04(17-016)p fm

Size: px

Start display at page:

Download "04(17-016)p fm"

대진 묘
6 years ago
Views:

1 ISSN (PRINT) ISSN (ONLINE) 약학회지제 61 권제 2 호 90~95 (2017) Yakhak Hoeji Vol. 61, No. 2 DOI /psk 종설 Short Report 오가피속식물잎의식물화학성분비교 안혜정 * 육창수 ** 김형춘 ***,# 고성권 *,# 고연 ( 高硏 ) 인삼연구소, * 세명대학교한방식품영양학부, ** 경희대학교약학대학, *** 강원대학교약학대학 (Received January 16, 2017; Revised March 24, 2017; Accepted March 25, 2017) Measurement of Characteristic Phytochemical Levels in Different Acanthopanax Species by HPLC Hye Jung An*, Chang Soo Yook**, Hyoung Chun Kim***,#, and Sung Kwon Ko # *Ginseng Research Center, Koyeon, Sejong 30100, Korea **The Department of Oriental Medical Food & Nutrition, Semyung University, Jecheon 27136, Korea ***College of Pharmacy, Kyung Hee University, Seoul 02453, Korea ****College of Pharmacy, Kangwon National University, Chunchon 24341, Korea Abstract This study was carried out to obtain the basic information that can be used to index Acanthopanax in ten species of China and Korea. The phytochemical components from the leaf of Acanthopanax species, were measured by the HPLC analysis. Protocatechuic acid, eleutheroside B, eleutheroside E, scopolin, rutin, hyperoside, chiisanoside, oleanolic acid were found in ethanol extracts from the leaf of Acanthopanax species. Total phenolic compound of Acanthopanax sieboldianum leaf (2.499%) was about 5.7 times higher than those of Acanthopanax divaricatus f. flavi-flos leaf (0.436%). As a result, the order of the rutin content was 1) sieboldianum (2.019%), 2) gracillstylus (1.087%), 3) seoulense (0.073%). On the other hand, total terpenoid of Acanthopanax divaricatus leaf (9.602%) from Korea was about 24 times higher than those of gracillstylus leaf (0.400%) from China. And also, the order of the chiisanoside content was 1) divaricatus (9.190%), 2) senticosus var. subinermis (8.767%), 3) divaricatus f. distigmatis (8.743%). Keywords leaf, Acanthopanax species, Acanthopanax sieboldianum, rutin, chiisanoside, Acanthopanax divaricatus 오가피 ( 五加皮, 五加木 ) 는지금으로부터 4,500여년전부터전승되어온한약물학서인신농본초경에처음으로기재되었고, 한국에서는오가피 [ sessiliflorum( sessiliflorus)] 또는동속식물 ( 오갈피과 Araliaceae) 의뿌리줄기및가지껍질을약전생약으로사용하고있다. # Corresponding Author Hyoung Chun Kim College of Pharmacy, Kangwon National University, Chunchon , Korea Tel.: Fax.: kimhc@kangwon.ac.kr Sung kwon Ko Department of Oriental Medical Food & Nutrition, Semyung University, Jecheon , Korea Tel.: Fax.: skko@semyung.ac.kr 한국에서자생하고있는오갈피나무로오가피 ( sessiliflorum), 지리오가피 ( chiisanensis), 서울오가피 ( seoulense), 중부오가피 ( sessiliflorum f. chungbuensis), 가시오가피 ( senticosus), 민가시오가피 ( senticosus var. subinermis), 섬오가피 ( koreanum), 흰털오가피 ( divaricatus var. albeofructus), 황오가피 ( divaricatus f. flavi-flos), 개오가피 ( divaricatus), 당오가피 ( sieboldianum), 이주오가피 ( divaricatus f. distigmatis) 등이있고, 중국전역에서약용되고있는오가피의기원식물은세주오가피 [Acanthopanax gracillstylus( 細柱五加 )] 를비롯한그동속식물인가시오가피 ( senticosus) 와중국남부, 대만, 베트남에자생하는세잎오가피 ( trifoliatus) 등이있다. 현재중국의약전생약으로는세주오가피, 가시오가피를사용하고있다. 또한, 오갈피나무의식물분류학적인분류로는무경종 ( 단경 ) 오가피로는오가피, 지리오가피, 서울오가피, 중부오가피가있고, 90

오가피잎의성분비교 91 유경종오가피로는가시오가피, 민가시오가피, 섬오가피, 세주오가피, 흰털오가피, 황오가피, 이주오가피, 개오가피, 당오가피등이이에해당한다. 1) Acanthopanax 속식물의생리활성에관한연구로는면역및항암효과, 성기능강화작용, 항당뇨작용, 간장애개선작용, 진정작용, 항스트레스작용등이보고되었다.

