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1.
Plant Cell Physiol ; 64(12): 1551-1562, 2023 Dec 21.
Artigo em Inglês | MEDLINE | ID: mdl-37801291

RESUMO

Folate, also known as vitamin B9, is an essential cofactor for a variety of enzymes and plays a crucial role in many biological processes. We previously reported that plastidial folate prevents starch biosynthesis triggered by the influx of sugar into non-starch-accumulating plastids, such as etioplasts, and chloroplasts under darkness; hence the loss of plastidial folate induces the accumulation of starch in plastids. To understand the molecular mechanism underlying this phenomenon, we screened our in-house chemical library and searched their derivatives to identify chemicals capable of inducing starch accumulation in etioplasts. The results revealed four chemicals, compounds #120 and #375 and their derivatives, compounds #120d and #375d, respectively. The derivative compounds induced starch accumulation in etioplasts and suppressed hypocotyl elongation in dark-grown Arabidopsis seedlings. They also inhibited the post-germinative growth of seedlings under illumination. All four chemicals contained the sulfonamide group as a consensus structure. The sulfonamide group is also found in sulfa drugs, which exhibit antifolate activity, and in sulfonylurea herbicides. Further analyses revealed that compound #375d induces starch accumulation by inhibiting folate biosynthesis. By contrast, compound #120d neither inhibited folate biosynthesis nor exhibited the herbicide activity. Protein and metabolite analyses suggest that compound #120d abrogates folate-dependent inhibition of starch accumulation in etioplasts by enhancing starch biosynthesis.


Assuntos
Arabidopsis , Arabidopsis/metabolismo , Ácido Fólico/metabolismo , Amido/metabolismo , Plastídeos/metabolismo , Plântula/metabolismo , Sulfonamidas/metabolismo
2.
Data Brief ; 28: 105032, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-31909126

RESUMO

The data presented here are related to the research paper entitled "Rare sulfated purine alkaloid glycosides from Bruchidius dorsalis pupal case" [1]. In this data article, we provide 1D and 2D nuclear magnetic resonance (NMR) spectroscopy and electrospray ionization mass spectrometry (ESIMS) data of three undescribed sulfated purine alkaloids, locustoside A disulfate, saikachinoside B disulfate, and saikachinoside A trisulfate isolated from the pupal case of the wild bruchid seed beetle Bruchidius dorsalis (Chrysomelidae, Bruchinae) infesting the seed of Gleditsia japonica Miquel (Fabaceae).

3.
Chem Biodivers ; 15(8): e1800154, 2018 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-29907997

RESUMO

Three new sulfated isoguanine alkaloid glycosides, designated as saikachinoside A monosulfate (1), saikachinoside A disulfate (2), and locustoside B disulfate (3), have been isolated from the pupal case of the wild bruchid seed beetle Bruchidius dorsalis (Chrysomelidae, Bruchinae) infesting the seed of Gleditsia japonica Miq. (Fabaceae). Their structures were determined by spectroscopic methods and the inhibitory activity of 2 and 3 against acid phosphatase was evaluated.


Assuntos
Alcaloides/farmacologia , Besouros/química , Gleditsia/química , Glicosídeos/farmacologia , Purinas/farmacologia , Sementes/química , Fosfatase Ácida/antagonistas & inibidores , Fosfatase Ácida/metabolismo , Alcaloides/química , Alcaloides/isolamento & purificação , Animais , Relação Dose-Resposta a Droga , Inibidores Enzimáticos/química , Inibidores Enzimáticos/isolamento & purificação , Inibidores Enzimáticos/farmacologia , Glicosídeos/química , Glicosídeos/isolamento & purificação , Conformação Molecular , Pupa/química , Purinas/química , Purinas/isolamento & purificação , Relação Estrutura-Atividade , Sulfatos/química , Triticum/enzimologia
4.
Phytochemistry ; 143: 145-150, 2017 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-28813687

RESUMO

Three previously undescribed isoguanine glycosides with an N3-prenyl group, designated locustoside B, saikachinoside B, and saikachinoside C, have been isolated from the seed of Gleditsia japonica Miquel (Fabaceae) along with two known compounds, locustoside A and saikachinoside A. Their structures were determined from spectroscopic data and X-ray crystallographic analysis. The inhibitory activity against acid phosphatase was evaluated.


Assuntos
Gleditsia/química , Sementes/química , Fosfatase Ácida/antagonistas & inibidores , Alcaloides , Cristalografia por Raios X , Fabaceae/química , Glicosídeos/química , Japão , Conformação Molecular , Ressonância Magnética Nuclear Biomolecular
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