Subscribe to RSS
DOI: 10.1055/s-0030-1250122
© Georg Thieme Verlag KG Stuttgart · New York
Two New Lignans from the Roots of Pulsatilla koreana
Publication History
received April 26, 2010
revised June 8, 2010
accepted June 12, 2010
Publication Date:
19 July 2010 (online)
Abstract
Two new lignans, (2R,3R)-2β-(4′′-hydroxy-3′′-methoxybenzyl)-3α-(4′-hydroxy-3′-methoxybenzyl)-γ-butyrolactone 2-O-(β-D-glucopyranoside) (1) and (1S,2R,3S)-dimethyl-1,2,3,4-tetrahydro-3,6,7-trihydroxy-1-(3′,4′-dihydroxyphenyl)naphthalene-2,3-dicarboxylate (2) together with nine known compounds (3–11) were isolated from the ethyl acetate fraction of the roots of Pulsatilla koreana. Their chemical structures were established based on physicochemical and spectroscopic data analyses. All isolates were investigated for their inhibition effects against the classical pathway of the complement system. Among them, compound 6 showed significant inhibitory activity with an IC50 value of 75.9 µM, compounds 8 and 9 had moderate effects with IC50 values of 182.2 and 166.5 µM, respectively.
Key words
Pulsatilla koreana - Ranunculaceae - lignan - anticomplement activity
References
- 1 Kirschfink M. Controlling the complement system in inflammation. Immunopharmacology. 1997; 38 51-62
- 2 Julia A E, Tony E H. Complement factors and their receptors. Immunopharmacology. 1997; 38 3-15
- 3 Kuby J. Complement in immunology, 2nd ed. New York; WH Freeman Company 1994: 336-355
- 4 Bae K H. The medicinal plants of Korea. Seoul; Kyo-Hak Press 1999: 139
- 5 Zhang X Q, Liu A R, Xu L X. Determination of ranunculin in Pulsatilla chinensis and synthetic ranunculin by reversed phase HPLC. Yao Hsueh Hsueh Pao. 1990; 25 932-935
- 6 Ye W C, Ou B X, Ji N N, Zhao S X, McKervey M A, Stevenson P. Patensin, a saponin from Pulsatilla patens var. multifida. Phytochemistry. 1995; 39 937-939
- 7 Ye W C, Ji N N, Zhao S X, Jing H L, Ye T, McKervey M A, Stevenson P. Triterpenoids from Pulsatilla chinensis. Phytochemistry. 1996; 42 799-802
- 8 Lee H S, Beon M S, Kim M K. Selective growth inhibitor toward human intestinal bacteria derived from Pulsatilla cernua root. J Agric Food Chem. 2001; 9 4656-4661
- 9 Mimaki Y, Kuroda M, Asano T, Sashida Y. Triterpene saponins and lignans from the roots of Pulsatilla chinensis and their cytotoxic activity against HL-60 cells. J Nat Prod. 1999; 62 1279-1283
- 10 Bang S C, Kim Y, Lee J H, Ahn B Z. Triterpenoid saponins from the roots of Pulsatilla koreana. J Nat Prod. 2005; 68 268-272
- 11 Agrawal P K, Rastogi R P. A new neolignan and other phenolic constituents from Cedrus deodara. Phytochemistry. 1980; 19 1260-1261
- 12 Sakushima A, Coskun M, Maoka T. Hydroxybenzoic acids from Boreava orientalis. Phytochemistry. 1995; 40 257-261
- 13 Lee S Y, Min B S, Kim J H, Lee J, Kim T J, Kim C S, Kim Y H, Lee H K. Flavonoids from the leaves of Litsea japonica and their anti-complement activity. Phytother Res. 2005; 19 273-276
- 14 Srinivasan R, Chandrasekar M J N, Nanjan M, Suresh B. Antioxidant activity of Caesalpinia digyna root. J Ethnopharmacol. 2007; 113 284-291