2 오가피잎의성분비교 91 유경종오가피로는가시오가피, 민가시오가피, 섬오가피, 세주오가피, 흰털오가피, 황오가피, 이주오가피, 개오가피, 당오가피등이이에해당한다. 1) Acanthopanax 속식물의생리활성에관한연구로는면역및항암효과, 성기능강화작용, 항당뇨작용, 간장애개선작용, 진정작용, 항스트레스작용등이보고되었다. 1) 오가피성분에관한연구는 Ovodov가오가피의근피추출물에서 eleutheroside A, B, B- 1, C, D, E, G, I, K, M 등의 saponin을분리하여보고 2,3) 한이후, lignan, coumarin, diterpene, triterpene, phenolic compound 등의천연물질들이잎또는열매에풍부하게함유되어주목받고있다. 4) 특히, eleutheroside E는관절염개선작용, 5) 2형당뇨개선작용, 6) 을나타내었으며, eleutheroside B(syringin) 는항암작용, 7) 간장보호작용, 8) 항염증작용, 9) 항피로작용, 10) 항당뇨작용, 11) 진통작용 12) 등이보고되었다. 한편, Acanthopanax 속식물의잎에대한약리연구로는위장보호작용, 13) 항산화작용, 14,15) 소염진통작용, 16-18) α-glucosidase 억제작용, 19,20) 조골세포분화증가작용, 21) 항암작용, 22) 항균작용, 23) 심근경색개선작용, 24) 혈당강하작용 25) 이보고되었다. 또한, Acanthopanax 속식물의잎에대한성분연구로는 Acanthopanax nipponicus 의잎으로부터 Triterpenoid saponin인 nipponosides A-E를보고하였고, 26) Acanthopanax trifoliatus forma tristigmatis의잎으로부터 pentacyclic lupane triterpene glycoside인 acanthodiolglycoside를보고하였으며, 27) Acanthopanax divaricatus var. albeofructus의잎으로부터 3,4-seco-lupane triterpenoids인 24-hydroxychiisanogenin, 22-alpha-hydroxychiisanogenin를분리하였고, 28) Acanthopanax senticosus의잎으로부터 flavonoid인 quercetin, quercitrin, rutin 을분리보고하였으며, 29) Acanthopanax japonicus의잎으로부터 oleanene type triterpene glycosides인 acanjaposide A-I를보고하였고, 30-32) Acanthopanax gracillstylus 의잎으로부터 Lupane-triterpene glycosides인 wujiapioside B, acankoreoside C, acantrifoside A, acankoreoside A, acankoreoside D를분리하였으며, 33,34) Acanthopanax koreanum의잎으로부터 Lupane-triterpene glycosides인 3alpha,30-dihydroxylup-20(29)- en-23,28-dioic acid 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta- D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester, 3alpha, 30-dihydroxylup-23-al-20(29)-en-28-oic acid 28-O-[alpha-Lrhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-Dglucopyranosyl] ester, (20S) 3alpha-hydroxylup-23-al-28,29-dioic acid 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-- >6)-beta-D-glucopyranosyl] ester를분리하였으며, 35) Acanthopanax trifoliatus의잎으로부터 caffeoyl quinic acid를분리하였다. 36) 오가피속식물잎의성분비교연구에있어서는 Zhang 37) 등이 flavonoid 및 phenol성성분 (5-caffeoylquinic acid, 4-caffeoylquinic acid, rutin, quercetin-3-o-glucoside, kaempferol-3-rutinoside, 3,4- dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, 1,5-dicaffeoylquinic acid, 4,5-dicaffeoylquinic acid) 에대한연구를시행하였지만, triterpene, lignan, phenylpropanoid, flavonoid 성분등식물화학성분 (protocatechuic acid, eleutheroside B, eleutheroside E, rutin, hyperoside, scopolin, chiisanoside, oleanolic acid) 전반에대한비교연구가체계적으로진행되고있지않은점에착안하여, 10 종의오가피잎의식물화학성분의함량을분석하여오가피잎건강기능식품개발의기초기반정보를제공하고자하였다. 실험방법실험재료본연구에사용한오가피속식물은개오가피 ( divaricatus), 당오 Fig. 1 Photograph of the leaf of Acanthopanax Species J. Pharm. Soc. Korea

