Nuclear magnetic resonance spectroscopy data of isolated compounds from Acacia farnesiana (L) Willd fruits and two esterified derivatives.

In the present article we describe the spectroscopic data of 1H and 13C Nuclear Magnetic Resonance of 11 compounds including: Nine natural products from the hexanic-chloroformic and methanolic extracts of Acacia farnesiana fruit and two esterified derivatives (22E-stimasta-5,22-dien- 3β-acetyl and methyl 3,4,5-triacetyloxybenzoate). Data linked to the research work entitled "Chemical composition of fruits of Acacia farnesiana (L) Willd and its activity against Mycobacterium tuberculosis and dysentery bacteria" (Hernández et al., 2019) [1].

Specifications table

Value of the data

The spectroscopic characterization of natural products reported in this article is important in the metabolic chemical characterization processes of plants of the same family, genus or different plant species.

It is possible the chracterization of new o related phytochemicals by comparision with the provided spectroscopic data.

Data

1H and 13C Nuclear Magnetic Resonance techniques allowed the characterization of isolated compounds from the hexanic, chloroformic and methanolic extracts of Acacia farnesiana and esterified derivatives. NMR spectra data is shown, as well as the detailed description of the spectroscopic signals (chemical shift, integration, coupling constants, multiplicity and signal assignment), see Fig. 1, Fig. 2, Fig. 3, Fig. 4, Fig. 5, Fig. 6, Fig. 7, Fig. 8, Fig. 9, Fig. 10, Fig. 11, Fig. 12, Fig. 13, Fig. 14, Fig. 15, Fig. 16, Fig. 17, Fig. 18, Fig. 19, Fig. 20, Fig. 21, Fig. 22 with this article.

Fig. 1

22E-stimasta-5,22-dien-3β-ol, NMR 1H (400 MHz CDCl3) δ ppm: 0.69 (s, 3H, Me-18), 0.79 (d, J=6.92 Hz, 3H, Me-27), 0.80 (t, J=7.1 Hz, 3H, Me-29), 0.83 (d, J=7.32 Hz, 3H, Me-26), 0.86 (d, J=3.8 Hz, 2H, H-28), 0.92 (d, J=6.4 Hz, 2H, H-9, H-24), 1.01 (s, 3H, Me-19), 1.02 (d, J=7. 72 Hz, 3H, Me-21), 1.10 (m, 1H, H-14), 1.04 (m, 2H, H-1), 1.07 (m, 2H, H-15), 1.11 (m, 1H, H-14), 1.13 (m, 1H, H-17), 1.16 (m, 1H, H-12), 1.28 (m, 1H, H-16), 1.41 (m, 1H, H-20), 1.53 (m, 2H, H-7), 1.54 (m, 1H, H-11), 1.83 (m, 1H, H-25), 1.84 (m, 2H, H-2), 1.85 (m, 1H, H-16), 1.99 (m, 1H, H-8), 2.0 (m, 2H, H-12), 2.28 (m, 2H, H-4), 3.52 (m, 1H, H-3), 5.01 (dd, J=15.1, 8.6 Hz, 1H, H-23), 5.15 (dd, J=15.1, 8.5 Hz, 1H, H-22), 5.35 (brd, J=4.72 Hz, 1H, H-6).

Fig. 2

22E-stimasta-5,22-dien-3β-ol, NMR 13C (100 MHz, CDCl3) δ ppm: 12.05 (C18), 12.25 (C29), 19.03 (C27), 19.40 (C19), 21.08 (C11, C26), 21.21 (C21), 24.36 (C15), 25.41 (C28), 28.92 (C16), 31.67 (C2), 31.88 (C7, C8), 31.90 (C25), 36.51 (C10), 37.26 (C1), 39.78 (C12), 40.49 (C20), 42.22 (C13), 42.31 (C4), 50.14 (C9), 51.24 (C24), 55.96 (C17), 56.87 (C14), 71.81 (C3), 121.71 (C6), 129.28 (C23), 138.32 (C22), 140.76 (C5).

