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PubMed1997

Oligosaccharide polyesters from roots of Polygala fallax.

Five new oligosaccharide polyesters, fallaxoses A-E, along with four known ones, reiniose D, senegose G, tenuifolioses C and P, were isolated from the roots of Polygala fallax. Fallaxoses A-E were elucidated as 3-O-{4-O-[beta-D-glucopyranosyl-(1-->4)- alpha-L-rhamnopyranosyl]-feruloyl}-beta-D-fructofuranosyl- (2-->1)-(4,6-di-O-benzoyl)-alpha-D-glucopyranoside, 3-O-{4-O-[beta-D-glucocopyranosyl-(1-->3)-(2-O-acetyl)- alpha-L-rhamnopyranosyl]-feruloyl}-beta-D-fructofuranosyl-(2-->1)- (4, 6-di-O-benzoyl)-alpha-D-glucopyranoside, 1-O-p-coumaroyl-(3-O-benzoyl)-beta-D-fructofuranosyl-(2-->1)- [beta-D-glucopyranosyl-(1-->2)]-[6-O-acetyl-beta-D-glucopyranosyl- (1-->3)]-(4-O-p-coumaroyl)-alpha-D-glucopyranoside, 1-O-p-coumaroyl-(3-O-benzoyl)-beta-D-fructofuranosyl-(2-->1)- [beta-D-glucopyranosyl-(1-->2)]-[6-O-acetyl-beta-D-glucopyranosyl-(1-->3 )]-(4-O-feruloyl)-alpha-D-glucopyranoside, 1-O-feruloyl-(3-O-benzoyl)-beta-D-fructofuranosyl-(2-->1)- [beta-D-glucopyranosyl-(1-->2)]-[beta-D-glucopyranosyl- (1-->3)-(6-O-acetyl)-beta-D-glucopyranosyl-(1-->3)]- (6-O-feruloyl)-alpha-D-glucopyranoside, respectively, by spectroscopic and chemical means.

Carbohydrate Conformation↗
PubMed1998

Polygalasaponins XLII-XLVI from roots of Polygala glomerata.

Five new oleanane-type saponins, polygalasaponins XLII-XLVI, along with two known saponins were isolated from the roots of Polygala glomerata Lour. The structures of polygalasaponins XLII-XLVI were elucidated as 3-O-beta-D-glucopyranosyl presenegenin 28-O-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl- (1-->2)-{4-O-[(E)-3,4-dimethoxycinnamoyl]}-beta-D-fucopyranosyl ester, 3-O-beta-D-glucopyranosyl presenegenin 28-O-beta-D-galactopyranosyl-(1-->4)-beta-D-xylopyranosyl-(1-->4)- alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-arabinopyranosyl- (1-->3)]-[4-O-(E)-p-methoxycinnamoyl]-beta-D-fucopyranosyl ester, 3-O-beta-D-glucopyranosyl presenegenin 28-O-beta-D-galactopyranosyl-(1-->4)-beta-D-xylopyranosyl-(1-->4)- alpha-L-rhamnopyranosyl-(1-->2)-[beta-D-glucopyranosyl- (1-->3)]-{4-O-[(E)-3,4-dimethoxycinnamoyl]}-beta-D-fucopyranosyl ester, 3-O-beta-D-glucopyranosyl presenegenin 28-O-beta-D-galactopyranosyl-(1-->4)-beta-D-xylopyranosyl-(1-->4)- alpha-L-rhamnopyranosyl-(1-->2)-[6-O- acetyl-beta-D-glucopyranosyl-(1-->3)]-{4-O- [(E)-3,4-dimethoxycinnamoyl]}-beta-D-fucopyranosyl ester, 3-O-beta-D- glucopyranosyl presenegenin 28-O-beta-D-galactopyranosyl-(1-->4)- beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl- (1-->2)-[6-O-acetyl-beta-D-glucopyranosyl-(1-->3)]-{4-O-[(Z)-3, 4-dimethoxycinnamoyl]}-beta-D-fucopyranosyl ester, respectively, on the basis of spectroscopic and chemical evidence.

Carbohydrate Sequence↗
PubMed1998

Oligosaccharide polyesters from roots of Polygala glomerata.

