Antiplatelet aggregation activity of compounds isolated from Guttiferae species in human whole blood

Figures & data

Figure 1.  Structures of compounds from Guttiferae species with significant antiplatelet aggregation effects.

Table 1.  Percentage inhibition of isolated compounds from Guttiferae species on platelet aggregation in human whole blood induced by arachidonic acid (AA) (0.5 mM), collagen (2 μg/mL), and adenosine diphosphate (ADP) (10 μM).

Compound	Concentration (μg/mL)	AA	Collagen	ADP
4-Hydroxyxanthone (1)	100	22.2 ± 0.0	18.2 ± 0.6	100.0 ± 0.0^c
	50			57.1 ± 0.9
	25			35.7 ± 0.7
	12.5			21.4 ± 0.4
1,3,7-Trihydroxyxanthone (2)	100	77.3 ± 2.3^b	30.8 ± 0.6	85.7 ± 1.4^a
1,3,6,7-Tetrahydroxyxanthone (3)	100	100.0 ± 0.0^b	34.6 ± 0.6	21.2 ± 0.7
6-Deoxyjacareubin (4)	100	53.6 ± 0.6	10.6 ± 0.9	18.6 ± 0.8
2-(3-Methylbut-2-enyl)-1,3,5-trihydroxyxanthone (5)	100	72.2 ± 0.9^a	33.7 ± 3.5	18.1 ± 1.2
	50	55.6 ± 1.7
	25	37.0 ± 0.8
	12.5	33.3 ± 1.1
2-(3-Methylbut-2-enyl)-1,3,5,6-tetrahydroxyxanthone (6)	100	100.0 ± 0.0^c	59.1 ± 2.1	100.0 ± 0.0^a
	50	50.0 ± 0.6	36.4 ± 0.5	55.7 ± 1.4
	25	30.0 ± 1.2	18.2 ± 0.8	28.6 ± 1.0
	12.5	10.0 ± 1.0	4.6 ± 1.3	14.3 ± 0.7
2-(3-Hydroxy-3-methylbutyl)-1,3,5,6-tetrahydroxyxanthone (7)	100	61.1 ± 0.0^c	36.0 ± 0.6	78.6 ± 1.1^b
Macluraxanthone (8)	100	28.6 ± 0.7	7.7 ± 1.4	100.0 ± 0.3^a
	50			85.7 ± 1.4
	25			57.1 ± 1.0
	12.5			21.4 ± 0.7
Rubraxanthone (9)	100	55.6 ± 0.0^b	100.0 ± 0.0^a	100.0 ± 0.0^c
	50	33.3 ± 1.4	90.9 ± 1.0	64.3 ± 1.2
	25	22.2 ± 1.0	63.6 ± 0.5	28.6 ± 0.8
	12.5	11.1 ± 0.7	27.3 ± 0.4	10.0 ± 0.4
Neoflavonoid (10)*	100	25.0 ± 0.7	3.6 ± 1.0	57.1 ± 1.0^a
	50			28.6 ± 1.2
	25			14.3 ± 1.0
	12.5			7.0 ± 0.7
Pyranoamentoflavone (11)	100	11.1 ± 0.6	41.8 ± 2.1	57.1 ± 0.7^c
	50			50.0 ± 1.2
	25			42.9 ± 1.0
	12.5			7.1 ± 0.7
GB-1a (12)^†	100	23.8 ± 0.6	15.4 ± 2.1	100.0 ± 0.0^a
	50			42.9 ± 1.2
	25			21.4 ± 1.0
	12.5			14.3 ± 0.0
Isocowanol (13)	100	16.7 ± 0.0	18.2 ± 0.9	20.0 ± 2.1
Amentoflavone (14)	100	10.0 ± 0.0	31.7 ± 2.1	38.1 ± 0.6
Quercetin (15)	100	75.6 ± 0.7^c	73.5 ± 1.0^c	85.7 ± 1.0^b
Quercetin 3-O-rhamnoside (16)	100	28.6 ± 8.0	25.0 ± 0.7	28.6 ± 0.7
Kaempferol 3-O-rhamnoside (17)	100	28.6 ± 2.8	42.5 ± 0.7	7.1 ± 2.0
β-Sitosterol (18)	100	19.0 ± 0.7	37.5 ± 1.0	4.7 ± 0.6
Friedelin (19)	100	8.3 ± 0.7	35.7 ± 2.4	21.4 ± 1.5
Canophyllol (20)	100	8.3 ± 1.1	35.7 ± 1.8	7.1 ± 1.1
Aspirin	25	100.0 ± 0.0	31.3 ± 0.7	42.9 ± 1.0
	12.5	70.1 ± 0.7
	6.25	60.5 ± 0.5
	3.13	36.5 ± 1.0

Aspirin was used as a positive control. Concentration of aspirin in reaction mixture: 25 μg/mL. Values are presented as mean ± SE (n = 3); ^ap < 0.05, ^bp < 0.01, and ^cp < 0.001 as compared with the respective control.

*Neoflavonoid: (+)-(2R, 3S, 16S)-2,3-dimethyl-5-hydroxy-6-(3-methylbut-2-enyl)-7-methoxy-8-(2-carboxyl-1-phenylethyl)-2,3-dihydrobenzopyran.

^†GB-1a: 5,7,4′,5″,7″,4′″-hexahydroxy[3–8″]biflavanone.

Table 2.  IC₅₀ values (μM) of isolated compounds on platelet aggregation induced by arachidonic acid (AA) (0.5 mM), collagen (2 μg/mL), and adenosine diphosphate (ADP) (10 μM).

Compound	AA	Collagen	ADP
4-Hydroxyxanthone (1)	—	—	136.2 ± 3.7
1,3,7-Trihydroxyxanthone (2)	208.0 ± 5.1	—	69.5 ± 4.2*
1,3,6,7- Tetrahydroxyxanthone (3)	127.0 ± 2.6	—	—
6-Deoxyjacareubin (4)	247.8 ± 6.3	—	—
2-(3-Methylbut-2-enyl)-1,3,5-trihydroxyxanthone (5)	115.9 ± 3.4*	—	—
2-(3-Methylbut-2-enyl)- 1,3,5,6- tetrahydroxyxanthone (6)	113.0 ± 2.9**	228.9 ± 4.6	106.5 ± 4.7
2-(3-Hydroxy-3-methylbutyl)-1,3,5,6- tetrahydroxyxanthone (7)	203.0 ± 3.8	—	109.9 ± 3.3
Macluraxanthone (8)	—	—	56.0 ± 2.6**
Rubraxanthone (9)	209.9 ± 2.8	47.0 ± 3.5*	82.3 ± 2.7*
Neoflavonoid (10)	—	—	88.0 ± 5.0*
Pyranoamentoflavone (11)	—	—	95.1 ± 5.1*
GB-1a (12)	—	—	74.4 ± 4.7*
Quercetin (15)	181.0 ± 4.1	200.5 ± 1.9	188.0 ± 5.6
Aspirin	27.3 ± 2.5	—	—

Data represent mean ± SE of three independent experiments performed in triplicate. *p < 0.05, **p < 0.01 as compared with the control.