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Honey locust (Gleditsia triacanthos) flowers and its bioactive constituents
Abstract
Honey locust, Gleditsia triacanthos L. (Fabaceae), is one of the popular deciduous trees native to central North America. Its leaves and seeds have been used in traditional food and medicine by Native Americans. Extracts of Gleditsia spp. have been reported to possess medicinal properties and used in treating rheumatoid arthritis, cancer and a variety of other illnesses. Phytochemical studies on its leaves and seeds have reported the presence of triterpenoids, alkaloids, flavonoids, galactomannans and tannins. However, there are no reports on its flowers for the presence of bioactive constituents. In our study, the hexane, ethyl acetate and methanolic extracts of the flowers of honey locust tree showed antioxidant, antiinflammatory and antitumor activities. Purification of these active extracts yielded 4 new compounds, together with 15 known compounds. Their structures were elucidated by spectral analyses. All pure isolates inhibited lipid peroxidation (LPO) by 20 – 94%, and cyclooxygenase enzymes, COX-1 by 35 – 55% and COX-2 by 23 –38% at 25 µg/mL. The tumor cell proliferation inhibitory activity of these compounds was determined agianst AGS (gastric), DU-145 and LNCaP (prostate), HCT-116 (colon), MCF-7 (breast), and NCI-H460 (lung) human tumor cell lines. All isolates tested at 25 µg/mL showed some degree of inhibition against tumor cell progression.
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Gleditsia triacanthos L. is a deciduous tree belonging to family Fabaceae. It possesses important biological activities as anti-mutagenic, anticancer, cytotoxic and treating rheumatoid arthritis. The total ethanol extract (EtOHE) and successive extracts (petroleum ether, chloroform, ethyl acetate, and aqueous ethanol) were prepared from the leaves. Eight flavone glycosides and two flavone aglycones named vicenin-I(1), vitexin(2), isovitexin(3), orientin(4), isoorientin(5), luteolin-7-O-ß-glucopyranoside(6), luteolin-7-O– ß- galactopyranoside(7), apigenin-7-O-ß-glucopyranoside(8), luteolin(9) and apigenin(10) were isolated from the aqueous ethanol extract of G. triacanthos L. leaves. Potent cytotoxic activity of the EtOHE extract against liver (IC50=1.68μg), breast (IC50=0.74μg), cervix (IC50=1.28μg), larynex(IC50=0.67μg) and colon (IC50=2.50μg) cancer cell lines. Cytotoxic activity of compounds 2, 4, 6 and 8 against, liver, breast and colon cancer cell lines was also proved. Evaluation of the invivo antioxidant activity of the EtOHE and successive extracts revealed that the highest activity was exhibited by 100mg of EtOHE (97.89% potency) as compared with vitaminE (100% potency). Compound 6 showed 91.8% free radical scavenging activity.
Mori Cortex Radicis (MCR, Moraceae) is used traditionally in the treatment ofjaundice, hematemesis, edema, and pollakisuria in Korea. In this study, the antiinflammatory effects of MCR extract were investigated using RAW 264.7 cells. The simultaneous analysis of five components present (neochlorogenic acid, chlorogenic acid, cryptochlorogenic acid, caffeic acid, and p-coumaric acid) in the MCR extract was performed using high-performance liquid chromatography (HPLC) coupled with photodiode array (PDA) detection. We determined the effects of MCR extract and its components on the production of nitric oxide (NO), prostaglandin E2 (PGE2), and mRNA expression of cyclooxygenase-2 (COX-2) in RAW 264.7 cells. MCR extract suppressed the production of NO and PGE2 in RAW 264.7 cells in a dose-dependent manner. None of the five components of the MCR extract had any influence on the production of NO. However, caffeic acid and p-coumaric acid inhibited the production of PGE2 and mRNA expression of COX-2 in RAW 264.7 cells. Our results suggest that MCR extract may offer potential as a therapeutic agent for the treatment of inflammation. The method we have established will help to improve the quality control of MCR extracts.
A cycloartane triterpenoid having a new 33-carbon skeleton, named cyclopodmenyl acetate, was isolated from the rhizomes of a fern Polypodium vulgare Linne, and its structure was established to be 24, 24, 27-trimethyl-9, 19-cyclolanost-25-en-3β-yl acetate (1a).
