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Two Novel Flavanones from Greigia sphacelata
Abstract
As part of our continuing phytochemical investigations of plants from arid environments in Chile, the aerial parts of Greigia sphacelata were examined. Two novel flavanones, 5,7,3'-trihydroxy-6, 4',5'-trimethoxyflavanone (1) and 5,3'-dihydroxy-6,7,4', 5'-tetramethoxyflavanone (2), as well as eight known compounds-1, 3-O-di-trans-p-coumaroylglycerol (3), 1-O-trans-p-coumaroylglycerol (4), a mixture of 1-(omega-feruloyldocosanoyl)glycerol (5) and 1-(omega-feruloyltetracosanoyl)glycerol (6), trans-ferulic acid 22-hydroxydocosanoic acid ester (7), arborinone (8), arborinol (9), and isoarborinol (10)-were isolated.
... On which they have been made. few investigations to date (four scientific publications, the last one from 2020) [19] About this fruit, it has been reported that it presents various types of antioxidants, mainly polyphenols, flavanones (5,7,3´trihydroxy-6,4,5´-trimethoxyflavanone and 5,3´-dihydroxy-6,7,4,5´-tetramethoxyflavanone) [20] In this work, a methodology was developed to determine the antioxidant capacity in wild fruits using Greigia sphacelata as the first model through the pulse difference voltammetry technique, a technique in which the potential is fixed and is superimposed on slowly changing the potential base. The current is measured at two points; before the application of the pulse, and at the end of the pulse [21,22]. ...
The study and determination of the antioxidant capacity of the Greigia Sphacelata fruit were carried out. G. sphacelata is an endemic fruit of central-southern Chile, better known as Chupón or Quiscal. Spectrophotometric and modified ORAC test were developed for antioxidant capacity determinations, and later an electrochemical method was developed by differential impulse voltammetry (DPV) with a vitreous carbon electrode for the quantification of the antioxidant capacity expressed in equivalent of the Trolox standard in µmolL-1. Once the voltammetric test was developed, the correlation study between both methods used to determine the antioxidant capacity of Greigia sphacelata was carried out. The results of the determination of the antioxidant capacity of Greigia sphacelata by ORAC test report an antioxidant capacity of 3525 µmol/100gequivalents of Trolox. Concerning the concentration obtained by the electrochemical methodology, 724 µmol/100g Trolox equivalents is obtained for a linear correlation r = 0.969 with the spectrophotometric method.
... Few reports have investigated the chemical properties of G. sphacelata. From the aerial parts of G. sphacelata flavanones (5,7,3'-trihydroxy-6, 4',5'-trimethoxyflavanone, and 5,3'-dihydroxy-6,7,4',5'tetramethoxyflavanone), glycerol derivatives (1-O-trans-p-coumaroylglycerol, 1,3-O-di-trans-pcoumaroylglycerol, 1-(ω-feruloyl-docosanoyl) glycerol, and 1-(ω-feruloyl-tetracosanoyl) glycerol), and trans-ferulic acid, arborinone, 22-hydroxydocosanoic acid ester, isoarborinol and arborinol have been isolated and characterized [11]. To our knowledge, there are no reports on the chemical characterization or antioxidant and enzyme inhibitory properties of the natural products obtained from G. sphacelata fruits. ...
Greigia sphacelata (Ruiz & Pav.) Regel (Bromeliaceae) is a Chilean endemic plant popularly known as “quiscal” and produce an edible fruit consumed by the local Mapuche communities named as “chupón”. In this study, several metabolites including phenolic acids, organic acids, sugar derivatives, catechins, proanthocyanidins, fatty acids, iridoids, coumarins, benzophenone, flavonoids and terpenes were identified in G. sphacelata fruits using ultrahigh performance liquid chromatography-photodiode array detection coupled with a Orbitrap mass spectrometry (UHPLC-PDA-Orbitrap-MS) analysis for the first time. The fruits showed moderate antioxidant capacities (i.e., 487.11 ± 26.22 μmol TE/g dry weight) in the stable radical DPPH assay, 169.08 ± 9.81 TE/g dry weight in the ferric reducing power assay, 190.32 ± 6.23 TE/g dry weight in the ABTS assay, and 76.46 ± 3.18 % inhibition in the superoxide anion scavenging assay. The cholinesterase inhibitory potential was evaluated against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). From the findings, promising results were observed for pulp and seeds. Our findings suggest that G. sphacelata fruits are a rich source of diverse secondary metabolites with antioxidant capacities. In addition, the inhibitory effects against AChE and BChE suggest that natural products or food supplements derived from G. sphacelata fruits are of interest Mofor their neuroprotective potential.
