Activity-Guided Isolation of Saponins from Kalopanax pictus with Anti-inflammatory Activity.

Abstract

Kalopanax pictus NAKAI (Araliaceae) is a deciduous tree found in countries of the Orient. The stem bark of Kalopanax pictus has been used in traditional medicine to treat neuralgia, rheumatic arthritis, lumbago, 1) furuncle, carbuncle, wound,2) diarrhea and scabies.3) Phytochemical studies demonstrated the presence of saponins, 4) polyacetylenes, 5) phenylpropanoid glycosides, 5) lignans, 5) as well as simple phenolic glycosides.5) During an ongoing collaborative search for novel anti-inflammatory agents originating from plants, an ethyl acetate fraction of the stem bark of Kalopanax pictus exhibited significant anti-inflammatory activity in a vascular permeability test.6) Anti-rheumatic activity on adjuvant-induced arthritis in rats 7) and antinociceptive 8) and antioxidative activities 9) of EtOAc fraction and kalopanaxsaponins A and I were reported. However, this plant has not been investigated previously for systematic isolation of its anti-inflammatory components. We report herein the bioassay-guided chromatographic fractionation of an ethyl acetate soluble extract of K. pictus, which has led to the isolation of two anti-inflammatory saponins together with a novel inactive saponin. Results and DiscussionResults of the activity-guided isolation from K. pictus extract are summarized in Chart 1. From the ethyl acetate soluble fraction (Fr.) which showed potent activity in the vascular permeability test, eleven subfractions (Frs. 1-11) were obtained and the activity was tested using doses proportional to the yields obtained in the isolation procedure. As shown in Table 1, only Fr. 8 showed significant inhibition of vascular permeability at 250 mg/kg. This fraction was further divided into 5 subfractions (Frs. 8-A-8-E) by column chromatography. Fractions 8-B and 8-D elicited inhibition of vascular permeability at doses of 120 and 100 mg/kg, respectively, while Frs. 8-A and 8-E were negative (Fig. 1). Fraction 8-C was a mixture of Frs. 8-B and 8-D. Fraction 8-B was crystallized from MeOH to give compound 1. Repeated column chromatography of Fr. 8-D followed by recrystallization yielded compounds 2 and 3. Compounds 1 and 2 at doses of 50 mg/kg showed potent inhibition of vascular permeability (Fig. 2), while compound 3 exhibited no activity. ϩ peak at m/z 789.4405. The IR spectrum of 2 showed absorption bands at 1700 cm Ϫ1 for carboxylic acid and strong absorption bands at 3436 and 1053 cm Ϫ1 suggestive of an oligoglycosidic structure. On acid hydrolysis of 2 with 5% aqueous hydrochloric acid (HCl)-60% dioxane solution, 2 yielded L-arabinose and Lrhamnose, which were identified by GLC analysis of the trimethylsilyl thiazolidine derivatives as the sugars 11) and an aglycon, caulophyllogenin.12) It showed signals for six angular methyl groups at d 0.98, 1.04, 1.05, 1.08, 1.17 and 1.79 (all singlets for C-25, 29, 26, 24, 30 and 27 CH 3 groups), as well as signals for two anomeric protons at d 5.13 (d, Jϭ6.2 Hz) and 6.26 (br s) in the 1 H-NMR spectrum. Comparison of the 1 H-and 13 C-NMR spectra of 2 with those of 1 sh...

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