Glucosylated caffeoylquinic acid derivatives from the flower buds of Lonicera japonica

Abstract

Three new glucosylated caffeoylquinic acid isomers (1–3), along with six known compounds, have been isolated from an aqueous extract of the flower buds of Lonicera japonica. Structures of the new compounds were determined by spectroscopic and chemical methods as (−)-4-O-(4-O-β-d-glucopyranosylcaffeoyl)quinic acid (1), (−)-3-O-(4-O-β-d-glucopyranosylcaffeoyl)quinic acid (2), and (−)-5-O-(4-O-β-d-glucopyranosylcaffeoyl)quinic acid (3), respectively. In the preliminary in vitro assays, two known compounds methyl caffeate and 2ʹ-O-methyladenosine showed inhibitory activity against Coxsackie virus B3 with IC50 values of 3.70 μmol/L and 6.41 μmol/L and SI values of 7.8 and 12.1, respectively.

Novel caffeoylquinic acid derivatives from Lonicera japonica Thunb. flower buds exert pronounced anti-HBV activities

“…9 Previous phytochemical investigations have been reported for different types of chemical constituents, including avonoids, caffeoylquinic acids, iridoids, saponins, and other compounds. [9][10][11][12] Furthermore, caffeoylquinic acids are major constituents of L. japonica. 13,14 However, the caffeoylquinic acid derivatives form L. japonica and their anti-HBV activities are lacking in systematic research.…”

“…To clarify the anti-HBV activity of caffeoylquinic acids from the ower buds of L. japonica Thunb., as well as four new caffeoylquinic acids (1)(2)(3)(4), together with ve simple caffeic acids (5)(6)(7)(8)17), and fourteen known caffeoylquinic acids (9)(10)(11)(12)(13)(14)(15)(16)(18)(19)(20)(21)(22)(23) are systematically isolated and identied ( Fig. 1).…”

Antiviral glycosidic bisindole alkaloids from the roots ofIsatis indigotica

“…13 C NMR spectral data (d) for isatindigobisindolosides A (1) -G (7) a . Data were measured in DMSO-d 6 for 1 -4, 6, and 7 and in CD3 OD for 5 at 125 MHz for 1, 2, and 4-6 and at 150 MHz for 3 and 7.…”

“…NMR spectra were obtained at 500 MHz or 600 MHz for 1 H, and 125 MHz or 150 MHz for13 C, respectively, on Inova 500 or SYS 600 (Varian Associates Inc., Palo Alto, CA, USA) or Bruker 600 NMR spectrometers (Bruker Corp., Karlsruhe, Germany) in DMSO-d 6 or MeOH-d 4 , with solvent peaks used as references. ESI-MS and HR-ESI-MS data were measured using an AccuToFCS JMS-T100CS spectrometer (Agilent Technologies, Ltd., Santa Clara, CA, USA).…”

Characterization of Nine Compounds Isolated from the Acid Hydrolysate of Lonicera fulvotomentosa Hsu et S. C. Cheng and Evaluation of Their In Vitro Activity towards HIV Protease

“…Lonicera species have been shown to possess hepatoprotective, antiallergic, anti-inflammatory, antibacterial, and antiviral activities [6][7][8]. Various active ingredients, such as caffeoylquinic acid, secoiridoids, flavonoids, cerebrosides, nitrogen-containing iridoid glycosides, and triterpene glycosides, have been isolated and characterized from Lonicera species [9][10][11][12][13][14]. In addition, a number of triterpene derivatives, caffeoylquinic acid derivatives, and flavonoids have exhibited potent inhibitory effects against human immunodeficiency virus (HIV)-1 integrase and prevented HIV-1 replication in tissue culture [15][16][17][18][19].…”