Oleanolic Acid Glycosides Research Articles

Effects of oleanolic acid glycosides on gastrointestinal transit and ileus in mice

The effects of various oleanolic acid glycosides obtained from medicinal herbs on gastrointestinal transit (GIT) and ileus were investigated in fasted mice. Ileus was induced by the peritoneal-irritation or by the laparotomy with manipulation. One hour after the oral administration, three oleanolic acid 3- O-monodesmosides (oleanolic acid 3- O-glucuronide ( 3, 50 mg/kg), momordin Ic ( 4, 25 and 50 mg/kg), and momordin I ( 6, 25 mg/kg)) significantly accelerated GIT, but two oleanolic acid 3- O-monodesmosides (28-deglucosyl-chikusetsusaponins IV ( 8) and V ( 10)), oleanolic acid 3,28- O-bisdesmosides (momordin IIc ( 5), chikusetsusaponins IV ( 7) and V ( 9)), and their common aglycon (oleanolic acid ( 1)) (50 mg/kg) showed no significant effect. On the other hand, oleanolic acid 28- O-monodesmoside (compound O ( 2, 50 mg/kg)) significantly inhibited GIT. 4 (5–25 mg/kg) and 6 (12.5 and 25 mg/kg) also significantly prevented the inhibition of GIT induced by the peritoneal injection of acetic acid. 2 and 9 (50 mg/kg) significantly potentiated the inhibition of GIT, whereas 1, 3, 5, 7, 8, and 10 (50 mg/kg) showed no significant effect. 3, 4, 6, and 10 (50 mg/kg) significantly prevented the inhibition of GIT induced by laparotomy with manipulation, while 1, 2, 5, 7, 8, and 9 (50 mg/kg) showed no significant effect. These results indicate that the 3- O-glycoside moiety seems to be essential to show the GIT accelerating activity, and the 28- O-glucoside moiety reduce the activity. The accelerations of GIT by 3, 4, and 6 were completely abolished by the pretreatment with streptozotocin (100 mg/kg, iv), but not by the pretreatment with capsaicin (75 mg/kg in total, sc). These results suggest that sympathetic nervous system, but not capsaicin-sensitive sensory nerves, be involved in the enhancements of GIT by 3, 4, and 6. It is worthy to study their therapeutical effect in the prevention of the inhibition of GIT, including ileus, in clinic. ©

Structure-Related Inhibitory Activity of Oleanolic Acid Glycosides on Gastric Emptying in Mice

We examined the effects of various oleanolic acid oligoglycosides obtained from traditional herbs on gastric emptying in non-nutrient meal- or nutrient meal-loaded mice. Test samples were given orally to fasted mice 0.5h before loading of test meals. Oleanolic acid 3-O-monodesmosides [oleanolic acid 3-O-glucuronide (3, 12.5–50mg/kg), momordin Ic (4, 25 and 50mg/kg), momordin I (6, 12.5–50mg/kg), and 28-O-deglucosyl-chikusetsusaponins IV (8, 12.5–50mg/kg) and V (10, 50mg/kg)] were found to show inhibitory effects on gastric emptying in 1.5% CMC-Na test meal-loaded mice. 4, 6, and 8 also inhibited gastric emptying in mice given 40% glucose test meal, milk test meal, and 60% ethanol test meal. 3 inhibited gastric emptying in mice given milk test meal or 60% ethanol test meal, but lacked significant inhibition in 40% glucose test meal-loaded mice. 10 (50mg/kg) also slightly inhibited gastric emptying in milk test meal-loaded mice, but lacked the significant inhibition in mice given 40% glucose or 60% ethanol test meal. Whereas oleanolic acid 3,28-O-bisdesmosides [momordin IIc (5), chikusetsusaponins IV (7) and V (9)], oleanolic acid 28-O-monodesmoside [compound O (2)], and their common aglycon [oleanolic acid (1)] showed no such effects at dose of 50mg/kg. 28-O-Deglucosyl-chikusetsusaponin V (10) showed a little inhibition in these experiments. These results indicate that both the 3-O-monodesmoside structure and 28-carboxyl group were confirmed to be essential for such activity, and the 28-ester glucoside moiety and 2′-O-β-d-glucopyranoside moiety reduce the activity. ©

Effects of oleanolic acid glycoside on gastric lesions induced by ethanol and indomethacin

Effects of oleanolic acid glycoside on gastric lesions induced by ethanol and indomethacin

Studies on Kochiae Fructus. V. Antipruritic effects of oleanolic acid glycosides and the structure-requirement.

