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PubMed2006

Antinociceptive properties of coumarins, steroid and dihydrostyryl-2-pyrones from Polygala sabulosa (Polygalaceae) in mice.

We have investigated the possible antinociceptive action of the extract, fractions and pure compounds obtained from the whole plant Polygala sabulosa A. W. Bennett (Polygalaceae) in acetic acid-induced visceral pain in mice. Intraperitoneal injection of animals with the hydroalcoholic extract and fractions (CH(2)Cl(2), EtOAc, n-BuOH, aqueous fraction) (1-100 mg kg(-1)) caused a dose-related and significant inhibition of the acetic acid-induced visceral nociceptive response. The CH(2)Cl(2), EtOAc and n-BuOH fractions were more potent than the hydroalcoholic extract and aqueous fraction. The isolated compounds dihydrostyryl-2-pyrones (1, 2, 3), styryl-2-pyrone (7), alpha-spinasterol (9), scopoletin (10) and two esters of the coumarin (scopoletin) obtained semisynthetically, acetylscopoletin (10a) and benzoylscopoletin (10b) (0.001-10 mg kg(-1)), exhibited significant and dose-related antinociceptive effects against acetic acid-induced visceral pain. The results distinguished, for the first time, the extract, fractions and pure compounds obtained from P. sabulosa that produced marked antinociception against the acetic acid-induced visceral nociceptive response, supporting the ethnomedical use of P. sabulosa.

Abdominal Pain↗

PubMed2004

Cognitive improving and cerebral protective effects of acylated oligosaccharides in Polygala tenuifolia.

We studied the cognitive improving and cerebral protective constituents in the roots of Polygala tenuifolia Willdenow, a well-known Chinese traditional medicine prescribed for amnesia, neurasthenia, palpitation, noctural emission and insomnia. Tenuifoliside B (1), which is one of the acylated oligosaccharides in the roots of P. tenuifolia, showed the cerebral protective effect on potassium cyanide (KCN)-induced anoxia in mice, widely used as an animal model for cerebrovascular disease, and also had an ameliorative effect on the scopolamine-induced impairment of performance in passive avoidance task in rats. Compound 1 significantly enhanced oxotremorine-induced tremors in mice, suggesting that it ameliorated the scopolamine-induced impairment of passive avoidance response by enhancing the cholinergic system. These findings show that compound 1 has cognitive improving and cerebral protective effects.

Acylation↗

PubMed2004

Anti-stress effects of 3,4,5-trimethoxycinnamic acid, an active constituent of roots of Polygala tenuifolia (Onji).

3,4,5-trimethoxycinnamic acid (TMCA) is one of the constituents in Onji (roots of Polygala tenuifolia WILLD), an herbal medicine used for sedative in Japanese traditional Kampo medicine. Our previous study revealed that oral administration of this compound prolongs sleeping time induced by hexobarbital in mice to exhibit sedative action. In the present study, we investigate the effects of TMCA on the stress induced with repeated cold exposure or intracerebroventricular injection of corticotrophin-releasing hormone (CRH). Both types of stress significantly reduced the sleeping time induced with pentobarbital in rat, which was significantly prolonged by intraperitoneal injection of TMCA. The intracerebroventricular injection of CRH significantly augmented the content of norepinephrine (NE) in locus coeruleus (LC) of rats, which was significantly suppressed by the intracerebroventricular injection of TMCA. These findings suggest that TMCA would exhibit sedative effects by suppressing NE content in LC.

Animals↗

PubMed2005

Four new phenones from the cortexes of Polygala tenuifolia.

From the 95% EtOH extract of the cortexes of Polygala tenuifolia, four new phenones and three known xanthones were isolated. The structures of the four new phenones were identified as 4-O-[alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl]-2-hydroxyl-6-methoxybenzophenone (tenuiphenone A, 1), 3,5-di-C-beta-glucopyranosyl-2,4,6,3'-tetrahydroxybenzophenone (tenuiphenone B, 2), 2',4',6'-trihydroxyphenyl-(24Z)-triacontene-1-one (tenuiphenone C, 3), 2',4',6'-trihydroxyphenyl-(26Z)-dotriacontene-1-one (tenuiphenone D, 4) respectively, on the basis of spectroscopic analyses. The isolation of 1 and 2 supplied an evidence for the hypothesis that xanthone was biosynthesized from benzophenone in the plants.

Benzophenones↗

PubMed2006

Two new triterpenoid saponins isolated from Polygala japonica.

