MaquiBright™ standardized maqui berry extract significantly increases tear fluid production and ameliorates dry eye-related symptoms in a clinical pilot trial.

AIM: Dry eye symptoms, resulting from insufficient tear fluid generation, represent a considerable burden for a largely underestimated number of people. We concluded from earlier pre-clinical investigations that the etiology of dry eyes encompasses oxidative stress burden to lachrymal glands and that antioxidant MaquiBright™ Aristotelia chilensis berry extract helps restore glandular activity. METHODS: In this pilot trial we investigated 13 healthy volunteers with moderately dry eyes using Schirmer test, as well as a questionnaire which allows for estimating the impact of dry eyes on daily routines. Study participants were assigned to one of two groups, receiving MaquiBright™ at daily dosage of either 30 mg (N.=7) or 60 mg (N.=6) over a period of 60 days. Both groups presented with significantly (P<0.05) improved tear fluid volume already after 30 days treatment. Schirmer test showed an increase from baseline 16.3±2.6 mm to 24.4±4.8 mm (P<0.05) with 30 mg MaquiBright™ and from 18.7±1.9 mm to 27.6±3.4 mm with 60 mg (P<0.05), respectively. Following treatment with 30 mg MaquiBright™ for further 30 days, tear fluid volume dropped slightly to 20.5±2.8 mm, whereas the improvement persisted with 60 mg treatment at 27.1±2.7 mm after 60 days treatment (P<0.05 vs. baseline). RESULTS: The burden of eye dryness on daily routines was evaluated employing the "Dry Eye-related Quality of life Score" (DEQS), with values spanning from zero (impact) to a maximum score of 60. Participants had comparable baseline values of 41.0±7.7 (30 mg) and 40.2±6.3 (60 mg). With 30 mg treatment the score significantly decreased to 21.8±3.9 and 18.9±3.9, after 30 and 60 days, respectively. With 60 mg treatment the DEQS significantly decreased to 26.9±5.3 and 11.1±2.7, after 30 and 60 days, respectively. Blood was drawn for safety analyses (complete blood rheology and -chemistry) at all three investigative time points without negative findings. CONCLUSION: In conclusion, while daily supplementation with 30 mg MaquiBright™ is effective, the dosage of 60 significantly increased tear fluid volume at all investigative time points and decreased dry eye symptoms to almost a quarter from initial values after two months treatment.

[Antigenicity and phototoxicity of water-soluble extract from Salacia reticulata (Celastraceae)].

The antigenicity and phototoxicity of water-soluble extract from Salacia reticulata (SRE) were examined in guinea pigs. In a study of active systemic anaphylaxis reaction, neither the oral administration group (64 or 320 mg/kg, 5 times/week, 3 weeks) nor the subcutaneous administration group (64 mg/kg, 1 time/week, 3 weeks) exhibited any anaphylactic reaction. Moreover, sensitization with serum obtained from these animals did not induce passive cutaneous anaphylaxis reaction in normal animals. In a phototoxicity study, oral administration of SRE (320 mg/kg) induced neither erythema nor edema. These results suggest that SRE is not antigenic or phototoxic.

Phytoestrogens from the roots of Polygonum cuspidatum (Polygonaceae): structure-requirement of hydroxyanthraquinones for estrogenic activity.

The methanolic extract from the roots of Polygonum (P.) cuspidatum was found to enhance cell proliferation at 30 or 100 microg/mL in MCF-7, an estrogen-sensitive cell line. By bioassay-guided separation from P. cuspidatum with the most potent activity, emodin and emodin 8-O-beta-D-glucopyranoside were isolated as active principles. The methanolic extracts from Polygonum, Cassia, Aloe, and Rheum species, which were known to contain anthraquinones, also showed the MCF-7 proliferation. As a result of the evaluation of various anthraquinones from plant sources and synthetic anthraquinones, aloe-emodin, chrysophanol, chrysophanol 8-O-beta-D-glucopyranoside, and 1,8-dihydroxyanthraquinone showed weak activity. On the other hand, alizalin and 2,6-dihydroxyanthraquinone as well as emodin having the 2- and/or 6-hydroxyl groups showed potent activity. These results show that the unchelated hydroxyl group is essential for strong activity. Emodin and 2,6-dihydroxyanthraquinone also inhibited 17beta-estradiol binding to human estrogen receptors (ERs) with K(i) values of 0.77 and 0.31microM for ERalpha and 1.5 and 0.69 microM for ERbeta. These findings indicate that hydroxyanthraquinones such as emodin are phytoestrogens with an affinity to human estrogen receptors.