We examined the antipruritic effects of various oleanolic acid glycosides from natural medicines such as Kochiae Fructus (the fruit of Kochia scoparia SCHRAD.) and Momordicae Radix (the roots of Momordica cochinchinensis SPRENG.) using a compound 48/80-induced pruritic model in mice. Oleanolic acid 3-O-monodesmosides showed an antipruritic effect, while oleanolic acid 3,28-O-bisdesmosides and their common sapogenol oleanolic acid lacked the activity. This evidence indicated that the 3-O-glycoside moiety and the 28-carboxyl group in oleanolic acid glycosides were essential for exhibiting the antipruritic effect. Furthermore, it was found that the 3-O-glucuronides showed more potent activity than the corresponding 3-O-glucosides.

Antidiabetic principles of natural medicines. III. Structure-related inhibitory activity and action mode of oleanolic acid glycosides on hypoglycemic activity.

We examined the structure-related activity of oleanolic acid glycosides with respect to their inhibitory effect on the increase in serum glucose in oral glucose-loaded rats and their mechanism of action using oleanolic acid 3-O-glucuronide and momordin Ic. Both the 3-O-monodesmoside structure and 28-carboxyl group were confirmed to be essential for such activity, and the 3-O-glucuronide was more potent than 3-O-glucoside. On the other hand, the 28-ester glucoside moiety and 6'-methyl ester of the glucuronide moiety reduced such activity. Oleanolic acid 3-O-glucuronide and momordin Ic, both of which inhibited the increase in serum glucose in oral glucose-loaded rats, did not lower serum glucose in normal or intraperitoneal glucose-loaded rats, or alloxan-induced diabetic mice. These glycosides were found to suppress gastric emptying in rats, and also inhibit glucose uptake in the rat small intestine in vitro. These results indicate that oleanolic acid 3-O-glucuronide and momordin Ic, given orally, have neither insulin-like activity nor insulin releasing-activity. They exhibit their hypoglycemic activity by suppressing the transfer of glucose from the stomach to the small intestine and by inhibiting glucose transport at the brush border of the small intestine.

Specificity of the tonoplast transport of the oleanolic acid monoglycosides in the vacuoles from Calendula officinalis leaves.

The specificity of two separate tonoplast permeases transporting oleanolic acid glycosides was investigated in vacuoles isolated from leaf protoplasts of marigold (Calendula officinalis) with the use of chemically synthesized analogs. The results indicate that the proper structure of both parts of oleanolic acid monoglycoside, i.e. aglycon and the sugar moiety, are required for binding to a specific tonoplast carrier.

Triterpene glycosides ofHedera taurica XVI. Structures of glycosides St-A, St-B1, St-B2, St-C, St-D1, St-D2, St-E, St-F1, and St-F2 from the stems of Crimean ivy

From the stems of Crimean ivyHedera taurica Carr. (fam. Araliaceae) we have isolated previously known glycosides of oleanolic acid — the 3-O-[O-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside], the 3-O-β-D-glucopyranuronoside, and the 3-O-[O-β-D-galactopyranosyl-(1→2)-β-D-glucopyranuronoside]; known glycosides of hederagenin — the 3-O-α-L-arabinopyranoside, the 3-β-D-glucopyranoside, the 3-O-[O-β-D-glucopyranosyl-(1→2)-O-α-L-arabinopyranoside], and the 3-O-β-D-glucopyranuronoside; and also the new triterpene glycoside St-D2, hederagenin 3-O-[O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside].

