Nuclear magnetic resonance spectroscopy and mass spectrometry data for sulfated isoguanine glycosides

Abstract

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).

Specifications Table

Subject area	chemistry
More specific subject area	natural products
Type of data	Figure
How data was acquired	NMR spectroscopy: JEOL A400; ESIMS: Thermo Fisher Scientific LTQ Orbitrap XL mass spectrometer.
Data format	Raw and analyzed
Experimental factors	The undescribed sulfated purine alkaloids were purified by column chromatography.
Experimental features	The isolated compounds were characterized by ESIMS and NMR spectroscopy
Data source location	Higashi-Hiroshima, Japan
Data accessibility	Data are available with this article
Related research article	Y. Uyama, E. Ohta, Y. Harauchi, T. Nehira, H. Ômura, H. Kawachi, A. Imamura-Jinda, M. M. Uy, S. Ohta, Rare sulfated purine alkaloid glycosides from Bruchidius dorsalis pupal case, Phytochemistry Letters 35 (2020) 10–14.

Value of the Data •The data presents NMR data and ESIMS data of newly isolated sulfated purine alkaloids and could be used by other researchers. •The provided information on the spectroscopic data of sulfated purine alkaloids could be useful for the analysis of spectra and determination of the structure of other sulfated purine alkaloids. •This data can serve as a benchmark for other researchers to elucidate the structures of sulfated purine alkaloids.

1. Data

The data set presented in this article focuses on characterization of the sulfated purine alkaloids described in [1]. The article provides the information on the spectroscopic data of the sulfated purine alkaloids 1–3 isolated from the pupal case produced by the bruchid beetle Bruchidius dorsalis inside the seed of Gleditsia japonica (Fig. 1). The ¹H NMR spectra of 1–3 are shown in Fig. 2a, Fig. 3a, Fig. 4a, respectively. The ¹³C NMR and DEPT spectra of 1–3 are shown in Fig. 2b, Fig. 3b, Fig. 4b, respectively. 2D ¹H–¹H COSY spectra of 1–3 are shown in Fig. 2c, Fig. 3c, Fig. 4c, respectively. 2D ¹H–¹H NOESY spectra of 1–3 are shown in Fig. 2d, Fig. 3d, Fig. 4d, respectively. 2D ¹H–¹³C heteronuclear single quantum coherence (HSQC) spectra of 1–3 are shown in Fig. 2e, Fig. 3e, Fig. 4e, respectively. 2D ¹H–¹³C heteronuclear multiple-bond correlation (HMBC) spectra of 1–3 are shown in Fig. 2f, Fig. 3f, Fig. 4f, respectively. ESIMS data of 1–3 are shown in Fig. 2g, Fig. 3g, Fig. 4g, respectively. Analyses of the spectra of 1–3 are described in the research article [1]. It has been reported that 3 inhibited starfish blastulation during embryonic development [1].

Fig. 1.

Structures of sulfated isoguanine glycosides isolated from pupal case produced by bruchid beetle Bruchidius dorsalis inside Gleditsia japonica seeds.

Fig. 2a.

¹H NMR (400 MHz, CD₃OD–D₂O, 1:9) of 1.

Fig. 3a.

¹H NMR (400 MHz, CD₃OD–D₂O, 1:9) of 2.

Fig. 4a.

¹H NMR (400 MHz, CD₃OD–D₂O, 1:9) of 3.

Fig. 2b.

¹³C NMR and DEPT (100 MHz, CD₃OD–D₂O, 1:9) of 1.

Fig. 3b.

¹³C NMR and DEPT (100 MHz, CD₃OD–D₂O, 1:9) of 2.

Fig. 4b.

¹³C NMR and DEPT (100 MHz, CD₃OD–D₂O, 1:9) of 3.

Fig. 2c.

¹H–¹H COSY of 1.

Fig. 3c.

¹H–¹H COSY of 2.

Fig. 4c.

¹H–¹H COSY of 3.

Fig. 2d.

¹H–¹H NOESY of 1.

Fig. 3d.

¹H–¹H NOESY of 2.

Fig. 4d.

¹H–¹H NOESY of 3.

Fig. 2e.

¹H–¹³C HSQC of 1.

Fig. 3e.

¹H–¹³C HSQC of 2.

Fig. 4e.

¹H–¹³C HSQC of 3.

Fig. 2f.

¹H–¹³C HMBC of 1.

Fig. 3f.

¹H–¹³C HMBC of 2.

Fig. 4f.

¹H–¹³C HMBC of 3.

Fig. 2g.

(−)HRESIMS of 1.

Fig. 3g.

(−)HRESIMS of 2.

Fig. 4g.

(−)HRESIMS of 3.

Although some sulfated guanosine analogs, such as the kainate receptor inhibitor HF-7 [2], have been isolated from the venom of spiders [3], sulfated nucleoside derivatives from natural sources other than spiders are rare [1,4].

2. Experimental design, materials, and methods

2.1. Samples

Samples were isolated according to a previously reported method [1].

2.2. Description of the NMR experiments

Compounds 1–3 were dissolved in 0.6 mL of a mixture of CD₃OD and D₂O (1:9). All NMR spectra were acquired using a JEOL A400 spectrometer (400 MHz for ¹H, 100 MHz for ¹³C). NMR analysis was performed using the ALICE2 software (JEOL, Tokyo, Japan). ¹H and ¹³C NMR chemical shifts were referenced to residual solvent peaks: δ_H 3.30 (residual CHD₂OD) and δ_C 49.0 for CD₃OD. HRESIMS were carried out using a Thermo Fisher Scientific LTQ Orbitrap XL mass spectrometer at the Natural Science Center for Basic Research and Development (N-BARD), Hiroshima University.

3. Sulfated isoguanine glycosides 1–3

3.1. 6-Amino-7-(2,4-di-O-sulfo-β-d-glucopyranosyl)-3,7-dihydro-3-(3-methyl-2-buten-1-yl) -2H-purin-2-one (locustoside A disulfate) (1)

1D NMR, 2D NMR, and HRESIMS spectra of the compound 1 are shown in Fig. 2a, Fig. 2b, Fig. 2c, Fig. 2d, Fig. 2e, Fig. 2f, Fig. 2ga–g.

3.2. 6-Amino-7-(6-O-d-apio-β-d-furanosyl-2,4-di-O-sulfo-β-d-glucopyranosyl)-3,7-dihydro-3-[(2Z)-4-hydroxy-3-methyl-2-buten-1-yl])-2H-purin-2-one (saikachinoside B disulfate) (2)

1D NMR, 2D NMR, and HRESIMS spectra of the compound 2 are shown in Fig. 3a, Fig. 3b, Fig. 3c, Fig. 3d, Fig. 3e, Fig. 3f, Fig. 3ga–g.

3.3. 6-Amino-3,7-dihydro-3-[(2Z)-4-hydroxy-3-methyl-2-buten-1-yl]-7-(2,4,6-tri-O-sulfo-β-d-glucopyranosyl)-2H-purin-2-one (saikachinoside A trisulfate) (3)

1D NMR, 2D NMR, and HRESIMS spectra of the compound 3 are shown in Fig. 4a, Fig. 4b, Fig. 4c, Fig. 4d, Fig. 4e, Fig. 4f, Fig. 4ga–g.

Conflict of interest

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.