Terpene Glycosides from the Roots of Sanguisorba officinalis L. and Their Hemostatic Activities

Abstract

Guided by a hemostasis bioassay, seven terpene glycosides were isolated from the roots of Sanguisorba officinalis L. by silica gel column chromatography and preparative HPLC. On the grounds of chemical and spectroscopic methods, their structures were identified as citronellol-1-O-α-L-arabinofuranosyl-(1→6)-β-D-glucopyranoside (1), geraniol-1-O-α-L-arabinofuranosyl-(1→6)-β-D-glucopyranoside (2), geraniol-1-O-α-L-arabinopyranosyl-(1→6)-β-D-glucopyranoside (3), 3β-[(α-L-arabinopyranosyl)oxy]-19α-hydroxyolean-12-en-28-oic acid 28-β-D-glucopyranoside (4), 3β-[(α-L-arabinopyranosyl)-oxy]-19α-hydroxyurs-12-en-28-oic acid 28-β-D-glucopyranoside (ziyu-glycoside I, 5), 3β,19α-hydroxyolean-12-en-28-oic acid 28-β-D-glucopyranoside (6) and 3β,19α-di-hydroxyurs-12-en-28-oic acid 28-β-D-glucopyranoside (7). Compound 1 is a new mono-terpene glycoside and compounds 2, 3 and 5 were isolated from the Sanguisorba genus for the first time. Compounds 1–7 were assayed for their hemostatic activities with a Goat Anti-Human α2-plasmin inhibitor ELISA kit, and ziyu-glycoside I (5) showed the strongest hemostatic activity among the seven terpene glycosides. This is the first report that ziyu-glycoside I has strong hemostatic activity.

Chemical Composition, Antioxidant and Antimicrobial Activities of Sanguisorba officinalis L. Extracts

“…Triterpene glycosides displayed antioxidant properties, including suppression of lipid peroxide and hydroxyl radical generation and upregulation of the superoxide dismutase activity [17]. Terpene glycosides exhibited hemostatic activity, the strongest one being shown by ziyu-glycoside I [18]. The aqueous extract of S. officinalis showed neuroprotective effects on the transient focal ischemia in rats, and the methanol extract also exhibited neuroprotective effect on the oxidative stress induced by amyloid beta protein [19 -21].…”

“…The ziyu-glucoside II showed an anticancer effect on the human gastric carcinoma BGC-823 cells [24], and an antiproliferative effect on human breast tumor cell lines MCF-7 and MDA-MB 231 [25]. The methanol extract of S. officinalis inhibited the growth of prostate cancer cell PC 3 and induced apoptotic cell death by downregulation of McI-1 protein expression and Bax oligomerization [18]. The aqueous extract of S. officinalis turned out to be effective in in vitro inhibition of the hepatitis B virus DNA polymerase activity and suppressed the hepatitis B virus surface antigen (HBsAg) [26,27].…”

Comprehensive characterization of the in vitro and in vivo metabolites of ziyuglycoside I in rat microsome, intestinal flora, excretion specimen and fresh tissues based on LC–Q-TOF/MS

“…A variety of bioactive ingredients, including saponins, flavonoids, tannins, anthraquinones and steroids, were isolated from S. officinalis, and their pharmacological effects on anti-wrinkle, hemostatic and anti-inflammatory properties had been studied [3][4][5]. Saponin components such as triterpenes and their glycosides, gallic acid, and disaccharide have been confirmed as major active ingridients in S. officinalis L. [6][7][8].…”

Aqueous extract of Sanguisorba officinalis blocks the Wnt/β-catenin signaling pathway in colorectal cancer cells

“…Since DY from Jiangsu province (D1) exerted the most signicant inhibitory effects on the Wnt pathway with an IC 50 value at 2.20 AE 0.74 mg ml À1 (Table s2 †), D1 was used for subsequent studies. To nd out the potential active constituents in DY, we investigated the anti-Wnt effects of tannins (RZ) and saponins (ZG), which respectively take proportions of around 17% and 4% of total contents in DY, 17,18 as well as their representative constituents, namely GA, CA, EA, ziyuglycoside I and ziyuglycoside II. 15,19 Results indicate that RZ and ZG inhibited Wnt signaling in the concentration range of 0.5-40 mg ml À1 (Fig.…”