Bioassay guided investigation of whole parts of Polygala japonica afforded two new triterpenoid saponins, characterized as 3-O-beta-D-glucopyranosyl medicagenic acid 28-O-{beta-D-xylopyranosyl(1-->4)-[beta-D-apiofuranosyl(1-->3)]-alpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl} ester (1), 3-O-beta-D-glucopyranosyl 2-oxo-olean-12-en-23, 28-dioic acid 28-O-{beta-D-xylopyranosyl(1-->4)-[beta-D-apiofuranosyl(1-->3)]-alpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl} ester (2), together with four known triterpenoid saponins (3-6). Their structures were elucidated by spectroscopic and chemical methods. Saponins 3, 4 and 5 showed significant anti-inflammation effects on carrageenan-induced acute paw edema in mouse.

Molecular Structure↗

PubMedDate not supplied

Two xanthones from Polygala paniculata and confirmation of the 1-hydroxy-2,3,5-trimethoxy-xanthone at trace level by HRGC-MS.

Polygala paniculata L. yielded the xanthones 1-hydroxy-5-methoxy-2,3-methylenedioxyxanthone (1) and 1,5-dihydroxy-2,3-dimethoxyxanthone (2), together with coumarin murragatin and flavonol rutin. Their structures were established by chemical and spectroscopic methods (EIMS, IR, 1H and 13C NMR, NOE difference spectroscopy). By posterior analysis of an apolar crude extract using high resolution gas chromatography coupled to mass spectrometry (HRGC-MS) it was possible to characterize two sterol (spinasterol and delta25-spinasterol) and the minor 1-hydroxy-2,3,5-trimethoxyxanthone (3). Thus, the xanthone 3 was confirmed through of co-injection HRGC-MS of the respective extract with a certified standard obtained by methylation of 2 with diazomethane.

Chromatography, Gas↗

PubMed2000

[Studies on chemical constituents of fat oil of Polygala tenuifolia].

OBJECTIVE: To study the chemical constituents of fat oil from root of Polygala tenuifolia Willd. METHOD: The components were separated and identified by gas chromatograpy-mass spectrometry and elucidated on the standard mass spectral data and the percentages were determined by gas chromatographic area normalization method. RESULT: Eighteen constituents were separated and sixteen of them were identified. CONCLUSION: The major components of the fat oil were established first time as oleic acid, linoleic acid, palmitic acid, eicosenoic acid and stearic acid, which make up 87.0%, 7.31%, 3.27%, 1.07%, 0.91% of fat oil respectively.

Fatty Acids↗

PubMed2003

[Blood-activating and anti-inflammatory actions of Polygala fallax].

OBJECTIVE: To observe the blood-activating and anti-inflammatory actions of Polygala fallax Hesml. (PFH) in this paper. METHODS: A series of experiments were performed to show the blood-activating and anti-inflammatory actions of PFH, including acute blood-stagnation model in rats induced by dextran of high molecular mass, observation on microcirculation in mice, platelet aggregation in vitro in rabbits, acute inflammation in mice induced by xylene or histamine, and PC-DTH. RESULTS: PFH could remarkably decrease the whole blood relative viscosity. PFH could significantly dilate the micro-artery and micro-vein, increase the opening number of capillary in mice. However, PFH had no obvious effect on platelet aggregation induced by ADP in rabbits. PFH could significantly inhibit the increase of capillary permeability induced by histamine in mice, and decrease the mice ear-swelling induced by xylene. PFH could remarkably inhibit the induction-phase and attack-phase of PC-DTH in mice. CONCLUSION: The results suggested that PFH could improve the hemorrheologic character in blood-stagnation state, invigorate the micro-circulation, and inhibit inflammation process.

Animals↗

PubMed2003

[Studies on chemical constituents in roots of Polygala tenuifolia].

OBJECTIVE: To study the chemical constituents from the roots of Polygala tenuifolia. METHOD: Column chromatographic techniques were employed for isolation and purification of chemical constituents of the plant and the structures were elucidated by spectroscopic analysis. RESULT: Five chemical constituents were isolated and elucidated as 4-C-beta-glucopyranosyl-1,3,6-trihydroxy-7-methoxyxanthone (1), 4-C-[beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranosyl]-1,3,6- trihydroxy-7-methoxyxanthone (2), presenegenin (3), presenegenin-3-O-beta-D-glycopyranoside (4) and daucosterol (5), respectively. CONCLUSION: Compounds 1,3,4 and 5 were isolated from this plant for the first time. Compound 1 is a new natural product.