3 92 안혜정 육창수 김형춘 고성권 가피 ( sieboldianum), 민가시오가피 ( senticosus var. subinermis), 서울오가피 ( seoulense), 세주오가피 ( gracillstylus), 이주오가피 ( divaricatus f. distigmatis), 오가피 ( sessiliflorum), 지리오가피 ( chiisanensis), 황오가피 ( divaricatus f. flavi-flos), 흰털오가피 ( divaricatus var. albeofructus) 를사용하였다. 사용한각각의오가피잎은경희대학교약학대학약초원과경희대학교내곡동약초원에서 2013년 11월 23일에채집하였고, 식물분류학적동정은경희대학교육창수교수가확인해주었으며, 제품표본 (Fig. 1) 은세명대학교한방식품자원학연구실에보관하고있다. 엑스의조제오가피속식물의잎을각각동결건조하여얻어진건조물각각 2g에에틸알코올 200 ml를가하여 2회반복환류추출후여과하고감압농축하여에틸알콜엑스를얻었다. HPLC-성분의분석 Zhao 등의방법 4) 에따라표품과직접비교하여성분의함량및조성을각시료당 3회반복실험하여결과의재현성을확인하여분석하였다. 표품은 Chromadex(U.S.) 와 Chemfaces(U.S.) 로 Fig. 2 HPLC profiles of phytochemical components detected from the leaf of Acanthopanax species. Vol. 61, No. 2, 2017