Dimeric sesquiterpene thioalkaloids with potent immunosuppressive activity from the rhizome of Nuphar pumilum: structural requirements of nuphar alkaloids for immunosuppressive activity.

Potent immunosuppressive dimeric sesquiterpene thioalkaloids, 6-hydroxythiobinupharidine, 6,6'-dihydroxythiobinupharidine, 6-hydroxythionuphlutine B and 6'-hydroxythionuphlutine B, were isolated from the rhizome of Nuphar pumilum together with five inactive quinolizidine alkaloids, neothiobinupharidine, nupharidine, deoxynupharidine, 7-epideoxynupharidine and nupharolutine. These dimeric sesquiterpene thioalkaloids were found to significantly inhibit anti-sheep erythrocyte plaque forming cell formation in mouse splenocytes at 1 microM. At this concentration. 6-hydroxythiobinupharidine, 6-hydroxythionuphlutine B and 6'-hydroxythionuphlutine B did not show cytotoxic effects to mouse splenocytes, and 6,6'-dihydroxythiobinupharidine also showed only minor or minimal cytotoxicity. By comparison of the inhibitory activity of several Nuphar alkaloids on anti-sheep erythrocyte plaque forming cell formation, some structural requirements of Nuphar alkaloids for immunosuppressive activity were obtained. Namely, the 6- or 6'-hydroxyl group at the quinolizidine ring of dimeric sesquiterpene thioalkaloids is essential for the immunosuppressive effect. The number of hydroxyl groups appears to be related to the cytotoxicity, and the influence on splenocytes is greater with increasing numbers of hydroxyl groups.

[Polyphenol constituents from Salacia species: quantitative analysis of mangiferin with alpha-glucosidase and aldose reductase inhibitory activities].

Mangiferin, three catechins, and two catechin dimers were isolated from the roots of Salacia reticulata (SRE), and examined their inhibitory activities against several carbohydrate metabolize enzymes (sucrase, maltase, isomaltase, alpha-amylase, and aldose reductase). Among them, mangiferin was found to inhibit sucrase, isomaltase, and aldose reductase from rat with IC50 values of 87, 216 and 1.4 micrograms/ml, respectively. The inhibitory activities of mangiferin are competitive for sucrase and isomaltase with inhibitor constant (Ki) 55 micrograms/ml and 70 micrograms/ml, respectively. In order to determine the mangiferin contents in the water extracts from the roots of S. reticulata, a quantitative analytical method by means of HPLC was developed and the mangiferin contents in SRE were determined to be in the range of 0.9-2.3% by the application of this method. A high linear correlation (r = 0.934) was observed between the mangiferin contents and the sucrase inhibitory activity. In addition, this analytical procedure of mangiferin was found to be applicable for other Salacia species (S. oblonga, S. chinensis, and S. prinoides). Thus, the quantitative HPLC analysis of mangiferin was supposed to be suitable for the quality control of Salacia species and its products.

Alcohol absorption inhibitors from bay leaf (Laurus nobilis): structure-requirements of sesquiterpenes for the activity.

Through a bioassay-guided separation using inhibitory activity on blood ethanol elevation in oral ethanol-loaded rat, various sesquiterpenes having an alpha-methylene-gamma-butyrolactone moiety, costunolide (1), dehydrocostus lactone (2), zaluzanin D (3), reynosin (4), santamarine (5), 3alpha-acetoxyeudesma-1,4(15),11(13)-trien-12,6alpha-+ ++olide (6) and 3-oxoeudesma-1,4,11(13)-trien-12,6alpha-olide (7), were isolated as the active principle from the leaves of Laurus nobilis (bay leaf, laurel). In order to characterize the structure requirement for the activity, several reduction products (2a-2d) and amino acid adducts (2e, 2f) of the alpha-methylene-gamma-butyrolactone moiety were synthesized from 2 and the inhibitory activities of these sesquiterpenes, together with alpha-methylene-gamma-butyrolactone (12) and its related compounds (13-16), were examined. These results indicated that the gamma-butyrolactone or gamma-butyrolactol moiety having alpha-methylene or alpha-methyl group was essential for the inhibitory activity on ethanol absorption. Since 1, 2 and 12 showed no significant effect on glucose absorption, these sesquiterpenes appeared to selectively inhibit ethanol absorption. In addition, the acute toxicities of 1 and 2 in a single oral administration were found to be lower than that of 12.

