scholarly journals Identification of a Novel Pyrrole Alkaloid from the Edible Mushroom Basidiomycetes-X (Echigoshirayukidake)

Molecules ◽  
2020 ◽  
Vol 25 (21) ◽  
pp. 4879
Author(s):  
Toshio Sakamoto ◽  
Ayaka Nishida ◽  
Naoki Wada ◽  
Yutaka Nakamura ◽  
Shinji Sato ◽  
...  

Three pyrrole alkaloid derivatives were isolated from the edible mushroom Basidiomycetes-X (Echigoshirayukidake) by water extraction followed by ethyl acetate fractionation. The chemical structures determined by MS and NMR were 4-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl] butanoic acid (compound I), 4-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl] butanamide (compound II), and 5-(hydroxymethyl)-1H-pyrrole-2-carboxaldehyde (compound III). Compound I was found to be the major component, followed by compound II, and compound III was the minor component. The dry powder of Basidiomycetes-X contained approximately 825 μg g−1 compound I and 484 μg g−1 compound II. Compound II was found to be a novel pyrrole aldehyde homologue not previously reported and thus is a specific component of this mushroom.

Molecules ◽  
2020 ◽  
Vol 25 (24) ◽  
pp. 5835
Author(s):  
Min-Ji Ryu ◽  
Minjeong Kim ◽  
Moongi Ji ◽  
Chaeyoung Lee ◽  
Inho Yang ◽  
...  

Lycii Fructus is a traditional medicine used to prevent liver and kidney diseases, which commonly derives from Lycium chinense and Lycium barbarum. Here, the extracts and ethyl acetate-soluble fractions of L. chinense fruits exhibited better hepatoprotective effects than those of L. barbarum, which was likely due to differences in their composition. Therefore, GC-MS and HPLC analyses were conducted to characterize the metabolite differences between L. chinense and L. barbarum. Based on amino acid (AA) and phenolic acid (PA) profiling, 24 AAs and 9 PAs were identified in the two species. Moreover, each species exhibited unique and readily distinguishable AA and PA star graphic patterns. HPLC analysis elucidated composition differences between the ethyl acetate-soluble layers of the two compounds. Further, NMR analysis identified their chemical structures as 4-(2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl)butanoic acid and p-coumaric acid. The higher content of 4-(2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl)butanoic acid was detected in L. chinense, whereas the content of p-coumaric acid was higher in L. barbarum. Therefore, the differences in the relative contents of these two secondary metabolites in the ethyl acetate-soluble layer of Lycii Fructus could be a good marker to discriminate between L. chinense and L. barbarum.


1975 ◽  
Vol 146 (1) ◽  
pp. 191-204 ◽  
Author(s):  
G H Tait

1. Micrococcus denitrificans excretes three catechol-containing compounds, which can bind iron, when grown aerobically and anaerobically in media deficient in iron, and anaerobically in medium with a high concentration of Ca2+. 2. One of these compounds was identified as 2,3-dihydroxybenzoic acid (compound I), and the other two were tentatively identified as N1N8-bis-(2,3-dihydroxybenzoyl)spermidine (compound II) and 2-hydroxybenzoyl-N-L-threonyl-N4[N1N8-bis-(2,3-dihydroxybenzoyl)]spermidine (compound III). 3. The equimolar ferric complex of compound III was prepared; compound III also forms complexes with Al3+, Cr3+ and Co2+ ions. 4. Cell-free extracts from iron-deficient organisms catalyse the formation of compound II from 2,3-dihydroxybenzoic acid and spermidine, and of compound III from compound II, L-threonine and 2-hydroxybenzoic acid; both reactions require ATP and dithiothreitol, and Mg2+ stimulates activity. The enzyme system catalysing the formation of compound II has optimum activity at pH 8.8 Fe2+ (35muM), Fe3+ (35muM) and Al3+ (65muM) inhibit the reaction by 50 percent. The enzyme system forming compound III has optimum activity at pH 8.6. Fe2+ (110 μM), Fe3+ (110 μM) and Al3+ (135 μM) inhibit the reaction by 50 percent. 5. At least two proteins are required for the formation of compound II, and another two proteins for its conversion into compound III. 6. The changes in the activities of these two systems were followed after cultures became deficient in iron. 7. Ferrous 1,10-phenanthroline is formed when a cell-free extract from iron-deficient cells is incubated with the ferric complex of compound III, succinate, NADH and 1,10-phenanthroline under N2.


