Four alkaloids from Portulaca oleracea L. and their anti-inflammatory.

Four alkaloids were isolated from Portulaca oleracea L., including two new compounds, 2-(4-amino-6-hydroxy-1,6-dihydropyrimidin-5-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol, named Olerapyrimidine (1) and (2 R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-((6-hydroxypyridin-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triol, named Olerapyridine (2), and two known compounds including 1H-imidazole (3) and (5S, 6 R, 7S, 8 R)-5-amino-(2Z,4Z)-1,2,3-trihydroxybuta-2,4-dienyloxy-pentane-6,7,8,9-tetraol (4) from P. oleracea for the first time. Their structures were determined by spectroscopic methods, including UHPLC-ESI-Q-TOF/MS, 1D and 2D NMR spectra. Both Olerapyrimidine and Olerapyridine at 20 µM could inhibit the inflammatory factors, IL-1ß and TNF-α in the RAW 264.7 cells induced by LPS.

Comparative analysis of chloroplast genomes of Pulsatilla species reveals evolutionary and taxonomic status of newly discovered endangered species Pulsatilla saxatilis.

BACKGROUND: Pulsatilla saxatilis, a new species of the genus Pulsatilla has been discovered. The morphological information of this species has been well described, but its chloroplast genome characteristics and comparison with species of the same genus remain to be reported. RESULTS: Our results showed that the total length of chloroplast (cp.) genome of P. saxatilis is 162,659 bp, with a GC content of 37.5%. The cp. genome contains 134 genes, including 90 known protein-coding genes, 36 tRNA genes, and 8 rRNA genes. P. saxatilis demonstrated similar characteristics to other species of genus Pulsatilla. Herein, we compared cp. genomes of 10 species, including P. saxatilis, and found that the cp. genomes of the genus Pulsatilla are extremely similar, with a length of 162,322-163,851 bp. Furthermore, The SSRs of Pulsatilla ranged from 10 to 22 bp in length. Among the four structural regions of the cp. genome, most long repeats and SSRs were detected in the LSC region, followed by that in the SSC region, and least in IRA/ IRB regions. The most common types of long repeats were forward and palindromic repeats, followed by reverse repeats, and only a few complementary repeats were found in 10 cp. genomes. We also analyzed nucleotide diversity and identified ccsA_ndhD, rps16_trnK-UUU, ccsA, and rbcL, which could be used as potential molecular markers for identification of Pulsatilla species. The results of the phylogenetic tree constructed by connecting the sequences of high variation regions were consistent with those of the cp. gene phylogenetic tree, and the species more closely related to P. saxatilis was identified as the P. campanella. CONCLUSION: It was determined that the closest species to P. saxatilis is P. campanella, which is the same as the conclusion based on pollen grain characteristics, but different from the P. chinensis determined based on morphological characteristics. By revealing information on the chloroplast characteristics, development, and evolution of the cp. genome and the potential molecular markers, this study provides effective molecular data regarding the evolution, genetic diversity, and species identification of the genus Pulsatilla.

Two new alkaloids from Portulaca oleracea L. and their anti-inflammatory and anticholinesterase activities.

Two new alkaloids identified as 2-(((S,Z)-1-(1H-azirin-1-yl)-5-methylhex-1-en-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol and (S,Z)-1-(1H-azirin-1-yl)-5-methylhex-1-en-3-ol, named olerazirin A (1), olerazirin B (2), together with five known alkaloids, identified as cyclo (L-Val-L-Ala) (3), cyclo-(glycyl-L-leucine) (4), cyclo-(Gly-Phe) (5), cyclo (Ser-Phe) (6), (3S,6S)-3-[(1R)-1-hydroxyethyl]-6-(phenyl-methyl)-2,5-piperazinedione (7) were obtained from Portulaca oleracea L. using a range of chromatographic techniques, 1D and 2D NMR, and high-resolution electrospray ionisation time-of-flight mass spectroscopic methods, in which the compounds 3-7 were isolated from P. oleracea for the first time. In addition, the results showed that the compounds 1 and 2 have anti-inflammatory activities and compounds 1-3 and 5-7 exhibit the anticholinesterase activities.