Medicinal foodstuffs. XVIII. Phytoestrogens from the aerial part of Petroselinum crispum MIll. (Parsley) and structures of 6"-acetylapiin and a new monoterpene glycoside, petroside.

In the course of our screening for natural estrogenic compounds from Occidental medicinal herbs, the extracts of several herbs were found to show proliferative activity in MCF-7 (an estrogen-sensitive breast cancer cell line). Among these active herbs, the methanolic extract from the aerial parts of Petroselinum crispum (parsley) showed potent estrogenic activity, which was equal to that of isoflavone glycosides from soybean. Through bioassay-guided separation, we isolated several flavone glycosides and a new flavone glycoside, 6"-acetylapiin, with estrogenic activity together with a new monoterpene glucoside, petroside. The structures of 6"-acetylapiin and petroside were characterized by the chemical and physicochemical evidence. Estrogenic activities of these flavone glycosides were found to be enhanced by removal of their glycoside moieties. The EC50 values (concentration needed to enhance the MCF-7 proliferation 50% compared to non-estrogen treated cell) of their aglycones are as follows, apigenin (1.0 microM), diosmetin (2.9 microM), and kaempferol (0.56 microM). The estrogenic activities of these flavones are nearly equal to those of the isoflavones, daidzein (0.61 microM) and genistein (0.60 microM). The methanolic extract of parsley, apiin, and apigenin restored the uterus weight in ovariectomized mice when orally administered for consecutive 7 days.

Characteristics of monocarboxylates as energy substrates other than glucose in rat brain slices and the effect of selective glial poisoning - a 31P NMR study.

In rat brain slices we examined the differences in the levels of high-energy phosphates in the presence of various energy substrates by using 31P NMR with a time resolution of 4 min at 25 degrees C. In parallel experiments we recorded population excitatory postsynaptic potentials (EPSPs) from granule cells in rat hippocampal slices. During high K(+) stimulation (8 min) phosphocreatine (PCr) decreased to a low level and recovered to the control level in standard artificial cerebrospinal fluid (ACSF) in about 10 min. Population EPSPs disappeared following high-K(+) stimulation and recovered in standard ACSF. In iodoacetic acid (IAA)-pretreated slices, whereas glucose was unable to support energy metabolism, the PCr level, which decreased following high-K(+) stimulation, recovered in ACSF containing lactate or pyruvate. The half-time of recovery of PCr levels in ACSF containing lactate was longer than that containing glucose. Population EPSPs in standard ACSF were maintained for more than 1 h, but those in ACSF containing lactate decreased gradually by about half in 40 min. In IAA-pretreated slices, when further treated with fluorocitrate (100 microM) for 2 h, the recovery of the PCr level in ACSF containing lactate after high-K(+) stimulation was completely abolished, whereas the recovery of the PCr level in ACSF containing pyruvate was unaffected. These results indicate that neurons can utilize pyruvate as well as glucose, but not lactate, as exogenous energy substrates, and that lactate may be metabolized to pyruvate in glial cells and transported to neurons to be utilized as an energy substrate.

The role of thunberginol A, an isocoumarin constituent of Hydrangeae Dulcis Folium, on the signal transmission pathway for rat mast cell degranulation.

The role of the signal transmission pathway of thunberginol A (TA) in mast cell degranulation was examined using rat peritoneal mast cells. First of all, we investigated the cellular distribution of TA using fluorescent microscopy. This indicated that TA is immediately incorporated into cells and distributes in cytosol around the nucleus. We then investigated the effect of TA on mast cell protein tyrosine phosphorylation, which is part of the signal transduction cascade for degranulation. TA non-specifically inhibited the tyrosine phosphorylation induced by compound 48/80 (Co. 48/80), at 10 to 100 microM, and orthovanadate/hydrogen peroxide at more than 50 microM in a dose-dependent manner. As far as the intracellular Ca2+ change in fluo-3-loaded cells was concerned, TA (10 microM) suppressed the rise in Ca2+ induced by antigens, ionomycin and thapsigargin, while TA did not suppress the rise induced by Co. 48/80. This evidence suggests that TA mainly inhibits extracellular Ca2+ influx, but TA does not act on the intracellular Ca2+ mobilization from the endoplasmic reticulum. We also investigated the influence of TA on the cytoskeleton and membrane changes using mast cells and erythrocytes. TA (10 microM) inhibited the cytoskeletal assembly formation in dicyanovinyl julolidin-loaded mast cells induced by Co. 48/80. Moreover, TA suppressed the hypotonic hemolysis of erythrocytes, from 3 to 1000 microM, in a dose-dependent manner. These results suggest that inhibition of protein tyrosine phosphorylation, extracellular Ca2+ influx and cytoskeletal assembly formation, and membrane stabilization are involved in the inhibitory effect of TA in mast cell degranulation.