Fig. 3

22E-stimasta-5,22-dien-3β-acetyl, NMR 1H (400 MHz, CDCl3) δ ppm: 0.69 (s, 3H, Me-18), 0.79 (d, J=6.96 Hz, 3H, Me-27) 0.80 (t, J=7.04 Hz, 3H, Me-29), 0.82 (d, J=1.74 Hz, 2H, H-28), 0.83 (d, J=7.2 Hz, 3H, Me-26),), 0.91 (m, 1H, H-24) 0.92 (d, J=6.54 Hz, 1H, H-9), 1.02 (s, 3H, Me-19), 1.021 (d, J=6.36 Hz, 3H, Me-21), 1.12 (m, 1H, H-14), 1.13 (m, 2H, H-15), 1.16 (m, 2H, H-1), 1.17 (m, 1H, H-17), 1.18 (m, 1H, H-12), 1.28 (m, 1H, H-16), 1.42 (m, 1H, H-20), 1.53 (m, 2H, H-11), 1.54 (m, 2H, H-7), 1.83 (m, 1H, H-25), 1.84 (m, 2H, H-2), 1.87 (m, 1H, H-16), 1.98 (m, 1H, H-8), 1.99 (m, 2H, H-12), 2.03 (s, 3H, CH3CO), 2.32 (m, 2H, H-4), 4.6 (m, 1H, H-3), 5.01 (dd, J=15.16, 8.64 Hz, 1H, H-23), 5.15 (dd, J=15.16, 8.6 Hz, 1H, H-22), 5.37 (brd, J=4.64, 1H, H-6).

Fig. 4

22E-stimasta-5,22-dien-3β-acetyl. NMR 13C (100 MHz, CDCl3) δ ppm: 12.04 (C18), 12.24(C29), 18.98 (C27), 19.30 (C19), 21.01 (C11), 21.08 (C26), 21.21 (C21), 21.44 (CH3CO), 24.35 (C15), 25.40 (C28), 27.77 (C2), 28.90 (C16), 31.86 (C7, C8), 31.88 (C25), 36.59 (C10), 36.99 (C1), 38.12 (C4), 39.62 (C12), 40.49 (C20), 42.20 (C13), 50.05 (C9), 51.23 (C24), 55.93 (C17), 56.78 (C14), 74.0 (C3), 122.63 (C6), 129.28 (C23), 138.31 (C22), 139.65 (C5), 170.56 (CH3CO).

Fig. 5

Tetracosanoic acid (2S)-2, 3-dihydroxypropyl ester, NMR 1H (400 MHz, CDCl3) δ ppm: 0.88 (t, J=6.78 Hz, 3H, Me-24), 1.25 (sa, 38H, (CH2)19, C4-C22), 1.50 (sa, 1H, OH-3´), 1.63 (m, 4H, H-3, H-23), 2.04 (s, 1H, OH-2´), 2.35 (t, J=7.58 Hz, 2H, H-2), 3.60 (dd, J=11.46, 5.78 Hz, 1H, H-3´β), 3.70 (dd, J=11.46, 3.98 Hz, 1H, H-3´α), 3.94 (m, 1H, H-2´), 4.15 (dd, J=11.68, 6.12 Hz, 1H, H-1´β), 4.21 (dd, J=11.64, 4.6 Hz, 1H, H-1´α).

Fig. 6

Tetracosanoic acid (2S)-2, 3-dihydroxypropyl ester, NMR 13C (100 MHz, CDCl3) δ ppm: 14.35 (C24), 22.91 (C23), 25.13 (C3), 29.34 (C4), 29.46 (C5), 29.58 (C8), 29.67 (C9), 29.82 (C21), 29.86 (C6), 29.88 (C7), 29.92 (C10-C20), 32.14 (C22), 34.37 (C2), 63.53 (C3´), 65.38 (C1´), 70.48 (C2´), 174.61 (C1).