Triterpene glycosides ofHedera taurica XV. Structures of glycosides St-I3, St-I4a, St-I4b, and St-I5 from the stems of Crimean ivy

From the stems of Crimean ivyHedera taurica Carr. (fam. Araliaceae) we have isolated the new triterpene glycosides St-I3, St-I5, and St-I4a, which are, respectively, the 3–0-β-D-glucopyranoside 28-O-[O-α-L-rhamnopyranosyl-(1→4)-O-(6-O-acetyl-β-D-glucopyranosyl)-(1→6)-O-β-D-glucopyranosides] of oleanolic acid and of hederagenin and the 3-O-β-D-glucopyranuronoside 28-O-β-gentiobioside of oleanolic acid, and also the previously known 3-O-[O-β-D-galactopyranosyl-(1→2)-β-D-glucopyranuronoside 28-O-β-D-glucopyranoside] of oleanolic acid (glycoside Rb-4).

Control of water-borne parasitic diseases with natural products: the potential of Dialium guineense as a molluscicide.

The molluscicidal activity of the fruit and leaves of Dialium guineense was found to be due to glycosides of the triterpenoid oleanolic acid. Three glycosides were isolated from the fruit and a fourth from the leaves and are known compounds. The amount of total saponins present in D. guineense makes it a good candidate for a readily available molluscicide in Nigerian villages.

Bioactive saponins and glycosides. VII. On the hypoglycemic principles from the root cortex of Aralia elata Seem.: structure related hypoglycemic activity of oleanolic acid oligoglycoside.

The hypoglycemic component, elatoside E, was isolated from the root cortex of Aralia elata SEEM. (Araliaceae) together with elatoside F and eight known oleanolic acid glycosides, elatosides A and C, oleanolic acid 3-O-[alpha-L-arabinofuranosyl (1-->4)]-beta-D-glucopyranosiduronic acid, oleanolic acid 3-O-beta-D-glucopyranosiduronic acid, stipuleanosides R1 and R2, and chikusetsusaponins IV and IVa. The structures of elatosides E and F were determined on the basis of chemical and physicochemical evidence as oleanolic acid 3-O-[beta-D-xylopyranosyl (1-->2)][beta-D-glucopyranosyl (1-->3)]-alpha-L-arabinopyranoside and its 28-O-beta-D-glucopyranosyl ester, respectively. The hypoglycemic activity of oleanolic acid and nine oleanolic acid oligoglycosides from the root cortex of Aralia elata was determined by monitoring inhibition effect on the elevation of plasma glucose level by oral sucrose tolerance test in rats, and some structure-activity relationships of oleanolic acid glycoside were obtained.

Ginsenosides increase secretion of lipoprotein lipase by 3T3-L1 adipocytes.

Treatment of 3T3-L1 adipocytes with either an oleanolic acid glycoside or a 20(S)-protopanaxatriol glycoside increased the secretion of lipoprotein lipase activity into the medium dose-dependently. At a concentration of 100 micrograms/ml, ginsenosides Ro, Re, Rg1, and Rh1 increased the secretion of lipase activity into the medium by 119, 107, 56, and 32%, respectively. The ratio of lipase activity in the medium to cellular lipase activity was 4.7% in control cells and 8.6% in ginsenoside Ro-treated cells, 8.3% in ginsenoside Re-treated cells, 7.0% in ginsenoside Rg1-treated cells, and 6.3% in ginsenoside Rh1-treated cells. Ginsenoside Rb2, which is a 20(S)-protopanaxadiol glycoside, increased the secretion of lipase activity by 16% at 25 micrograms/ml, and the ratio of lipase activity in the medium to cellular lipase activity was higher in ginsenoside Rb2-treated cells than in control cells. However, at 100 and 200 micrograms/ml, ginsenoside Rb2 decreased the secretion of lipase activity in parallel with cellular lipase activity. Ginsenoside Rd also decreased the secretion of lipase activity in the same dose-dependent manner. Thus, the effective dose for the secretion of lipoprotein lipase activity with ginsenosides varies with their aglycone structure.