Glucosides↗

PubMed2004

[Studies on the chemical constituents in root bark of Polygala tenuifolia (II)].

OBJECTIVE: To study the chemical constituents of Polygala tenuifolia. METHOD: Isolations were performed on various chromatography columns and structure elucidations were aided by spectral data and chemical property analyses. RESULT: Four compounds were isolated from the roots of P. tenuifolia. Their structures were identified as sibiricose A5 (1), sibiricose A6 (2), tenuifoliside A (3) and 3',6-disinapoyl sucrose (4). CONCLUSION: Compounds 1 and 2 were isolated from this plant for the first time.

Plant Roots↗

PubMed2005

[Different mechanisms mediated the potentiation uterine smooth muscle caused by Polygala tenuifolia decoction progesterone in virginal rats].

OBJECTIVE: To research the effects of Polygala tenuifolia decoction on myoelectric activity of uterine smooth muscle and contractile activity of uterine smooth muscle strips of virginal rats. METHOD: To record the effects of P. tenuifolia decoction on myoelectric activity of uterine smooth muscle and contractile activity of uterine smooth muscle strips of virginal rats with biolap 410 biological system. Five blocking agents were used to study their mechanisms respectively. RESULT: Different dosages of water extract of P. tenuifolia (0.02, 0.04, 0.08 g x kg(-1)), could significantly potentiate uterine myoelectric activity and contractile activity of virginal rats. CONCLUSION: The effect of P. tenuifolia on myoelectric activity of uterine smooth muscle and contractile activity of uterine smooth muscle strips in rats may be mainly associated with H1 receptor, L-voltage-dependant calcium channels or prostaglandin synthese, its nothing to M receptor.

Adrenergic alpha-Antagonists↗

PubMed2006

[Studies on chemical constituents from roots of Polygala tricornis].

OBJECTIVE: To study the chemical constituents from the roots of Polygala tricornis. METHOD: Compounds were isolated by repeated silica gel column chromatography and their structures were determined by spectral analysis and physicochemical properties. RESULT: Six compounds were isolated from the roots of P. tricornis, and their structures were identified as p-hydroxy benzoic acid (I), glucosyringic acid (II), 1-O-p-coumaroyl-D-glucopyranose (III), cis-coniferin (IV), cis-syringin (V) and vacciniin (VI). CONCLUSION: Compounds I approximately VI were obtained from this plant for the first time.

Benzoates↗

PubMed2006

[Fingerprint of Polygala tenuifolia by high performance liquid chromatography].

AIM: To study and establish the fingerprint of Polygala tenuifolia by RP-HPLC. METHODS: The fingerprint of P. tenuifolia was built by using Kromasil C18 as column and acetonitrile-0.05% phosphoric acid aqueous in gradient as mobile phase. The flow rate was 1.0 mL x min(-1), and the detecting wavelength was set at 318 nm. Total 14 batches of P. tenuifolia from different habitats were detected, and different commodities and preparative methods were compared. RESULTS: Samples from different habitats were of high similarities, and the qualities of "yuanzhitong" and "yuanzhirou" were better than that of "yuanzhigun", while the fingerprints of P. tenuifolia with different preparative methods have not obvious differences. Moreover, the standard fingerprint of P. tenuifolia was originated from the "Computer Aided Similarity Evaluation" software, and 29 common peaks existed in the fingerprint. Each peak in the fingerprint was separated very well under the above chromatographic condition, with good accuracy, stability and repeatability, satisfied to the requests of fingerprint. CONCLUSION: The RP-HPLC fingerprint method can be used in the quality control of P. tenuifolia.

Chromatography, High Pressure Liquid↗

PubMed1977

Cytotoxic and tumor inhibitory agent from Polygala macradenia Gray (Polygalaceae): 4'-demethyldeoxypodophyllotoxin.

The chloroform fraction of Polygala macradenia exhibited activity against the P-388 lymphocytic leukemia and human epidermoid carcinoma of the nasopharynx test systems. The constituent responsible for this activity was a lignan, 4'-demethyldeoxypodophyllotoxin (C21H20O7). The identity was proven by elemental analysis; PMR, IR, mass spectrometric, and melting-point determinations; and preparation of a derivative.

Animals↗

PubMed1997

Antinociceptive properties of the hydroalcoholic extract and preliminary study of a xanthone isolated from Polygala cyparissias (Polygalaceae).