4 오가피잎의성분비교 93 부터구입한 protocatechuic acid, eleutheroside B, eleutheroside E, rutin, hyperoside, scopolin, chiisanoside, oleanolic acid를사용하였다. 사용한 HPLC 장치는 Shimadzu LC-20AD(Shimadzu, Japan) 이며, 칼럼은 KNAUER Eurospher 5μ C A(Knauer, mm, Germany) 을사용하였다. 이동상은 acetonitrile(hplc급, Sigma, U.S.) 과 HPLC용증류수 (0.05% phosphate) 이며, 페놀성성분은 acetonitrile의비율을 0%(0 min) 에서 10%(10 min), 35 %(60 min), 그리고마지막으로다시 0% 로조절하였고, 전개온도는 26 o C, 유속은분당 0.9 ml, 크로마토그램은시마즈 SPD- 20A 검출기를이용하여 220 nm에서검출하였다. 또한, 테르페노이드성분은 acetonitrile의비율을 10%(0 min) 에서 50%(30 min), 100%(35 min), 그리고마지막으로다시 0% 로조절하였고, 전개온도는 26 o C, 유속은분당 1.0 ml, 크로마토그램은시마즈 SPD- 20A 검출기를이용하여 210 nm에서검출하였다. 결과및고찰본연구는오가피속식물잎의식물화학성분을 HPLC법 (Fig. 2) 으로비교분석하여오가피속식물잎의성분정체성을확인하고자하였다. 성분비교분석은 Zhao 등의방법 4) 에따라서생리활성물질의분리방법을결정하였다. 페놀성성분비교분석결과, 페놀성성분의총합함량에있어서는 Table 1에서보는바와같이유경종오가피인당오가피잎이 2.499% 로가장높은함량을보여주었고, 그다음으로개오가피잎과세주오가피잎이각각 1.486%, 1.377% 로높은함량을나타내었다. 이와같은결과는당오가피잎 (2.499%) 의페놀성성분총함량은황오가피잎 (0.436%) 보다약 5.7배높은함량을나타내었다. 중요한생리활성성분으로관절염개선작용, 5) 2형당뇨개선작용 6) 을나타내는리그난계성분인 eleutheroside E의경우, 유경종오가피인이주오가피잎이 0.964% 로가장높은함량을나타내었으며, 개오가피잎 (0.903%), 오가피잎 (0.533%) 의순으로높은함량을나타내었다. 또한, 페닐프로파노이드계성분인 eleutheroside B의경우무경종오가피인오가피잎이 0.072% 로가장높은함량을나타내었으며, 세주오가피잎 (0.070%), 당오가피잎 (0.069%) 의순으로높은함량을나타내었다. Prothocatechuic acid의함량에있어서는개오가피잎이 0.021% 로서가장높은함량을나타내었으며, 오가피잎 (0.014%), 세주오가피잎 (0.013%) 의순으로높은함량을나타내었다. 또한, 쿠마린계성분인 scopolin의경우는황오가피잎이 0.097% 로가장높은함량을나타내었으며, 당오가피잎 (0.052%) 와지리오가피잎이 0.046% 로그뒤를이었다. 플라보노이드계성분인 rutin의경우, Fig. 2에서보는바와같이당오가피잎 2.019% 로서가장높은함량을나타내었으며, 세주오가피잎 (1.087%), 서울오가피잎 (0.078%) 의순으로높은함량을나타내었다. 한편, 세주오가피잎 (1.087%) 의함량은 Zhang 37) 등이보고한 0.133%, 0.698%, 0.297% 의함량보다높은함량을나타내었다. Hyperoside에있어서는개오가피잎이 0.439% 로서가장높은함량을나타내었으며오가피잎 (0.243%), 흰털오가피잎 (0.214%) 순으로높은함량을나타내었다. 한편, 테르페노이드성분의총합함량에있어서는 Table 1에서보는바와같이유경종오가피인개오가피잎이 9.602% 로가장높은함량을보여주었고, 그다음으로민가시오가피잎과이주오가피잎이각각 9.294%, 9.023% 로높은함량을나타내었다. 이와같은결과는개오가피잎 (9.602%) 의테르페노이드성분총함량 Table I The phytochemical components from the leaf of Acanthopanax Species(%,w/w). Phytochemical components divaricatus senticosus var. sieboldianum subinermis seoulense divaricatus gracillstylus f. distigmatis sessiliflorum chiisanensis divaricatus f. flavi-flos divaricatus var. albeofructus Protocatechuic acid 0.021± ± ± ± ± ± ± ± ± ±0.000 Eleutheroside B 0.033± ± ± ± ± ± ± ± ± ±0.001 Scopolin 0.036± ± ± ± ± ± ± ± ± ±0.002 Eleutheroside E 0.903± ± ± ± ± ± ± ± ± ±0.007 Rutin 0.053± ± ± ± ± ± ± ± ± ±0.002 Hyperoside 0.439± ± ± ± ± ± ± ± ± ±0.000 Total(phenolic compounds) Chiisanoside 9.190± ± ± ± ± ± ± ± ± ±0.038 Olenolic acid 0.413± ± ± ± ± ± ± ± ± ±0.029 Total (terpenoids) J. Pharm. Soc. Korea

