Modulation of intracellular expression of IFNγ and IL-2 in culture of splenic T lymphocytes by some flavonoid glycosides of Alchornea floribunda

Figures & data

Figure 1. Chemical structures of the isolated compounds.

Table 1. NMR spectroscopic data of compounds 1–3.

	1		2		3
Position	δC	δH (J, Hz)	δC	δH (J, Hz)	δC	δH (J, Hz)
2	83.7	5.25 d (9.4)	82.0	5.52 d (3.5)	83.9	5.14 (10.6)
3	77.2	4.92 d (9.4)	77.3	4.48 d (3.5)	76.5	4.80 (10.6)
4	196.5	–	195.0	–	196.3	–
5	165.6	–	165.9	–	165.8	–
6	97.4	5.91 brs	97.3	5.89 d (2.0)	97.7	5.93 d (2.0)
7	169.2	–	168.9	–	169.3	–
8	96.4	5.90 brs	96.5	5.92 d (2.0)	96.5	5.91 d (1.6)
9	164.3	–	164.2	–	164.6	–
10	102.8	–	102.5	–	102.7	–
1'	129.1	–	128.5	–	129.0	–
2'	116.0	6.96 brs	116.6	7.06 d (2.0)	115.8	6.97 d (2.0)
3'	146.4	–	145.9	–	146.8	–
4'	147.4	–	146.75	–	147.8	–
5'	116.3	6.77 brs	116.0	6.71 d (8.2)	116.5	6.80 d (8.1)
6'	121.2	6.82 d (7.7)	121.0	6.84 dd (1.9, 8.2)	129.0	6.85 dd (2.0, 8.1)
(3-O)
1''	103.5	3.93 d (7.6)	104.5	4.52 d (7.7)	101.6	3.85 d (3.9)
2''	72.4	3.52 m	72.6	3.52 d (7.6)	71.3	3.59 dd (3.9, 6.0)
3''	74.7	3.29 m	74.9	3.46 d	73.3	3.55 m
4''	70.4	3.71 brs	70.3	3.81 d (3.0)	67.1	3.80 dt (3.4, 7.7)
5''	77.1	3.28 m	77.2	3.50 d (5.6)	63.6	3.92 dd (7.1, 1.7)
						3.38 dd (3.7, 1.7)
6''	62.4	3.65 d	62.6	3.70 d (6.9) HA	–	–
				3.65 d HB

Spectra was measured in CD₃OD at 600 (¹H) and 150 (¹³C) MHz.

Table 2. NMR spectroscopic data of compounds 4–7.

Position	4 (δH) (J, Hz)	5 (δH) (J, Hz)	6 (δH) (J, Hz)	7 (δH) (J, Hz)
2	–	–	–	–
3	–	–	–	–
4	–	–	–	–
5	–	–	–	–
6	6.14 br s	6.20 d (2.0)	6.18 br s	6.21 br s
7	–	–	–	–
8	6.31 br s	6.38 d (2.0)	6.35 br s	6.40 br s
9	–	–	–	–
10	–	–	–	–
1'	–	–	–	–
2'	7.71 br s	7.77 d (8.7)	7.33 d br s	7.77 d (2.0)
3'	–	6.93 d (8.7)	–	–
4'	–	–	–	–
5'	6.85 d (8.5)	6.93 d (8.7)	6.91 d (8.1)	6.89 d (8.5)
6'	7.58 d (8.5)	7.77 d (8.7)	7.30 dd (8.2)	7.60 dd (2.0, 8.4)
(3-O)
1''	5.18 d (7.8)	5.38 brs	5.35 br s	5.17 d (6.6)
2''	3.47 d	4.22 br s	4.23 br s	3.92 t
3''	3.32	3.71 dd	3.76 dd	3.66 dd
4''	3.20	3.20	3.35 t	3.83 br s
5''	3.58	3.40	3.42 dt (6.1)	3.48 d Ha
				3.84 d Hb
6''	3.56 Ha	0.92 d (5.4, 3H)	0.94 d (6.1, 3H)	–
	3.81 Hb

Spectra were measured in CD₃OD at 500 (¹H) MHz.

Figure 2. Intracellular cytokine staining showing modulation of activated CD4⁺T-lymphocytes (A) and CD8⁺T-lymphocytes (B) secreting interferon-gamma (IFN-γ) and interleukin-2 at 25 μg/mL compound potency. Also shown are cells which are double positive for IFN-γ and IL-2 secretion (IFN-γ/IL-2).

Figure 3. Intracellular cytokine staining showing modulation of activated CD4⁺T-lymphocytes (A) and CD8⁺T-lymphocytes (B) secreting interferon-gamma (IFN-γ) and interleukin-2 at 6.25 μg/mL compound potency. Also shown are cells double-positive for IFN-γ and IL-2 secretion (IFN-γ/IL-2).