Antioxidant and anti-inflammatory potentials of Ammodaucus leucotrichus Coss. & Durieu seeds' extracts: In vitro and in vivo studies.

ETHNOPHARMACOLOGICAL RELEVANCE: Ammodaucus leucotrichus Coss. & Durieu (Apiaceae) is traditionally used in southern Algeria as a remedy against a wide range of disease due to its health-promoting properties. AIM OF THE STUDY: To investigate anti-oxidant and anti-inflammatory potentials of plant methanolic extract and its fractions in vitro and in vivo. MATERIALS AND METHODS: Anti-radical activity was assessed in vitro using ABTS•+, superoxide anion (O2•-) and nitric oxide radical (•NO). Lipid peroxidation inhibition was also investigated in the linoleic acid system. Enzyme inhibition assay was performed against α-amylase and α-glucosidase. The anti-inflammatory effect of extracts was screened in vitro through thermal induction of human serum albumin, and in vivo on a skin acute inflammation model induced by λ-carrageenan paw injection, xylene and croton oil topical application. Analgesic effect was evaluated by acetic acid-induced writhing test. RESULTS: The highest contents of polyphenols and flavonoids was recorded by the crude extract (77.14 ± 0.01 µg GAE/mg E and 19.59 ± 0.08 µg QE/mg E, respectively). Among the extracts, ethyl acetate extract showed a promising anti-radical activity of ABTS•+, O2•- and •NO, in addition to a remarkable inhibition activity of the tested enzymes. Meanwhile, all extracts effectively protected linoleic acid against lipid peroxidation and human serum albumin structure in thermal condition even at low concentration (0.31 mg/ml). Oral administration of 200 mg/kg of crude extract successfully inhibited acetic acid induced nociception and reduced edema formation induced by xylene and carrageenan. However, a dose-dependent manner was observed to decrease ear edema by a microscopic examination in croton oil induced acute inflammation. Nitrite and malondialdehyde levels together with catalase activity were modulated in the presence of plant-derived bioactive compounds. CONCLUSIONS: This study showed that Ammodaucus leucotrichus is potentially rich source of anti-oxidant and anti-inflammatory bioactive compounds.

Secondary metabolite contents and safety assessment study of the aqueous extract from the Algerian Echium trygorrhizum Pomel roots.

ETHNOPHARMACOLOGICAL RELEVANCE: Species of Echium trygorrhizum Pomel, belonging to the Boraginaceae family, grow wild in North Africa. This plant is used in traditional Algerian medicine for the treatment of Diabetes, Jaundice and Tonsillitis. AIM OF THE STUDY: To our knowledge, no work has been done on the phytochemistry and biological activities of this plant. Moreover, no study has yet corroborated that the use of this plant is safe. Therefore, the present study was carried out to gather information on the various medicinal uses of this plant and to evaluate the total phenolic content and assess its safety after acute and sub-acute toxicity tests with rodents (mice and rats). MATERIAL AND METHODS: An ethnopharmacological survey was carried out using a direct questionnaire. It included some questions relating to the plant. The content of polyphénols, flavonoids and tannins present in the aqueous extract was determined by colorimetric methods. In the acute toxicity tests, three groups each containing five males and five females Albino mice were formed. The control group received water, while the test groups received different doses of aqueous extract (2000 and 5000) mg/kg body weight. In the subacute toxicity study, different doses (250, 500 and 1000 mg/kg) of the aqueous extract were administered to male and female rats for 28 consecutive days. Hematological analysis, biochemical parameters estimation and histopathological examination have been determined at the end of the treatment. RESULTS: Data from the ethnopharmacological survey showed that 25, 31% of people used this plant in Algeria as a traditional medicine for the treatment of Jaundice (100%), Diabetes (28, 33%) and Tonsillitis (10%). Results also revealed that aqueous extract contains high amounts of polyphenols, flavonoids and tannins. The extract did not cause any toxicity during the 14-days observation period after a single dose of 5000 mg/kg was administered to mice, with LD50 values greater than 5000 mg/kg. In a further step, the administration of the aqueous extract at all dose levels (250, 500, and 1000 mg/kg) to male and female rats during the 28-days study did not result in any deaths or behavioral changes, and there were no changes in body weight, relative organ weights, or food consumption as a result of this experiment. However, male rats showed a significant difference in relative liver weight in the high dose group (1000 mg/kg) (p < 0.05) and the satellite group (p < 0.01). In female rats, liver weight significantly increased only in the satellite group compared with the control group (p < 0.01). The results showed an increase in red blood cells (RBC), hemoglobin (Hb), and hematocrit (Hct) in the female groups. However, a clear decrease was observed in plasma ALP enzyme activities in females treated with the doses of 250 and 1000 mg/kg (p < 0.05) after the treatment periods. CONCLUSION: The study indicated that the single dose of 5 g/kg AQE can be considered relatively safe as it did not cause death or any signs of toxicity in mice. Repeated oral administration of AQE at doses below 250 g/kg/day for 28 consecutive days can be considered relatively safe.

