Aqueous Acetone Extract Research Articles

Short communication: Aqueous-acetone extraction improves the drawbacks of using dimethylsulfoxide as solvent for photometric pigment quantification in Quercus ilex leaves

Aim of study: We evaluated the use of dimethylsulfoxide (DMSO) for the photometric determination of chlorophyll (Chla and Chlb) and carotenoids in Quercus ilex L. leaves by comparative analysis using aqueous-acetone extraction.Area of study: a Q. ilex dehesa in Las Majadas del Tietar, Cáceres, SpainMaterial and methods: Q. ilex leaves were sampled during two vegetative periods. Field SPAD-502 Chlorophyll measurements and photometric chlorophyll determinations were performed. Two procedures were used: extraction of intact foliar discs at 65ºC with DMSO and fine foliar powder with cold aqueous-acetone.Main results: DMSO produced Chlb overestimation and different fitting performance for SPAD vs pigment calibrations (R2=0.64, RMSE=0.20, p<0.0001 for Chla (µg/cm2); R2=0.33, RMSE=0.23, p<0.0001 for Chlb (µg/cm2) and R2=0.50, RMSE=0.23, p<0.0001 for carotenoids (µg/cm2)). Aqueous-acetone provided more accurate predictions (R2=0.90, RMSE=0.16, p<0.0001 for Chla and R2=0.91, RMSE=0.16, p<0.0001 for Chlb, R2=0.90, RMSE=0.02, p<0.0001 for carotenoids) and mean ratio Chla/Chlb=3.6 inside the range for sun exposed leaves.Research highlights: Oxidizing conditions and polyphenol concentrations in Q. ilex leaves generated brown colorations in the DMSO extraction procedure, interfering with the photometric measurements in the red-orange region. Aqueous-acetone extraction was free from interference. DMSO should be avoided for pigment determination in Q. ilex leaves or when comparing different tree species.

Structures and Antibacterial Properties of Isorugosins H-J, Oligomeric Ellagitannins from Liquidambar formosana with Characteristic Bridging Groups between Sugar Moieties.

Three new ellagitannin oligomers, isorugosins H (1), I (2), and J (3), together with 11 known hydrolyzable tannins were isolated from an aqueous acetone extract of the fresh leaves of Liquidambar formosana. Their chemical structures were elucidated based on spectroscopic data and chemical conversion into known hydrolyzable tannins. The bridging mode of the valoneoyl groups between their sugar moieties has been identified only in this plant species. Additionally, the effects of the isorugosins isolated from this species on drug-resistant bacteria were evaluated and showed that isorugosin A (4) exhibited the most potent antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA). The isorugosins also had a suppressing effect on pigment formation in Pseudomonas aeruginosa. The isorugosin-protein complexes were analyzed using size-exclusion chromatography and polyacrylamide gel electrophoresis to clarify the relationship of their antibacterial properties with their protein interaction potency as hydrolyzable tannins. The results suggested that the antibacterial properties of hydrolyzable tannins are not simply a result of their binding activity to proteins, but are due to other factors such as the accessibility of polyphenolic acyl groups to bacterial membranes.

Antimicrobial activity of water and acetone extracts of some Eucomis taxa.

To evaluate the antibacterial and antifungal properties of acetone and water extracts of selected Eucomis taxa. The bulbs of Eucomis bicolor, Eucomis comosa (E.comosa) and E. comosa cv. were dried and examples from each experimental treatment were ground separately into powder. Each sample was divided into two groups with equal amounts of powder, and respectively extracted with water and a 70% solution of aqueous acetone. The crude water extracts were then filtered through a 0.2μm filter. The 70% aqueous acetone extracts were next concentrated at 40°C. After the evaporation of the acetone, the samples were additionally filtered through a 0.2μm filter. The antibacterial and antifungal activities of the extracts against chosen microorganisms were then determined. The results of the study demonstrated that the water and acetone extracts of Eucomis bulbs have an influence on the viability of Staphylococcus aureus and Bacillus atrophaeus strains. In the case of mediums containing E. comosa and E. comosa cv. extracts, a decrease in the number of gram-positive bacteria was dependent on the extract concentration. The best results were obtained in the case of the 25% extracts. The water and acetone extracts of Eucomis bulbs did not cause a decrease in the number of Escherichia coli cells. Additionally, antifungal activity against Aspergillus niger, Botrytis cinerea, Stachybotrys chartarum, Mucor circinelloides and Rhizopus oryzae cells were also not observed. The tested gram-negative and fungi microorganisms show resistance towards acetone and water extracts of Eucomis bulbs. The highest activity is found in the case of Aspergillus clavatus, Staphylococcus aureus and Bacillus atrophaeus strains, which shows water and acetone extracts of 25%.

