A New Lignan Glycoside from Juniperus rigida

다국어 초록 (Multilingual Abstract)

A new lignan glycoside, named juniperigiside (1) was isolated from the CHCl3 soluble fraction of the MeOH extract of stems and leaves of Juniperus rigida S.et Z. Compound 1 was identified by 1D- and 2D-NMR spectroscopy as well as CD analysis as (2R,3S)-2,3-dihydro-7-methoxy-2-(4'-hydroxy-3'-methoxyphenyl)-3-hydroxymethyl-5-benzofuranpropanol 4'-O-(3-O-methyl)-α-L-rhamnopyranoside. Five known lignans, icariside E4 (2), desoxypodophyllotoxin (3), savinin (4), thujastandin (5), and (−)-nortrachelogenin (6) in addition to five known labdane diterpenes including trans-communic acid (7), 13-epi-torulosal (8), 13-epi-cupressic acid (9), imbricatoric acid (10), and isocupressic acid (11) were also isolated and their structures were characterized by comparing their spectroscopic data with those in the literature. All compounds were isolated for the first time from this plant, and 5 and 6 were first reported from the genus Juniperus. The isolated compounds were tested for cytotoxicity against four human tumor cell lines in vitro using a Sulforhodamin B bioassay. Compounds 3, 4, 7, and 8 showed considerable cytotoxicity against four human cancer cell lines in vitro.

참고문헌 (Reference)

1 이영섭, "노간주나무 에탄올추출물의 지방 흡수 억제 및 지방분해 효능" 한국생약학회 41 (41): 216-220, 2010

2 Fukuyama, Y., "Two new benzofuran-type lignans from the wood of Viburnum awabuki" 44 : 1418-1420, 1996

3 Kuo, Y. H., "Three labdane-type diterpenes from the bark of Juniperus formosana HAY. var. concolor HAY" 44 : 1242-1244, 1996

4 Murakami, K., "The structure of thujastandin, a new lignan from Thuja standishii (GORD.) CARR" 13 : 265-, 1967

5 Yanagawa, T., "Terpenoids. xxix. diterpenes in the wood of Juniperus rigida" 17 : 306-310, 1971

6 Liu, C. M., "Terpenoids from stems and leaves of Cupressus gigantea" 8 : 405-410, 2010

7 Li, S., "Reassignment of relative stereochemistry at C-7 and C-8 in arylcoumaran neolignans" 46 : 929-934, 1997

8 Gardner, D. R., "Ponderosa pine needle-induced abortion in beef cattle: identification of isocupressic acid as the principal active compound" 42 : 756-761, 1994

9 Pan, H., "Phenolic extractives from root bark of Picea abies" 39 : 1423-1428, 1995

10 Yuen, M. S. M., "On the absolute structure of optically active neolignans containing a dihydrobenzo[b]furan skeleton" 54 : 12429-12444, 1998

11 Skehan, P., "New colorimetric cytotoxicty assay for anticancer- drug screening" 82 : 1107-1112, 1990

12 Nakanishi, T., "Neolignan and flavonoid glycosides in Juniperus communis var, depressa" 65 : 207-213, 2004

13 Hosup Yeo, "Lignans of Rosa multiflora Roots 287" 대한약학회 27 (27): 287-290, 2004

14 Takaku, N., "Lignans of Chamaecyparis obtusa" 47 : 476-482, 2001

15 Achenbach, H., "Lignans and other constituents from Carissa edulis" 22 : 749-753, 1983

16 Su, W. C., "Labdanes from Cryptomeria japonica" 37 : 1109-1114, 1994

17 Ito, C., "Isolation of 6,7-demethylenedesoxypodophyllotoxin from Hernandia ovigera" 40 : 1318-1321, 1992

18 Matsuda, N., "Isolation and absolute structures of the neolignan glycosides with the enantiomeric aglycones from the leaves of Viburnum awabuki K. KOCH" 44 : 1122-1123, 1996

19 Miyase, T., "Ionone and lignan glycosides from Epimedium diphyllum" 28 : 3483-3485, 1989

20 Nishibe, S., "Introduction of an alcoholic hydroxyl group into 2,3-dibenzylbutyrolactone lignans with oxidizing agents and carbon- 13 nuclear magnetic resonance spectra of the oxidation products" 28 : 850-860, 1980

21 Chang, S.-T., "Cytotoxicity of extractive from Taiwania cryptomerioides heartwood" 55 : 227-232, 2000

22 Hanari, N., "Comparison of terpenes in extracts from the resin and the bark of the resinous stem canker of Chamaecyparis obtusa and Thujopsis dolabrata var. hondae" 48 : 56-63, 2002

23 Lee, T. B., "Coloured Flora of Korea" Hyang-Moon Publishing Co 150-, 2003

24 Kim, T. H., "Aromatic constituents from the heartwood of Santalum album L" 53 : 641-644, 2005

25 Chen, J. J., "Aporphine alkaloids and cytotoxic lignans from the roots of Illigera luzonensis" 72 : 523-532, 2011

26 Gordien, A. Y., "Antimycobacterial terpenoids from Juniperus communis L. (Cuppressaceae)" 126 : 500-505, 2009

27 Tomita, B., "Allo-cedrol : a new tricarbocyclic sesquiterpene alcohol" 12 : 1409-1414, 1973

28 Kato, A., "(+)-Nortrachelogenin, a new pharmacologically active lignan from Wikstroemia indica" 42 : 159-162, 1979