Effects of phyllodulcin, hydrangenol, and their 8-O-glucosides, and thunberginols A and F from Hydrangea macrophylla SERINGE var. thunbergii MAKINO on passive cutaneous anaphylaxis reaction in rats.

We examined the antiallergic effects of phyllodulcin, hydrangenol, and their 8-O-glucosides, and thunberginols A and F isolated from the processed leaves (Hydrangeae Dulcis Folium) and dried leaves of Hydrangea macrophylla SERINGE var. thunbergii MAKINO using the passive cutaneous anaphylaxis (PCA) reaction. With the exception of phyllodulcin, these constituents were found to significantly inhibit the PCA reaction. Although thunberginol A showed the most potent inhibitory effect, hydrangenol was considered to be the principal antiallergic component in the processed leaves, after taking into account their contents.

Structure-requirements of isocoumarins, phthalides, and stilbenes from Hydrangeae Dulcis Folium for inhibitory activity on histamine release from rat peritoneal mast cells.

We examined the structure-activity relationships of isocoumarins, phthalides and stilbenes isolated from Hydrangeae Dulcis Folium and related compounds for the inhibition of histamine release in rat peritoneal mast cells. The activities of isocoumarins such as thunberginols A and B were more potent than those of dihydroisocoumarins such as hydrangenol and thunberginol G. The double bond at the 3-position seemed to be essential to potentiate the activity. The hydroxyl groups at the 8-, 3'- and 4'-positions of isocoumarin were essential for the activity, while the hydroxyl group at the 6-position was scarcely needed. Since the activities of benzylidenephthalides such as thunberginol F were more potent than those of hydramacrophyllols A and B, the presence of a double bond at the 3-position was needed to increase the activity. Moreover, the hydroxyl group at the 8-position was essential for the activity. On the time course study, thunberginols A, B and F completely inhibited histamine release by pretreatment at 100 microM for 1 to 15 min, whereas DSCG inhibited histamine release only following 1-min pretreatment at 1000 microM. These results suggested that the mechanisms of the inhibitory effect of thunberginols are different from that of DSCG.

Chemical constituents from the leaves of Hydrangea macrophylla var. thunbergii (III): Absolute stereostructures of hydramacrosides A and B, secoiridoid glucoside complexes with inhibitory activity on histamine release.

Following the characterization of dihydroisocoumarin constituents, two secoiridoid glucoside complexes, called hydramacrosides A and B, were isolated from the leaves of Hydrangea macrophylla Seringe var. thunbergii Makino. The absolute stereostructures of hydramacrosides A and B were elucidated on the basis of chemical and physicochemical evidence, which included the application of the 13C-NMR glycosylation shift rule of 1,1'-disaccharides and the modified Mosher's method. Hydramacrosides A and B exhibited an inhibitory effect on histamine release from rat mast cells induced by an antigen-antibody reaction.

Development of bioactive functions in Hydrangeae Dulcis Folium. VII. Immunomodulatory activities of thunberginol A and related compounds on lymphocyte proliferation.

Immunomodulatory activities of constituents isolated from Hydrangeae Dulcis Folium and their related compounds on lymphocyte proliferation were investigated using splenocytes and lymph node cells. Thunberginol A (TA) significantly suppressed B lymphocyte proliferation stimulated by lipopolysaccharide (LPS) at 10(-5) M. However TA at a lower concentration (10(-6) M) and the other compounds, except hydrangenol and 3'-hydroxyhydrangeaic acid, tended to potentiate B lymphocytes proliferation (10(-5) M). On the other hand, thunberginol A significantly suppressed T lymphocyte proliferation stimulated by concanavalin A (Con A), but did not suppress phytohemagglutinin (PHA). Hydrocortisone and cyclosporin A strongly suppressed T lymphocyte proliferation induced by both Con A and PHA. These results suggest that thunberginol A acts on both B and T lymphocytes and may have a suppressive mechanism different from the known immunosuppressants. The cytotoxicity of TA for splenocytes seemed weaker than known immunosuppressants resulting from viability tests using MTT assay and the measurement of lactate dehydrogenase (LDH) released in the medium. Moreover, TA suppressed antigen-specific T lymphocyte proliferation in mice lymph node cells immunized with keyhole limpet hemocyanin (KLH). Thus, these findings show that TA has a suppressive effect on lymphocyte activation, and this inhibitory effect of TA seems to contribute to its suppressive effect on type IV allergies.