Metabolism of [3-3H]oleanolic acid in the isolated Calendula officinalis leaf cells and transport of the synthesized glycosides to the cell wall and the extracellular space.

It has been shown for the first time that [3-3H]oleanolic acid glycosides formed in the cytosol of C. officinalis leaf cells are transported to the extracellular space in the form of pentaglucoside VI (44%), whereas glucuronides derived from [3-3H]oleanolic acid 3-O-monoglucuronide (29%) as well as a part of glucosides (24%) were transported into the cell walls.

ChemInform Abstract: Elatoside E, a New Hypoglycemic Principle from the Root Cortex of Aralia elata SEEM.: Structure‐Related Hypoglycemic Activity of Oleanolic Acid Glycosides.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Oleanolic acid saponins from root-bark of Aralia elata

Five new oleanolic acid glycosides, tarasaponins III–VII, were isolated from the dried root-bark of Aralia elata together with stipuleanoside R 2, in addition to eight saponins previously reported. They were characterized as oleanolic acid 3- O-[β- d-xylopyranosyl(1→2)][β- d-glucopyranosyl(1→3)]-α- l-arabinopyranoside, β- d-glucopyranosyl oleanolate 3- O-[β- d-glucopyranosyl(1→2)][α- l-arabinofuranosyl(1→4)]-β- d-glucuronopyranoside, β- d-glucopyranosyl oleanolate 3- O-[β- d-xylopyranosyl(1→2)][β- d-glucopyranosyl(1→3)]-β- d-glucuronopyranoside, β- d-glucopyranosyl oleanolate 3- O-[β- d-xylopyranosyl(1→2)][β- d-galactopyranosyl(1→3)]-β- d-glucopyranosyl oleanolate 3- O-[β- d-xylopyranosyl(1→2)][β- d-glucopyranosyl(1→3)-α- l-arabinopyranoside, respectively.

Oleanolic acid saponins from root bark of Aralia elata

Three new oleanolic acid glycosides, tarasaponins I–III, were isolated as their methyl esters from the root bark of Aralia elata together with four known glycosides, the methyl esters of chikusetsusaponins IVa, IV, 28-desglucosyl-chikusetsursaponin IV and pseudoginsenoside RT 1. Tarasaponins I–III were characterized as oleanolic acid 3- O-[ β- d-glucopyranosyl (1→3)][ α- l-arabinofuranosyl(1→4)]- β- d-glucuronopyranoside, oleanolic acid 3- O-[ β- d-xylopyranosyl(1→2)][ β- d-galactopyranosyl(1→3)]- β- d-glucuronopyranoside and β- d-glucopyranosyl oleanolate 3- O- β- d-galactopyranosyl(1→3)- β- d-glucuronopyranoside, respectively.

Elatoside E, a new hypoglycemic principle from the root cortex of Aralia elata Seem.: structure-related hypoglycemic activity of oleanolic acid glycosides.

A new inhibitor named elatosides E (which was shown to affect the elevation of plasma glucose level by oral sugar tolerance test in rats) was isolated from the root cortex of Aralia elata Seem. together with elatoside F. The structures of elatosides E and F were elucidated on the basis of chemical and physicochemical evidence. The hypoglycemic activities of oleanolic acid and nine oleanolic acid glycosides obtained from the root cortex of Aralia elata have been examined, and some structure-activity relationships have been found.

Phytochemical studies of seeds of medicinal plants. III. Ursolic acid and oleanolic acid glycosides from seeds of Patrinia scabiosaefolia Fischer.