Terminalia bellirica (Gaertn.) Roxb. fruit mitigates CCl4 induced oxidative stress and hepatotoxicity in rats

Terminalia bellirica (Gaertn.) Roxb. is a medicinal plant used for the treatment of various ailments in the traditional system of medicine like Ayurveda where it has been prescribed as a rejuvenator and general health tonic. The fruit of the plant is one of the components of the age old ayurvedic formulation-‘Triphala’. The present study evaluates curative effect of aqueous acetone extract of Terminalia bellirica fruits (AATB) against CCl4 induced oxidative stress and liver damage in an animal model. Two doses of the fruit extract (200mg/kg body weight and 400mg/kg body weight) were investigated for the beneficial effects. At the end of the treatment, liver function markers (ALT, AST, ALP, GGT, LDH, total bilirubin, total protein, albumin, globulin, albumin-globulin ratio) as well as hepatic oxidative stress markers (SOD, CAT, GSH) were evaluated. Treatment with AATB significantly restored the parameters towards normal level as compared to the elevated biochemical markers in the CCl4 treated animals. Reversal to normal tissue architecture was observed in histological evaluation. The results of AATB (400mg/kg) were found comparable with that of standard drug silymarin in all the parameters. The above findings suggest the therapeutic potential of the plant in alleviating hepatic oxidative stress and tissue damage, hence the traditional use of the plant in this regard stands justified.

Pharmacological evaluation of two South African commercial herbal remedies and their plant constituents

Amandla impilo immune booster and sejeso are two widely used South African commercial herbal remedies that are prepared from a mixture of several plants. They are used as multipurpose treatments for curing various diseases and ailments including gastrointestinal disorders, and diabetes (amandla impilo). This study was aimed at determining the pharmacological potential of the two herbal remedies, and eleven constituent plant species used in their preparation. Water and 70% aqueous acetone were used for extraction, and 30 extracts in total were evaluated for antibacterial activity against Campylobacter jejuni, Escherichia coli, Shigella flexneri and Staphylococcus aureus from the American Type Culture Collection. Extracts that exhibited antibacterial activity with minimum inhibitory concentration (MIC) values less than 1mg/ml against at least three bacterial strains were evaluated for cytotoxicity against monkey kidney (Vero) cells. Amandla impilo immune booster and its plant constituents were evaluated for antidiabetic potential against the alpha-glucosidase enzyme. The MIC values ranged from 0.195–12.50mg/ml, and the best value was demonstrated by 70% aqueous acetone extracts of Elephantorrhiza burkei roots against S. aureus and S. flexneri as well as Peltophorum africanum bark and leaves against S. flexneri (MIC=0.195mg/ml). The 70% aqueous acetone leaf extracts of Gunnera perpensa and P. africanum, as well as the water extract of Hypoxis obtusa corms were not toxic to Vero cells. However, 70% aqueous acetone extracts of E. burkei roots, H. obtusa corms and P. africanum bark showed slight toxicity towards the cells, and thus should be administered cautiously. Amandla impilo immune booster exhibited stronger alpha-glucosidase inhibitory activity (40.08μg/ml) than the positive control, acarbose (1040.00μg/ml), providing credence for the antidiabetic use of this concoction. Interestingly, water extracts of G. perpensa leaves and rhizomes (2.61 and 2.72μg/ml respectively), 70% acetone extracts of G. perpensa leaves (5.69μg/ml), Watsonia densiflora bulbs (9.08μg/ml), Combretum krausii bark and leaves (19.38μg/ml), G. perpensa rhizomes (18.00μg/ml), W. densiflora bulbs (14.82μg/ml) and Mimusops obovata bark (17.25μg/ml) showed stronger inhibition of the enzyme, demonstrating more antidiabetic potential individually than the commercial mixture they make. In conclusion, the observed antibacterial and antidiabetic activity of some plants, if supported by further studies, might justify their inclusion in the makeup of the tested herbal remedies. Although amandla impilo and sejeso showed low antibacterial activity, more research determining potential toxicity and antibacterial activity against bacterial strains, not tested in this study, is required as these two concoctions are used in traditional medicine practice against various diseases. This study confirmed the antidiabetic potential of amandla impilo, therefore, further studies on its antidiabetic activity and possible synergistic potential due to mixing of plant extracts are required.

