Chemical Constituents from the Roots and Stems of Erycibe obtusifolia and Their In Vitro Antiviral Activity

Abstract

Three new quinic acid derivatives, 4-O-caffeoyl-3-O-sinapoylquinic acid methyl ester (1), 5-O-caffeoyl-4-O-syringoylquinic acid methyl ester (2), and 4-O-caffeoyl-3-O-syringoylquinic acid methyl ester (3), as well as four new coumarin glycosides, 7-O-(3-O-sinapoyl-β-D-glucopyranosyl)-6-methoxycoumarin (12), 7-O-(6-O-sinapoyl-β-D-glucopyranosyl)-6-methoxycoumarin (13), 7-O-(2-O-sinapoyl-β-D-glucopyranosyl)-6-methoxycoumarin (14), and 7-O-(6-O-syringoyl-β-D-glucopyranosyl)-6-methoxycoumarin (15), together with eight known compounds (4–11) were isolated from the roots and stems of Erycibe obtusifolia. Their structures were elucidated on the basis of spectroscopic analysis and chemical evidence. All the compounds were screened for their in vitro antiviral activity against respiratory syncytial virus with a cytopathic effect reduction assay. Among them, the di-O-caffeoyl quinates 8–11 displayed a potent in vitro anti-respiratory syncytial virus effect.

Key words

Erycibe obtusifolia - Convolvulaceae - quinic acid derivative - coumarin glycoside - antivirus activity - respiratory syncytial virus

^* These authors contributed equally to this work.

• References

• 1 Tan JN, Gao ZX. Advances in studies on Caulis erycibes . J Guangxi Acad Sci 2008; 24: 49-52
• 2 Cao H, Wang MJ. Determination of scopoletin in Dinggongteng injection by HPLC. Pharm Clin Res 2007; 15: 129-130
• 3 Liu J, Feng ZM, Xu JF, Wang YH, Zhang PC. Rare biscoumarins and a chlorogenic acid derivative from Erycibe obtusifolia . Phytochemistry 2007; 68: 1775-1780
• 4 Yao TR, Chen ZN. Chemical investigation of Chinese medicinal herb, Bao Gong Teng. The isolation and preliminary study on a new myotic constituent, Bao Gong Teng A. Acta Pharm Sin 1979; 14: 731-735
• 5 Pan R, Dai Y, Gao XH, Xia YF. Scopolin isolated from Erycibe obtusifolia Benth stems suppresses adjuvant-induced rat arthritis by inhibiting inflammation and angiogenesis. Int Immunopharmacol 2009; 9: 859-869
• 6 Zeng SJ, Zhang YB, Peng DW, Wu YP, Yu KM, Zhou WB. Studies of the mechanism of lowering intraocular pressure on Erycibele alkaloid. Chin J Ophthalmol 1999; 35: 171-173
• 7 Li YL, But PPH, Ooi VEC. Antiviral activity and mode of action of caffeoylquinic acids from Schefflera heptaphylla (L.) Frodin. Antiviral Res 2005; 68: 1-9
• 8 Li YL, Jiang RW, Ooi LSM, But PPH, Ooi VEC. Antiviral triterpenoids from the medicinal plant Schefflera heptaphylla . Phytother Res 2007; 21: 466-470
• 9 Wang Y, Chen M, Zhang J, Zhang XL, Huang XJ, Wu X, Zhang QW, Li YL, Ye WC. Flavone C-glycosides from the leaves of Lophatherum gracile and their in vitro antiviral activity. Planta Med 2012; 78: 46-51
• 10 Geng HW, Zhang XL, Wang GC, Yang XX, Wu X, Wang YF, Ye WC, Li YL. Antiviral dicaffeoyl derivatives from Elephantopus scaber . J Asian Nat Prod Res 2011; 13: 665-669
• 11 Tanaka T, Nakashima T, Ueda T, Tomii K, Kouno I. Facile discrimination of aldose enantiomers by reversed-phase HPLC. Chem Pharm Bull 2007; 55: 899-901
• 12 Song S, Li YX, Feng ZM, Jiang JS, Zhang PC. Hepatoprotective constituents from the roots and stems of Erycibe hainanesis . J Nat Prod 2010; 73: 177-184
• 13 Kim HJ, Kim EJ, Seo SH, Shin CG, Jin C, Lee YS. Vanillic acid glycoside and quinic acid derivatives from Gardeniae Fructus. J Nat Prod 2006; 69: 600-603
• 14 Li B, Huang MJ, Li YL, Zeng GY, Tan JB, Zhou YJ. Antioxidant constituents of Sarcandra glabra (Thunb.) Nakai. J Shenyang Pharm Univ (Shenyang Yaoke Daxue Xuebao) 2009; 26: 900-903
• 15 Ono M, Masuoka C, Odake Y, Ikegashira S, Ito Y, Nohara T. Antioxidative constituents from Tessaria integrifolia . Food Sci Technol Res 2000; 6: 106-114
• 16 Wang YF, Liu B. Preparative isolation and purification of dicaffeoylquinic acids from the Ainsliaea fragrans champ by high-speed counter-current chromatography. Phytochem Anal 2007; 18: 436-440
• 17 Ojwang JO, Wang YH, Wyde PR, Fischer NH, Schuehly W, Appleman JR, Hinds S, Shimasaki CD. A novel inhibitor of respiratory syncytial virus isolated from ethnobotanicals. Antiviral Res 2005; 68: 163-172