NMR and ESIMS data for bisabolane-type sesquiterpenoids

Abstract

The data presented here are related to the research paper entitled “Norbisabolane and bisabolane sesquiterpenoids from the seeds of Angelica keiskei” [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 norbisabolane- and bisabolene-type sesquiterpenoids, ashitabaol B-D isolated from the seeds of Angelica keiskei.

Specifications Table

Subject area	chemistry
More specific subject area	natural products
Type of data	Figure
How data was acquired	NMR spectroscopy: JEOL A400; ESIMS: Shimadzu LCMS-IT-TOF and Thermo Fisher Scientific LTQ Orbitrap XL.
Data format	Raw and analyzed
Experimental factors	The undescribed sesquiterpenoids 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	S. Ohta, Y. Yuasa, N. Aoki, E. Ohta, T. Nehira, H. Ômura, M. M. Uy, Norbisabolane and bisabolane sesquiterpenoids from the seeds of Angelica keiskei, Phytochemistry Letters 33 (2019) 94–101.

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

1. Data

The data set presented in this article focuses on characterization of the norbisabolane- and bisabolane-type sesquiterpenoids described in Ref. [1]. The article provides the information on the spectroscopic data of the sesquiterpenoids 1–3 isolated from the seeds of Angelica keiskei (Fig. 1). The ¹H NMR spectra of 1–3 are shown in Fig. 2, Fig. 3, Fig. 4a, respectively. The ¹³C NMR and DEPT spectra of 1–3 are shown in Fig. 2, Fig. 3, Fig. 4b, respectively. 2D ¹H–¹H COSY spectra of 1–3 are shown in Fig. 2, Fig. 3, Fig. 4c, respectively. 2D NOESY spectra of 1–3 are shown in Fig. 2, Fig. 3, Fig. 4d, respectively. 2D ¹H–¹³C heteronuclear single quantum coherence (HSQC) spectra of 1–3 are shown in Fig. 2, Fig. 3, Fig. 4e, respectively. 2D ¹H–¹³C heteronuclear multiple-bond correlation (HMBC) spectra of 1–3 are shown in Fig. 2, Fig. 3, Fig. 4f, respectively. ESIMS data of 1–3 are shown in Fig. 2, Fig. 3, Fig. 4g, respectively. Analyses of the spectra of 1–3 are described in the research article [1].

Fig. 1.

Structures of norbisabolane- and bisabolane-type sesquiterpenoids isolated from the seeds of A. keiskei.

Fig. 2.

a. ¹H NMR (400 MHz, CDCl₃) of 1, b. ¹³C NMR and DEPT (100 MHz, CDCl₃) of 1, c. ¹H–¹H COSY of 1, d. NOESY of 1, e. HSQC of 1, f. HMBC of 1, g. (+)ESIMS of 1.

Fig. 3.

a. ¹H NMR (400 MHz, CDCl₃) of 2, b. ¹³C NMR and DEPT (100 MHz, CDCl₃) of 2, c. ¹H–¹H COSY of 2, d. NOESY of 2, e. HSQC of 2, f. HMBC of 2, g. (+)ESIMS of 2.

Fig. 4.

a. ¹H NMR (400 MHz, CDCl₃) of 3, b. ¹³C NMR and DEPT (100 MHz, CDCl₃) of 3, c. ¹H–¹H COSY of 3, d. NOESY of 3, e. HSQC of 3, f. HMBC of 3, g. (+)ESIMS of 3.

2. Experimental design, materials, and methods

NMR spectra were acquired using a JEOL A400 spectrometer (400 MHz for ¹H, 100 MHz for ¹³C). ¹H and ¹³C NMR chemical shifts were referenced to residual solvent peaks: δ_H 7.26 (residual CHCl₃) and δ_C 77.0 for CDCl₃. ESIMS were carried out using a Shimadzu LCMS-IT-TOF mass spectrometer and a Thermo Fisher Scientific LTQ Orbitrap XL mass spectrometer at the Natural Science Center for Basic Research and Development (N-BARD), Hiroshima University.

3. Sesquiterpenoids 1–3

3.1. (Z)-2-((3R,3aR,7aS)-3-Hydroxy-3,6-dimethyl-3,3a,4,5-tetrahydrobenzofuran-2(7aH)-ylidene)acetaldehyde (ashitabaol B) (1)

1D NMR, 2D NMR, and ESIMS spectra of the compound 1 are shown in Fig. 2a–g.

3.2. (E)-2,6-Dihydroxy-2-(4-hydroxy-4-methylcyclohex-2-en-1-yl)-6-methylhept-4-en-3-one (ashitabaol C) (2)

1D NMR, 2D NMR, and ESIMS spectra of the compound 2 are shown in Fig. 3a–g.

3.3. (5S,6R)-6-((R,E)-2,6-Dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-5-hydroxy-3-methylcyclohex-2-enone (ashitabaol D) (3)

1D NMR, 2D NMR, and ESIMS spectra of the compound 3 are shown in Fig. 4a–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.