식용식물자원으로부터 활성물질의 탐색-XXII. 사자발쑥 (Artemisia princeps PAMPANINI)의 지상부로부터 Triterpenoid의 분리 = Development of Biologically Active Compounds from Edible Plant Sources XXII. Triterpenoids from the Aerial Parts of Sajabalssuk (Artemisia princeps PAMPANINI)

다국어 초록 (Multilingual Abstract)

The aerial parts of Sajabalssuk (Artemisia princeps PAMPANINI, Sajabalssuk) was extracted with
80% aqueous MeOH, and the concentrated extract was partitioned with EtOAc, n-BuOH and
H2O, successively. From the EtOAc fraction, three cycloartane-type triterpnoids and one ursanetype
triterpenoid were isolated through the repeated silica gel, ODS and Sephadex LH-20 column
chromatographies. From the results of physico-chemical data including NMR, MS and IR, the
chemical structures of the triterpenoids were determined as wrightial (1), wrightial acetate (2), 27-
norcycloart-20(21)-ene-25-al-3β-ol acetate (3) and ursolic acid (4). No report has been found for isolation
of compound 3 in the literature so far, and compounds 1, 2 and 3 were the first to be isolated
from Sajabalssuk (Artemisia princeps PAMPANINI, Sajabalssuk). Also, compound 1 showed
Acyl-CoA:Cholesterol acyltransferase (hACAT-1) and hACAT-2 inhibitory activity with the IC50
values of 33.0 and 45.0 μg/ml, respectively. Compounds 2 and 3 inhibited hACAT-1 activity with
the IC50 values of 12.0 and 16.0 μg/ml, respectively.

다국어 초록 (Multilingual Abstract)

The aerial parts of Sajabalssuk (Artemisia princeps PAMPANINI, Sajabalssuk) was extracted with
80% aqueous MeOH, and the concentrated extract was partitioned with EtOAc, n-BuOH and
H2O, successively. From the EtOAc fraction, three cycloartane-type triterpnoids and one ursanetype
triterpenoid were isolated through the repeated silica gel, ODS and Sephadex LH-20 column
chromatographies. From the results of physico-chemical data including NMR, MS and IR, the
chemical structures of the triterpenoids were determined as wrightial (1), wrightial acetate (2), 27-
norcycloart-20(21)-ene-25-al-3β-ol acetate (3) and ursolic acid (4). No report has been found for isolation
of compound 3 in the literature so far, and compounds 1, 2 and 3 were the first to be isolated
from Sajabalssuk (Artemisia princeps PAMPANINI, Sajabalssuk). Also, compound 1 showed
Acyl-CoA:Cholesterol acyltransferase (hACAT-1) and hACAT-2 inhibitory activity with the IC50
values of 33.0 and 45.0 μg/ml, respectively. Compounds 2 and 3 inhibited hACAT-1 activity with
the IC50 values of 12.0 and 16.0 μg/ml, respectively.

참고문헌 (Reference)

1 류수노, "약쑥 함유 Eupatilin과 Jaceosidin 성분의 분석" 한국작물학회 49 (49): 452-456, 2004

2 최병범, "쑥 추출물의 아미노산, 당 분석 및 항산화 효과에 관한 연구" 한국식품영양학회 17 (17): 86-91, 2004

3 방면호, "식용식물자원으로부터 활성물질의 탐색-XIV.사자발쑥(Artemisia herba)의 전초로부터 flavonoid 화합물의 분리" 한국응용생명화학회 48 (48): 418-420, 2005

4 방면호, "식용식물자원으로부터 활성물질의 탐색 XVI.사자발쑥(Artemisia herba)의 전초로부터 sterol 화합물의 분리" 한국응용생명화학회 49 (49): 140-144, 2006

5 Ramchandra, P., "Wrightial, a new terpene from Wrightia tnictoria" 56 : 1811-1812, 1993

6 Pathak, A. K., "Ursolic acid inhibits STAT3 activation pathway leading to suppression of proliferation and chemosensitization of human multiple myeloma cells" 5 : 943-955, 2007

7 Khan, M. T. H., "Tyrosinase inhibitory cycloartane type triterpenoids from the methanol extract of the whole plant of Amberboa ramosa Jafri and their structure-activity relationship" 14 : 938-943, 2006

8 Anjaneyulu, V., "Triterpenoids from Mangifera indica" 24 : 2359-2367, 1985

9 De Pascual, T. J., "Triterpenes from Euphorbia broteri" 26 : 1767-1776, 1987

10 Gao, X., "Synthetic triterpenoids inhibit growth and induce apoptosis in human glioblastoma and neuroblastoma cells through inhibition of prosurvival Akt, NF-κB and Notch1 signaling" 84 : 147-157, 2007

11 Achiwa, Y., "Regulation of the phosphatidylinositol 3-Kinase-Akt and the mitogenactivated protein kinase pathways by ursolic acid in human endometrial cancer cells. Biosci. Biotechnol" 71 : 31-37, 2007

12 Simin, K., "Phytochemical investigation of Perovskia abrotanoides" 73 : 77-83, 2007

13 Yin, M. C., "Nonenzymatic antioxidative and antiglycative effects of oleanolic acid and ursolic acid" 55 : 7177-7181, 2007

14 Zhang, H. J., "Natural anti-HIV agents. Part IV. Anti-HIV constituents from Vatica cinerea" 66 : 263-268, 2003

15 Shin, D. H., "Investigation of medicinal substance from in vitro cultured cells and leaves of Artemisia princeps var. orientalis" 13 : 69-76, 2005

16 Lee, T. B., "In coloured flora of Korea" Hyang Mun Sa 2003

17 Singh, C., "Higher isoprenoids. V. Partial syntheses from cycloartenol, cyclolaudenol. Part 1. Mangiferolic acid, ambolic acid" 33 : 817-819, 1977

18 Cho, Y. H., "Essential oil composition and antibacterial activity of Artemisia capillaris, Artemisia argyi, and Artemisia princeps. Kor" 13 : 313-320, 2001

19 Madureira, A. M., "Effect of cycloartanes on reversal of multidrug resistance and apoptosis induction on mouse lymphoma cells" 24 : 859-864, 2004

20 Chinou, I., "Cytotoxic activity of origanum dictamnus" 78 : 342-344, 2007

21 Ferreira, M. J., "Cycloartane triterpenes from Euphorbia tuckeyana" 15 : 363-369, 2001

22 Gabriela, M. C., "Cycloartane Derivatives from Tillandsia usneoides" 59 : 343-347, 1996

23 Reiko, T., "Bioactive steroids from the whole herb of Euphorbia chamaesyce" 63 : 99-103, 2000

24 Horiuchi, K., "Antimicrobial activity of oleanolic acid from Salvia officinalis and related compounds on vancomycinresistant enterococci (VRE)" 30 : 1147-1149, 2007

25 Rosa, C. S., "Antihistaminic and antieicosanoid effects of oleanolic and ursolic acid fraction from Helichrysum picardii" 62 : 459-462, 2007

26 Tatsuzaki, J., "Anti-tumor agents 255: Novel glycyrrhetinic aciddehydrozingerone conjugates as cytotoxic agents. Bioorganic Medi" 15 : 6193-6199, 2007