... As part of our ongoing search for new anti-cancer and anti-HIV-1 agents from plants, a MeOH-EtOAc (1:1) fraction, obtained by dissolving a crude MeOH extract from leaves and twigs of G. sessiliflora, was separated by chromatography, followed by recrystallization to afford three new compounds, sessiliflorin (1), 5,3′,5′-trihydroxy-6,7,4′-trimethoxyflavanone (10) and 5-hydroxy-6,7,3′,4′,5′-pentamethoxyflavanone (11). Furthermore, eight known cycloartane triterpenoids, (23E)-25-hydroxycycloart-23-ene-3β,25-diol (2) (Khan et al., 2006), 3β-hydroxy-5α-cycloart-24(31)-en-28-oic acid (3) (Banskota et al., 2000), 23-deoxojessic acid (4) (Banskota et al., 2000), sootepenoic acid (5) (Pudhom et al., 2012), coronalolide methyl ester (6) (Silva et al., 1997), sootepin A (7) (Nuanyai et al., 2009), tubiferolide methyl ester (8) , coronalolide (9) (Silva et al., 1997); as well as ten known flavonoids, 6-methoxynaringenin (12) (Spring et al., 1997), 5,3′-dihydroxy-6,7,4′,5′-tetramethoxyflavanone (13) (Flagg et al., 2000), apigenin (14) (Benayache et al., 2014), hispidulin (15) (Osei-Safo et al., 2009), cirsimaritin (16) (Kawashty et al., 1999), salvigenin (17) (Chatuevedula and Prakash, 2013), 5-hydroxy-6,7,4′,5′-tetramethoxyflavone (18) (Akkal et al., 2003), 5,3′,5′-trihydroxy-6,7,4′trimethoxyflavone (19) (Kinoshita and Firman, 1996), 5,3′-dihydroxy-6,7,4′,5′-tetramethoxyflavone (20) (Kongkum et al., 2012) and umuhengerin (21) (Rwangabo et al., 1988), were also obtained and characterized. We herein report the isolation, structure elucidation, as well as the unpublished results on cytotoxic and anti-HIV-1 activities of the isolates. ...
A new cycloartane triterpenoid, sessiliflorin (1), together with two new flavanones, 5,3′,5′-trihydroxy-6,7,4′-trimethoxyflavanone (10) and 5-hydroxy-6,7,3′,4′,5′-pentamethoxyflavanone (11) were isolated from a me-thanol extract of leaves and twigs of Gardenia sessiliflora. In addition, the known cycloartane triterpenoids 2-9 and flavonoids 12-21 were also obtained from the same source. All structures were determined based on their spectroscopic data. Most of the tested compounds including the new compounds, 1, 10, and 11 showed anti-HIV-1 activity in the syncytium reduction assay with EC 50 values of < 8.02-171.61 μM and SI values of 1.12-9.72 except compound 7 which was found toxic. In the anti-HIV-1 RT assay, compound 5, 10, 13, and 14 displayed weak activities with 30.00-46.40% inhibition at 200 μg/mL, while 16 showed moderate activity with 52.50% inhibition at 200 μg/mL. For cytotoxic assay, 7 displayed cytotoxic activity in all tested cell lines except A549 cell line with IC 50 values of 0.6-4.8 μM, whereas 3-5 and 14 were found active in P-388 cell line with IC 50 values of 1.2-7.5 μM. However, compounds 5 and 7 were also found toxic to HEK 293 cell line.
