Prenylated purine alkaloids from seeds of Gleditsia japonica

Harauchi, Yui; Kajimoto, Tadashi; Ohta, Emi; Kawachi, Hiroyuki; Imamura-Jinda, Aya; Ohta, Shigeru

doi:10.1016/j.phytochem.2017.08.006

Cited by 18 publications

(8 citation statements)

References 15 publications

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“…13CNMR data of glucose moiety were δ 87.4 (C-1''), δ 79.7 (C-5''), δ 76.5 (C-3''), δ 72.9 (C-2''), δ 68 (C-4''), and δ 60.4(C-6''). UV, 1H NMR, and 13C NMR data were in agreement with the published data [10].…”

Section: Compound 1 Locustoside Asupporting

confidence: 89%

Anti-proliferative activity and phytochemical study of the methanolic extract from the pods of Gleditsia caspica Desf

MIRZAEIDARBAND,

SAMADISHAMS,

HAMEDEYAZDAN

et al. 2024

jrp

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Gleditsia caspica Desf. (Caesalpinaceae) is traditionally used to treat diverse diseases. This research paper aims to investigate anti-proliferative properties and phytochemical compounds of methanolic extract from the pods of G. caspica. MTT test was used to measure in vitro anti-proliferative effect of the soxhlet-extracted methanolic extract of G.caspica pods with the concentration ranging from 25-1000 µg/ml against A549 cell line. The extract was applied to SPE, HPLC preparative system, and spectral analysis ( 1 HNMR, 13 CNMR, and UV) for fractionation, purification, and identification of phytoconstituents, respectively. The results indicated that the extract prevented proliferation of A549 cell line dependent on time and concentration. After 48 h and 72 h, there was a significant decrease in cell viability initiated from 100 and 500 (µg/ml) concentrations in comparison to untreated control. Phytochemical assessment of the extract resulted in two alkaloids, locustoside A and saikachinoside A, and four flavonoids quercetin-3,7-diglucoside, luteolin-4',7-diglucoside, quercetin-3-glucoside, and quercetin. This experiment was an activity-guided phytochemical study. In prior studies, quercetin and quercetin-3-β-D-glucoside showed in vitro inhibitory effect on proliferation of A549 cell line. However, the cytotoxic properties of the other identified compounds have not been reported. Cytotoxic properties of G.caspica was previously attributed to saponins, while isolated flavonoids and alkaloids could be responsible for the extract's cytotoxic effects. This paper first explored cytotoxic activity of methanolic extract from the pods of G.caspica on A549 cell line and identified flavonoids and alkaloids of this plant.

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Section: Compound 1 Locustoside Asupporting

confidence: 89%

Anti-proliferative activity and phytochemical study of the methanolic extract from the pods of Gleditsia caspica Desf

MIRZAEIDARBAND,

SAMADISHAMS,

HAMEDEYAZDAN

et al. 2024

jrp

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“…Plants known as Gleditsia have long been applied as a traditional treatment for some ailments, including diarrhea, headache, and swelling, in various countries, especially China, South Korea, and Japan (Niknam et al, 2021). Up to date, different species of this genus are known, such as Gleditsia japonica (Japanese honey locust) (Harauchi et al, 2017), Gleditsia sinensis Lam. , and Gleditsia triacanthos (Zhang et al, 2016).…”

Section: Introductionmentioning

confidence: 99%

A new source of galactomannan isolated from Gleditsia caspica (Persian honey locust) seeds: Extraction and comprehensive characterization

Niknam

Mousavi

Kiani

2021

J. Food Process. Preserv.

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The dominant objective of this study was to extract and purify galactomannan from Gleditsia caspica seeds. In addition to chemical analysis and investigation of the basic physicochemical and functional properties of the extracted galactomannan, other tests have been performed to determine the structural and thermal properties. The FT-IR spectra authenticated availability of O-H, C-H, and C-O stretching vibrations in the galactomannan conformation. The extracted galactomannan had amorphous structure with very low crystallinity which was obtained from XRD analysis. The obtained DSC and TGA plots showed thermal events including one endothermic and one exothermic peak that are typical for natural polysaccharides. The H-NMR analysis of the extracted galactomannan demonstrated peaks at δ 4.901 and 4.705 ppm, which were affiliated with availability of H-1 (α) (α-galactopyranosyl) and H-2 (β) (β-mannopyranosyl). The images obtained from SEM confirmed that the galactomannan surface was relatively smooth and uniform. Novelty Impact StatementThe galactomannan was extracted and purified from Gleditsia caspica seeds.Comprehensive characterization of obtained galactomannan authenticated its chance to be applied as thickeners or stabilizers in food formulations as a new source of plant-based hydrocolloid.

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“…Isoguanine has been reported as a skeleton for several biologically important alkaloids [18,19,20]. Some interesting results were obtained on a compound with the 4-aminopyrazolo[1,5- a ][1,3,5]triazin-2-one skeleton (a triazine-based 5-aza-9-deaza-isostere of isoguanine) [21].…”

Section: Introductionmentioning

confidence: 99%

Fused Heterocyclic Systems with an s-Triazine Ring. 34. Development of a Practical Approach for the Synthesis of 5-Aza-isoguanines

et al. 2019

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Purine isosteres present excellent opportunities in drug design and development. Using isosteres of natural purines as scaffolds for the construction of new therapeutic agents has been a valid strategy of medicinal chemistry. Inspired by the similarity to isoguanine, we attempted to develop a practical method for the preparation of 5-aza-isoguanines. Several synthetic approaches were explored to establish a robust general protocol for the preparation of these compounds. The significant difference in the reactivity of the C-5 and C-7 electrophilic centers of 1,2,4-triazolo[1,5-a][1,3,5]triazines (5-azapurines) towards nucleophiles was demonstrated. The most practical and general method for the preparation of 5-aza-isoguanines involved a regioselective reaction of ethoxycarbonyl isothiocyanate with a 5-aminotriazole. The intramolecular ring closure of the resulted product followed by the S-methylation afforded 7-methylthio-2-phenyl-1,2,4-triazolo[1,5-a][1,3,5]triazin-5-one, which could be effectively aminated with various amines. The resulted 5-aza-isoguanines resemble a known purine nucleoside phosphorylase inhibitor and could be interesting for further investigations as potential anticancer agents.

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Prenylated purine alkaloids from seeds of Gleditsia japonica

Cited by 18 publications

References 15 publications

Anti-proliferative activity and phytochemical study of the methanolic extract from the pods of Gleditsia caspica Desf

Anti-proliferative activity and phytochemical study of the methanolic extract from the pods of Gleditsia caspica Desf

A new source of galactomannan isolated from Gleditsia caspica (Persian honey locust) seeds: Extraction and comprehensive characterization

Fused Heterocyclic Systems with an s-Triazine Ring. 34. Development of a Practical Approach for the Synthesis of 5-Aza-isoguanines

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