Polygala cyparissias (Polygalaceae) grows abundantly on Brazil's Atlantic coast, belonging to the typical underbrush vegetation of dunes and have been used in folk medicine for treatment of several diseases, such as disturbances of bowel and kidney. The hydroalcoholic extract of P. cyparissias (HE, 3 to 60 mg kg(-1), i.p. or 25 to 200 mg kg(-1), p.o.) produced significant and graded inhibition of acetic acid-induced abdominal constrictions, with mean ID50 values of 6 and 72 mg kg(-1), respectively. The HE (at this same range of doses) also produced dose-related inhibition of both the early and the late phase of formalin-induced licking. The calculated mean ID50 values for the early phase were: >60 and >200 mg kg(-1), while for the late phase they were 11 and 101 mg kg(-1), respectively, by i.p. and p.o. routes. The HE also caused dose-related inhibition of formalin-induced edema formation (P<0.01). The HE (3 to 60 mg kg(-1), i.p. or 50 to 200 mg kg(-1), p.o.) produced significant and dose-related inhibition of the neurogenic nociception caused by topical injection of capsaicin, with mean ID50 values of 12 and 71 mg kg(-1), respectively. Given orally, the HE (50 to 200 mg kg(-1)) prevented in a dose-dependent manner, bradykinin (3 nmol/paw) and substance P (10 nmol/paw)-induced hyperalgesia in the rat paw, with mean ED50 values of 122 and 121 mg kg(-1), respectively, but was ineffective in the hot-plate model of nociception. The antinociception caused by the HE, in contrast to that of morphine (5 mg kg(-1), s.c.), was not reversed by naloxone (5 mg kg(-1), i.p.) when assessed in the acetic acid writhing test. The HE, at antinociceptive doses, did not affect motor coordination of animals when assessed in the rota-rod model. The xanthone isolated from P. cyparissias, identified as 1,7-dihydroxy-2,3-dimethoxy xanthone (0.3 to 30 mg kg(-1), i.p.), produced dose-related inhibition of acetic acid-induced abdominal constriction, with mean ID50 value of 1.5 mg kg(-1). These data show that the active principle(s) present in the HE of P. cyparissias, elicited pronounced antinociception when assessed by i.p. or p.o. routes, against both inflammatory and neurogenic nociception, and was able to prevent bradykinin and substance P-induced hyperalgesia. Its precise mechanism of action still remains unclear.

Abdominal Pain↗

PubMed2000

Styryl- and dihydrostyryl-2-pyrones derivatives from Polygala sabulosa.

Two dihydrostyrylpyrones and a styrylpyrone were isolated from Polygala sabulosa, together with five known styrylpyrones. Their structures were established on the basis of spectral evidence as 4-methoxy-6-(11,12-methylenedioxy-14-methoxydihydrostyryl)-2-pyrone, 4-methoxy-6-(11,12-methylenedioxy-10,14-dimethoxydihydrostyryl)-2-pyrone, and 4-methoxy-6-(11,12-methylenedioxy-14-methoxystyryl)-2-pyrone.

Molecular Structure↗

PubMed1993

Sinapic acid esters from Polygala virgata.

Three sinapoyl glycosides have been isolated from the roots of Polygala virgata. The structures were established on the basis of UV, mass 1H and 13C NMR spectral data, including homonuclear and heteronuclear 2D shift correlation and selective INEPT experiments. alpha-D-(3-O-Sinapoyl)fructofuranosyl-alpha-D-(3-O-acetyl-6-O-s inapoyl)glucopyranoside and beta-D-(3,O-sinapoyl)fructofuranosyl-alpha-D-(4-O-acetyl-6-O-si napoyl)glucopyranoside are new natural products, whereas beta-D-(3-O-sinapoyl)fructofuranosyl-alpha-D-(6-O-sinapoyl) glucopyranoside has already been reported from other plants.

Carbohydrate Sequence↗

PubMed2002

Xanthone O-glycosides from Polygala tenuifolia.

Four xanthone O-glycosides, polygalaxanthones IV-VII were isolated from the roots of Polygala tenuifolia Willd., together with eight known compounds. The structures of the four xanthone O-glycosides were established as 6-O-[alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl]-1-hydroxy-3,7-dimethoxyxanthone (polygalaxanthone IV), 6-O-[alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl]-1,3-dihydroxy-7-methoxyxanthone (polygalaxanthone V), 6-O-(beta-D-glucopyranosyl)-1,2,3,7-tetramethoxyxanthone (polygalaxanthone VI), and 3-O-[alpha-D-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl]-1,6-dihydroxy-2,7-dimethoxyxanthone (polygalaxanthone VII), respectively, on the basis of analysis of spectroscopic evidence.

Glycosides↗