Three isomeric pairs of ursolic acid (1, 3, and 5) and oleanolic acid (2, 4, and 6) glycosides were isolated as predominant constituents from seeds of Patrinia scabiosaefolia Fischer (Valerianaceae). Based on chemical and spectral evidence, their structures were established to be 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl] ursolic acid (1) and oleanolic acid (2), 3-O-[beta-D-glucopyranosyl-(1-->3)-alpha-L-arabinopyranosyl] ursolic acid (3) and oleanolic acid (4), and 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-[beta-D-glucopyranosyl- (1-->3)]-alpha-L-arabinopyranosyl] ursolic acid (5) and oleanolic acid (6), respectively. Glycosides 1, 5, and 6 are new compounds and named as patrinia-glycosides A-I, B-I, and B-II, respectively. Glycoside 3 is a known but is the first naturally occurring product. Ursolic acid glycosides were first found from this plant specimen.

The transport of [3-3H]oleanolic acid and its monoglycosides to isolated vacuoles of protoplasts from Calendula officinalis leaves

Intact vacuoles isolated from C. officinalis leaf protoplasts were supplied with [3-3H]oleanolic acid, its 3-O-monoglucoside and 3-O-monoglucuronide. It was found that both monoglycosides were transported into vacuolar space whereas free oleanolic acid only bound with the tonoplast. The effects of pH of the medium and the presence of ATP on transport of monoglycosides, as well as the competition between oleanolic acid glycosides in their transport to isolated vacuoles, were studied. The results indicate that different mechanisms underlie the transport of both series of oleanolic acid glycosides to the vacuoles.

Studies on the Constituents of Actinostemma lobatum MAXIM. VI. Structures of Lobatosides I, J and K, Oleanolic Acid and Gypsogenin Glycosides Isolated from the Seed.

Two new gypsogenin glycosides, named lobatosides I and J, and one oleanolic acid glycoside, lobatoside K, were isolated from the seed of Actinostemma lobatum MAXIM. (Cucurbitaceae), and thier structures were elucidated to be as follows based on chemical and spectral evidence.Lobatoside I : 3-O-[O-β-D-galactopyranosyl-(1→2)-β-D-glucopyranosyluronic acid]gypsogenin 28-{O-β-D-glucopyranosyl-(1→3)-[O-β-D-xylopyranosyl-(1→4)]-O-α-L-rhamnopyranosyl-(1→2)-β-D-fucopyranosyl}ester.Lobatoside J : 3-O-[O-β-D-galactopyranosyl-(1→2)-β-D-glucopyranosyluronic acid]gypsogenin 28-{O-β-D-xylopyranosyl-(1→3)-O-β-D-xylopyranosyl-(1→4)-[O-β-D-glucopyranosyl-(1→3)]-O-α-L-rhamnopyranosyl-(1→2)-β-D-fucopyranosyl}ester.Lobatoside K is an oleanolic acid glycoside. The structure of the sugar moiety is the same as that of lobatoside I.

Studies on the constituents of Aster scaber Thunb. III. Structures of scaberosides B7, B8 and B9, minor oleanolic acid glycosides isolated from the root.

Three new oleanolic acid 3,28-O-bisdesmosides, scaberosides B7, B8 and B9, were isolated as minor saponins from the root of Aster scaber THUNB. (Compositae), and their structures were determined based on spectral and chemical evidence as follows. Scaberoside B7 is 3-O-beta-D-glucopyranosyluronic acid oleanolic acid 28-[O-beta-D-apiofuranosyl-(1----3)-[O-beta-D-xylopyranosyl-(1---- 4)-O-alpha-L-rhamnopyranosyl-(1----2)-alpha-L-arabinopyranosyl] ester, scaberoside B8, 3-O-beta-D-glucopyranosyl oleanolic acid 28-[O-beta-D-xylopyranosyl-(1----4)-O-alpha-L-rhamnopyranosyl-(1----2)-a lpha-L-arabinopyranosyl] ester, and scaberoside B9, 3-O-beta-D-glucopyranosyluronic acid oleanolic acid 28-[O-alpha-L-rhamnopyranosyl-(1----2)-[O-beta-D-xylopyranosyl-(1----6)] -beta-D-glucopyranosyl] ester. Scaberosides B7 and B9 were obtained as their methyl esters.