HPLC-MS profiling of the multidrug-resistance modifying resin glycoside content of <i>Ipomoea alba</i> seeds

Castañeda-Gómez, Jhon; Rosas-Ramírez, Daniel; Cruz-Morales, Sara; Fragoso-Serrano, Mabel; Pereda-Miranda, Rogelio

doi:10.1016/j.bjp.2017.05.003

Jhon Castañeda-Gómez

Grupo Químico de Investigación y Desarrollo Ambiental, Programa de Licenciatura en Ciencias, Facultad de Educación, Universidad Surcolombiana, Neiva, Colombia

Daniel Rosas-Ramírez

Departamento de Química de Biomacromoléculas, Instituto de Química, Universidad Nacional Autónoma de México, Mexico City, Mexico

Sara Cruz-Morales

Departamento de Farmacia, Facultad de Química, Universidad Nacional Autónoma de México, Mexico City, Mexico

Mabel Fragoso-Serrano

Departamento de Farmacia, Facultad de Química, Universidad Nacional Autónoma de México, Mexico City, Mexico

Rogelio Pereda-Miranda ^** Corresponding author. E-mail:pereda@unam.mx (R. Pereda-Miranda).

Departamento de Farmacia, Facultad de Química, Universidad Nacional Autónoma de México, Mexico City, Mexico

* Corresponding author. E-mail:pereda@unam.mx (R. Pereda-Miranda).

Authors’ contributions

JCG and SCM performed the isolation of novel compounds and completed their structure elucidation. DRR prepared derivatives and accomplished HPLC-MS dereplication. MFS performed the bioassays and supervised HPLC procedures. RPM planned the study and contributed to the preparation of the document final version.

Conflicts of interest

The authors declare no conflicts of interest.

Compound	t_R (min)	Formula	MW	ESI [M + Na]⁺	FAB [M-H]^-	Fragment ions (FAB negative mode, m/z)
1 (Albinoside X)	83.3	C₄₈H₇₈O₂₀	974.508	997	973	891, 809, 663, 517, 389, 243
2 (Albinoside XI)	147.1	C₅₀H₈₂O₂₀	1002.539	1025	1001	919, 837, 691, 545, 417, 271
3 (Albinoside I)	23.1	C₅₁H₈₆O₂₆	1114.532	1137	1113	1013, 971, 825, 679, 533, 389, 243
4 (Albinoside II)	99.7	C₅₄H₈₈O₂₄	1120.558	1153	1119	1037, 891, 745, 517, 389, 243
5 (Albinoside III)	128.2	C₅₇H₉₆O₂₄	1164.620	1187	1163	1081, 935, 853, 707, 561, 417, 271
6 (Albinoside IV)	38.2	C₄₉H₈₂O₂₄	1054.513	1077	1053	971, 907, 825, 679, 533, 389, 243
7 (Albinoside V)	49.6	C₅₄H₉₀O₂₅	1138.569	1161	1137	1037, 891, 809, 791, 745, 663, 517, 389, 243
8 (Albinoside VI)	29.9	C₄₅H₇₆O₂₂	968.470	991	967	867, 679, 551, 533, 389, 243
9 (Albinoside VII)	44.6	C₄₅H₇₆O₂₁	952.477	975	951	851, 809, 663, 535, 517, 389, 371, 243
10 (Albinoside VIII)	63.1	C₄₈H₇₈O₂₁	990.496	1013	989	907, 825, 679, 533, 389, 243
11 (Albinoside IX)	109.1	C₅₀H₈₂O₂₁	1018.527	1041	1017	935, 853, 707, 561, 417, 271

