New Triterpenoid Saponins from the Herb Hylomecon japonica

Abstract

Background: Hylomecon japonica, a plant of the Papaveraceae family which is well-known for the alkaloids they produce, is a perennial plant widely distributed in the northeast, central and east regions of China. Although a variety of chemical constituents, including alkaloids, flavonoids, and megastigmoids, have been isolated from H. japonica, the investigation of saponins in H. japonica has not been reported until now. Methods: Various separation techniques, including polyporous resin column chromatography, silica gel column chromatography and hemi-preparative HPLC were applied to the isolation of triterpenoid saponins, and chemical methods such as acid hydrolysis and spectroscopic methods including HRESIMS and NMR were applied to their structure elucidation, and the XTT reduction method was used to assay cytotoxicity. Results: Two new triterpenoid saponins, named hylomeconoside A (1) and B (2) which were identified as 3-O-β-d-galactopyranosyl-(1→2)-β-d-glucuronopyranosyl-gypsogenin-28-O-β-d-xylopyranosyl-(1→3)-β-d-xylopyranosyl-(1→4)-α-l-rhamnopyranosyl-(1→2)-β-d-quinovopyranoside (1) and 3-O-β-d-galactopyranosyl-(1→2)-β-d-glucuronopyranosyl-gypsogenin-28-O-β-d-xylopyranosyl-(1→3)-β-d-xylopyranosyl-(1→4)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranoside (2), and two known triterpenoid saponins identified as dubioside C (3) and lucyoside P (4) on the basis of spectroscopic and chemical evidence, were isolated from H. japonica. Compound 1 exhibited moderate cytotoxicity on MGC-803 and HL-60 cells, with IC50 values of 43.8 and 32.4 μg·mL−1, respectively. Conclusions: Compounds 1 and 2 are new saponins, and 1 is considered to be one of the antitumor principles in this plant. This is the first time that triterpenoid saponins have been isolated from plants of the Papaveraceae family.

Antitumor Triterpenoid Saponin from the Fruits of Avicennia marina

“…As previously described [ 37 ] with some minor modifications, compound 1 (10 mg) was hydrolyzed with 2 M HCl/dioxane (1:1, 4 mL) under reflux for 8 h. After partitioned with CHCl 3 (2 mL × 3), the aqueous layer was neutralized with 2 M NaOH and then dried to give a monosaccharide mixture. A solution of the sugar mixture in pyridine (2 mL) was added to l -cysteine methyl ester hydrochloride (about 1.5 mg) and kept at 60 °C for 1 h. Then trimethylsilylimidazole (1.5 mL) was added to the reaction mixture.…”

Predicting the Potential Distribution of Hylomecon japonica in China under Current and Future Climate Change Based on Maxent Model

“…In this study, a total of 102 occurrences of H. japonica were collected from the following sources: (1) the Global Biodiversity Information Facility Data Portal [23]; (2) the Specimen Resources Sharing Platform for Education [24]; (3) the Chinese Virtual Herbarium [25]; (4) Chinese plant species information System [26]; (5) relevant literature [2,6,27,28] and field investigation. In addition, only one was retained when the obtained geographic information of the sample repeated.…”

“…Various alkaloids, phenols, flavonoids, saponins and other active compounds isolated from H. japonica have been reported. A new species of endophytic bacteria belonging to sphingomonas was isolated from the rhizome of H. japonica [4][5][6]. Although many pharmacological studies, including anti-inflammatory, anticancer and antibacterial activities, have been reported [7][8][9], the investigation of the medicinal value and mechanism of H. japonica is far from enough.…”

Habitat Suitability Study of Hylomecon Japonica Based on Maxent Model in China

“…Various alkaloids, phenols, avonoids, saponins and other active compounds isolated from H. japonica have been reported. And a new species of endophytic bacteria belonging to sphingomonas was isolated from the rhizome of H. japonica [4][5][6]. Although many pharmacological studies, including anti-in ammatory, anticancer and antibacterial activities, have been reported [7][8][9], the investigation of the medicinal value and mechanism of H. japonica is far from enough.…”