Immunomodulatory activity of thunberginol A and related compounds isolated from Hydrangeae Dulcis Folium on splenocyte proliferation activated by mitogens.

We investigated the immunomodulatory effects of antiallergic constituents from Hydrangeae Dulcis Folium, the processed leaves of Hydrangea macrophylla SERINGE var. thunbergii MAKINO, on splenocyte proliferation in mice. Thunberginol A and hydrangenol significantly suppressed T lymphocyte proliferation induced by concanavalin A. Thunberginol A also suppressed B lymphocyte proliferation induced by lipopolysaccharide, but other constituents induced significant increases. These inhibitory effects of thunberginol A on splenocyte proliferation seemed to contribute to the suppressive effect on type IV allergy.

Bioactive constituents of Chinese natural medicines. IV. Rhodiolae radix. (2).: On the histamine release inhibitors from the underground part of Rhodiola sacra (Prain ex Hamet) S. H. Fu (Crassulaceae): chemical structures of rhodiocyanoside D and sacranosides A and B.

The methanolic extract of the underground part of Rhodiola sacra (PRAIN ex HAMET) S. H. Fu was found to show inhibitory activity on the histamine release from rat peritoneal exudate cells induced by an antigen-antibody reaction. From the methanolic extract with the inhibitory activity on histamine release, a new cyanoglycoside called rhodiocyanoside D and two new monoterpene glycosides called sacranosides A and B were isolated, together with eight known compounds, rhodiocyanoside A, heterodendrin, lotaustralin, rhodioloside, 2-phenylethyl alpha-L-arabinopyranosyl(1-->6)-beta-D-glucopyranoside, 2-methyl-3-buten-2-yl beta-D-glucopyranoside, kenposide A, and rhodiooctanoside. The structures of new compounds were determined on the basis of chemical and physicochemical evidence, which included the synthesis of sacranoside A from (-)-myrtenol. All major chemical constituents from R. sacra inhibited the histamine release and, among them, lotaustralin and rhodiooctanoside were found to show potent inhibitory activity.

Medicinal foodstuffs. VI. 1) Histamine release inhibitors from kidney bean, the seeds of Phaseolus vulgaris L.: chemical structures of sandosaponins A and B.

Two new olean-12-ene-type triterpene oligoglycosides, named sandosaponins A and B, were isolated from kidney bean, the seed of Phaseolus vulgaris L., together with three known saponins, soyasaponins I and V and dehydrosoyasaponin 1. The structures of sandosaponins A and B were determined on the basis of chemical and physicochemical evidence, which included the chemical derivation of sandosapogenol from a known sapogenol, soyasapogenol B. Five saponins obtained from kidney bean were found to inhibit histamine release from rat exudate cells induced by an antigen-antibody reaction and, among them, sandosaponins A and B showed the most potent inhibitory activity.

Bioactive constituents of Chinese natural medicines. II. Rhodiolae radix. (1). Chemical structures and antiallergic activity of rhodiocyanosides A and B from the underground part of Rhodiola quadrifida (Pall.) Fisch. et Mey. (Crassulaceae).

Two bioactive cyanoglycosides, rhodiocyanosides A and B, and two oligoglycosides, rhodioflavonoside [gossypetin 7-O-beta-D-glucopyranosyl(1-->3)-alpha-L-rhamnopyranoside] and rhodiooctanoside [octyl alpha-L-arabinopyranosyl(1-->6) beta- D-glucopyranoside), were isolated from the Chinese natural medicine "Si Lie Hong Jing Tian" (Shiretsukoukeiten in Japanese), the underground part of Rhodiola quadrifida (Pall.) Fisch. et Mey., together with four known compounds: rhodioloside, n-hexyl beta-D-glucopyranoside, gossypetin 7-O-alpha-L-rhamnopyranoside, and tricetin. The chemical structures of new glycosides were determined on the basis of chemical and physicochemical evidence. Rhodiocyanosides A and B exhibited inhibitory activity on the histamine release from rat peritoneal exudate cells sensitized with anti-2,4-dinitrophenyl IgE. Additionally, rhodiocyanoside A, the major constituent of this natural medicine, was also found to show antiallergic activity in a passive cutaneous anaphylaxis test in rat.

