며, 필수아미노산은비슷한함량을나타냈다. 백합과의 phenol 성분인 p-coumaric acid 와 ferulic acid 의정량분석한결과, 참나리인경은 ethyl acetate 분획물에서높게나타났고하늘말나리인경은 ether 분획물에서높게나타났다. Ferulic acid 의함량은참나리와하늘말나리인경에서비슷하게나타났으며, p-coumaric acid 함량은참나리인경에비해서하늘말나리인경에서높게나타났다. 이들결과로써하늘말나리도참나리와마찬가지로한약재 백합 ( 百合 ) 으로쓰여질수있으리라사료된다. References AOAC (Association of official analytical chemists) Official methods of analysis. (15th ed.), Washington D.C., USA. pp Cao, G., E. Sofic and L. Ronald Antioxidant capacity of tea and common vegetables. J. Agric. Food Chem. 44:

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8 韓資植誌 Korean J. Plant Res. 27(2) : 125~132(2014) Antioxidant compounds and activities of foxtail millet, proso millet and sorghum with different pulverizing methods. Kor. J. Soc. Food Sci. Nutr. 40: (in Korean). Sim, E.J., J.K. Lee, Y.S. Choi and J.H. Kim Analysis of genetic variation in diploid and triploid populations of Lilium lancifolium Thunb. native to Korea using RAPD markers. Korean Association for Flower Industry Development 14: Sin, H.S Food analysis. Sinkwang publishng Co., Seoul, Korea. pp (in Korean). Song, B.S Natural habitat and ploidy distribution of Lilium lancifolium in Islands of bay of Kyonggi, Korea. MS Thesis, Kangwon National University, Korea (in Korean). Wilson, A.M., T.M. Work, A.A. Bushway and R.J. Bushway HPLC determination of fructose, glucose and sucrose in potatoes. J. Food Sci. 46:300. (Received 19 November 2013 ; Revised 13 January 2014 ; Accepted 14 January 2014) -132-

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