Seven new sucrose and oligosaccharide esters, glomeratoses A-G, together with four known compounds, 3-O-[(E)-3,4,5-trimethoxycinnamoyl]-beta-D-fructofuranosyl-(2-->1) - (6-O-benzoyl)-alpha-D-glucopyranoside, 3-O-(E)-sinapoyl-beta-D-fructofuranosyl-(2-->1)-[6-O-(E)-sinapo yl]-alpha-D- glucopyranoside, tenuifoliside C and reiniose G were isolated from the roots of Polygala glomerata. Glomeratoses A-G were elucidated as 3-O-[(E)-3,4,5-trimethoxycinnamoyl]-beta-D-fructofuranosyl-(2-->1) -alpha-D- glucopyranoside, 3-O-(E)-sinapoyl-beta-D-fructofuranosyl-(2-->1)-[6-O-(E)-p- coumaroyl]-alpha-D-glucopyranoside, 3-O-[(E)-3,4,5-trimethoxycinnamoyl]-beta-D-fructofuranosyl-(2-->1) -[6-O-(E)- p-coumaroyl]-alpha-D-glucopyranoside, 3-O-[(E)-3,4,5-trimethoxycinnamoyl]-beta-D-fructofuranosyl-(2-->1) -[6-O-(E)- 3,4,5-trimethoxycinnamoyl]-alpha-D-glucopyranoside, 1-O-{6-O-[3-O-(E,E)-(beta, beta'-bis-sinapoyl)-beta-D-fructofuranosyl]}-alpha- D-glucopyranoside intramolecular ester, 1-O-(E)-p-coumaroyl-(3-O-benzoyl)-beta-D- fructofuranosyl-(2-->1)-[beta-D-glucopyranosyl-(1-->2)]-[6-O-acetyl-beta -D- glucopyranoysl-(1-->3)]-[4-O-(E)-feruloyl]-(6-D-acetyl)-alph a-D- glucopyranoside, 1-O-(E)-p-coumaroyl-(3-O-benzoyl)-beta-D-fructofuranosyl-(2-->1)-[ beta-D- glucopyranosyl-(1-->2)]-[6-O-acetyl-beta-D-glucopyranoside-(1-->3)]-{4-O - [4-O-beta-D-glucopyranosyl-(E)-feruloyl]}-[6-O-(E)-p-coumaroyl+ ++]-alpha- D-glucopyranosyl, respectively, on the basis of chemical and spectral evidence.

Carbohydrate Conformation↗
PubMed2000

Isolation and evaluation of immunological adjuvant activities of saponins from Polygala senega L.

We have identified saponins in the root of Polygala senega L., a plant indigenous to the Canadian prairies, which display immunopotentiation activity to protein and viral antigens. By two-step extraction and hemolytic activity-guided fractionation by silica flush chromatography six saponin fractions were generated and their HPLC profiles determined. Two dominant fractions, designated as PS-1 and PS-2, were tested for adjuvant activity in mice immunized with ovalbumin, and hens immunized with rotavirus. The resulting adjuvant activity was compared with that of Quil A saponin. The P. senega saponins increased specific antibody levels to the antigens, in both mice and hens. In mice, there was a preferential increase of the IgG2a subclass, and upon in vitro secondary antigen stimulation, high IL-2 and IFN-gamma levels were observed in spleen cell cultures from P. senega saponins-immunized animals. The saponins were tested for their toxicity by lethality in mice and were found to be less toxic at the same dose than their counterpart Quil A. The results of this study indicated the potential of P. senega saponins as vaccine adjuvants to increase specific immune responses.

Adjuvants, Immunologic↗
PubMed2001

Onjisaponins, from the root of Polygala tenuifolia Willdenow, as effective adjuvants for nasal influenza and diphtheria-pertussis-tetanus vaccines.

Active substances from hot water extracts from 267 different Chinese and Japanese medicinal herbs were screened for mucosal adjuvant activity with influenza HA vaccine in mice. The extract from the root of Polygala tenuifolia was found to contain potent mucosal adjuvant activity. The active substances were purified and identified as onjisaponins A, E, F, and G. When each onjisaponin (10 microg) was intranasally (i.n.) inoculated with influenza vaccine (10 microg) in mice, serum hemagglutination-inhibiting (HI) antibody titers increased 3-14 times over control mice administered vaccine alone after 4 weeks. When each onjisaponin (10 microg) was i.n. inoculated with the vaccine (10 microg) followed by i.n. vaccination of the vaccine alone after 3 weeks, serum HI antibody titers increased 27-50 fold over those mice given i.n. vaccinations without onjisaponins. These same conditions also significantly increased nasal anti-influenza virus IgA antibody titers. Two inoculations with onjisaponin F (1 microg) and influenza HA vaccine (1 microg) at 3 weeks intervals, significantly increased serum HI antibody and nasal anti-influenza virus IgA and IgG antibody titers after only 1 week over mice given HA vaccine alone after the secondary vaccination. Intranasal vaccination with onjisaponin F inhibited proliferation of mouse adapted influenza virus A/PR/8/34 in bronchoalveolar lavages of infected mice. Separate intranasal vaccinations with onjisaponins A, E, F, and G (10 microg) each and diphtheria-pertussis-tetanus (DPT) vaccine (10 microg) of mice followed by i.n. vaccination with DPT vaccine alone after 4 weeks showed significant increases in serum IgG and nasal IgA antibody titers after 2 weeks following secondary vaccination over mice vaccinated with DPT vaccine alone. All onjisaponins showed little hemolytic activity at concentrations up to 100 microg/ml. The results of this study suggest that onjisaponins may provide safe and potent adjuvants for intranasal inoculation of influenza HA and DPT vaccines.

Adjuvants, Immunologic↗
PubMed1998

Effect of Polygala tenuifolia root extract on the tumor necrosis factor-alpha secretion from mouse astrocytes.