Phytochemical Screening, In vitro Antioxidant and Enzyme Inhibitory Properties, and Acute Toxicity of Extracts from the Aerial Parts of Ephedra nebrodensis, a Source of Bioactive Compounds.

BACKGROUND: Due to the strong association between the chemistry of medicinal plants and their biological properties, it is important to determine their phytochemical composition to justify experimental tests. OBJECTIVE: The aim of this study was to evaluate the in vitro antioxidant and the enzyme inhibitory properties and to identify the bioactive compounds present in the extracts of Ephedra nebrodensis growing in Algeria. METHODS: Total phenolic and flavonoids content in these extracts were quantified by Folin- Ciocalteu and aluminum chloride methods. The antioxidant capacity was assessed using DPPH, ABTS, ß-carotene/linoleic acid, CUPRAC and FRAP assays, and in vitro cholinesterase activity against acetylcholinesterase and butyrylcholinesterase were evaluated. The chemical constituents of the extracts were analyzed by high-performance liquid chromatography coupled with mass spectrometric detection and gas chromatography. For the acute toxicity study, extracts were administered to mice at single dose of 2 g/kg and 5 g/kg by gavage. RESULTS: Plant extracts were rich in phenolic compounds. Ethyl acetate extract presented the highest phenolic (238.44 ± 1.50 µg GAE /mg of extract) and flavonoid (21.12 ± 0.00 µg QE /mg of extract) contents. Likewise, ethyl acetate extract showed potent radical scavenging and reducing properties. Ethanol-acetone extract showed inhibitory activity against acetylcholinesterase, and was a potent inhibitor of butyrylcholinesterase. In all extracts, flavonoids were the most abundant compounds. The phytochemical investigation showed the presence of alkaloids (ephedrine and pseudo-ephedrine). In the acute toxicity, the LD50 was superior to 5 g/kg body weight. There were no alterations in the histology of the liver and kidneys. CONCLUSION: This study demonstrated a good antioxidant potential and anticholinesterase activity of aerial parts of E. nebrodensis.

Antioxidant, Anti-inflammatory, and Analgesic Activities of Alcoholic Extracts of Ephedra nebrodensis From Eastern Algeria

Objectives: Ephedra nebrodensis (Ephedraceae) presents a wide range of biological activities. It is used to treat respiratory problems and hepatic pathologies in traditional medicine. The aim of this study is to evaluate the antioxidant, in vitro and in vivo anti-inflammatory and analgesic properties of two hydro-alcoholic extracts of E. nebrodensis in mice. Materials and Methods: The antioxidant capacity of hydro-methanolic (HM) and hydro-ethanolic (HE) extracts of E. nebrodensis was evaluated via assays of their superoxide radical scavenging capacity and ferrous ion chelating activity. The in vitro anti-inflammatory activity of the extracts (5, 10, and 20 mg/kg) was also determined using the bovine serum albumin denaturation test. Croton oil-induced ear edema was then employed to evaluate the in vivo anti-inflammatory effect of the extracts (200 and 400 mg/kg). Finally, the analgesic activity of the extracts (200 and 400 mg/kg) was determined by the acetic acid-induced torsion test. Results: The hydro-alcoholic extracts of E. nebrodensis present significant antioxidant activity. The HE and HM could inhibit protein denaturation by 82.99%±20.21% and 56.25%±2.12%, respectively. The extracts (HM and HE) also show strong anti-inflammatory effects in vivo and could reduce ear edema by 70.37%±2.00% and 72.22%±1.94%, respectively. The HM extract (72.51%±2.43%) demonstrates greater pain inhibitory effects than HE (70.76%±2.58%). Conclusion: The hydro-alcoholic extracts of E. nebrodensis produce antioxidant, anti-inflammatory, and analgesic effects. These results confirm the traditional use of the herb in the treatment of various diseases.