2009 ◽  
Vol 65 (3) ◽  
pp. m121-m127 ◽  
Author(s):  
Juan Carlos Muñoz ◽  
Ana María Atria ◽  
Maria Teresa Garland ◽  
Ricardo Baggio

The structures of three new polymeric lanthanide complexes, poly[[bis(2,2′-bipyridine)-μ4-itaconato-di-μ3-itaconato-digadolinium(III)] tetrahydrate], {[Gd2(C5H4O4)3(C10H8N2)2]·4H2O}n, (I), poly[diaqua(2,2′-bipyridine)di-μ3-itaconato-μ2-itaconato-digadolinium(III)], [Gd2(C5H4O4)3(C10H8N2)(H2O)2]n, (II), and poly[[bis(2,2′-bipyridine)-μ4-itaconato-di-μ3-itaconato-diholmium(III)] dihydrate], {[Ho2(C5H4O4)3(C10H8N2)2]·2H2O}n, (III), have been solved from twinned specimens. Compound (I) presents a two-dimensional polymeric structure parallel to (011) built up around two independent nine-coordinated Gd centres displaying similar GdO7N2environments, with both N-donor atoms in each provided by a chelating 2,2′-bipyridine (bpy) unit. The coordinating O atoms are from three different itaconate (ita) anions (itaconic acid is 2-methylidenebutanedioic acid). Compound (II) also presents two independent Gd centres (one ten- and the other eight-coordinated), but the overall formula and individual coordinations are different from those of (I). The chemical unit is in this case completed by one bpy ligand, three ita anions (one of them displaying a new, hitherto unreported, μ3-O,O′:O′,O′′:O′′′ binding mode) and two aqua ligands. The whole structure is built up around a twofold rotation axis passing through both cations, as well as through the centre of the bpy ligand and one of the ita anions, thus making only half of the chemical unit independent. Finally, compound (III) presents a single independent Ho centre, a bpy unit and one and a half ita anions (one of them bisected by a twofold rotation axis) in the asymmetric unit, plus two (disordered) nonbonded solvent water molecules. In compounds (II) and (III), those ita anions bisected by a symmetry element incompatible with the internal symmetry of the ligand exhibit disorder in the C=CH2group.


Molecules ◽  
2021 ◽  
Vol 26 (3) ◽  
pp. 603
Author(s):  
Prashanth Sandineni ◽  
Hooman Yaghoobnejad Asl ◽  
Weiguo Zhang ◽  
P. Shiv Halasyamani ◽  
Kartik Ghosh ◽  
...  

Herein, we report the syntheses of two lithium-vanadium oxide-fluoride compounds crystallized from the same reaction mixture through a time variation experiment. A low temperature hydrothermal route employing a viscous paste of V2O5, oxalic acid, LiF, and HF allowed the crystallization of one metastable phase initially, Li2VO0.55(H2O)0.45F5⋅2H2O (I), which on prolonged heating transforms to a chemically similar yet structurally different phase, Li3VOF5 (II). Compound I crystallizes in centrosymmetric space group, I2/a with a = 6.052(3), b = 7.928(4), c = 12.461(6) Å, and β = 103.99(2)°, while compound II crystallizes in a non-centrosymmetric (NCS) space group, Pna21 with a = 5.1173(2), b = 8.612(3), c = 9.346(3) Å. Synthesis of NCS crystals are highly sought after in solid-state chemistry for their second-harmonic-generation (SHG) response and compound II exhibits SHG activity albeit non-phase-matchable. In this article, we also describe their magnetic properties which helped in unambiguous assignment of mixed valency of V (+4/+5) for Li2VO0.55(H2O)0.45F5⋅2H2O (I) and +4 valency of V for Li3VOF5 (II).