We investigated whether an aqueous extract of Polygala tenuifolia root (PTAE) inhibits secretion of tumor necrosis factor-alpha (TNF-alpha) from primary cultures of mouse astrocytes. PTAE dose-dependently inhibited the TNF-alpha secretion by astrocytes stimulated with substance P (SP) and lipopolysaccharide (LPS). Interleukin-1 (IL-1) has been shown to elevate TNF-alpha secretion from LPS-stimulated astrocytes while having no effect on astrocytes in the absence of LPS. We therefore also investigated whether IL-1 mediated inhibition of TNF-alpha secretion from primary astrocytes by PTAE. Treatment of PTAE to astrocytes stimulated with both LPS and SP decreased IL-1 secretion to the level observed with LPS alone. Moreover, incubation of astrocytes with IL-1 antibody abolished the synergistic co-operative effect of LPS and SP. These results suggest that PTAE may inhibit TNF-alpha secretion by inhibiting IL-1 secretion and that PTAE has an anti-inflammatory activity on the central nervous system curing some pathological disease states.

Animals↗
PubMed2000

Tetrasaccharide multi-esters and xanthone glycosides from the roots of Polygala wattersii.

Ten new tetrasaccharide multi-esters, watteroses A-J (1-10), and two new xanthone glycosides, wattersiixanthones A (11) and B (12), were isolated from the roots of Polygala wattersii, together with 11 known compounds (10 oligosaccharide multi-esters and a xanthone glycoside). The structures of new compounds were elucidated on the basis of chemical and spectroscopic evidence.

China↗
PubMed2000

Oligosaccharide esters from the roots of Polygala arillata.

Two new sucrose esters, arillatoses A (1) and B (2), and four new trisaccharide esters, arillatoses C-F (3-6), were isolated from the roots of Polygala arillata, together with four known sucrose esters, glomeratose E (7) and sibiricoses A(1) (8), A(5) (9), and A(6) (10). The structures of the new compounds were elucidated on the basis of chemical and spectroscopic evidence.

China↗
PubMed1999

Biologically active triterpene saponins from callus tissue of Polygala amarella.

A new bioactive saponin (1), together with a known saponin (polygalasaponin XXVIII) has been isolated from the callus tissue culture of Polygala amarella. Based on spectroscopic data, especially direct and long-range heteronuclear 2D NMR analysis and on chemical transformations, the structure of 1 was elucidated as 3-O-beta-D-glucopyranosyl presenegenin-28-O-beta-D-galactopyranosyl-(1 --> 3)-beta-D-xylopyranosyl-(1 --> 4)-alpha-L-rhamnopyranosyl-(1 --> 2)-[beta-D-glucopyranosyl-(1 --> 3)]-beta-D-fucopyranoside. Both saponins showed significant immunological properties based on the enhancement of granulocyte phagocytosis in vitro.

Adjuvants, Immunologic↗
PubMed1999

Sucrose esters and xanthone C-glycosides from the roots of Polygala sibirica.

Six new sucrose esters, sibiricoses A(1)-A(6) (1-6), two new xanthone C-glycosides, sibiricaxanthones A (7) and B (8), and a new acetophenone glycoside, sibiricaphenone (9), were isolated from the roots of Polygala sibirica together with six known glycosides. The structures of new compounds were elucidated on the basis of chemical and spectroscopic evidence. The structure of the known xanthone glycoside, polygalaxanthone III (10), was revised.

Carbohydrate Sequence↗
PubMed1996

Hypoglycemic effect of the rhizomes of Polygala senega in normal and diabetic mice and its main component, the triterpenoid glycoside senegin-II.

The hypoglycemic effect of the rhizomes of Polygala senega L. var. latifolia Torrey et Gray (Polygalaceae) was investigated in normal and KK-Ay mice, one of the model animals of non-insulin dependent diabetes mellitus (NIDDM). The n-butanol extract of senega rhizomes (SN) (5 mg/kg) reduced the blood glucose of normal mice from 191 +/- 3 to 120 +/- 3 mg/dl 4 hours after intraperitoneal administration (P < 0.001), and also showed a significant decrease in the glucose level of KK-Ay mice from 469 +/- 38 to 244 +/- 14 mg/dl under similar conditions (P < 0.001). But streptozotocin-induced diabetic mice did not experience a change in the blood glucose after administration of SN. We propose that the hypoglycemic effect of SN occurs without altering the insulin concentration. Moreover, SN needs the presence of insulin in order to act. In addition, one of the active components of the hypoglycemic effect was identified as a triterpenoid glycoside, senegin-II.

Animals↗
PubMed1994

Xanthone C-glycoside and acylated sugar from Polygala tenuifolia.

A new xanthone C-glycoside, polygalaxanthone III (1), and a new acylated sugar, tenuifoliside E (2) were isolated from the roots of Polygala tenuifolia. Their structures were characterized as 4-C-[beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranosyl]-1, 3,6-trihydroxy-7-methoxyxanthone (1) and beta-D-(1-O-acetyl-3-O-feruloyl-6-O-sinapoyl)-fructofuranosy l-alpha-D-(2,4,6- O-triacetyl)glucopyranoside (2), respectively, on the basis of chemical and spectral evidence including two dimensional nuclear magnetic resonance (2D-NMR) studies.

Disaccharides↗