In vivo toxicity evaluation of aqueous acetone extract of Terminalia bellirica (Gaertn.) Roxb. fruit

Terminalia bellirica (Gaertn.) Roxb. (Family: Combretaceae), known as Bhibhitaki in Sanskrit and locally known as Behera in India is one of the oldest medicinal plants which has widely been used in the traditional system of medicine, especially in Ayurveda for centuries. The dried fruit of Terminalia bellirica is used for treating various ailments. Aqueous acetone extract of Terminalia bellirica (Gaertn.) Roxb fruits (AATB), showed antioxidant potential in our screening study is selected for the present in vivo toxicity evaluation. Acute administration of AATB was done in female Wistar Albino rats as a single dose up to 2000 mg/kg body weight. At the end of the study, Blood was collected for biochemical and hematological analyses, while histological examinations were performed on liver and kidney. There was no alteration in the behavioral pattern, food and water intake in the treated animals. The relative organ weight, biochemical parameters, hematological parameters and histopathological analysis were also found normal. All the parameters of the toxicity evaluation were found to be normal and the data suggests aqueous acetone extract of Terminalia bellirica fruit is safe, to be used as a traditional herbal formulation for its antioxidant potential and other health benefits.

Triterpenoid Acids as Important Antiproliferative Constituents of European Elderberry Fruits

ABSTRACTIn Europe, both the fruits and flowers of Sambucus nigra L. have been used against cold, as well as laxative, diaphoretic, and diuretic remedies. There are also a number of commercially available food products that contain elderberry juice, puréed or dried elderberries. Recent comprehensive literature data on pharmacology and chemistry of Sambuci fructus have encouraged us to screen extracts with different polarities from this plant material against cancer cell lines. The cytotoxic activity of the ethyl acetate and aqueous acetone extracts from elderberries as well as detected triterpenoids on human colon adenocarcinoma cell line (LoVo) and human breast cancer cell line (MCF-7) was investigated by sulforhodamine B assay. Moreover, cell migration assay was conducted for triterpenoid fraction and pure compounds. Aqueous acetone extract possessed much lower IC50 value in cancer cell lines compared to ethyl acetate extract. The latter manifested high cytotoxicity against studied cell lines, suggesting that nonpolar compounds are responsible for the cytotoxic activity. Indeed, the phytochemical analysis revealed that ursolic and oleanolic acids are the main triterpenoids in the mentioned extract of which ursolic acid showed the highest activity with IC50 values of 10.7 µg/mL on MCF-7 and 7.7 µg/mL on LoVo cells.

Ellagitannins of Davidia involucrata. I. Structure of Davicratinic Acid A and Effects of Davidia Tannins on Drug-Resistant Bacteria and Human Oral Squamous Cell Carcinomas.

We isolated a new ellagitannin, davicratinic acid A (5), together with four known ellagitannins, davidiin (1), granatin A (2), pedunculagin (3), and 3-O-galloylgranatin A (4), from an aqueous acetone extract of dried Davidia involucrata leaves. The known ellagitannins were identified based on spectroscopic data. The structure of davicratinic acid A (5), a monomeric ellagitannin possessing a unique, skew-boat glucopyranose core, was established based on spectroscopic data. Additionally, we examined the effects of several tannins with good yields from this plant on drug-resistant bacteria and human oral squamous cell carcinomas, and found that davidiin (1) exhibited the most potent antibacterial and antitumor properties among the tannins examined.

Biochemical and Molecular Study of Carpobrotus edulis Bioactive Properties and Their Effects on Dugesia sicula (Turbellaria, Tricladida) Regeneration.

The traditional medicinal properties of Carpobrotus edulis are well recognized, particularly in Tunisia where it is used for wound healing. Thus, in this study, biochemical and molecular properties of its leaves' bioactive aqueous-acetone extract were investigated. The total phenolic content (TPC) of the extract was estimated to be 184±5mg/100g of fresh matter (FM). The qualitative and quantitative polyphenolic profile was determined by ultra performance liquid chromatography with diode array detection (UPLC-DAD) and showed that chlorogenic acid was the major compound (43.7%). The extract exhibits potent antioxidant capacities with IC50=56.19 and 58.91μg/ml, as accessed via the anionic DPPH and cationic ABTS radical scavenging assays, respectively. The extract has high antibacterial properties, especially against the Gram+ Staphylococcus aureus and Bacillus cereus strains. To investigate the extract effect on regeneration, the flatworm Dugesia sicula Lepori, 1948, was used as a model. The macroscopic analysis of planarian cultures in ordinary medium containing phenolic extract at non-toxic concentrations illustrated that the extract caused morphological changes. Additionally, the molecular study through the fluorescence-activated cell sorting (FACS) technique showed that C. edulis polyphenols can harm the stem cells' development. These results emphasize the ecotoxicological impact of phenolic rejections in the environment on flatworms' physiology.