... A limited number of poly-oxygenated flavonoids have previously been identified from plants belonging to Bromeliaceae (Bringmann et al., 2000;Flagg et al., 2000; Lowe et al., 2017). Several studies have shown that rutin has anticancer effects (Lin et al., 2012 be useful in treating leukaemia, however, they underlined that much more confirmative research is needed (Lin et al., 2012). ...
Neoglaziovia variegata is endemic to northeastern Brazil. The drought resistant plant produces edible fruits and is used as a fibre plant by rural communities in the Caatinga region where a variety of products are made from the white, soft and flexible fibres. Extracts of N. variegata have been reported to be of low toxicity and to exhibit antinociceptive effect, photoprotective potential, antioxidant effect, gastroprotective effects and antibacterial effect against both Gram-positive and Gram-negative bacteria, however, the chemical constituents of this species are mainly unknown. The novel poly-oxygenated flavone glucoside 5,6,7,4'-tetrahydroxy-3',5'-dimethoxy-flavone 7-O-b-glucopyranoside in addition to the rare poly-oxygenated flavone 5,4'-dihydroxy-6,7,3'-trimethoxyflavone 4'-O-b-glucopyranoside and the flavonol quercetin 3-O-(6''-rhamnopyranosyl-b-glucopyranoside) have been characterised from the leaves of N. variegata. Torgils Fossen. A novel poly-oxygenated flavone glucoside from aerial parts of the Brazilian plant Neoglaziovia variegata (Bromeliaceae). (http://creativecommons.org/licenses/by-nc-nd/4.0/). 5,6,7,4'-tetrahydroxy-3',5'-dimethoxy-flavone, which comprises the core structure of the novel compound, is a new flavonoid aglycone in nature. The structure determinations were based on extensive use of 2D NMR spectroscopic techniques and high-resolution mass spectrometry. Both substances exhibited toxicity towards MOLM-13 acute myeloid leukaemia cells.
Obesity, heart disease, diabetes, and cancer are just a few chronic diseases for which proper nutrition has been demonstrated to be a crucial factor in preven-tion. Flavonoids, found in many fruits and vegetables, are a type of dietary polyphenol with potent antioxidant activity and anti-carcinogenic characteris-tics. Flavonoids and foods rich in flavonoids have been shown in recent years to have profound effects on cognitive function, aging, and neurodegenerative diseases like Alzheimer's. Foods high in flavonoids, such as green tea, choco-late, blueberries, and other fruits and vegetables, have ameliorated symptoms of cognitive impairment, Alzheimer's disease, and dementia in several animal models. As a result of their ability to prevent neuronal death generated by neu-rotoxic chemicals such as free radicals and β-amyloid proteins. Furthermore, flavonoids are also effective in slowing the evolution of clinical signs of neuro-degenerative illnesses. In addition, flavonoids can improve lipid profiles by preventing the oxidation of low-density lipoproteins, and these antioxidant ca-pabilities are responsible for their therapeutic impacts. Finally, the potential of flavonoids to induce vasodilation and control apoptotic processes in the endo-thelium is another way in which they benefit the cardiovascular system. This review aims to offer up-to-date information on categorizing these compounds, their primary methods of action in the human body, and their positive impacts on the management of neurodegenerative diseases, cardiovascular disorders, and other life-threatening diseases.
A comprehensive phytochemical research on roots of Caragana grandiflora, a native plant to Iran, resulted in isolation of ten compounds including four phenolic compounds (2, 4, 5, 8), two fatty alcohols (1, 6), one fatty acid (9), one triterpene (3), one glyceride derivatives (7) and one fatty acid methyl ester (10), from which eight compounds (1, 2, 4–6 and 8–10) were isolated from the genus Caragana and two compounds (5 and 10) from the family Fabaceae, for the first time. All compounds (1–10) were described from Caragana grandiflora for the first time. Chemical structures of the purified compounds were identified through FT-IR, NMR and MSS, and spectral data comparison with literature reported evidences.
Our findings provide valuable information in reporting the rare existence of natural fatty acid methyl ester (10) in the Fabaceae family. Moreover, the chemotaxonomic significance of these compounds was discussed.
