Flavonoids of Calligonum polygonoides and their cytotoxicity

Figures & data

Table 1. The ¹H- and ¹³C NMR data for compound 1 in CD₃OD.

	1
Position	δC, type	δH (J in Hz)
2	157.7, C	–
3	133.9, C	–
4	177.7, C	–
5	161.5, C	–
6	98.6, CH	6.16 (brd)
7	164.4, C	–
8	93.5, CH	6.33 (brd)
9	156.9, C	–
10	104.1, C	–
1’	121.0,C	–
2’	130.9, CH	8.01 (d, 8.4)
3’	114.6, CH	6.85 (d, 7.6)
4’	160.2, C	–
5’	114.6, CH	6.85 (d, 7.6)
6’	130.9, CH	8.01 (d, 8.4)
1″	103.2, CH	5.29 (d, 6.8)
2″	74.0, CH	3.53–3.64^a
3″	76.0, CH	3.53–3.64^a
4″	71.3, CH	3.53–3.64^a
5″	75.7, CH	3.82 (d, 9.6)
6’″	168.7, C	–
1””	64.8, CH2	4.06 (m)
2””	30.1, CH2	1.51 (m)
3””	18.6, CH2	1.26 (dq, 14.8, 7.2)
4””	12.6, CH3	0.83 (t, 7.2)

^aOverlapped signals.

Figure 1. Chemical structures of flavonoids isolated from the hydroalcoholic extract of Calligonum polygonoides.

Figure 2. Dose–response curves for cytotoxic effects of the flavonoids isolated from the hydroalcoholic extract of Calligonum polygonoides. Numbers written above each graph correspond to chemical structures in Figure 1. Cytotoxicity was assessed on HepG2 (solid line) and MCF-7 (dotted line).

Table 2. Cytotoxic activity (IC₅₀, μg/mL) of flavonoids isolated from Calligoum polygonoides.

Compound	HepG2^a	MCF-7^a
Kaempferol-3-O-β-D-(6″-n-butyl glucuronide)	17.44	40.01
Kaempferol-3-O-β-D-(6″-methyl glucuronide)	125.54*	85.51
Quercetin 3-O-β-D-(6″-n-butyl glucuronide)	60.46*	61.4
Quercetin -3-O-β-D-(6″-methyl glucuronide)	42.31**	109.1**
Quercetin-3-O-glucuronide	35.73	14.32
Kaempferol-3-O-glucuronide	64.87*	33.23
Quercetin-3-O-rhamnopyranoside	84.17**	30.84
Kaempferol-3-O-glucopyranoside	9.21*	26.9
Quercetin-3-O-glucopyranoside	66.09*	38.18
Taxifolin	21.25	15.9
Catechin	20.83	27.78
Dehydrodicatechin A	131.2**	67.09*
Quercetin	4.88	0.87
Kaempferol	46.18*	27.81
Adriamycin^b	3.07	4.51

^aMCF-7 (human Caucasian breast adenocarcinoma) and HepG-2 (human hepatocellular carcinoma cell line).

^bAdriamycin (doxorubicin) was used as a positive control.

* Significantly different than control at p < 0.05.

** Significantly different than control at p < 0.01.

Figure 3. Structure elements in flavonoids that increase (solid circle) or decrease (dotted circle) cytotoxic activity against breast cancer cells.