Author(s):  
Olha Sereda ◽  
Helen Stoeckli-Evans

The title compounds,catena-poly[[[bis[(R)-propane-1,2-diamine-κ2N,N′]copper(II)]-μ-cyanido-κ2N:C-[tris(cyanido-κC)(nitroso-κN)iron(III)]-μ-cyanido-κ2C:N] monohydrate], {[Cu(Lpn)2][Fe(CN)5(NO)]·H2O}n, (I), and poly[[hexa-μ-cyanido-κ12C:N-hexacyanido-κ6C-hexakis[(R)-propane-1,2-diamine-κ2N,N′]dichromium(III)tricopper(II)] pentahydrate], {[Cu(Lpn)2]3[Cr(CN)6]2·5H2O}n, (II) [where Lpn = (R)-propane-1,2-diamine, C3H10N2], are new chiral cyanide-bridged bimetallic coordination polymers. The asymmetric unit of compound (I) is composed of two independent cation–anion units of {[Cu(Lpn)2][Fe(CN)5)(NO)]} and two water molecules. The FeIIIatoms have distorted octahedral geometries, while the CuIIatoms can be considered to be pentacoordinate. In the crystal, however, the units align to form zigzag cyanide-bridged chains propagating along [101]. Hence, the CuIIatoms have distorted octahedral coordination spheres with extremely long semicoordination Cu—N(cyanido) bridging bonds. The chains are linked by O—H...N and N—H...N hydrogen bonds, forming two-dimensional networks parallel to (010), and the networks are linkedviaN—H...O and N—H...N hydrogen bonds, forming a three-dimensional framework. Compound (II) is a two-dimensional cyanide-bridged coordination polymer. The asymmetric unit is composed of two chiral {[Cu(Lpn)2][Cr(CN)6]}−anions bridged by a chiral [Cu(Lpn)2]2+cation and five water molecules of crystallization. Both the CrIIIatoms and the central CuIIatom have distorted octahedral geometries. The coordination spheres of the outer CuIIatoms of the asymmetric unit can be considered to be pentacoordinate. In the crystal, these units are bridged by long semicoordination Cu—N(cyanide) bridging bonds forming a two-dimensional network, hence these CuIIatoms now have distorted octahedral geometries. The networks, which lie parallel to (10-1), are linkedviaO—H...O, O—H...N, N—H...O and N—H...N hydrogen bonds involving all five non-coordinating water molecules, the cyanide N atoms and the NH2groups of the Lpn ligands, forming a three-dimensional framework.


Author(s):  
Assi M. ◽  
Usta J. ◽  
Mounimne Y. ◽  
Aboul Ela M. ◽  
El Lakany A.

Objective: Cancer represents the second leading cause of death after stroke and heart diseases. Plant extracts have long been used in traditional medicine for the prevention and treatment of many illnesses, including some types of cancer. The aim of this study was to evaluate the antiproliferative effects of ethyl acetate fractions of two Lebanese herbs: Inula viscosa (I. vis) and Inula vulgaris (I. vul).Methods: Plants were extracted with ethanol followed by ethyl acetate, then dried and tested on three cell lines including CaCO2, HepG2, and MCF7, to check for their viability and antiproliferative activity, using trypan blue exclusion and 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assays. Proton (1H) and carbon (13C) nuclear magnetic resonance spectrometry (NMR) were used to identify the compounds that have been isolated from both Inula species.Results: The current findings were consistent for both trypan blue and MTT assays. The results showed that the most potent effect for I. vul was HepG2 (IC50 20 µg/ml, 27 µg/ml), and for I. vis on MCF7 (9 µg/ml, 15 µg/ml) and CaCO2 (12 µg/ml, 22 µg/ml) in the two mentioned assays respectively. However, insignificant differences were observed among the studied plants for each of the evaluated cells indicating comparable potencies. Quercetin, quercetin glycoside, and epicatechin derivatives were isolated by fractionation on column chromatography and identified using NMR spectroscopy.Conclusion: The antiproliferative activities of the two plants could be related to their content that is significant for high levels of secondary metabolites. The identification of those compounds is necessary to establish a relationship between their chemical structures and their activities.


2019 ◽  
Vol 57 (1) ◽  
pp. 7
Author(s):  
Duc Long Le ◽  
Huu Tung Nguyen ◽  
Thi Thom Nguyen ◽  
Gyung Ja Choi ◽  
Dinh Hoang Vu ◽  
...  

Abstract-HCTN_16Methanol extract of the roots of Scutellaria baicalensis effectively inhibited the bacterial growth of human pathogenic bacteria Staphylococcus aureus ATCC 6538, Bacillus cereus ATCC 21768 and Bacillus subtilis ATCC 6633 at MICs of 2,000 µg/mL. n-Hexane, ethyl acetate and aqueous residues were prepared by successively partitioning the methanol extract with n-hexane and ethyl acetate. Among them, only ethyl acetate layer showed antibiotic effect; whereas n-hexane and aqueous layers were inactive against tested bacteria. The ethyl acetate residue was fractionated by silica gel column chromatography to afford three flavonoids and an oligosaccharide. Their chemical structures were elucidated as wogonin (SB1), baicalein (SB4), baicalin (SB5) and tetrasaccharide (SB10) on the basis of the analysis of NMR and MS spectroscopic data. The isolates were evaluated for in vitro inhibitory effect against human pathogenic bacteria using micro dilution bioassay method. Baicalein (SB4) showed a broad-spectrum inhibition against various human pathogenic bacteria. In particular, it was found to potently inhibit S. aureus ATCC 6538 and B. cereus ATCC 21768 with MICs of 9.5 and 38 µg/mL, respectively. The study results demonstrated antibiotic effect of the extracts from the roots of S. baicalensis and characterization of compounds isolated from the plant materials.


