Flavone C-glycosides from the Leaves of Lophatherum gracile and Their In Vitro Antiviral Activity

Abstract

Four new flavone C-glycosides, luteolin 6-C-α-L-arabinopyranosyl-7-O-β-D-glucopyranoside (1), apigenin 6-C-β-D-galactopyranosiduronic acid (1 → 2)-α-L-arabinopyranoside (2), luteolin 6-C-β-D-galactopyranosiduronic acid (1 → 2)-α-L-arabinopyranoside (3), and luteolin 6-C-β-D-glucopyranosiduronic acid (1 → 2)-α-L-arabinofuranoside (4), along with three known ones, were isolated from the leaves of Lophatherum gracile. The structures of the new compounds were elucidated by extensive spectroscopic methods as well as acid hydrolysis. All the flavone glycosides isolated from this plant were screened for their in vitro antiviral activity against respiratory syncytial virus (RSV) with cytopathic effect (CPE) reduction assay, and several flavone 6-C-monoglycosides showed potent in vitro anti-RSV effect.

Key words

Lophatherum gracile - Gramineae - flavone C-glycoside - antivirus activity - RSV

References

• 1 Xiao P G. Modern Chinese Materia Medica. Vol. 3. Beijing: Chemical Industry Press; 2002: 335-338
• 2 Ohmoto T, Ikuse M, Natori S. Triterpenoids of the Gramineae.  Phytochemistry. 1970;  9 2137-2148
• 3 Chen Q, Wu L J, Wang J, Li H. Studies on the chemical constituents of Lophatherum gracile Brongn.  J Shenyang Pharm Univ (Shenyang Yaoke Daxue Xuebao). 2002;  19 23-24
• 4 Lusebrink J, Schildgen V, Schildgen O. Novel therapies for an old virus: treatment of RSV infections in the 21st Century.  Expert Rev Anti Infect Ther. 2009;  7 1125-1129
• 5 Naithani R. Antiviral activity of phytochemicals: a comprehensive review.  Mini Rev Med Chem. 2008;  8 1106-1133
• 6 Zhang J, Wang Y, Zhang X Q, Zhang Q W, Ye W C. Chemical constituents from the leaves of Lophatherum gracile.  Chin J Nat Med (Zhongguo Tianran Yaowu). 2009;  7 428-431
• 7 Wang Y, Zhang D M, Ye W C, Yin Z Q, Fung K P, Zhao S X, Yao X S. Triterpenoid saponins from Androsace umbellata and their anti-proliferative activities in human hepatoma cells.  Planta Med. 2008;  74 1280-1284
• 8 Reed J L, Muench H. A simple method of estimating fifty percent endpoints.  Am J Trop Med Hyg. 1938;  27 493-497
• 9 Li Y L, But P P H, Ooi V E C. Antiviral activity and mode of action of caffeoylquinic acids from Schefflera heptaphylla (L.) Fordin.  Antiviral Res. 2005;  68 1-9
• 10 Cattopadhyay D, Chawla-Sarkar M, Chatterjee T, Dey R S, Bay P, Chakraborti S, Khan M T H. Recent advancements for the evaluation of anti-viral activities of natural products.  New Biotechnol. 2009;  25 347-368
• 11 Elbandy M, Miyamoto T, Lacaille-Dubois M A. Sulfated lupane triterpene derivatives and a flavone C-glycoside from Gypsophila repens.  Chem Pharm Bull. 2007;  55 808-811
• 12 Hasegawa T, Tanaka A, Hosoda A, Takano F, Ohta T. Antioxidant C-glycosyl flavones from the leaves of Sasa kurilensis var. gigantean.  Phytochemistry. 2008;  69 1419-1424
• 13 Flamini G, Pardini M, Morelli I, Ertugrul K, Dural H, Bagci Y, Kargioglu M. Flavonoid glycosides from Centaurea pseudoscabiosa subsp. pseudoscabiosa from Turkey.  Phytochemistry. 2002;  61 433-437
• 14 Gonrad J, Förster-Fromme B, Constantin M A, Ondrus V, Mika S, Mert-Balci F, Klaiber I, Pfannstiel J, Möller W, Rösner H, Förster-Fromme K, Beifuss U. Flavonoid glucuronides and a chromone from the aquatic macrophyte Stratiotes aloides.  J Nat Prod. 2009;  72 835-840
• 15 Peng J Y, Fan G R, Wu Y T. Studies on chemical constituents of Patrinia villosa.  China J Chin Mater Med. 2006;  31 128-130
• 16 Davoust D, Massias M, Molho D. Carbon-13 NMR investigation of flavonoid C-β-D-glucosides. Detection of a conformational equilibrium.  Org Magn Reson. 1980;  13 218-219
• 17 Sun W X, Li X, Li N, Meng D L. Chemical constituents of the extraction of bamboo leaves from Phyllostachys nigra (Lodd. ex Lindl.) Munro var. henonis (Mitf.) Stepf. ex Rendle.  J Shenyang Pharm Univ (Shenyang Yaoke Daxue Xuebao). 2008;  25 39-43
• 18 Li Q M, Van den Heuvel H, Delorenzo O, Corthout J, Pieters L A, Vlietinck A J, Claeys M. Mass spectral characterization of C-glycosidic flavonoids isolated from a medicinal plant (Passiflora incarnata).  J Chromatogr. 1991;  562 435-463
• 19 Li Y L, Ma S C, Yang Y T, Ye S M, But P P H. Antiviral activities of flavonoids and organic acid from Trollius chinensis Bunge.  J Ethnopharmacol. 2002;  79 365-368
• 20 Cai S Q, Wang R F, Yang X W, Shang M Y, Ma C M, Shoyama Y. Antiviral flavonoid-type C-glycosides from the flowers of Trollius chinensis.  Chem Biodivers. 2006;  3 343-348

1 These authors contributed equally to this work.