New Guaiane, Megastigmane and Eudesmane-Type Sesquiterpenoids and Anti-Inflammatory Constituents from Youngia japonica

Abstract

Eleven sesquiterpenoids have been isolated from the whole plants of Youngia japonica (Asteraceae). Among these sesquiterpenoids, five were identified as new compounds on the basis of spectroscopic methods and chemical analysis. Their structures were 3-oxo-8α-(4-hydoxyphenyl)acetoxy-10(14),11(13)-guaiadien-12,6-olide (1), 3β-[3-(4-hydroxyphenyl)acetyl-β-D-glucopyranosyloxy]-8α-hydroxy-4(15),10(14),11(13)-guaiatrien-12,6-olide (2), 3β-[3-(4-hydroxyphenyl)acetyl-β-D-glucopyranosyloxy]-4(15),10(14),11(13)-guaiatrien-12,6-olide (3), 3α,5β,6α-trihydroxy-4α-(β-D-glucopyranosyloxy)-7-megastigmen-9-one (4), and 3α-(β-D-glucopyranosyloxy)-4(15),11(13)-eudesmadien-12-oic acid (5). The three known components 3β-(β-D-glucopyranosyloxy)-8α-(4-hydroxyphenyl)acetoxy-4(15),10(14),11(13)-guaiatrien-12,6-olide (8), 3β-(β-D-glucopyranosyloxy)-4(15),10(14),11 (13)-guaiatrien-12,6-olide (9), and 3α-hydroxy-4α-(β-D-glucopyranosyloxy)-5,7-megastigmadien-9-one (11) showed inhibitory activity against the proliferation of T and B lymphocytes of mice in vitro at concentrations of 1 × 10 ^{- 7}, 1 × 10 ^{- 6}, and/or 1 × 10 ^{- 5} M without obvious cytotoxicity. Compound 9, the major component of the plant extract, exhibited weak anti-inflammatory activity at a dosage of 50 mg/kg (p. o.) in in vivo anti-inflammatory experiments of mice.

Key words

Youngia japonica - Asteraceae - sesquiterpenoid - immunosuppressive activity - anti-inflammatory activity

References

• 1 Jiangsu New Medical C ollege, Dictionary of Chinese herb m edicines. Shanghai; Shanghai Scientific and Technologic Press 1986: p. 2066
• 2 Adegawa S, Miyase T, Fukushima S. Sesquiterpene glycosides from Youngia denticulate (Houtt.) kitam.  Chem Pharm Bull. 1986;  34 3769-73
• 3 Samek Z, Holub M, Drozdz B, Iommi G, Corbella A, Gariboldi P. Sesquiterpenic lactones of the Cynara scolymus L. species.  Tetrahedron Lett. 1971;  50 4775-8
• 4 Bohlmann F, Van N. Sesquiterpenlactone und Polyine aus der Gattung Arctotis .  Phytochemistry. 1977;  16 487-8
• 5 Miyase T, Ueno A, Noro T, Kuroyanagi M, Fukushima S. Studies on sesquiterpene glycosides from Crepis japonica Benth.  Chem Pharm Bull. 1985;  33 4451-6
• 6 Miyase T, Fukushima S. Sesquiterpene lactones from Ainsliaea acerifolia Sch. Bip. and A. dissecta Franch. et Sav.  Chem Pharm Bull. 1984;  32 3043-6
• 7 Miyase T, Yamaki K, Fukushima S. Studies on sesquiterpenes from Macroclinidium trilobum makino. 1.  Chem Pharm Bull. 1984;  32 3912-7
• 8 Romo de Vivar A, Cabrera A, Ortega A, Romo J. Constituents of zaluzania species - II structures of zaluzanin C and zaluzanin D.  Tetrahedron. 1967;  23 3903-7
• 9 Shimizu S, Miyase T, Ueno A, Usmanghani K. Sesquiterpene lactone glycosides and ionone derivative glycosides from Sonchus asper .  Phytochemistry. 1989;  28 3399-3402
• 10 Xiang D, Li X. Antitumor activity and immuno-potentiating actions of Achyranthes bidentata polysaccharides.  Acta Pharmacol Sin. 1993;  14 556-61
• 11 Winter C, Risley E, Nuss C. Carrageenin-induced edema in hind paw of the rat as an assay for anti-inflammatory drugs.  Proc Soc Exp Biol Med. 1962;  111 544-7
• 12 Ceccherelli P, Curini M, Marcotullio M, Menghini A. Sesquiterpene acids from Dittrichia viscosa .  Phytochemistry. 1985;  24 2987-9
• 13 Kupchan S, Kelsey J, Maruyama M, Cassady J, Hemingway J, Knox J. Tumor inhibitors. XLI. structural elucidation of tumor-inhibitory sesquiterpene lactones from Eupatorium rotundifolium .  J Org Chem. 1969;  34 3876-83
• 14 Sun C, Syu W, Don M, Lu J, Lee G. Cytotoxic sesquiterpene lactones from the root of Saussurea lappa .  J Nat Prod. 2003;  66 1175-80
• 15 Zidorn C, Ellmerer E, Konwalinka G, Schwaiger N, Stuppner H. 13-Chloro-3-O-β-D-glucopyranosylsolstitialin from Leontodon palisae: the first genuine chlorinated sesquiterpene lactone glucoside.  Tetrahedron Lett. 2004;  45 3433-6