Binglang, the fruit of Areca catechu L, has a long history as an important Chinese herbal medicine. Two new alkaloids (1 and 2), along with forty-one known compounds (3-43) were isolated from the dried fruit of Areca catechu L. The structures were elucidated on basis of the IR, UV, MS and 1D, 2D NMR spectroscopic data. Compounds 26 and 33 showed weak cytotoxicity against human gastric cancer cell line (BGC-823) with IC50 of 15.91 μM and 20.13 μM, respectively.
Oenothera rosea L´Hér. ex Ait is a species traditionally used in the treatment of inflammation, headache, stomach pain, infections, among others. The aim of this study was evaluating the acute anti-inflammatory activity of the aqueous extract of O. rosea by 2,4,6-trinitrobenzene sulfonic acid (TNBS)-induced colitis. Rats were randomized into six groups: (I) Sham; (II) EtOH; (III) TNBS; and (IV–VI) 250, 500 and 750 mg/Kg, respectively. The colonic injury was induced (groups III–VI) by intrarectal instillation of 0.25 mL of TNBS (10 mg) in 50% ethanol. Groups I and II received an enema (0.25 mL) of physiological saline solution or 50% ethanol, respectively. Treatments were administered by oral gavage 48, 24 and 1 h prior, and 24 h after the induction. The inflammatory response was assessed considering the macroscopic and microscopic damage, the serum nitric oxide (NO), the colonic IL-1β levels, and the myeloperoxidase (MPO) activity. Moreover, we performed an LC–MS-based metabolite profiling, and a docking on the MPO. Doses of 500 and 750 mg/Kg showed a protective effect in the TNBS-induced colonic damage. This activity was related to the downregulation of evaluated parameters. Also, considering previous reports, 29 metabolites of 91 detected were selected for the docking, of which Isolimonic acid (29) and Kaempferol 3-(2′′,4′′-diacetylrhamnoside) (10) showed the highest affinity to MPO. The aqueous extract of O. rosea protected the TNBS-induced colonic damage in rats, an effect that could be associated with the presence of polyphenolic compounds, alkaloids, and terpenes; as well as their ability to down-regulate MPO activity.
This review describes aspects of the Bromeliaceae family dealing the traditional applications, biological activities and distribution of secondary metabolites in distinct subfamilies. Some species are used with medicinal purposed in the treatment of respiratory, diabetes or inflammation diseases, and gastrointestinal disorders. Special emphasis on cycloartane triterpenoids and flavonoids, typical metabolites of this family, are presented. Bromeliaceae is unique amongst the monocotyledons in the frequency and variety of flavonoids with hydroxylation or methoxylation at the 6-position. Other compound classes as steroids, hidroxycinnamic acids, phenylpropane diglycerides, lignans, are presented.
Flavanones are one of the most interesting naturally occurring flavonoids in view of their structural pattern as well as
biological and pharmacological potentials. The present review deals with natural flavanones reported from 1998 to mid 2007,
along with their biological and pharmacological activities. The review includes more than 160 new naturally occurring
flavanones from 135 references. The reported flavonoids belong to thirty-six plant families.
Keywords: Naturally occurring flavanones, distribution, pharmacological studies, biological activities.
A new sucrose ester named beta-D-(1-O-acetyl-3-O-cis-feruloyl)fructofuranosyl alpha-D-2',3',6'-O-triacetylglucopyranoside 1 and a novel phenylpropanoid glycerol named 1-O-cis-feruloyl-3-O-trans-p-coumaroylglycerol 2, have been isolated from Sparganium stoloniferum. Their structures were elucidated by spectroscopic methods.