Background and AimsAroma precursors in grape juice include glycosylated terpenoids or benzenoids. The separation of these polar substances has been achieved by several chromatographic techniques but often after the esterification of the sugar hydroxyls. We aimed to develop a high-performance liquid chromatography method to isolate the glycoconjugates in their natural form. Methods and ResultsThe glycoside fraction was extracted from fresh grape juice, treated with lead (II) acetate to precipitate phenolic compounds and finally separated by hydrophilic interaction liquid chromatography. Three compounds were isolated, and their structures elucidated by means of spectroscopic data; one revealed previously unreported structural features. Conclusions
Our hydrophilic interaction liquid chromatography method has been proven effective for the purification of the complex blend of many chemical compounds that contribute to grape and wine flavour. Significance of the StudyThe present article proposes a new, straightforward procedure for the isolation of flavour glycoconjugates.
The arid plant Prosopis cineraria (Fabaceae) is known as Khejri in India or the golden tree of Indian deserts. The dried pods are consumed as a vegetable and leaves as traditional medicine to cure a wide range of diseases in the state of Rajasthan, India. The pods of this plant have not been investigated for their bioactive components, hence we have done so in this study. The dried pods were boiled with water to afford the aqueous extract. Extraction of the residue gave methanolic extract. The lipid peroxidation (LPO) and cyclooxygenase enzymes (COX-1 and -2) inhibitory activities of extracts and major compounds present in the bioactive extracts were then determined. Purification of bioactive extracts yielded compounds 1–7. The absorbance of 1–7 at 570nm ranged between 0.15 and 0.45 at 50μg/mL whereas vitamin C and tert-butylhydroquinone (TBHQ) at 25μg/mL gave an absorbance of 0.5 in the MTT [3-(4,5-dimethylthiazole-2-yl)-2,5-diphenyltetrazolium bromide] assay. At 25μg/mL concentration, compounds 1–7 inhibited LPO, COX-1 and -2 enzymes between the ranges of 15–87%, 21–67% and 16–59%, respectively. This is the first report of the chemical and biological activities of the edible part of this plant.
The carbohydrate and lipid compositions of seeds from Gleditsia triacanthos L. cultivated in Uzbekistan are investigated. Water-soluble polysaccharide (galactomannan), pectinic substances, and hemicellulose are isolated. Their physicochemical properties and monosaccharide composition are found. The content and fatty-acid composition of neutral, glyco-, and phospholipids are determined.
Summary The complete structure of the triterpene glycoside triacanthoside C (I) isolated from the pericarps of the honeylocust,Gleditschia triacanthos L. (family Leguminosae) has been established as a hexaoside of oleanolic acid.
From the green pods of the honeylocust, in addition to the ten triacanthosides described previously, oleanolic and echinocystic
acids have been isolated, and also five other triterpene glycosides-gleditschosides A, B, C, D, and E. Gleditschoside A, C36H58O8, is oleanolic acid β-D-glucopyranoside (VII), gleditschoside B, C36H58O9 is echinocystic acid β-D-glucopyranoside (VIII), gleditschoside C, C41H66O12, is oleanolic acid 3-O-[α-L-arabinopyranosyl-(1→3)-O-β-D-glucopyranoside] (V), gleditschoside E, C41H66O13, is echinocystic acid 3-O-[α-L-arabinopyranosyl-(1→3)-O-β-D-glucopyranoside] (VI), and gleditschoside D, C46H74O16, is oleanolic acid 3-O-[β-D-xylopyranosyl-(1→4)-O-α-L-arabopyranosyl-(1→3)-O-β-D-glucopyranoside]. Gleditschosides A, B,
C, D, and E have also been detected in the leaves of the plant.