Two novel ketone alkaloids from Portulaca oleraceaL. and their anti-inflammatory activities.

Eleven compounds were obtained from Portulaca oleracea L., including two novel ketone alkaloids, (1, 2), 4-hydroxy-3-methoxybenzamide (3) (isolated for the first time), ß-adenosine (4), oleracrylimide A and B (5, 6), oleracein H, C, D, Q and A (7-11). The two novel ketone alkaloids were identified as 5-acetyl-5-methylcyclopent-2-ene-1-carboxamide (1), named oleraciamide H, and (2 R,3S,4R,5R)-5-((R)-1,2-dihydroxyethyl)-3,4-dihydroxytetrahydrofuran-2-yl glycinate (2), named oleracone Q by spectroscopic methods, including 1D, 2D NMR and compound fingerprints. Additionally, their anti-inflammatory activities were tested via RAW 264.7 cells induced by LPS and found that they could significantly inhibit the release of IL-1ß and TNF-α.

Two novel alkaloids from Portulaca oleracea L. and their anti-inflammatory bioactivities.

Two novel alkaloids were identified as (E)-N-(4-3,4-dihydroxy-6-(hydroxymethyl)-5-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-2,5-dihydroxyphenyl)-3-(4-hydroxyphenyl)acrylamide (1), named Oleracrylimide D, (E)-N-(4-3,4-dihydroxy-6-(hydroxymethyl)-5-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-2,5-dihydroxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)acrylamide (2), named Oleracrylimide E, isolated from Portulaca oleracea L. The structures were identified by spectroscopic methods, including 1D NMR, 2D NMR, and UHPLC-ESI-QTOF/MS methods, also, the anti-inflammatory bioactivities of the compounds were studied by ELISA method.

A new alkaloid and two organic acids from Portulaca oleracea L. and their bioactivities.

A new alkaloid, identified as 1-benzyl-2-nitroso-1,2,3,4-tetrahydroisoquinoline-6,7-diol, named oleraisoquinoline (1), and five organic acids and two esters, identified as 5-(hydroxymethyl)furan-2-carboxylic acid (2), 1H-pyrrole-2,5-dicarboxylic acid (3), (7E,10E)-octadeca-7,10-dienoic acid (4), (10E,13E)-octadeca-10,13-dienoic acid (5), (7E,10E)-hexadeca-7,10-dienoic acid (6), methyl tridecanoate (7) and methyl (9E,12E)-octadeca-9,12-dienoate (8), were isolated from Portulaca oleracea L., among which compounds 2 and 4‒7 were isolated for the first time. Moreover, the anti-inflammatory activities of compounds 1‒3 were studied, especially, compound 1 presented good inhibitory effects on the production of inflammatory factors IL-1ß and TNF-α.

A new alkaloid from Portulaca oleracea L. with its anti-inflammatory activity.

A new isoindole alkaloid, 6-hydroxy-2-(4'''-hydroxy-3'''-methoxyphenethyl)-4-(4'-hydroxy-3'-methoxyphenyl)-7-methoxy-1H-benzo[f]isoindole-1,3(2H)-dione, named oleraisoindole B was isolated from Portulaca oleracea L., its structure was elucidated using NMR and UHPLC-ESI-Q-TOF/MS spectroscopic methods, and presented anti-inflammatory activity at 5 µM.

A novel skeleton alkaloid from Portulaca oleracea L. and its bioactivities.

A novel skeleton alkaloid was obtained from Portulaca oleracea L., which was identified as 10,11-dihydroxybenzo[5',6'] pentaleno[1',2':3,4]pyrrolo[2,1-b]oxazol-7(11bH)-one, named oleracone M, and its structure was determined using UHPLC-ESI-QTOF/MS, 1D NMR and 2D NMR spectroscopy, and circular dichroism. Then the bioactivities of the compound were investigated including the anti-inflammatory, anti-acetylcholinesterase and antioxidant activities. The results showed that the novel skeleton alkaloid exhibited the potent effect on inhibiting the secretion of IL-1ß at 10 µM, anticholinesterase activity with IC50 value of 49.58 µM, and antioxidant activity with IC50 value of 66.43 µM.