Fig. 7

Stigmasta-5,22-dien-3β-O-D-glucopyranoside, NMR 1H (400 MHz, DMSO-d6) δ ppm: 0.64 (s, 3H, Me-18), 0.79 (t, J= 7.40 Hz, 3H, Me-29), 0.80 (d, J= 7.64 Hz, 3H, Me-27), 0.81 (m, 1H, H-9), 0.83 (m, 1H, H-24), 0.89 (d, J= 6.24 Hz, 3H, Me-26), 0.95 (s, 3H, Me-19), 0.99 (d, J= 6.36 Hz, 3H, Me-21), 1.03 (m, 1H, H-17), 1.07 (m, 2H, H-15), 1.09 (m, 1H, H-9), 1.14 (m, 2H, H-12), 1.19 (d, J= 7.1 Hz, 1H, H-4), 1.22 (m, 2H, H-11), 1.37 (m, 2H, H-2), 1.40 (m, 1H, H-20), 1.46 (m, 1H, H-25), 1.49 (m, 2H, H-7), 1.62 (dd, J= 6.4, 11.6, 1H, H-8), 1.78 (m, 1H, H-16), 1.80 (m, 1H, H-4), 1.93 (m, 1H, H-16), 2.11 (m, 1H, H-1), 2.36 (dd, J= 3.0, 13.3 Hz, 1H, H-1), 2.88 (m, 1H, H-2´), 3.01 (m, 2H, H-5´), 3.04 (m, 2H, 4´), 3.11 (m, 1H, H-3´), 3.46 (m, 1H, H-3), 3.48 (m, 1H, H-6´a), 3.63 (dd, J= 10.7, 5.4 Hz, 1H, H-6´b), 4.21 (d, J= 7.72 Hz, 1H, H-1´), 4.45 (t, J= 5.6 Hz, 1H, OH-6´), 4.88 (sa, 1H, OH-4´), 4.89 (sa, 1H, OH-2´), 4.91 (d, J = 4.5 Hz, 1H, OH-3´), 5.01 (dd, J= 15, 8.72, Hz, 1H, H-23), 5.15 (dd, J= 15.04, 8.62 Hz, 1H, H-22), 5.32 (sa, 1H, H-6).

Fig. 8

Stigmasta-5,22-dien-3β-O-D-glucopyranoside. NMR 13C (100 MHz, DMSO-d6): δ (ppm): 11.69 (C29), 11.80 (C18), 18.63 (C21), 18.85 (C27), 18.95 (C19), 19.12 (C26), 22.62 (C11), 23.88 (C28), 24.88 (C15), 29.26 (C16), 31.38 (C7, C8), 31.43 (C24, C25), 33.35 (C2), 35.49 (C20), 36.23 (C10), 36.83 (C4), 38.30 (C1), 39 (C12), 41.87 (C13), 49.61 (C9), 55.43 (C17), 56.27 (C14), 61.11 (C6´), 70.12 (C2´), 73.48 (C4´), 76.76 (C5´), 76.92 (C3´), 76.98 (C3), 100.78 (C1´), 121.24 (C6), 130.74 (C23), 138.06 (C22), 140.47 (C5).

Fig. 9

Stigmasta-5,22-dien-3β-O-D-tetraacetylglucopyranoside, NMR 1H (400 MHz, CDCl3) δ ppm: 0.67 (s, 3H, Me-18), 0.80 (t, J=7.24 Hz, 3H, Me-29), 0.83 (d, J=7.04 Hz, 3H, Me-27), 0.91 (d, J=6.44 Hz, 3H, Me-26), 0.98 (s, 3H, Me-19), 1.02 (d, J=6.64 Hz, 3H, Me-21), 2.00 (s, 3H, CHCO-3´), 2.02 (s, 3H, CHCO-2´), 2.05 (s, 3H, CHCO-4´), 2.08 (s, 3H, CHCO-6´), 3.48 (m, 1H, H-3), 3.67 (m, 1H, H-2´), 4.1 (dd, J=12.2, 2.88 Hz, 1H, H-6´a), 4.26 (dd, J=12.22, 4.82 Hz, 1H, H-6´b), 4.59 (d, J=8.0 Hz, 1H, H-1´), 4.96 (t, J= 9.48 Hz, 1H, H-3´), 5.03 (dd, J= 14.16, 5.56 Hz, 1H, H-23), 5.07 (t, J= 9.68 Hz, 1H, H-5´), 5.13 (dd, J=15.16, 6.52 Hz, 1H, H-22), 5.20 (t, J=9.52 Hz, 1H, H-4´) 5.36 (da, J=4.84 Hz, 1H, H-6).