In this work, three different extraction procedures were performed in Gleditsia triacanthos seeds in order to obtain extracts that were characterized in terms of the yield of extraction, total phenolic content and antioxidant properties. The extracts have been shown to contain considerable amounts of phenolic compounds (between 4.93 and 12.34mggalicacidgextract−1) and antioxidant activity between 18.77 and 71.59%. Different concentrations of one of the extracts (extract presenting simultaneously the best values of total phenolic content, radical scavenging activity and the concentration of the compounds that caused a 50% inhibition of the radical scavenging activity) were incorporated into G. triacanthos galactomannan solutions and films were cast from these. A 22 full factorial design was done to evaluate the effect of the galactomannan and extract concentrations in film properties. Galactomannan concentrations ranging from 0.5 to 1.5% and extract concentrations ranging from 0 to 1.0%, were used and the evaluated film properties as: water vapour permeability, colour, total phenolic compounds content and antioxidant activity. This work has shown that G. triacanthos can be used not only as a source of galactomannan films suitable to incorporate antioxidant compounds for further application in the food industry but also as a source of the active compounds to be incorporated.
The seeds of Gleditsia triacanthos (Fabaceae) are a source of galactomannans with a variable mannose:galactose (Man:Gal) ratio that depends on the isolation and purification methods. In this study, three processes were used: (1)—treatment with boiling water (M1); (2)—concentration with boiling 2 N NaOH (M2) and (3)—swelling with water and later manual removal of the endosperm (M3). The functional properties of the hydrocolloids obtained by the three isolating methods were compared with those exhibited by xanthan and guar gums, which are widely used as food additives. The product obtained by boiling water (M1) had the lowest yield, although that hydrocolloid showed high water absorption capacity and solubility, high emulsifying and foaming capacities, and imparted high stability to the dispersions (foams and emulsions). These properties could be influenced by its high Man:Gal ratio and protein content.
The rhizome of “Mango Ginger”, Curcuma mangga (Zingiberaceae), is a dietary ingredient in India and its popularity is similar to the rhizomes of Curcuma longa (Zingiberaceae), the “turmeric root”. In Indian folk medicine, the rhizomes of C. mangga have been used as medicine to treat a variety of diseases for centuries. However, it has not been investigated for its bioactive constituents. In our study, the aqueous, methanolic and ethyl acetate extracts of its rhizome showed antioxidant, anti-inflammatory and anti-tumour activities. Purification of these active extracts yielded bioactive labdane diterpenoids labda-8(17)-12-diene-15,16-dial (1), calcaratarin A (2), communic acid (3), copallic acid (4), zerumin B (5), 14,15,16-trinor-labdan-8,12-diol (6) and two decalins (7–8). The structures were elucidated by spectral analyses. All pure isolates inhibited lipid peroxidation (LPO) by 12–45% at 25 μg/ml. In cyclooxygenase enzymes (COX-1 and -2) inhibitory assays, compounds 1–4 showed selective COX-2 enzyme inhibition by 39–55% where as 5–8 showed selectivity to COX-1 between 45% and 53%. The tumour cell proliferation inhibition by these compounds was determined by using NCI-H460 (lung), HCT-116 (colon), AGS (gastric), SF-268 (CNS) and MCF-7 (breast) human tumour cell lines. All isolates tested at 25 μg/ml showed some degree of inhibition against tumour cell progression.
The synthesis of 28-O-b-D-glucuronide betulinic acid, an acyl glucuronide derivative, was successfully carried out for the first time using commercially available peracetylated methyl glucuronate bromide under phase-transfer conditions. The target compound could be used in an anticancer prodrug monotherapy (PMT)strategy since it is non-cytotoxic, non-haemolytic, more water soluble than betulinic acid, it possesses a good in vitro stability in phosphate buffer and can be hydrolyzed in the presence of b-D-glucuronidase releasing in vitro betulinic acid, a promising anticancer agent.