5 94 안혜정 육창수 김형춘 고성권 은중국의세주오가피잎 (0.400%) 보다약 24배높은함량을나타내었다. 항염작용, 38,39) 혈소판응집억제작용, 40) 항균작용 41) 이보고된 chiisanoside의경우는개오가피잎이 9.190% 로가장높은함량을보여주었고, 그다음으로민가시오가피잎과이주오가피잎이각각 8.767%, 8.743% 로높은함량을나타내었다. 또한, oleanolic acid의경우는민가시오가피잎이 0.527% 로가장높은함량을보여주었고, 그다음으로개오가피잎과오가피잎이각각 0.413%, 0.314% 로높은함량을나타내었다. 이와같은결과는 Zhang 37) 등이 5-caffeoylquinic acid, 4- caffeoylquinic acid, rutin, quercetin-3-o-glucoside, kaempferol-3- rutinoside, 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, 1,5- dicaffeoylquinic acid, 4,5-dicaffeoylquinic acid 에대한비교분석연구를시행하였지만, triterpene, lignan, phenylpropanoid, flavonoid 성분등식물화학성분 (protocatechuic acid, eleutheroside B, eleutheroside E, rutin, hyperoside, scopolin, chiisanoside, oleanolic acid) 전반에대한비교연구를진행하여오가피잎의식물화학성분의정체성확인에기여하는결과라고사료된다. 결론오가피속식물잎의페놀성성분의총함량과오가피잎의주생리활성성분중하나인 rutin의함량에있어서당오가피가가장높은함량을나타내었고, 테르페노이드성분의총함량과 chiisanoside의함량에있어서는개오가피가가장높은함량을나타내었다. 따라서, 향후, 이를활용한기능성강화오가피잎제품개발이기대된다. 감사의말씀 본연구는농림부고부가가치식품기술개발사업의지원에의해이루어진것임 References 1) Yook, C. S. : Medicinal Herbs of Acanthopanax in Asia., Kyungwon Media., Seoul, p. 1 (2001). 2) Ovodov, Y. S., Frolova, G. M., Nefedova, M. Y. and Elyakov, G. B. : The glycosides of Eleutherococcus senticosus Max. I. Isolation and some properties of eleutherosides B and E. Khim. prirodn. soedin. 1, 3 (1996). 3) Ovodov, Y. S. and Flolova, G. M. : Triterpenoidal glycosides of Eleuterococcus sessiliflorus leaves II. Khim. Prirodnih. Soedin. 1, 618 (1971). 4) Zhao, L. S., An, Q., Qin, F. and Xiong, Z. L. : Simulataneous determination of six constituents in the fruit of Acanthopanax sessiliflorus (Rupr. et maxim.) seem. by HPLC-UV. Nat. Prod. Res. 7, 500 (2014). 5) He, C., Chen, X., Zhao, C., Qie, Y., Yan, Z. and Zhu, X. : Eleutheroside E ameliorates arthritis severity in collageninduced arthritis mice model by suppressing inflammatory cytokine release. Inflammation. 5, 1533 (2014). 6) Ahn, J., Um, M. Y., Lee, H., Jung, C. H., Heo, S. H. and Ha, T. Y. : Eleutheroside E, an active component of Eleutherococcus senticosus, ameliorates insulin resistance in type 2 diabetic db/ db mice. Evid. Based Complement Alternat. Med. 2013, (2013). 7) Lall, N., Kishore, N., Binneman, B., Twilley, D., Plessis- Stoman, D., Boukes, G. and Hussein, : Cytotoxicity of syringin and 4-methoxycinnamyl alcohol isolated from Foeniculum vulgare on selected human cell lines. Nat. Prod. Res. 29, 1752 (2015). 8) Gong, X., Zhang, L., Jiang, R., Wang, C. D., Yin, X. R. and Wan, J. Y. : Hepatoprotective effects of syringin on fulminant hepatic failure induced by D-galactosamine and lipopolysaccharide in mice. J. Appl. Toxicol. 34, 265 (2014). 9) Song, Y. Y., Li, Y. and Zhang, H. Q. : Therapeutic effect of syringin on adjuvant arthritis in rats and its mechanisms. Yao Xue Xue Bao. 45, 1006 (2010). 10) Li, C., Wang, X. Y., Hu, X. W., Fang, H. T. and Qiao, S. Y. : Determination of eleutheroside B in antifatigue fraction of Acanthopanax senticosus by HPLC. Zhongguo Zhong Yao Za Zhi. 33, 2800 (2008). 11) Niu, H. S., Liu, I. M., Cheng, J. T., Lin, C. L. and Hsu, F. L. : Hypoglycemic effect of syringin from Eleutherococcus senticosus in streptozotocin-induced diabetic rats. Planta Med. 74, 109 (2008). 12) Choi, J., Shin, K. M., Park, H. J., Jung, H. J., Kim, H. J., Lee, Y. S., Rew, J. H. and Lee, K. T. : Anti-inflammatory and antinociceptive effects of sinapyl alcohol and its glucoside syringin. Planta Med. 70, 1027 (2004). 13) Kim, H., Kim, M. G. and Leem, K. H. : Extrusion process of Acanthopanax senticosus leaves enhances the gastroprotective effect of compound 48/80 on acute gastric mucosal lesion in rats. J. Tradit. Chin. Med. 36, 187 (2016). 14) Zhang, X. D., Liu, X. Q., Kim, Y. H. and Whang, W. K. : Chemical constituents and their acetyl cholinesterase inhibitory and antioxidant activities from leaves of Acanthopanax henryi : potential complementary source against Alzheimer's disease. Arch. Pharm. Res. 37, 606 (2014). 15) Nhiem, N. X., Kim, K. C., Kim, D., Hyun, J. W., Kang, H. K., Van, Kiem. P., Van, Minh. C., Thu, V. K., Tai, B. H., Kim, J. and Kim, Y. H. : Phenylpropanoids from the leaves of Acanthopanax koreanum and their antioxidant activity. J. Asian Vol. 61, No. 2, 2017