In-vivo anti-inflammatory activity and safety assessment of the aqueous extract of Algerian Erica arborea L. (Ericaceae) aerial parts.

ETHNOPHARMACOLOGICAL RELEVANCE: Erica arborea known as Khlenj in Algeria is a small shrub belonging to Ericaceae family. E. arborea Aqueous extract (EAAE) is used in traditional medicine for anti-inflammatory, diuretic, antimicrobial, and antiulcer purposes. AIM OF THE STUDY: To our knowledge, no data reveal the combination between in-vivo anti-inflammatory and toxicological studies of EAAE. For this purpose, the aim of this study is to evaluate the biological activity cited above and assess its safety. MATERIAL AND METHODS: Anti-inflammatory activity was undergone using carrageenan-induced paw edema and croton oil-induced ear edema. The acute and sub-acute toxicity were conducted following the OECD guidelines 423 and 407, respectively. Phytochemical identification was carried out using HPLC-DAD-MS. Quantitative evaluation of polyphenols; flavonoids and antioxidant activity of EAAE were also determined. RESULTS: Oral administration of EAAE (250 and 500 mg/kg) significantly (p < 0.05) reduced the edema induced by carrageenan. Administration of EAAE dosed at 250 and 500 mg/kg exhibited efficacy in reducing edema induced by croton oil. The acute administration of EAAE at doses of 2000 and 5000 mg/kg did not cause any mortality or adverse effects indicating that the LD50 is above 5000 mg/kg. The prolonged administration of EAAE (500 and 1000 mg/kg) showed a significant reduction in triglycerides levels in male and female rats whereas no significant changes in other biochemical and hematological parameters were observed. Histopathological damages were recorded in both liver and kidney animal's tissues of both sexes treated with medium and maximum doses of EAAE. Phytochemical characterization of EAAE revealed a high amount of phenolic compounds, HPLC-DAD-MS analysis led to the identification of chlorogenic acid and five flavonol glycosides: myricetin pentoside, quercetin-3-O-glucoside, myricetin-3-O-rhamnoside, quercetin-3-O-pentoside, and quercetin-3-O-rhamnoside. CONCLUSION: In the light of the results obtained in this study, EAAE corroborates the popular use to treat the anti-inflammatory impairments. EAAE can be considered as non-toxic in acute administration and exhibited a moderate toxicity in sub-acute administration. High phenolic content and in-vitro antioxidant activity observed indicate that EAAE may reduce oxidative stress markers in-vivo.

Antioxidant and anti-inflammatory effect of Asphodelus microcarpus methanolic extracts.

ETHNOPHARMACOLOGICAL RELEVANCE: Asphodelus microcarpus is an important medicinal plant belonging to family Liliaceae. This plant is used in traditional medicine to treat abscesses by local application of the powder; the roots are used against white spots, and specifically used for ear pain. AIM OF THE STUDY: The aim of the present study was to assess the in vitro antioxidant effects and the in vivo anti-inflammatory activity of the different parts methanolic extracts of the Asphodelus microcarpus: aerial part (APME), leaf (LME), stem flowers (SFME) and root (RME). MATERIAL AND METHODS: The antioxidant potency of extracts was evaluated by DPPH (2, 2-diphenyl-l-picrylhydrazyl), ABTS, ß-carotene bleaching assays, iron chelating, free hydroxyl radicals (HO•) assays, and reducing power. The anti-inflammatory effect of the extracts was evaluated using the carrageenan induced rat paw edema and xylene-induced ear edema in mice. RESULTS: The estimation of polyphenols and flavonoids showed that the leave methanolic extract contains a high amount of polyphenols and flavonoids: 755.3 ±â€¯0.036 mg Gallic acid equivalent and 42.2 ±â€¯0.043 mg Rutin equivalent/g of dried material, respectively. Oral administration of the APME and RME extract produced significant (p < 0.05) anti-edematogenic effect with a dose of 500 mg/kg in the carrageenan induced paw edema after 6 h (58.04%, 58.75%, respectively). APME, LME; SFME and RME extracts at 100, 300 and 500 mg/kg, exhibited significant (p < 0.05) inhibition of xylene induced ear edema. CONCLUSION: the present study confirms the use of A. microcarpus in traditional medicine as anti-inflammatory agent.

