Study of Methanol Extracts from Different Parts of Peganum harmala L. Using ¹H-NMR Plant Metabolomics

Table 1

¹H-NMR assignments of major metabolites in P. harmala extracts.

No.	Metabolite	δH (multiplicity, J)	Sample
1	Isoleucine	1.02 (d, 7.06), 0.95 (t, 7.15)	B^b
2	Valine	1.05 (d, 7.0), 0.99 (d, 7.0)	B^b
3	Threonine	4.25 (m), 1.33 (d, 6.55)	A^b
4	Alanine	3.57 (m), 1.48 (d, 7.3)	B^b
5	Lysine	3.6 (m), 1.65, 1.89 (m), 2.25 (m), 3.02, 3.4 (m)	F^b
6	Acetic acid	1.92 (s)	A^b
7	Proline	3.30–3.35 (m), 2.31–2.37 (m), 1.95–2.00 (m), 4.12 (dd, 8.63, 6.56)	A^b
8	4-Hydroxyisoleucine	4.25 (m), 2.167 (m), 3.835 (m), 2.22, 1.98 (m), 1.88 (m)	E^a
9	Succinic acid	2.43 (s), 2.43 (s)	F^b
10	Malic acid	2.71 (dd, 2.9, 15.62), 4.31 (dd, 3.1, 10.2)	F^b
11	Asparagine	4.03 (dd, 4.4, 7.25), 2.94 (m), 2.84 (m)	E^b
12	Choline	4.07, 3.21 (s)	C^b
13	Phosphorylcholine	3.23 (s)	A^b
14	Betaine	3.27 (s)	B^b
15	Sucrose	3.69 (s), 4.22 (d, 8.65), 4.06 (t, 8.89), 3.91 (m), 3.87 (d, 3.15), 5.42 (d, 3.8), 3.59 (m), 3.78 (t, 9.48), 3.49 (t, 9.28), 3.91(m)	A^b
16	β-Glucose	4.65 (d, 8.0)	A^b
17	Vasicine	3.77, 3.69 (m),2.15, 2.71 (m), 5.22 (t, 8.80), 7.11 (m), 7.36 (m), 7.28 (m), 7.19 (d, 7.5)	E^a
18	α-Glucose	5.24 (d, 3.83)	C^b
19	Maleic acid	6.01 (s)	B^b
20	Harmine	6.64 (d, 1.9), 6.69 (dd, 8.75, 2.25), 7.84 (d, 5.64), 2.55 (s), 7.69 (d, 5.42), 7.61 (d, 8.59), 3.84 (s)	D^a
21	Harmaline	6.46 (dd, 8.85, 1.94), 6.37 (d, 1.66), 7.0 (d, 8.64), 2.47 (s), 2.96(t, 8.83), 3.22(t, 8.83), 3.81(s)	D^a
22	Vasicinone	4.11, 3.91 (m), 1.99, 2.45 (m), 4.99 (t, 6), 7.71 (m), 7.93 (m), 7.64 (m), 8.25 (d, 6)	F^a
23	Formic acid	8.46 (s)	A^b

Note. “a” was determined by the ¹H-NMR, COSY, HSQC, and HMBC spectra. “b” was determined by the ¹H-NMR and HSQC spectra. s, singlet; d, doublet; t, triplet; m, multiplet; A, root; B, leaf; C, flower; D, seed; E, testa; F, stem.