Supersedes Agriculture Handbook no. 41, Check list of native and naturalized trees of the United States (Including Alaska), 1953 Incluye índice
The effects of topically applied curcumin, chlorogenic acid, caffeic acid, and ferulic acid on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced epidermal ornithine decarboxylase activity, epidermal DNA synthesis, and the promotion of skin tumors were evaluated in female CD-1 mice. Topical application of 0.5, 1, 3, or 10 mumol of curcumin inhibited by 31, 46, 84, or 98%, respectively, the induction of epidermal ornithine decarboxylase activity by 5 nmol of TPA. In an additional study, the topical application of 10 mumol of curcumin, chlorogenic acid, caffeic acid, or ferulic acid inhibited by 91, 25, 42, or 46%, respectively, the induction of ornithine decarboxylase activity by 5 nmol of TPA. The topical application of 10 mumol of curcumin together with 2 or 5 nmol of TPA inhibited the TPA-dependent stimulation of the incorporation of [3H]-thymidine into epidermal DNA by 49 or 29%, respectively, whereas lower doses of curcumin had little or no effect. Chlorogenic acid, caffeic acid, and ferulic acid were less effective than curcumin as inhibitors of the TPA-dependent stimulation of DNA synthesis. Topical application of 1, 3, or 10 mumol of curcumin together with 5 nmol of TPA twice weekly for 20 weeks to mice previously initiated with 7,12-dimethylbenz[a]anthracene inhibited the number of TPA-induced tumors per mouse by 39, 77, or 98%, respectively. Similar treatment of mice with 10 mumol of chlorogenic acid, caffeic acid, or ferulic acid together with 5 nmol of TPA inhibited the number of TPA-induced tumors per mouse by 60, 28, or 35%, respectively, and higher doses of the phenolic acids caused a more pronounced inhibition of tumor promotion. The possibility that curcumin could inhibit the action of arachidonic acid was evaluated by studying the effect of curcumin on arachidonic acid-induced edema of mouse ears. The topical application of 3 or 10 mumol of curcumin 30 min before the application of 1 mumol of arachidonic acid inhibited arachidonic acid-induced edema by 33 or 80%, respectively.
Genistein and daidzein, the two major soy isoflavones, principally occur in nature as their glycosylated or methoxylated derivatives, which are cleaved in the large intestine to yield the free aglycones and further metabolites. The objective of this study was to compare the antioxidant activities of genistein and daidzein with their glycosylated and methoxylated derivatives and also those of their human metabolites. The abilities of these compounds to inhibit lipid peroxidation in a liposomal system were evaluated using fluorescence spectroscopy, and structural criteria that enhance antioxidant activity were established. The peroxidation initiators employed in the study were Fe(II) and Fe(III) metal ions and aqueous-phase, azo-derived peroxyl radicals. Both the parent isoflavonoids and their metabolites were more effective at suppressing metal-ion-induced peroxidations than the peroxyl-radical-induced peroxidation. Antioxidant activities for the isoflavone metabolites were comparable to or superior to those for the parent compounds. Equol and its 4-hydroxy and 5-hydroxy derivatives were the most potent antioxidants in the study, suggesting that absence of the 2, 3-double bond and the 4-oxo group on the isoflavone nucleus enhances antioxidant activity. Additionally, the number and position of hydroxyl groups were determining factors for isoflavonoid antioxidant activity, with hydroxyl substitution being of utmost importance at the C-4' position, of moderate importance at the C-5 position, and of little significance at the C-7 position.
Microbial transformation of the antimelanoma agent betulinic acid (1) was studied. Preparative scale biotransformation with resting-cell suspensions of Cunninghamella species NRRL 5695 resulted in the production of a fungal metabolite of 1, which has been characterized as 28-O-beta-D-glucopyranosyl 3beta-hydroxy-lup-20(29)-en-28-oate (2) based on spectral and enzymic data. The in vitro cytotoxicity assay of metabolite 2 revealed no activity against several human melanoma cell lines.
Montmorency and Balaton tart cherries were lyophilized and sequentially extracted with hexane, ethyl acetate, and methanol. Methanolic extracts of dried Balaton and Montmorency tart cherries (Prunus cerasus) inhibited lipid peroxidation induced by Fe(2+) at 25 ppm concentrations. Further partitioning of this methanol extract with EtOAc yielded a fraction that inhibited lipid peroxidation by 76% at 25 ppm. Purification of this EtOAc fraction afforded eight polyphenolic compounds, 5,7,4'-trihydroxyflavanone (1), 5,7, 4'-trihydroxyisoflavone (2), chlorogenic acid (3), 5,7,3', 4'-tetrahydroxyflavonol-3-rhamnoside (4), 5,7,4'-trihydroxyflavonol 3-rutinoside (5), 5,7,4'-trihydroxy-3'methoxyflavonol-3-rutinoside (6), 5,7,4'-trihydroxyisoflavone-7-glucoside (7), and 6, 7-dimethoxy-5,8,4'-trihydroxyflavone (8), as characterized by (1)H and (13)C NMR experiments. The antioxidant assays revealed that 7-dimethoxy-5,8,4'-trihydroxyflavone (8) is the most active, followed by quercetin 3-rhamnoside, genistein, chlorogenic acid, naringenin, and genistin, at 10 microM concentrations.
