Journal of Diabetes Research

Research Article

Antihyperlipidemic, Antihyperglycemic, and Liver Function Protection of Olea europaea var. Meski Stone and Seed Extracts: LC-ESI-HRMS-Based Composition Analysis

Table 1

Secondary metabolites detected in the different Olea europaea meski stone and seed extracts.


No.	Rt (min)	Proposed EC		Δ in ppm	RDBeq	(Relative intensity %)	Tentative identification	Olea meski stone extracts		Olea meski seed extracts
No.	Rt (min)	Proposed EC		Δ in ppm	RDBeq	(Relative intensity %)	Tentative identification	MeOH	MeOH/H₂O	MeOH	MeOH/H₂O

1	2.54	C₁₄H₁₉O₈	315.10764	−2.87	5.5	153.0506 (100), 287.1157, 196.7752	Hydroxytyrosol hexoside	−	−	+	+
2	2.77	C₈H₉O₃	153.05582	0.64	4.5	123.0452 (100)	Hydroxytyrosol	−	−	++	+
3	3.27	C₁₄H₁₉O₇	299.11270	0.57	5.5	Nd	Salidroside	+	+	+	+
4	3.45	C₁₀H₁₃O₅	213.07648	−1.73	4.5	151.0763 (100), 196.8127, 183.0658	Hydroxylated products of the decarboxylated form of hydroxy elenolic acid(isomer I)	+	+	+	+
5	3.55	C₁₀H₁₃O₅	213.0765	−1.52	4.5	151.0763 (100), 196.8127, 183.0658	Hydroxylated products of the decarboxyl elenolic acid (isomer ΙI)	+	+	+	+
6	3.63	C₁₁H₁₃O₆	241.07126	−2.08	5.5	Nd	Elenolic acid	+	−	−	−
7	3.78	C₁₆H₂₁O₁₁	389.10782	−2.86	6.5	345.1174 (100), 287.1134, 196.8236	Oleoside	−	−	+	+
8	4.50	C₁₇H₂₃O₁₁	403.12350	−2.67	6.5	223.0603 (100), 359.1330, 333.0810, 179.0557.	Oleoside 11-methyl ester	+	+	++	++
9	5.82	C₂₅H₃₁O₁₄	555.17032	−0.482	10.5	537.1587 (100), 456.8495, 403.1225, 393.1173, 287.0841	Hydroxyoleuropein	+	+	+	+
10	5.90	C₃₁H₄₁O₁₈	701.22791	−1.40	11.5	539.1738 (100), 377.1226, 307.0786, 175.0913	Neo-nuzhenide	+	+	+	+
11	5.98	C₂₁H₁₉O₁₁	447.09225	−2.30	12.5	Nd	Luteolin hexosides	−	−	+	+
12	6.12	C₂₉H₃₅O₁₅	623.19629	−2.97	12.5	461.1638 (100)	Verbascoside	+	+	+	+
13	6.17	C₂₉H₃₅O₁₅	623.19672	−2.29	12.5	461.1639 (100)	Isoacteoside	+	+	+	+
14	6.47	C₂₅H₃₅O₁₃	543.20715	−2.13	8.5	525.1948 (100), 513.1946	Dihydro oleuropein	−	−	+	+
15	6.51	C₃₁H₄₁O₁₇	685.23309	−1.06	11.5	523.1719 (100), 453.1376, 421.1480, 299.1130	Nuzhenide	++	++	+++	+++
16	7.14	C₁₀H₁₁O₄	195.06624	−0.22	5.5	Nd	Hydroxytyrosol acetate	+	−	−	−
17	7.52	C₂₅H₃₁O₁₃	539.17572	−2.39	10.5	377.1223 (100), 307.0809, 275.0913	Oleuropein	+++	+++	+	+
18	7.63	C₂₅H₂₇O₁₃	535.14655	1.55	12.5	Nd	Comselogoside (p-Coumaroyl-6 oleoside)	−	−	+	+
19	8.35	C₂₅H₂₇O₁₃	523.18054	−2.97	10.5	361.1273 (100), 291.0858, 259.0962	Ligstroside	++	+	+	+
20	8.43	C₁₉H₂₁O₇	361.12854	−2.03	9.5	291.0861 (100), 259.0966	Monoaldehydic form of ligstroside aglycon	+	+	+	+
21	8.81	C₁₅H₉O₆	285.03976	−2.44	11.5	Nd	Luteolin	−	−	+	+
22	8.87	C₁₇H₁₉O₆	319.11795	−2.38	8.5	Nd	Oleacein	+	−	+	+
23	8.99	C₂₅H₃₅O₁₃	381.15448	−2.65	7.5	363.1430 (100), 349.1275, 331.1170, 287.121	Hydroxytyrosol acyclodihydroelenolate	−	−	+	+
24	10.64	C₁₈H₃₃O₅	329.23254	0.289	2.5	229.1438 (100), 311.2214, 293.2111, 211.1334	9,12,13-trihydroxy octadeca-7-enoic acid	++	−	−	−
25	15.61	C₁₉H₂₅O₈	377.12372	−1.25	9.5	345.0978 (100), 307.0822, 275.0924	Oleuropein aglycon	+	−	−	−
26	17.50	C₃₀H₄₇O₄	471.34674	−1.47	7.5	423.3267 (100), 405.3052, 393.3250	Maslinic acid	++	+	−	−
27	18.11	C₁₈H₃₁O₃	295.2378	0.39	3.5	251.2372 (100), 277.2162, 155.1440	Hydroxyoctadecadienoic acid	++	−	−	−
28	21.01	C₃₀H₄₇O₃	455.35178	−2.83	7.5	196.7925 (100), 287.0947, 407.3293	Oleanolic acid	++	+	−	−
29	21.19	C₂₀H₃₇O₂	309.1732	−0.41	2.5	287.1234 (100), 196.7988	Eicosanoic acid	++	−	−	−
30	22.21	C₂₁H₃₇O₄	353.2667	−1.35	4.5	287.0779 (100), 196.8279	Dihydroxyheneicosanoic acid	++	−	−	−
31	25.61	C₂₇H₂₉O₁₅	593.15009	−1.86	13.5	Nd	Luteolin-7-O-rutinoside	−	−	+	+

Rt: retention time; EC: elemental composition; RDBeq: ring double bond equivalent; : of the pseudomolecular ion; relative abondance; not detected.