Safety assessment of aqueous acetone extract of Clerodendrum infortunatum L. in Wistar rats

Clerodendrum infortunatum L. is a traditional medicinal plant used for the treatment of bronchitis, malarial fever, benign tumour etc. Antioxidant screening revealed that the aqueous acetone extract exhibited the greatest antioxidant activity. In the present study, toxicity analysis of the aqueous acetone extract was carried out in male Wistar rats to evaluate its impact on the liver and serum biochemical parameters. Male Wistar rats were divided into six groups and groups II to VI were treated with a single dose of 250, 500, 1000 and 2000 mg/kg body weight of aqueous acetone extract and silymarin, respectively. Group I served as the normal control. The rats were observed for 14 days. At the end, the blood was collected for the estimation of aspartate transaminase, alanine transaminase, gamma glutamate transaminase, alkaline phosphatase, lactate dehydrogenase, direct and total bilirubin, albumin, globulin, A/G ratio and total protein. Antioxidant parameters such as superoxide dismutase, catalase, reduced glutathione, lipid peroxidation and histopathological examination were carried out in liver tissue. All the biochemical parameters were found to be normal. Results suggest that the administration of aqueous acetone extract of C. infortunatum was safe and can be used as a new source of drug for the modern pharmaceutics.

Diarylpropanes and lignans from Horsfieldia tetratepala

Two new diarylpropanes (1–2), four known compounds, and a new artifact, were isolated from 70% aqueous acetone extract of the twigs of Horsfieldia tetratepala. Their structures were elucidated by spectroscopic analysis. Cytotoxicity evaluation against five cancer cell lines showed that none of these compounds was cytotoxic.

Melanogenesis inhibitory activity of a 7-O-9′-linked neolignan from Alpinia galanga fruit

An aqueous acetone extract from the fruit of Alpinia galanga (Zingiberaceae) demonstrated inhibitory effects on melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells (IC50=7.3μg/mL). Through bioassay-guided separation of the extract, a new 7-O-9′-linked neolignan, named galanganol D diacetate (1), was isolated along with 16 known compounds including 14 phenylpropanoids (2–15). The structure of 1, including its absolute stereochemistry in the C-7 position, was elucidated by means of extensive NMR analysis and total synthesis. Among the isolates, 1 (IC50=2.5μM), 1′S-1′-acetoxychavicol acetate (2, 5.0μM), and 1′S-1′-acetoxyeugenol acetate (3, 5.6μM) exhibited a relatively potent inhibitory effect without notable cytotoxicity at effective concentrations. The following structural requirements were suggested to enhance the inhibitory activity of phenylpropanoids on melanogenesis: (i) compounds with 4-acetoxy group exhibit higher activity than those with 4-hydroxy group; (ii) 3-methoxy group dose not affect the activity; (iii) acetylation of the 1′-hydroxy moiety enhances the activity; and (iv) phenylpropanoid dimers with the 7-O-9′-linked neolignan skeleton exhibited higher activity than those with the corresponding monomer. Their respective enantiomers [1′ (IC50=1.9μM) and 2′ (4.5μM)] and racemic mixtures [(±)-1 (2.2μM) and (±)-2 (4.4μM)] were found to exhibit melanogenesis inhibitory activities equivalent to those of the naturally occurring optical active compounds (1 and 2). Furthermore, the active compounds 1–3 inhibited tyrosinase, tyrosine-related protein (TRP)-1, and TRP-2 mRNA expressions, which could be the mechanism of melanogenesis inhibitory activity.