Acute, sub-acute toxicity and antioxidant activities (in vitro and in vivo) of Reichardia picroide crude extract.

ETHNOPHARMACOLOGICAL RELEVANCE: Reichardia picroide is a species mainly used for alimentary purposes, but it is traditionally known to be used as hypoglycemiant, diuretic, depurative, galactagogue and tonic. AIM OF THE STUDY: To date, there are no studies corroborating both its safety and antioxidant activities. The objective of the present study, thus, was to assess the safety profile of Reichardia picroide methanolic extract (RPE) and as well as on its antioxidant and antihemolytic activities. MATERIALS AND METHODS: The acute toxicity of RPE was carried out based on OECD guidelines 425. Signs accompanying toxicity and possible death of animals were monitored for two weeks to ascertain the median lethal dose (LD50) of the RPE. In sub-acute toxicity study, the extract was administered by gavage at the doses of 250, 500 and 1000mg/kg/day for 21 consecutive days. The antioxidant activity of RPE was investigated through various methods both in vitro and in vivo. RESULTS: The admistrated doses did not produce mortality or changes in general behaviors of the tested males and females mice. The LD50 was found to be superior to 5000mg/kg DW. Moreover, daily administration of RPE at doses ranged from 500 to 1000mg/kg could result in alteration of liver and kidney histology. Significant decrease in liver enzymes (ALT and AST), urea and creatinine levels in female plasma was recorded. The RPE was, in vitro, strong in DPPH scavenging and hemolytic inhibition, benificial in lipid peroxidation inhibition and reducing power. In addition, it exhibited, in vivo, a strong effect on GSH level increasing and lipid peroxidation inhibition in liver and kidney. CONCLUSIONS: It can be suggested, based on the results of this study, that the crude extract of Reichardia picroide was non-toxic in acute administration and the use of this extract is safe at doses ≤ 250mg/kg. This study supports the application of Reichardia picroides in alimentary and traditional medicine purposes. Moreover, antioxidant activity results suggested that Reichardia picroide had potent antioxidant activities and could be utilized as new natural antioxidant in food and therapeutics.

Chromatographic fractionation, antioxidant and antibacterial activities of Urginea maritima methanolic extract.

The present work concerns a phytochemical study of Urginea maritima L. from Algeria, and an evaluation of antioxidant activity of the methanolic extract (UMME) and its chromatographic fractions. UMME was fractionated using open glass chromatography on silica gel and antioxidant effects were evaluated using DPPH and ß-carotene/linoleate assays. The phytochemical screening revealed that the bulb of plant contains flavonoids, glycosides, tannins, reducing compounds, anthraquinones combined, anthocyanins, mucilage, triterpenes and steroids. DPPH method showed that the UMME has a scavenger effect on radical DPPH with an IC50=57.83±1.59µg/ml. The fractions isolated from U. maritima (L.) presented an IC50 ranging between 499.23 and 39.68µg/ml. In ß-carotene/linoleate test, UMME and fractions give an I% =69.56±0.08% and between 31.29±0.49% and 90.79±0.29%, respectively. UMME showed a high inhibitory effect on the xanthine oxidase (IC50=0.67±0.01 mg/ml) and on the cytochrome c reduction (IC50=0.68 mg/ml). Wide range of phytochemical constituents in Urginea maritima were detected in methanolic extract which exhibited antioxidant and antibacterial activity. This plant could serve as pilot for the development of novel agents for pathological disorders.

Antioxidant Potentials and Xanthine Oxidase Inhibitory Effect of Two Furanocoumarins Isolated from Tamus communis L.

In this investigation, the screening of two furanocoumarins; 5,8- dimethoxypsoralen (1) and heraclinin (2), isolated from the methanol root-extracts of Tamus communis L for their antioxidant activity and xanthine oxidase inhibitory effect was carried out, using different assays such as DPPH free radical scavenging effect, ß- carotene / linoleic acid, xanthine oxidase (XO) inhibition and in addition to blood total antioxidant capacity. Results revealed that the two compounds have significant DPPH radical scavenging activity and effective inhibition of linoleic acid oxidation in a dose-dependent manner; 5,8-dimethoxypsoralen exhibited the highest activity with an I% = 72.69 ± 1.88%. These results indicate that the isolated compounds inhibit xanthine oxidase activity and scavenge superoxide radicals with heraclinin (2) as the more potent xanthine oxidase inhibitor, and 5,8-dimethoxypsoralen (1) as the more effective on cytochrome c reduction, the two tested compounds can effectively protect erythrocytes against hemolytic injury induced by AAPH. These results are promising for further studies of the biological and pathological effects of these natural products.

