Calysolins V-IX, Resin Glycosides from Calystegia soldanella and Their Antiviral Activity Toward Herpes. -(ONO*, M.; TAKIGAWA, A.; KANEMARU, Y.; KAWAKAMI, G.; KABATA, K.; OKAWA, M.; KINJO, J.; YOKOMIZO, K.; YOSHIMITSU, H.; NOHARA, T.; Chem. Pharm. Bull. 62 (2014) 1, 97-105, http://dx.doi.org/10.1248/cpb.c13-00610 ; Sch. Agric., Kyushu Tokai Univ., Aso, Kumamoto 869-14, Japan; Eng.) -H. Toeppel 23-210
Four new resin glycosides having macrolactone structures (jalapins), named calysolins X (1)-XIII (4), were isolated from the leaves, stems, and roots of Calystegia soldanella ROEM. et SCHULT. (Convolvulaceae). Their structures were determined on the basis of spectroscopic data as well as chemical evidence. The sugar moieties of 1-4 were partially acylated by some organic acids, including tiglic acid, 2S-methylbutyric acid, and 2S,3S-nilic acid. Additionally, the antiviral activity of 1-4 toward herpes simplex virus type 1 was evaluated. All the compounds showed antiviral activity.Key words resin glycoside; jalapin; Calystegia soldanella; Convolvulaceae; calysolin; anti-herpes simplex virus activityis commonly found on the sandy beaches of seas and lakes located the temperate regions of the world. The roots of this plant are used in the treatment of arthritis.1) In our previous paper, we reported the isolation and structural elucidation of four new glycosidic acids, calysolic acids A-D, which were obtained along with the known glycosidic acid, soldanellic acid B, and three organic acids, 2S-methylbutyric, tiglic, and 2S,3S-nilic acids, upon alkaline hydrolysis of the crude resin glycoside fraction of the leaves, stems, and roots of C. soldanella.2) Further, we isolated nine genuine resin glycosides namely calysolins I-IX, all of which possessed characteristic macrolactone structures similar to those of the already known jalapins, 3) along with one known jalapin, soldanelline B, and their antiviral activities toward herpes simplex virus type 1 (HSV-1) were evaluated. 4,5) As a part of an ongoing study of the resin glycosides from this plant, the current study deals with the isolation and structural elucidation of four new resin glycosides named calysolins X (1)-XIII (4). Additionally, the antiviral activity of 1-4 toward HSV-1 is described herein.The fresh leaves, stems, and roots of C. soldanella were extracted using methanol (MeOH). This extract was suspended in H 2 O and then extracted successively using ethyl acetate (EtOAc) and n-butanol (BuOH). The EtOAc-soluble fraction was subjected to silica gel column chromatography and HPLC on octadecyl silica (ODS) and silica gel to yield 1-4.Calysolin X (1) was obtained as an amorphous powder. The negative-ion FAB-MS and positive-ion FAB-MS of 1 exhibited an [M-H] -ion peak at m/z 1051 and an [M+ Na] + ion peak at m/z 1075, respectively, indicating its molecular weight to be 1052. The molecular formula of 1 was found to be C 50 H 84 O 23 using high-resolution (HR)-positive-ion FAB-MS. Upon alkaline hydrolysis, 1 yielded a glycosidic acid and an organic acid fraction. The gas chromatography (GC) analysis of the organic acid fraction revealed the presence of tiglic and nilic acids. The glycosidic acid was identified as soldanelic acid B (5) by comparing with an authentic sample 2) using 1 H-NMR spectroscopy. The 1 H-NMR spectrum of 1 exhibited signals due to one H-2 of the niloyl residue, one H-3 of the tigloyl residue, and four anomeric protons. The 13 C-NMR spectrum...
Five new resin glycosides having macrolactone structures (jalapins), named calysolins V-IX (1-5), were isolated from the leaves, stems, and roots of Calystegia soldanella ROEM. et SCHULT. (Convolvulaceae). Their structures were determined on the basis of spectroscopic data as well as chemical evidence. The isolated compounds could be classified into two macrolactone types-one having a 22-membered ring (1-4) and the other with a 27-membered ring (5). The sugar moieties of 1-5 were found to exist in partially acylated forms comprising 2S-methylbutyric acid and tiglic acid. Compounds 4 and 5 are the first representatives of the calysolic acid C as the component glycosidic acid. Additionally, the antiviral activity of 1-5, together with calysolins I-IV and soldanelline B, which are previously isolated jalapins from this plant, toward herpes simplex virus type 1 was evaluated. All the compounds showed antiviral activity.Key words resin glycoside; jalapin; Calystegia soldanella; Convolvulaceae; calysolin; anti-herpes activityis widely distributed on the sandy beaches of seas and lakes in temperate regions of the world. The roots of this plant are used for the treatment of arthritis.1) In our previous investigations, we reported the isolation and structural elucidation of four new glycosidic acids, calysolic acids A-D, which were obtained along with the known glycosidic acid, soldanellic acid B, and three organic acids, 2S-methylbutyric, tiglic, and 2S,3S-nilic acids, upon alkaline hydrolysis of the crude resin glycoside fraction of the leaves, stems, and roots of C. soldanella.2) Further, we isolated four genuine resin glycosides named calysolins I-IV, all of which were found to possess characteristic macrolactone structures, as in already known jalapins, 3) along with one known jalapin, soldanelline B. 4) As part of an ongoing study of the resin glycosides from this plant, the present report deals with the isolation and structural elucidation of five new resin glycosides named calysolins V-IX. Additionally, the antiviral activity of calysolins I-IX and soldanelline B toward herpes simplex virus type 1 (HSV-1) 5) is described.The fresh leaves, stems, and roots of C. soldanella were extracted with methanol. The obtained extract was suspended in H 2 O and then extracted successively with ethyl acetate and n-butanol. The ethyl acetate-soluble fraction was subjected to silica gel column chromatography and HPLC on octadecyl silica (ODS) and naphthylethyl group bonded silica to yield five resin glycosides (1-5).Compound 1
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