Natural products from extreme marine environments: Searching for potential industrial uses within extremophile plants

Extremophile plants, halophytes in particular, still remain largely unexplored and underutilized despite their high potential as source of industrial raw materials like natural antioxidants in industries related to pharmaceutical, cosmetics and functional ingredients. The goal of this study was to explore the phenolic content and the in vitro antioxidant and tyrosine inhibition properties of polyphenol-rich extracts of twenty-one extremophile plant species collected in saline habitats of the South of Portugal (Algarve). Aqueous acetone extracts of Lithrum salicaria, Cladium mariscus, Frankenia laevis, F. pulverulenta, Limoniastrum monopetalum, Aster tripolium and Typha domigensis had remarkable levels of total phenolics (≥230mg GAE/g DW); Halopeplis amplexicaulis, Cladium mariscus, F. pulverulenta and Salsola vermiculata contained high levels of flavonoids (≥10mg RE/g DW); tannins peaked in T. domingensis and C. mariscus (≥35mg CE/g DW) and L. salicaria and A. tripolium had the upmost hydrocinamic acids content (≥60mg CAE/g DW). Overall L. salicaria had the highest antioxidant activity and only P. lentiscus had the capacity to inhibit tyrosinase. As the most bioactive extracts were not cytotoxic towards mammalian cell lines, our results suggest that several halophytes present in Southern Portugal could be used in the food and/or cosmetic industries.

Four New Monoterpenoid Glycosides from the Flower Buds of Magnolia biondii.

Four new monoterpenoid glycosides 1–4, named magnoliaterpenoid A–D, were isolated from a 50% aqueous acetone extract of flower buds of Magnolia biondii, along with one known compound, (1′R,3′S,5′R,8′S,2Z,4E)-dihydrophaseic acid 3-O-β-d-glucopyranoside (5). Their structures and relative configuration were identified by extensive spectroscopic analysis (IR, UV, MS, 1D and 2D NMR). The aglycones of these four new compounds possess seven-membered rings systems, which are very rare. A plausible biosynthetic route for the four new compounds was proposed via the biogenetic isoprene rule. Compounds 1, 2, 3, and 4 showed no antimicrobial activity at the concentration range of 1.95–250 µg/mL.

English

Plants have been used as major source of active compounds with medicinal importance since human civilization. These naturally occurring pharmacologically active agents have least or no toxicity to the host. The antibacterial activity of extracts (water, acetone and methanol) from six indigenous Indian plants: Acacia nilotica (Fabaceae), Albizia saman (Fabaceae), Azadirachta indica (Meliaceae), Carica papaya (Caricaceae), Cymbopogon citratus (Poaceae) and Mangifera indica (Anacardiaceae) were determined against the pathogenic bacteria (Staphylococcus aureus: ATCC 25923; Escherichia coli: ATCC 25922 and Klebsiella pneumonia: ATCC 700603). The antimicrobial study was carried out by the gel diffusion method and the results show that as compared to aqueous extract, methanolic and acetone extracts were more effective. Of all the studied plants, the methanolic extract of A. saman leaves inhibited the growth of all the three test organisms.   Key words: Antibacterial activity, pathogenic bacteria, indigenous plants.

In vitro and in vivo antioxidant activity of the pulp of Jatobá-do-cerrado

Oxygen metabolism in cells causes the production of free radicals, which produce damage, including changes in cell structure and function. Antioxidants are substances that, at low concentrations, slow down or prevent oxidation. Fruits and vegetables contribute to the dietary supply of these compounds. The flora of the Cerrado in Brazil has shown to have high levels of bioactive compounds. This study aimed to characterize the antioxidant activity of the pulp of jatoba-do-cerrado in vitro and in vivo.In vitro antioxidant activity of the aqueous, ethanol and aqueous acetone extracts was evaluated by the DPPH method. We determined total phenols by the Folin-Ciocalteu assay and tannins by the Folin-Denis method.In vivo antioxidant potential of the aqueous acetone extract was evaluated by the TBARS technique. The aqueous acetone extract had the highest antioxidant capacity, followed by the aqueous and ethanol extracts. The same pattern occurred in the extraction of phenols and in the extraction of tannins. In vivo administration of the aqueous acetone extract inhibited lipid peroxidation compared to the control group. The inhibition of peroxidation has increased by elevating the dosage concentration of the extracts, demonstrating a significant antioxidant potential in vivo as well as in vitro.

Hydrolyzable Tannins of Tamaricaceous Plants. 7.1 Structures and Cytotoxic Properties of Oligomeric Ellagitannins from Leaves of Tamarix nilotica and Cultured Tissues of Tamarix tetrandra.