Phenotypic and genotypic characterization of some lactic Acid bacteria isolated from bee pollen: a preliminary study.

In the present work, five hundred and sixty-seven isolates of lactic acid bacteria were recovered from raw bee pollen grains. All isolates were screened for their antagonistic activity against both Gram-positive and Gram-negative pathogenic bacteria. Neutralized supernatants of 54 lactic acid bacteria (LAB) cultures from 216 active isolates inhibited the growth of indicator bacteria. They were phenotypically characterized, based on the fermentation of 39 carbohydrates. Using the simple matching coefficient and unweighted pair group algorithm with arithmetic averages (UPGMA), seven clusters with other two members were defined at the 79% similarity level. The following species were characterized: Lactobacillus plantarum, Lactobacillus fermentum, Lactococcus lactis, Pediococcus acidilactici, Pediococcus pentosaceus, and unidentified lactobacilli. Phenotypic characteristics of major and minor clusters were also identified. Partial sequencing of the 16S rRNA gene of representative isolates from each cluster was performed, and ten strains were assigned to seven species: Lactobacillus plantarum, Lactobacillus fermentum, Lactococcus lactis, Lactobacillus ingluviei, Pediococcus pentosaceus, Lactobacillus acidipiscis and Weissella cibaria. The molecular method used failed to determine the exact taxonomic status of BH0900 and AH3133.

Comparison of xanthine oxidase levels in synovial fluid from patients with rheumatoid arthritis and other joint inflammations.

OBJECTIVE: To search whether xanthine oxido-reductase (XOR) present in the synovium is also liberated, to determine its activity in synovial fluid and to establish a possible relationship between XOR levels in rheumatoid arthritis (RA) and non-RA patients. METHODS: This study was carried out in the Laboratory of Immunology, University Ferhat Abbas, Setif, Algeria from 2001-2008. This study is a retrospective controlled study matching cases with RA to non rheumatoid joint inflammations. Synovial fluid (SF) samples were collected with consent of the patients, at Setif University Hospital, from adults suffering from RA (n=36) or only with joint inflammations (n=52). After its detection in SF with indirect enzyme-linked immunosorbent assay (ELISA) and dot-immunobinding, using anti-bovine XOR as first antibodies, XOR was assayed with capture ELISA. RESULTS: Xanthine oxidoreductase is found in all studied SF. Capture ELISA showed levels up to 0.762 and 0.143 mg/mL in SF of RA and other joint inflammations patients, respectively. In most cases, more than 50% of synovial XOR is present as oxidase form. Positive correlation was observed between enzyme level and the disease severity since RA patients had a significantly high enzyme amount compared to patients with other less severe arthritic pathologies. CONCLUSION: These results suggest that the enzyme could well be involved in joint inflammation probably by producing reactive oxygen species.

Antioxidant properties and xanthine oxidase inhibitory effects of Tamus communis L. root extracts.

This study was conducted to search for xanthine oxidase (XO) inhibitors from the root extracts of Tamus communis L. traditionally used in folk medicine in Algeria. Root extracts with different solvents were screened for purified milk xanthine oxidase inhibition. The root extracts (methanol, chloroform and ethyl acetate) and proteins, obtained in distilled water, inhibited bovine, sheep and human milk XO from three species in a concentration-dependent manner, with an additional superoxide scavenging capacity, which reached its highest level with ethyl acetate extract (IC(50) = 0.15, 0.04 and 0.09 g/L) for bovine XO, sheep XO and human XO, respectively. The antioxidant potential was confirmed with the non-enzymatic method, total radical-trapping antioxidant parameter (TRAP) assay, which showed that the Tamus communis L. extracts have a potential antioxidant activity in the same order obtained by using the reduction of cytochrome c, an enzymatic method, in which the antioxidant activity followed a decreasing order: ethyl acetate extract > chloroform extract > protein.

Anti-xanthine oxidase antibodies in sera and synovial fluid of patients with rheumatoid arthritis and other joint inflammations.