Two new natural products from Portulaca oleracea L. and their bioactivities.

Two new natural products, belonging to alkaloids, identified as ((2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl acetate (1) and (5-hydroxypyridin-2-yl)methyl acetate (2), were isolated from Portulaca oleracea L. The structures were identified by spectroscopic methods, including 1D, 2D NMR, and UHPLC-ESI-QTOF/MS methods. Meanwhile, the anti-inflammatory and anticholinesterase bioactivities were found in these two compounds.

Two new ester alkaloids from Portulaca oleracea L. and their bioactivities.

Two new ester alkaloids were isolated from Portulaca oleracea L., identified as (5-aminofuran-2-yl) methyl acetate (1) named oleracone N and 4(S)-ethyl 3-acetamido-3-(dihydroxyamino) propanoate (2) named oleracone O. The structures were elucidated via spectroscopic methods, including 1 D and 2 D NMR, UHPLC-ESI-QTOF/MS and CD spectrometry technique. It was suggested that both oleracone N and oleracone O could significantly inhibit inflammatory factors IL-1ß and TNF-α in RAW 264.7 cells induced by LPS.

Two novel amide alkaloids from Portulaca oleracea L. and their anti-inflammatory activities.

In this article, two novel amide alkaloids were identified as (E)-3-(4-hydroxy-3-methoxyphenyl)-1-(5-hydroxy-6-((3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1H-indol-1-yl)prop-2-en-1-one (1) and (E)-1-(5-hydroxy-6-((3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1H-indol-1-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one (2), the two compounds were named oleraindole E and oleraindole F, respectively. The structures were elucidated using 1D and 2D NMR and HR-ESI-TOF-MS spectra. Additionally, the anti-inflammatory activities were evaluated on RAW264.7 cells induced by LPS, compounds 1 and 2 exhibited anti-inflammatory activities at 20 µM.

A novel alkaloid from Portulaca oleracea L. and its anti-inflammatory activity.

A novel alkaloid identified as methyl 8,9-dihydroxy-11-oxo-6,11-dihydro-5H-benzo[d]pyrrolo[1,2-a]azepine-3-carboxylate, named portulacatone A (1) with six known compounds Oleracein E (2), 6,7-dihdroxy-3,4-dihydro-2H-isoquinolin-1-one (3), N-trans-p-coumaroytyramine (4), 9H-carbazole (5), isoaspergin (6) and flavoglaucin (7) were obtained from Portulaca oleracea L., while compounds (5-7) were isolated from the plant for the first time. The new structure was identified by using UHPLC-ESI-Q-TOF/MS, 1D, 2D NMR and the others were proved by 1H-NMR and 13C NMR that comparing with previous reports. It was suggested that the portulacatone A (1) can significantly inhibit the inflammatory factor, interleukin-1ß (IL-1ß) in the RAW 264.7 cells induced by LPS.

Two new homoisoflavones from Portulaca oleracea L. and their activities.

Two new compounds, identified as 3-(2-hydroxybenzyl)-6,8-dimethoxy-4H-chromen-4-one (1), named oleracone J and 3-(2-hydroxybenzyl)-6,8-dimethoxychroman-4-one (2), named oleracone K, were isolated from Portulaca oleracea L., and the structures of them were determined by spectroscopy, including one-dimensional and two-dimensional nuclear magnetic resonance, high-resolution electrospray ionisation time-of-flight mass spectrometry. The two compounds have scavenging activities in 1,1-diphenyl-2-picryl-hydrazyl (DPPH) radical quenching assay, with IC50 values of 18.34, 23.92 µM, and anticholinesterase activities with IC50 values of 59.08, 67.89 µM, respectively.

Seven compounds from Portulaca oleracea L. and their anticholinesterase activities.

A novel lignan, identified as 4-(3,4-dihydroxyphenyl)-6,7-dimethoxy-3a,4-dihydronaphtho[2,3-c]furan-1(3H)-one, named oleralignan A (1), together with six known compounds, loliolide (2), isololiolide (3), dehydrololiolide (4), daphnetin (5), esculetin (6), and trans-coumaric acid methyl ester (7) was obtained from Portulaca oleracea L., while compounds 3, 4, 6, and 7 were isolated from the plant for the first time. Their structures were elucidated using spectroscopic methods, including one- and two-dimensional NMR and high-resolution electrospray ionization time-of-flight mass spectrometry. In addition, the results of activity assay demonstrated that compounds 1-7 have anticholinesterase activities.