- 15 Tsukamoto H, Hisada S, Nishibe S. Lignans from bark of Fraxinus mandshurica var. japonica and F. japonica. Chem Pharm Bull. 1984; 32 4482-4489
- 16 Woo E R, Piao M S. Antioxidative constituents from Lycopus lucidus. Arch Pharm Res. 2004; 27 173-176
- 17 Tandon S, Rastogi R P. Wikstromol, a new lignan from Wikstroemia viridiflora. Phytochemistry. 1976; 15 1789-1791
- 18 Kato A, Hashimoto Y. (+)-Nortrachelogenin, a new pharmacologically active lignan from Wikstroemia indica. J Nat Prod. 1979; 42 159-162
- 19 Lopes L M X, Yoshida M, Gottlieb O R. Dibenzylbutyrolactone lignans from Virola sebifera. Phytochemistry. 1983; 22 1516-1518
- 20 Harmatha J, Buděšínsky' M, Trka A. Strukturnè bohatstvè a biologickğ vğznam lignanŭ a jim přèbuznğch rostlinnğch fenylpropanoidŭ. Collect Czech Chem Commun. 1982; 47 644-663
- 21 Rahman M M A, Dewick P M, Jackson D E, Lucas J A. Lignans of Forsythia intermedia. Phytochemistry. 1990; 29 1971-1980
- 22 Zhang Z, Guo D, Li C, Zheng J, Koike K, Jia Z, Nikaido T. Gaultherins A and B, two lignans from Gaultheria yunnanensis. Phytochemistry. 1999; 51 469-472
- 23 Baderschneider B, Winterhalter P. Isolation and characterization of novel benzoates, cinnamates, flavonoids, and lignans from riesling wine and screening for antioxidant activity. J Agric Food Chem. 2001; 49 2788-2798
- 24 Park S H, Oh S R, Jung K Y, Lee I S, Ahn K S, Kim J H, Kim Y S, Lee J J, Lee H K. Acylated flavonol glycosides with anti-complement activity from Persicaria lapathifolia. Chem Pharm Bull. 1999; 47 1484-1486
- 25 Jung K Y, Oh S R, Park S H, Lee I S, Ann K S, Lee J J. Anti-complement activity of tiliroside from the flower buds of Magnolia fargesii. Biol Pharm Bull. 1998; 21 1077-1078
- 26 Min B S, Lee S Y, Kim J H, Lee J K, Kim T J, Kim D H, Kim Y H, Joung H, Lee H K, Nakamura N, Miyashiro H, Hattori M. Anti-complement activity of constituents from the stem-bark of Juglans mandshurica. Biol Pharm Bull. 2003; 26 1042-1044
- 27 Thuong P T, Min B S, Jin W, Na M, Lee J, Seong R, Lee Y M, Song K, Seong Y, Lee H K, Bae K, Kang S S. Anti-complementary activity of ursane-type triterpenoids from Weigela subsessilis. Biol Pharm Bull. 2006; 29 830-833
- 28 Min B S, Lee I, Chang M J, Yoo J K, Na M, Hung T M, Thuong P T, Lee J, Kim J H, Kim J C, Woo M H, Choi J S, Lee H K, Bae K. Anticomplementary activity of triterpenoids from the whole plant of Aceriphyllum rossii against the classical pathway. Planta Med. 2008; 74 726-729
- 29 Min B S, Na M K, Oh S R, Ahn K S, Jeong G S, Li G, Lee S K, Joung H, Lee H K. New furofuran and butyrolactone lignans with antioxidant activity from the stem bark of Styrax japonica. J Nat Prod. 2004; 67 1980-1984
Prof. KiHwan Bae
College of Pharmacy
Chungnam National University
305-764 Daejeon
Korea
Phone: +82 4 28 21 59 25
Fax: +82 4 28 23 65 66
Email: baekh@cnu.ac.kr
Prof. Byung Sun Min
College of Pharmacy
Catholic University of Daegu
330 Geumnak 1-ri
712-702 Gyeongbuk
Korea
Phone: +82 5 38 50 36 13
Fax: +82 5 38 50 36 02
Email: bsmin@cu.ac.kr