Fig. 10

Stigmasta-5,22-dien-3β-O-D-tetraacetylglucopyranoside. NMR 13C (100 MHz, CDCl3) δ ppm: 11.89(C29), 12.02 (C18),18.81 (C21),19.07(C27), 19.39 (C19), 19.85 (C26), 20.65 (CHCO-6´), 20.68 (CHCO-4´), 20.76 (CHCO-3´), 20.80 (CHCO-2´), 21.08 (C11), 23.10 (C28), 24.33 (C15), 28.27 (C16), 29.48 (C24), 31.90 (C8, C25), 31.98 (C7), 33.98 (C-2), 36.16 (C20), 36.76 (C10), 37.23 (C1), 38.95 (C4), 39.77 (C12), 42.36 ( C13), 50.20 (C9), 56.09 (C17), 56.79 (C14), 62.15 (C6´), 68.53 (C4´), 71.54 (C3´), 71.73 (C5´), 72.96 (C3), 80.12 (C2´), 99.68 (C1´), 122.20 (C6), 129.34 (C23), 138.32 (C22), 140.40 (C5), 169.34 (CH3CO-3´), 169.44 (CH3CO-4´), 170.40 (CH3CO-2´), 170.74 (CH3CO-6´).

Fig. 11

Methyl gallate, NMR 1H (400 MHz, Acetone-d6) δ ppm: 3.78 (s, 3H, OMe), 7.11 (s, 2H, H-2, H-6), 8.17 (s, 3H, OH).

Fig. 12

Methyl gallate, NMR 13C (100 MHz, Acetone-d6) δ ppm: 51.01 (OMe), 108.92 (C2, C6), 120.93 (C1), 137.82 (C4), 145.16 (C3, C5), 166.27 (COOR).

Fig. 13

Methyl 3,4,5-triacetyloxybenzoate, NMR 1H (400 MHz, CDCl3) δ ppm: 2.32 (s, 9H, 3x CHCO), 3.92 (s, 3H, OMe), 7.82 (s, H-2, H 6).

Fig. 14

Methyl 3,4,5-triacetyloxybenzoate, NMR 13C (100 MHz, CDCl3) δ ppm: 20.17 (CHCO-4), 20.58 (CHCO-3, CHCO-5), 52.57 (OCH3), 122.22 (C2, C6), 128.29 (C1), 138.58 (C4), 143.39 (C3, C5), 164.90 (CH3CO-1), 166.44 (CH3CO-4), 167.61 (CH3CO-3, CH3CO-5).

Fig. 15

Gallic acid, NMR 1H (400 MHz, Acetone-d6) δ ppm: 3.08 (sa, 4H, OH-4), 7.14 (s, 2H, H-2, H-6), 8.22 (sa, 2H, OH-3, OH-5).

Fig. 16

Gallic acid, NMR 13C (100 MHz, Acetone-d6) δ ppm: 109.22 (C2, C6), 121.15 (C1), 137.77 (C4), 145.11 (C3, C5), 166.82 (COOH).

Fig. 17

(2S) -Naringenin 7-O-β-D-glucopyranoside, NMR 1H (400 MHz, DMSO-d6) δ ppm: 2.73 (dd, J= 17.1, 2.62 Hz, 1H, H-3β), 3.14 (m, 1H, H-3α), 3.22 (m, 2H, H-4´´, H-2´´), 3.37 (m, 2H, H-3´´, H-5´´), 3.42 (dd, J= 11.68, 5.64 Hz, 1H, H-6a´´), 3.65 (dd, J= 11.04, 4.68 Hz, 1H, H-6b´´), 4.54 (t, J= 5.56, 1H, OH-6”), 4.95 (d, J= 7.4 Hz, 1H, H-1´´), 5.01 (d, J= 5.2 Hz, 1H, OH-4´´), 5.08 (d, J= 4.72 Hz, 1H, OH-3´´), 5.33 (d, J= 4.88 Hz, 1H, OH-2´´), 5.50 (dd, J= 12.6, 2.48 Hz, 1H, H-2), 6.13 (d, J= 2.2, 1H, H-6), 6.15 (d, J= 1.96, 1H, H-8), 6.79 (d, J= 8.4 Hz, 2H, H-3´, H-5´), 7.32 (d, J= 8.44 Hz, 2H, H-2´, H-6´), 9.59 (s, 1H, OH-4´), 12.05 (s, 1H, OH-5).