The increase of multidrug-resistant Mycobacterium tuberculosis (MDR-TB) demands the search for alternative antimycobacterial drugs. The aim of this study was to evaluate plants used in Mexican traditional medicine to treat respiratory diseases for activity against MDR-TB. A group of 22 plants was screened for activity against Mycobacterium tuberculosis H37Rv and Mycobacterium avium at concentrations from 50 to 200 microg/mL. The antimycobacterial effect was determined by a microcolorimetric assay with Alamar blue dye. None of the aqueous extracts had antimycobacterial activity. Hexane extracts from Artemisia ludoviciana, Chamaedora tepejilote, Lantana hispida, Juniperus communis and Malva parviflora, and methanol extracts from Artemisia ludoviciana and Juniperus communis inhibited the growth of Mycobacterium tuberculosis. Mycobacterium avium was inhibited by Juniperus communis hexane extract and by Malva parviflora methanol extract. The active extracts were tested against monoresistant variants of Mycobacterium tuberculosis H37Rv (isoniazid, rifampin, streptomycin and ethambutol resistant) and the hexane extract of Lantana hispida showed the best activity. Lantana hispida hexane extract was also active against a group of MDR-TB clinical isolates. In contrast, it did not inhibit the growth of non-tuberculous mycobacteria. The hexane extract of Lantana hispida was fractionated by column chromatography and one of its fractions (FVI) inhibited the growth of all the MDR-TB clinical isolates at concentrations up to 25 microg/mL. This study supports the fact that selecting plants by ethnobotanical criteria enhances the probability of finding species with activity against mycobacteria, and our results point to Lantana hispida as an important source of potential compounds against MDR-TB.
More than 450 new flavonoid structures, reported from January 2001 until December 2003, are reviewed. They comprise anthocyanidins, flavones, flavonols, chalcones, dihydrochalcones, aurones, flavanones and dihydroflavonols, both as aglycones and as glycosides. The biological activity of some of the compounds is briefly discussed. There are 289 cited references.
Fractionation of the aerial parts of Chromolaena odorata afforded a new flavonoid, 5,7-dihydroxy-6,4'-dimethoxyflavanone, in addition to 14 known flavonoid compounds, six of which had not been isolated previously from this plant. The structure of the new compound was determined by spectroscopic methods particularly 2D-NMR analysis.
Aus den Blättern von Glycosmis arborea (Rutaceae) wurden zwei neue epimere pentacyclische Triterpene, Arborinol und Isoarborinol, isoliert. Durch chemischen Abbau und Anwendung physikalischer Methoden, insbesondere der kernmagnetischen Resonanz (NMR), der optischen Rotationsdispersion und der Massenspektroskopie konnte die Struktur der Ringe A, B und C der Arborinole aufgeklärt und die Existenz von zwei sekundären Methylgruppen im Rest des Moleküls nachgewiesen werden. Für Arborinol und Isoarborinol wird deshalb die Struktur von 3-Hydroxy-Δ9(11)-13β.14α-dimethyl-pentacyclischen Triterpenen (I bzw. III) angenommen; sie stellen damit einen neuen Triterpen-Typus dar.
The esters of n-fatty acids and ω-hydroxy n-fatty acids of β-sitosterol, D-glucose and ferulic acid (trans and cis) as well as β-sitosterol, fatty acids and β-sitosteryl-β-D-glucoside were isolated from three Virola species and identified by optical data and chemical reactions. A novel series of acidic esters derived from C22C29 ω-hydroxy fatty acids and cis- and trans-ferulic acid is reported for the first time. These compounds also occurred as the corresponding diester 1-monoglycerides whereas the ω-hydroxy acids themselves were also present as the corresponding glucosyl esters.
Three new phenolic acid derivatives, 1,3-O-di-trans-p-coumaroylglycerol, 1,2-O-di-trans-p-coumaroylglycerol and chokorin were isolated from stromata of Epichloe typhina on timothy plants Phleum pratense. Their structures were established by spectroscopic and chemical means.
This paper reports on the presence of arborinone, isoarborinol and some of their early diagenetic degradation products in a tropial lake. Isoarborinol and arborinne, two 3-oxygenated pentacyclic triterpenes whose origin was initially ascribed to higher plants, were found to be highly abundant in Lake Valencia (Venezuela) surface sediments. The primarily autochthonous origin of the organic matter in sediments from this hypereutrophic lake seems to indicate a microbial source for these compounds, as previously suggested by other authors. The structures of two novel tetracyclic aliphatic alkene degradation products of arborinone/isoarborinol are also proposed, and sediment core profiles for both parent and degradation products are discussed.