Development of bioactive functions in Hydrangeae dulcis folium. VI. Syntheses of thunberginols A and F and their 3'-deoxy-derivatives using regiospecific lactonization of stilbene carboxylic acid: structures and inhibitory activity on histamine release of hydramacrophyllols A and B.

Lactonization reaction of 2-carboxystilbene mediated by copper(II) chloride proceeded regiospecifically to give the five-membered lactone, while the bromolactonizations using N-bromosuccinimide and anodic oxidation were found to furnish the six-membered lactone. Using these regiospecific lactonization reactions as a key step, antiallergic and antimicrobial isocoumarins and the benzylidenephthalides thunberginols A and F and their 3'-deoxyanalogs were synthesized from phyllodulcin and hydrangenol. Two phthalides called hydramacrophyllols A and B were isolated from Hydrangeae Dulcis Folium and their stereostructures were determined on the basis of physicochemical and chemical evidence, which included the syntheses of hydramacrophyllols A and B from hydrangenol by the application of the lactonization method using copper(II) chloride. In addition, hydramacrophyllols A and B were found to exhibit an inhibitory effect on the histamine release from rat peritoneal exudate cells induced by antigen-antibody reaction.

Potent immunosuppressive principles, dimeric sesquiterpene thioalkaloids, isolated from nupharis rhizoma, the rhizoma of Nuphar pumilum (nymphaeaceae): structure-requirement of nuphar-alkaloid for immunosuppressive activity.

Potent immunosuppressants, the dimeric sesquiterpene thioalkaloids, 6-hydroxythiobinupharidine (2), 6,6'-dihydroxythiobinupharidine (3), 6-hydroxythionuphlutine B (5) and 6'-hydroxythionuphlutine B (6), were isolated from a natural medicine, Nupharis Rhizoma, the rhizoma of Nuphar pumilum (TIMM.) DC., through bioassay-guided separation together with five quinolizidine alkaloids (8, 9, 10, 11, 12). Dimeric sesquiterpene thioalkaloids (2, 3, 5, 6) were found to significantly inhibit anti-sheep erythrocyte plaque forming cell formation in mice spleen cells at 10(-6) M concentration. At this concentration, 2, 5 and 6 were found to exhibit no cytotoxicity to mice spleen cells, and 3 also showed only a little cytotoxicity. In addition, the inhibitory activity of several Nuphar alkaloids, dimeric sesquiterpene thioalkaloids (1, 4, 7, 8), and monomeric sesquiterpene alkaloids (9, 10, 11, 12) on anti-sheep erythrocyte plaque forming cell formation was examined and some structural requirement of Nuphar alkaloid for immunosuppressive activity was determined.

Development of bioactive functions in hydrangeae dulcis folium. V. On the antiallergic and antimicrobial principles of hydrangeae dulcis folium. (2). Thunberginols C, D, and E, thunberginol G 3'-O-glucoside, (-)-hydrangenol 4'-o-glucoside, and (+)-hydrangenol 4'-O-glucoside.

Following the characterization of thunberginols A, B, and F, six bioactive principles, thunberginols C, D, and E, thunberginol G 3'-O-glucoside, (-)-hydrangenol 4'-O-glucoside, and (+)-hydrangenol 4'-O-glucoside, were isolated from Hydrangeae Dulcis Folium, the processed leaves of Hydrangea macrophylla SERINGE var. thunbergii MAKINO, together with four kaempferol and quercetin oligoglycosides. Their chemical structures have been determined on the basis of chemical and physicochemical evidence. Thunberginols C, D, E, and G and (-)-hydrangenol 4'-O-glucoside showed antiallergic activity in the in vitro bioassay using the Schultz-Dale reaction. These components also exhibited inhibitory activities on the histamine release from rat mast cells and on the histamine-induced contraction in isolated guinea pig tracheal chain. In addition, thunberginols C, D, E, and G showed antimicrobial activities against oral bacteria.