Two new organic acids from Portulaca oleracea L. and their anti-inflammatory and anticholinesterase activities.

Two new organic acids, identified as (7E,9E,12E)-pentadecyl-7,9,12-trienoic acid, named Oleraceacid A (1), and 6,7-dihydroxy-4-(4-hydroxy-3,5-dimethoxyphenyl)-2-naphthoic acid, named Oleraceacid B (2), were isolated from Portulaca oleracea L.. The structures were verified by spectroscopic methods, including UHPLC-ESI-QTOF/MS, 1 D and 2 D NMR. Both Oleraceacid A (1) and Oleraceacid B (2) at 20 µM inhibited the inflammatory factor, IL-1ß in the RAW 264.7 cells induced by LPS, moreover, Oleraceacid A (1) can inhibit cholinesterase activity.

A new alkaloid from Portulaca oleracea L. and its anti-inflammatory activity.

A new alkaloid, identified as (E)-2-(4-hydroxyphenyl)-3-(pyridazin-3-yl)-acrylaldehyde, named oleradazine, was isolated from Portulaca oleracea L., and the structure was elucidated using spectroscopic methods, including 1D and 2D NMR spectroscopic and UHPLC-ESI-QTOF/MS methods. In addition, the compound was used to investigate its anti-inflammatory activity in lipopolysaccharide-stimulated macrophages. It was suggested that the oleradazine can significantly inhibit the inflammatory factors, interleukin 1ß and nitric oxide in lipopolysaccharide-stimulated RAW 264.7 cells by enzyme-linked immunosorbent assays.

Three novel alkaloids from Portulaca oleracea L. and their anti-inflammatory bioactivities.

Three novel alkaloids, identified as (E)-N-((2R)-3-(2,5-dihydroxy-4-((3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)-2-hydroxypropanoyl)-3-(4-hydroxyphenyl)acrylamide (1), named oleracrylimide A, (E)-N-((2R)-3-(2,5-dihydroxy-4-((3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)-2-hydroxypropanoyl)-3-(4-hydroxy-3-methoxyphenyl)acrylamide (2), named oleracrylimide B, and (E)-N-((2R)-3-(2,5-dihydroxy-4-((3,4,5-trihydroxy-6-(((3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)-2-hydroxypropanoyl)-3-(4-hydroxy-3-methoxyphenyl)acrylamide (3), named oleracrylimide C were isolated from Portulaca oleracea L. and the structures of the three novel compounds were determined by 1D and 2D NMR, circular dichroism, and UHPLC-ESI-QTOF/MS spectroscopic methods. Moreover, the bioactivities of anti-inflammation of the three compounds were investigated via testing RAW 264.7 macrophage cell stimulated by Lipopolysaccharide.

Two amide glycosides from Portulaca oleracea L. and its bioactivities.

Two novel amide glycosides, named oleraciamide E (1) and oleraciamide F (2), were isolated from the Portulaca oleracea L. Their structures were determined by means of 1D and 2D NMR spectroscopic and UHPLC-ESI-TOF-MS methods. Oleraciamide E (1) exhibited anticholinesterase activity with IC50 values of 52.43 ± 0.33 µM, and presented scavenging activity in 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical quenching assay, with the IC50 values of 24.64 ± 0.33 µM.

Three new alkaloids from Portulaca oleracea L. and their bioactivities.

Three novel alkaloids, named oleracone L (1), portulacatone B (2), and portulacatal (3), were isolated from P. oleracea L.. The structures were determined using UV, IR, 1D and 2D NMR spectroscopy and UHPLC-ESI-QTOF/MS. The three compounds in a dose-dependent manner significantly reduced the secretion of IL-1ß in the lipopolysaccharide-stimulated macrophages RAW 264.7 cell culture supernatant, moreover, exhibited the anticholinesterase activities.