Fig. 18

(2S) -Naringenin 7-O-β-D-glucopyranoside. NMR 13C (100 MHz, DMSO-d6) δ ppm: 42.55 (C3), 61.05 (C6´´), 69.98 (C4´´), 73.50 (C2´´), 76.80 (C3´´), 77.56 (C5´´), 79.13 (C2), 95.92 (C8), 96.97 (C6), 100.10 (C1´´), 103.73 (C10), 115.65 (C3´, C5´), 128.89 (C2´, C6´), 129.11 (C1´), 158.28 (C4´), 163.25 (C5), 163.41 (C9), 165.79 (C7), 197. 67 (C4).

Fig. 19

Pinitol, NMR 1H (400 MHz, D2O) δ (ppm): 3.18 (t, J=9.64 Hz, 1H, H-6), 3.44 (s, 3H, OCH3), 3.49 (t, J=9.64 Hz, 1H, H-1), 3.55 (dd, J=9.94, 2.38 Hz, 1H, H-2), 3.65 (dd, J=9.98, 2.42 Hz, 1H, H-5), 3.84 (m, 2H, H-3, H-4).

Fig. 20

Pinitol. NMR 13C (100 MHz, D2O) δ (ppm): 59.67 (OCH3), 69.76 (C5), 70.47 (C2), 71.40 (C3), 71.61 (C4), 72.07 (C1), 82.72 (C6).

Fig. 21

Sucrose, NMR 1H (400 MHz, D2O) δ (ppm): 3.43 (t, J=9.42 Hz, 1H, H-4), 3.52 (dd, J=10, 3.84 Hz, 1H, H-2), 3.63 (s, 2H, H-1´), 3.72 (t, J=9.56 Hz, 1H, H-3), 3.78 (d, J=2.96 Hz, 2H, H-6), 3.79 (d, J=2.8 Hz, 2H, H-6´), 3.83 (m, 1H, H-5), 3.86 (m, 1H, H-5´), 4.01 (t, J= 8.56 Hz, 1H, H-4´), 4.18 (d, J=8.76 Hz, 1H, H-3´), 5.38 (d, J=3.88 Hz, 1H, H-1).

Fig. 22

Sucrose. NMR 13C (100 MHz, D2O) δ (ppm): 62.59 (C6), 63.82 (C1´), 64.84 (C6´), 71.70 (C4), 73.55 (C2), 74.88 (C5), 75.05 (C3), 76.47 (C4´), 78.88 (C3´), 83.85 (C5´), 94.66 (C1), 106.17 (C2´).

Experimental design, materials and methods

One-dimensional nuclear magnetic resonance (NMR) spectra were obtained using the Bruker AVANCE III HD 400 MHz equipment. Deuterated solvents (CDCl3, DMSO-d6, acetone-d6 and D2O) were used based on the dissolution needs of the compounds to be studied and tetramethylsilane (TMS) as internal standard.

5–10 mg of each compound analyzed was weighed in analytical balance and 0.5 mL of deuterated solvent was added to sample until complete solubility. Then solution was placed in a clean and dry resonance tube.

To obtain the spectroscopic data of hydrogen nucleus (1H), a 400 MHz equipment frequency was used, while for the carbon nucleus (13C) a frequency of 100 MHz was used.

Subject area	Phytochemistry
Type of data	NMR spectra figures
How data was acquired	NMR equipment Bruker AVANCE III HD 400 MHz
Data format	Analysed
Experimental factors	Dissolution of the compounds in deuterated solvent CDCl3, DMSO-d6, Acetone-d6and D2O
Experimental features	NMR1H and13C chemical shift, integration, coupling constants and multiplicity
Data source location	Facultad de Ciencias Químicas
	Universidad Autónoma de Nuevo León. Guerreo y Progreso S/N. Col. Treviño, Monterrey, Nuevo León, México. C.P. 64570.
Data accessibility	All data are available in this document.
Related research article	Hernández, E., Garza, E., García, A., Avalos, F.G., Rivas, V. M., Rodríguez, J., Alcántar, V. M., Delgadillo, C., Camacho M. R. Chemical composition of Acacia farnesiana (L) wild fruits and its activity against Mycobacterium tuberculosis and dysentery bacteria. J. Ethnopharmacol 2019 230: 74–80 [1].