Position	1		2
	^δ _H	^δ _C	^δ _H	^δ _C
Qui-1	4.77 (d, J = 8.0 Hz)	103.2	4.75 (d, J = 8.0 Hz)	103.0
2	4.44 (dd, J = 9.0, 8.0 Hz)	77.1	4.45 (dd, J = 9.0, 8.0 Hz)	76.8
3	4.33 (dd, J = 9.0, 9.0 Hz)	79.6	4.33 (t, J = 9.0, 9.0 Hz)	79.4
4	3.63 (dd, J = 9.0, 9.0 Hz)	78.0	3.65 (dd, J = 9.0, 9.0 Hz)	77.7
5	3.67 (dq, J = 9.0, 6.0 Hz)	73.2	3.67 (dq, J = 9.0, 6.0 Hz)	72.9
6	1.59 (d, J = 6.0 Hz)	19.7	1.61 (d, J = 6.0 Hz)	19.1
Rha-1	5.89 (brs)	100.4	5.88 (brs)	100.2
2	4.79 (dd, J = 3.0, 2.0 Hz)	70.7	4.80 (dd, J = 3.0, 2.0 Hz)	70.5
3	5.76 (m^*)	79.7	5.75 (t, J = 8.8 Hz)	79.5
4	4.32 (dd, J = 9.9, 9.9 Hz)	86.1	4.33 (dd, J = 9.9, 9.9 Hz)	85.9
5	4.83 (dq, J = 9.9, 6.5 Hz)	68.9	4.84 (dq, J = 9.6, 6.5 Hz)	68.6
6	1.92 (d, J = 6.5 Hz)	19.3	1.93 (d, J = 6.5 Hz)	19.3
Rha'-1	5.64 (brs)	99.9	5.64 (brs)	99.8
2	5.88 (dd, J = 3.0, 2.0 Hz)	74.3	5.88 (dd, J = 3.0, 2.0 Hz)	73.9
3	4.15 (m^*)	81.9	4.34 (dd, J = 9.0, 3.0 Hz)	79.4
4	3.66 (dd, J = 9.9, 9.9 Hz)	75.9	3.68 (dd, J = 9.9, 9.9 Hz)	75.6
5	3.86 (dq, J = 9.9, 6.5 Hz)	72.6	3.85 (dq, J = 9.9, 6.5 Hz)	72.3
6	1.49 (d, J = 6.5 Hz)	18.8	1.49 (d, J = 6.5 Hz)	18.6
Fuc-1	5.29 (d, J = 7.6 Hz)	107.1	5.30 (d, J = 7.6 Hz)	106.9
2	4.33 (dd, J = 9.2, 7.6 Hz)	74.2	4.33 (dd, J = 9.6, 7.6 Hz)	73.7
3	4.25 (dd, J = 9.2, 3.0 Hz)	80.9	4.25 (dd, J = 9.2, 3.0 Hz)	81.7
4	5.63 (brs)	74.9	5.64 (brs)	74.7
5	3.93 (q, J = 6.0 Hz)	70.9	3.93 (q, J = 6.0 Hz)	70.7
6	1.32 (d, J = 6.4 Hz)	17.7	1.31 (d, J = 6.4 Hz)	17.4
conv-1		173.2
2a	2.82 (ddd, J = 10.4, 7.6, 2.0 Hz)	35.2
2b	2.43 (ddd, J = 10.4, 7.6, 2.0 Hz)
11	3.79-3.82 (m^*)	81.7
14	0.90 (t, J = 7.2 Hz)	14.8
jal-1				173.0
2a			2.88 (ddd, J = 16.4, 10.4, 6.0 Hz)	35.6
2b			2.43 (ddd, J = 16.4, 10.4, 6.0 Hz)
11			3.82-3.88 (m^*)	80.9
16			0.85 (t, J = 6.8 Hz)	14.7
tga-1		168.2		168.0
2		129.7		129.4
3	6.99 (dq, J = 7.2, 1.6 Hz)	138.3	6.99 (dq, J = 7.2, 1.6 Hz)	138.0
4	1.49 (d, J = 7.2 Hz)	14.9	1.49 (d, J = 7.2 Hz)	14.6
5	1.85 (brs)	13.1	1.81 (brs)	12.7
tga'-1		169.0		169.0
2		129.6		129.3
3	7.13 (dq, J = 7.2, 1.2 Hz)	138.8	7.13 (dq, J = 7.2, 1.2 Hz)	138.5
4	1.47 (d, J = 7.2 Hz)	15.1	1.45 (d, J = 7.2 Hz)	14.5
5	1.87 (brs)	13.0	1.86 (brs)	12.7

Compound^a a Serial dilutions from 0.00064 to 10 µg/ml of vinblastine in the presence or absence of glycolipid (25 µg/ml).	IC₅₀ (µg/ml)			Reversal fold^c c RF = IC50 Vinblastine/IC50 Vinblastine in the presence of glycolipid. Each value represents the mean ± SD from three independent experiments.
	MCF-7/Vin^-	MCF-7/Vin⁺	MCF-7 sens	RF_MCF-7/Vin ^-	RF_MCF-7/Vin ⁺	RF_MCF-7 _sens
Vinblastine	1.08 ± 0.06	1.37 ± 0.23	0.047 ± 0.01
1	0.98 ± 0.16	0.79 ± 0.098	0.015 ± 0.02	1.1	1.7	3.1
2	<0.00064	<0.00064	<0.00064	>1687.5	>2140.6	>73.4
Reserpine^b b Reserpine = 5 µg/ml as positive control.	0.037 ± 0.01	0.31 ± 0.19	0.003 ± 0.001	29.2	4.4	15.7

[1] * Corresponding author. E-mail:pereda@unam.mx (R. Pereda-Miranda).

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HPLC-MS profiling of the multidrug-resistance modifying resin glycoside content of Ipomoea alba seeds

ABSTRACT