6 오가피잎의성분비교 95 Nat. Prod. Res. 13, 56 (2011). 16) Hamid, R., Kee, T. H. and Othman, F. : Anti-inflammatory and anti-hyperalgesic activities of Acanthopanax trifoliatus (L) Merr leaves. Pharmacognosy Res. 5, 129 (2013). 17) Nhiem, N. X., Kiem, P. V., Minh, C. V., Tai, B. H., Quang, T. H., Soung, K. S., Koo, J. E., Koh, Y. S. and Kim, Y. H. : Antiinflammatory activity on LPS-stimulated dendritic cells of lupanetype triterpenoids from the leaves of Acanthopanax koreanum. Arch. Pharm. Res. 34, 1593 (2011). 18) Jung, H. J., Nam, J. H., Choi, J., Lee, K. T. and Park, H. J. : Antiinflammatory effects of chiisanoside and chiisanogenin obtained from the leaves of Acanthopanax chiisanensis in the carrageenan- and Freund's complete adjuvant-induced rats. J. Ethnopharmacol. 97, 359 (2005). 19) Wang, Z. B., Jiang, H., Xia, Y. G., Yang, B. Y. and Kuang, H. X. : α-glucosidase inhibitory constituents from Acanthopanax senticosus harm leaves. Molecules. 17, 6269 (2012). 20) Zhou, H., Xing, J., Liu, S., Song, F., Cai, Z., Pi, Z., Liu, Z. and Liu, S. : Screening and determination for potential α-glucosidase inhibitors from leaves of Acanthopanax senticosus harms by using UF-LC/MS and ESI-MS(n). Phytochem. Anal. 23, 315 (2012). 21) Park, S. H., Nhiem, N. X., Kiem, P. V., Choi, E. M., Kim, J. and Kim, Y. H. : A new norlupane triterpene from the leaves of Acanthopanax koreanum increases the differentiation of osteoblastic MC3T3-e1 cells. Arch. Pharm. Res. 33, 75 (2010). 22) Nguyen, X. N., Phan, V. K., Chau, V. M., Do, T. H., Buu, H. T., Pham, H. Y., Nguyen, H. T., Hyun, J. H., Kang, H. K. and Kim, Y. H. : Lupane-type triterpene glycosides from the leaves of Acanthopanax koreanum and their in vitro cytotoxicity. Planta Med. 76, 189 (2010). 23) Lee, S., Shin, D. S., Oh, K. B., Shin, K. H. : Antibacterial compounds from the leaves of Acanthopanax senticosus. Arch. Pharm. Res. 26, 40 (2003). 24) Sui, D. Y., Lu, Z. Z., Ma, L. N. and Fan, Z. G. : Effects of the leaves of Acanthopanax senticosus (Rupr. et Maxim.) Harms. on myocardial infarct size in acute ischemic dogs. Zhongguo Zhong Yao Za Zhi. 19, 746 (1994). 25) Sui, D. Y., Lu, Z. Z., Li, S. H. and Cai, Y. : Hypoglycemic effect of saponin isolated from leaves of Acanthopanax senticosus (Rupr. et Maxin.) Harms. Zhongguo Zhong Yao Za Zhi. 19, 683 (1994). 26) Miyakoshi, M., Shirasuna, K., Hirai, Y., Shingu, K., Isoda, S., Shoji, J., Ida, Y. and Shimizu, T. : Triterpenoid saponins of Acanthopanax nipponicus leaves. J. Nat. Prod. 62, 445 (1999). 27) Yook, C. S., Chang, S. Y., Lai, J. H., Ko, S. K., Jeong, J. H. and Nohara, T. : Lupane-glycoside of Acanthopanax trifoliatus forma tristigmatis leaves. Arch. Pharm. Res. 22, 629 (1999). 28) Oh, O. J., Chang, S. Y., Yook, C. S., Yang, K. S., Park, S. Y. and Nohara, T. : Two 3,4-seco-lupane triterpenes from leaves of Acanthopanax divaricatus var. albeofructus. Chem. Pharm. Bull. 48, 879 (2000). 