The paper reports on 73 medicinal plants of 30 families, traditionally used in Bulgarian phytotherapy. Some of the plants are applied in practice for the treatment of cardiovascular, gastrointestinal, respiratory, urogenital and other disorders. The popular plants used for treatment are growing in 20 forested regions in Bulgaria.
Several flavonoids and isoflavonoids isolated from Balaton tart cherry were assayed for prostaglandin H endoperoxide synthase (PGHS-1) enzyme or cyclooxygenase isoform-1 (COX-1) activity. Genistein showed the highest COX-1 inhibitory activity among the isoflavonoids studied, with an IC50 value of 80 microM. Kaempferol gave the highest COX-1 inhibitory activity among the flavonoids tested, with an IC50 value of 180 microM. The structure-activity relationships of flavonoids and isoflavonoids revealed that hydroxyl groups at C4', C5 and C7 in isoflavonoids were essential for appreciable COX-1 inhibitory activity. Also, the C2-C3 double bond in flavonoids is important for COX-1 inhibitory activity. However, a hydroxyl group at the position decreased COX-1 inhibitory activity by flavonoids.
Anti-oxidant bioassay-directed extraction of the fresh leaves and stems of Ocimum sanctum and purification of the extract yielded the following compounds; cirsilineol [1], cirsimaritin [2], isothymusin [3], isothymonin [4], apigenin [5], rosmarinic acid [6], and appreciable quantities of eugenol. The structures of compounds 1-6 were established using spectroscopic methods. Compounds 1 and 5 were isolated previously from O. sanctum whereas compounds 2 and 3 are here identified for the first time from O. sanctum. Eugenol, a major component of the volatile oil, and compounds 1, 3, 4, and 6 demonstrated good antioxidant activity at 10-microM concentrations. Anti-inflammatory activity or cyclooxygenase inhibitory activity of these compounds were observed. Eugenol demonstrated 97% cyclooxygenase-1 inhibitory activity when assayed at 1000-microM concentrations. Compounds 1, 2, and 4-6 displayed 37, 50, 37, 65, and 58% cyclooxygenase-1 inhibitory activity, respectively, when assayed at 1000-microM concentrations. Eugenol and compounds 1, 2, 5, and 6 demonstrated cyclooxygenase-2 inhibitory activity at slightly higher levels when assayed at 1000-microM concentrations. The activities of compounds 1-6 were comparable to ibuprofen, naproxen, and aspirin at 10-, 10-, and 1000-microM concentrations, respectively. These results support traditional uses of O. sanctum and identify the compounds responsible.
Neochlorogenic acid (3-CQA) and cryptochlorogenic acid (4-CQA), isolated from prune (Prunus domestica L.), were identified by NMR and MS analyses. In addition, the quantity of chlorogenic acid isomers in prune were measured by HPLC. These isomers, 3-CQA, 4-CQA, and chlorogenic acid (5-CQA), were contained in the ratio 78.7:18. 4:3.9, respectively. 4-CQA was identified and quantified in prune for the first time, and relatively high amounts of this isomer were characteristic. Antioxidative activities of the chlorogenic acid isomers, such as scavenging activity on superoxide anion radicals and inhibitory effect against oxidation of methyl linoleate, were also evaluated. Each isomer showed antioxidative activities which were almost the same.
Many hydroxyflavone derivatives have been found in nature and shown to have many biological functions. Because their function is changed by the position and number of hydroxyl group, their structural identification is a fundamental and necessary step for understanding their functions. In the present study, the complete 1H and 13C NMR spectral assignments were presented for 6 hydroxyflavones, and NMR data of additional 14 hydroxyflavone derivatives were compared with those of the 6 hydroxyflavones. In addition, the partially incorrect NMR data of two of the dihydroxyflavones whose NMR data were previously reported were corrected.
Herbs: Challenges in chemistry and biology
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Honey locust, Gleditsia triacanthos L.-Plant symbol. U.S. Department of Agriculture
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L.-Plant symbol. U.S. Department of Agriculture, Natural
Resources Conservation Service.