2019 ◽  
Vol 57 (2) ◽  
pp. 162
Author(s):  
Quan Minh Pham ◽  
Hoai Van Thi Tran ◽  
Lam Tien Do ◽  
Phuong Lan Doan ◽  
Inh Thi Cam ◽  
...  

Urena lobata L. is used in Vietnamese traditional medicine for the treatment of several diseases. Tree roots are used to treat rheumatism, dysentery, poor digestion, flu, tonsils, malaria, asthma, goiter. Flowers are used to treat chickenpox, fever, and mental disorders. Branches, leaves or whole trees used to treat injuries bruises, rheumatism, mastitis, bites. Phytochemical investigation of the n-hexan and ethyl acetate extract of Urena lobata L. led to the isolation of β-sitosterol (1), β-sitosterol-3-O-β-D-glucopyranoside (2), a-acetylamino-phenylpropyl a-benzoylamino-phenylpropanoate (3), quercetin (4), and trans-tiliroside (5). Their chemical structures were determined by spectroscopic methods including MS, 1D, 2D NMR and comparing with those reported in previous papers. Two compounds 3, 5 were isolated for the first time from Urena lobata plant.


Author(s):  
SHWETA R. GOPHANE ◽  
SAGAR R. JADHAO ◽  
PREETI B. JAMDHADE

Objective: Bergenia ciliata (family-Saxifragaceae) is a well-known herb for kidney stone. The main objective of the study was the identification of flavonoids along with ADME profile. Another supportive objective was to check inhibition of enzymes which perform active role in oxalate synthesis. Methods: The hydromethanolic extract was fractionated by liquid-liquid extraction to obtain ethyl acetate and ethyl ether fractions. The chemical structures of the purified compounds were identified by gas chromatography-mass spectrometry. Results: A total of 12 volatile chemical compounds belonging to hydrocarbons, esters, alcohols, fatty acids, ketones, etc. were identified and characterized in ethyl acetate fraction through GC-MS analysis Fractions enriched in flavonoids showed glycolate oxidase and lactate dehydrogenase enzyme inhibition with IC50 value (µg/ml) 65.76 and 69.84 respectively. The kinetic behaviour of the extracts that inhibit the Glycolate oxidase and Lactate dehydrogenase activity was determined by the Lineweaver-Burk plot. The mode of inhibition of the studied plant extract was type of a non-competitive inhibition. ADMET screening of compounds successfully passed all the parameters of screening. Conclusion: On the basis of the results, it was found that Bergenia ciliata (rhizome) may serve as a novel and rich source of therapeutic compounds and it can be further explored for urolithiasis treatment purposes.


2020 ◽  
Vol 13 (7) ◽  
pp. 3390-3397
Author(s):  
Regina Kemunto Mayaka ◽  
Alice Wanjiku Njue ◽  
Moses Kiprotich Langat ◽  
Peter Kiplagat Cheplogoi ◽  
Josiah Ouma Omolo

The emergence of antibiotic resistant pathogens has continuously increased, leading to a growing worldwide health threat due to infectious diseases. And therefore in our search for antibacterial and antifungal compounds from the polypore Ganoderma adspersum, the dried, ground fruiting bodies of G. adspersum were extracted with methanol and solvent removed in a rotary evaporator. The extract was suspended in distilled water, then partitioned using ethyl acetate solvent to obtain an ethyl acetate extract. The extract was fractionated and purified using column chromatographic method and further purification on sephadex LH20. The chemical structures were determined on the basis of NMR spectroscopic data from 1H and 13C NMR, HSQC, HMBC, 1H-1H COSY, and NOESY experiments. Antimicrobial activity against clinically important bacterial and fungal strains was assessed and zones of inhibition were recorded. Compound (1), ergosta-7,22-dien-3-one weakly inhibited the growth of Gram positive bacteria Streptococcus pneumonia and a fungus Cryptococcus neoformans. Compounds ergosta-7,22-dien-3-ol (2) and ergosta-5,7,22-trien-3-ol (3) also inhibited gram positive Streptococcus pyogenes bacteria.Keywords: Polypores, steroid compounds, antimicrobial activity.


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