29) Chen, M., Song, F., Guo, M., Liu, Z. and Liu, S. : Analysis of flavonoid constituents from leaves of Acanthopanax senticosus harms by electrospray tandem mass spectrometry. Rapid. Commun. Mass Spectrom. 16, 264 (2002). 30) Park, S. Y., Chang, S. Y., Oh, O. J., Yook, C. S. and Nohara, T. : nor-oleanene type triterpene glycosides from the leaves of Acanthopanax japonicus. Phytochemistry. 59, 379 (2002). 31) Park, S. Y., Choi, H. S., Yook, C. S. and Nohara, T. : A new lupane glycoside from the leaves of Acanthopanax koreanum. Chem. Pharm. Bull. 53, 97 (2005). 32) Park, S. Y., Yook, C. S. and Nohara, T. : New oleanene glycosides from the leaves of Acanthopanax japonicus. Chem. Pharm. Bull. 53, 1147 (2005). 33) Yook, C. S., Liu, X. Q., Chang, S. Y., Park, S. Y. and Nohara, T. : Lupane-triterpene glycosides from the leaves of Acanthopanax gracilistylus. Chem. Pharm. Bull. 50, 1383 (2002). 34) Liu, X. Q., Chang, S. Y., Park, S. Y., Nohara, T. and Yook, C. S. : A new lupane-triterpene glycoside from the leaves of Acanthopanax gracilistylus. Arch. Pharm. Res. 25, 831 (2002). 35) Choi, H. S., Kim, H. J., Nam, S. G., Kim, I. S., Lee, K. T., Yook, C. S. and Lee, Y. S. : Lupane glycosides from the leaves of Acanthopanax koreanum. Chem. Pharm. Bull. 56, 1613 (2008). 36) Sithisarn, P., Muensaen, S. and Jarikasem, S. : Determination of caffeoyl quinic acids and flavonoids in Acanthopanax trifoliatus leaves by HPLC. Nat. Prod. Commun. 6, 1289 (2011). 37) Zhang, X., Zhou, X., Liu, X., Li, X. and Whang, W. : Development and Application of an HPLC-UV Procedure to Determine Multiple Flavonoids and Phenolics in Acanthopanax Leaf Extracts. J. Chromatogr. Sci. 54, 574 (2016). 38) Won, J. H., Park, S. Y., Nam, S. G., Park, H. J., Choi, J. W. and Lee, K. T. : Inhibition of lipopolysaccharide-induced expression of inducible nitric oxide and cyclooxygenase-2 by chiisanoside via suppression of nuclear factor-kappab activation in RAW macrophage cells. Biol. Pharm. Bull. 28, 1919 (2005). 39) Jung, H. J., Nam, J. H., Choi, J., Lee, K. T. and Park, H. J. : Antiinflammatory effects of chiisanoside and chiisanogenin obtained from the leaves of Acanthopanax chiisanensis in the carrageenan- and Freund's complete adjuvant-induced rats. J. Ethnopharmacol. 97, 359 (2005). 40) Jin, J. L., Lee, S., Lee, Y. Y., Kim, J. M., Heo, J. E. and Yun-Choi, H. S. : Platelet anti-aggregating triterpenoids from the leaves of Acanthopanax senticosus and the fruits of sessiliflorus. Planta Med. 70, 564 (2004). 41) Lee, S., Shin, D. S., Oh, K. B. and Shin, K. H. : Antibacterial compounds from the leaves of Acanthopanax senticosus. Arch. Pharm. Res. 26, 40 (2003). J. Pharm. Soc. Korea

jaeryomading review.pdf

jaeryomading review.pdf 4 5 6 7 8 9 10 11 12 13 1. S. Kim, H. Y. Jeong, S. K. Kim, S. Y. Choi and K. J. Lee, Nano Lett. 11, 5438 (2011). 2. E. Menard, K. J. Lee, D. Y. Khang, R. G. Nuzzo and J. A. Rogers, Appl. Phys. Lett. 84,