OBJECTIVE: To study anti-bovine milk xanthine oxidoreductase XOR antibody levels in synovial fluid as well as in serum of patients suffering from rheumatoid affections to assess a possible correlation between antibody titres and severity of disease. METHODS: Sera and synovial fluids were collected from volunteer donors at Setif University Hospital, Setif, Algeria from 2001--2007 with the consent of patients. Human IgG and IgM levels of free and bound anti-bovine milk XOR antibodies were determined using bovine XOR as antigen, with enzyme-linked immunosorbent assay ELISA. RESULTS: Serum IgG anti-bovine milk XOR titres in 30 healthy normal subjects 2.74+/-2.31 microgram/mL are in agreement with that reported in the literature. Immunoglobulin G and IgM anti-bovine milk XOR antibody titres were found to be significantly higher in serum from patients with rheumatoid arthritis RA, and latex positives subjects. Synovial IgM antibody titres to bovine XOR were found to be significantly higher in rheumatoid arthritis patients compared to patients with other joint inflammations. CONCLUSION: In rheumatoid arthritis patients, high concentrations of antibodies against XOR were noticed. These antibodies may play a major role in RA by inhibiting both xanthine and NADH oxidase activities of XOR. They may also play a key role in eliminating XOR from serum and synovial fluid positive role but unfortunately, immune complex formation could also activate complement and participate in self maintenance of inflammation.

Effect of tannins from Quercus suber and Quercus coccifera leaves on ethanol-induced gastric lesions in mice.

The gastroprotective effects of 70% acetone extracts of Quercus suber and Quercus coccifera leaves and of tannins (pedunculagin, castalagin, phillyraeoidin A, and acutissimin B) purified from these extracts were examined in the mouse using the ethanol-induced gastric ulcer model. Both extracts (25, 50, and 100 mg/kg), given orally, prevented the formation of ethanol-induced lesions in the stomach. The percent protection varied between 68 and 91%. Purified tannins (50 mg/kg) were also effective in protecting the stomach against ethanol, and the percent protection varied from 66 to 83%. Castalagin was the most potent. Both extracts and all of the tannins tested (10, 25, and 50 microg/mL) strongly inhibited (55-65%) the lipid peroxidation of rabbit brain homogenate. These results suggest that the gastroprotective effects of extracts of Q. suber and Q. coccifera leaves and the purified tannins in this experimental model are related to their anti-lipoperoxidant properties.

Gastroprotective effects of honey and glucose-fructose-sucrose-maltose mixture against ethanol-, indomethacin-, and acidified aspirin-induced lesions in the rat.

The gastric cytoprotective properties of natural honey (monofloral and polyfloral specimens) and of a glucose-fructose-sucrose-maltose mixture (GFSM) was evaluated in the rat using absolute ethanol, indomethacin and acidified acetylsalicylic acid (ASA-HCl) as necrotising agents. Prior gastric administration of honey (2.5 g/kg) to animals induced a net reduction of hemorrhagic lesions length of the mucosa. Protection of the stomach elicited by both types of honey and GFSM was almost total against ethanol-induced lesions. Similar results were also observed when using ASA-HCl except that the percent protection was 87%. The percent reduction of indomethacin-induced gastric lesions was variable according to the nature of the test solution: GFSM mixture (41.1%) < polyfloral honey (55.2%) < monofloral honey (64.0%). Perfusion of the stomach with isotonic honey resulted in (1) a 70% reduction of the area of the lesions caused by ethanol, (2) the failure to prevent the transmural potential difference fall induced by ethanol, (3) an increase of basal and histamine-stimulated acid secretion. These results suggest that sugar rich solutions (GFSM and honey) may prevent gastric damage by a mechanism involving the release of some protective agents.

Dimeric and trimeric hydrolyzable tannins from Quercus coccifera and Quercus suber.

Three new hydrolyzable tannins, cocciferins D(1) (1), D(2) (2), and T(1) (4), were isolated from the leaves of Quercus coccifera. Cocciferin D(2) (2) and two additional new tannins, cocciferins D(3) (3) and T(2) (5), were also obtained from the leaves of Quercus suber. Their oligomeric structures were elucidated on the basis of spectroscopic methods and chemical evidence. Compounds 2, 3, and 5 were rare oligomers possessing glucose cores with both open-chain and pyranose forms.