Partially unacylated new oligomeric hydrolyzable tannins, nilotinin T2 (1, trimer) and nilotinin Q1 (2, tetramer), together with four known trimers, nilotinin T1 (3) and hirtellins T1-T3 (4-6), and a dimer, tamarixinin B (7), were isolated from the aqueous acetone extracts of leaves of Tamarix nilotica. Among them, the new trimer 1 and the known trimers 4 and 6, in addition to the partially unacylated new trimer nilotinin T3 (8), the known dimers nilotinin D3 (9) and tamarixinin C (10), and the monomer tellimagrandin I (11), were isolated from the cultured shoots of Tamarix tetrandra. The structures of the new hydrolyzable tannins were established by chromatographic analyses and extensive 1D and 2D NMR, HRESI-TOFMS, and ECD spectroscopic experiments. Among the new oligomeric tannins, the particular unacylated position of a glucose core is attributed to a possible biosynthetic route. Isolation of the same oligomeric tannins from cultured shoots of T. tetrandra emphasizes the unique biogenetic ability of the obtained cultures on production of the structurally and biologically characteristic tamaricaceous tannins commonly produced by the intact Tamarix plants. Additionally, tannins obtained in the present study together with gemin D (12) and 1,3-di-O-galloyl-4,6-O-(aS)-hexahydroxydiphenoyl-β-d-glucose (13), from our previous investigation of the leaves of T. nilotica, exhibited variable tumor-specific cytotoxic effects. The ellagitannin trimers 4, 6, and 8 and the dimer 9 exerted predominant tumor-selective cytotoxic effects with high specificity toward human promyelocytic leukemia cells.

Acylated neo-clerodane type diterpenoids from the aerial parts of Scutellaria coleifolia Levl. (Lamiaceae).

Twenty new neo-clerodane type diterpenoids, scutefolides G1-S (1-20), were isolated from the 70 % aqueous acetone extract of the aerial parts of Scutellaria coleifolia. Their structures were elucidated by extensive spectroscopic analyses. The absolute configurations of 1, 2, 7, 8, 14 and 15 were determined by means of the CD exciton chirality method. Compounds 1, 2, 5, 7, 8, 12, 14, 15, 18 and 19 were evaluated for their cytotoxic activities against four human cancer cell lines, and anti-bacterial activities against methicillin-resistant Staphylococcus aureus.

Phenolic and tocopherol content of autumn olive (Elaeagnus umbellate) berries

The objectives of this work were to characterize polyphenols and α- and γ-tocopherols in several commercial cultivars of Elaeagnus umbellate (autumn olive) berry. Acidic aqueous acetone extraction yielded the highest total phenol recovery, ranging from 190 to 275 mg gallic acid equivalents (GAE)/100 g fresh weight among berry cultivars. Berries were found to contain proanthocyanidins by reaction with 4-(dimethylamino)cinnamaldehyde. Normal phase HPLC analysis confirmed that the total proanthocyanidin content of berries ranged from 68 to 225 catechin equivalents/100 g dry weight. Proanthocyanidins were composed of 64 to 89% polymers with degree of polymerization >10, with lesser amounts of monomers through 5-mers. Total α- and γ-tocopherol ranged between 9 and 23 mg/100 g oil. The ratio of α- to γ-tocopherol varied from ~3:1 to 10:1 among autumn olive cultivars. Thus, the presence of highly polymerized proanthocyanidins and tocopherols should be considered in formulating functional foods with autumn olive berry.

Ellagitannins, gallotannins, and gallo-ellagitannins from the galls of Tamarix aphylla

Chromatographic separation of an aqueous acetone extract of the galls from Tamarix aphylla using gels resulted in isolation of an ellagitannin, phyllagallin M1 (13), a gallo-ellagitannin, phyllagallin D1 (14), and four gallotannins, phyllagallin M2 (15) and phyllagallins D2–D4 (16–18), in addition to four known ellagitannins and three phenolics of lower molecular weight structurally related to hydrolyzable tannins. The structures of the six new tannins were elucidated based on spectroscopic and chemical data. Among the phenolics, flavogallonic acid dilactone (8), which is presumed to be biogenetically produced by C–C oxidative coupling of an ellagic acid unit with a galloyl residue, shows an exceptional oxidative pattern of gallic acid residues in plants of the family Tamaricaceae. Although the ellagitannin tamarixellagic acid (4) was reported to be a constituent of the galls of T. aphylla, such compounds with anomalous location of the DHDG moiety at O-3 on the glucopyranose core have not been observed among the tannins of tamaricaceous plants.