LC-QTOF-MS analysis of xanthone content in different parts of Garcinia mangostana and its influence on cholinesterase inhibition

Figures & data

Table 1. Linearity, LOD and LOQ of the xanthones of Garcinia mangostana.

Compound	Regression equation	Linear range (ng/mL)	R^2	LOD (ng/mL)	LOQ (ng/mL)
Mangostanol (1)	y = 0.176164x ± 0.045660	1000–10000	0.9998	500	1000
3-Isomangostin (2)	y = 1.000952x ± 0.002474	25–1000	0.9999	5	25
Garcinone C (3)	y = 0.035076x ± 0.030565	5000–50000	0.9987	120	5000
γ-Mangostin (4)	y = 0.389182x ± 0.000753	1000–5000	0.9910	90	1000
8-Deoxygartanin (5)	y = 0.595092x ± 0.003890	25–500	0.9969	10	25
α-Mangostin (6)	y = 0.480042x ± 0.151938	1000–10000	0.9992	50	1000

Figure 1. Representative total ion chromatogram of the methanol extracts (A) and aqueous extracts (B) of different parts of Garcinia mangostana. (1) Mangostanol ; (2) 3-Isomangostin ; (3) Garcinone C ; (4) γ-Mangostin ; (5) 8-Deoxygartanin ; (6) α-Mangostin.

Figure 2. Fragmentation patterns of the xanthones. (1) Mangostanol, (2) 3-Isomangostin, (3) Garcinone C, (4) γ-Mangostin, (5) 8-Deoxygartanin, (6) α-Mangostin.

Table 2. Xanthone content in the methanol and aqueous extracts of different parts of Garcinia mangostana.

Sample			Content of bioactive xanthones (n = 3) (mg/g)													Relative distribution^c
	Yield (%)	Mangostanol (1)		3-Isomangostin(2)		Garcinone C (3)		γ-Mangostin (4)		8-Deoxygartanin (5)		α -mangostin (6)		Total		1	2	3	4	5	6
		Extract^a	RW^b	Extract^a	RW^b	Extract^a	RW^b	Extract^a	RW^b	Extract^a	RW^b	Extract^a	RW^b	Extract^a	RW^b
Methanol extract
Pericarp	35.6	8.6 ± 0.4	3.1	10.4 ± 0.6	3.7	0.5 ± 0.1	0.2	57.0 ± 12.7	20.2	11.5 ± 0.6	4.1	403.9 ± 13.1	143.7	521.2	185.5	0.8	1	0.06	5.4	1.1	38.6
Calyx	38.2	35.3 ± 2.6	13.5	7.7 ± 0.3	2.9	0.6 ± 0.0	0.2	37.2 ± 1.9	14.2	13.2 ± 1.2	5.0	221.0 ± 11.2	84.0	311.5	118.9	4.5	1	0.08	4.7	1.7	28.5
Aril	10.8	ND	ND	3.4 ± 0.2	0.4	0.004 ± 0.0	0.4 (μg/g)	0.1 ± 0.1	0.01	0.1 ± 0.0	0.01	1.2 ± 0.1	0.13	5.4	0.6	ND	1	ND	0.04	0.03	0.4
Stalk	21.7	46.9 ± 1.3	10.2	11.5 ± 0.3	2.5	1.0 ± 0.0	0.2	3.7 ± 0.1	0.8	19.5 ± 0.4	4.2	56.9 ± 1.7	12.3	73.0	15.8	4.0	1	0.09	0.3	1.6	4.9
Leaves	19.5	0.8 ± 0.1	0.2	3.9 ± 0.1	0.7	0.2 ± 0.0	0.04	3.7±.0.3	0.7	5.4 ± 0.2	1.1	2.4 ± 0.2	0.5	16.6	3.2	0.2	1	0.04	0.9	1.4	0.6
Bark	7.5	5.0 ± 0.5	0.4	10.0 ± 0.7	0.8	0.1 ± 0.0	7.5 (μg/g)	2.7 ± 0.6	0.2	15.6 ± 0.6	1.2	209.7 ± 16.9	15.7	242.3	18.2	0.5	1	0.01	0.3	1.5	20.9
Stem	14.8	8.7 ± 0.1	1.3	6.8 ± 0.3	1.0	0..1 ± 0.0	0.02	2.1 ± 0.01	0.3	6.1 ± 0.4	0.9	47.6 ± 5.4	7.0	71.5	10.6	1.2	1	0.01	0.3	0.9	6.9
Aqueous extract
Pericarp	8.6	0.06 ± 0.02	5.2 (μg/g)	3.6 ± 0.1	0.3	0.1 ± 0.0	8.6 (μg/g)	0.4 ± 0.04	0.03	0.1 ± 0.0	8.6 (μg/g)	2.5 ± 0.4	0.2	6.5	0.6	ND	1	0.02	0.1	0.03	0.6
Calyx	18.2	ND	ND	2.9 ± 0.1	0.5	ND	ND	ND	ND	0.004 ± 0.0	0.73 (μg/g)	ND	ND	2.9	0.5	ND	1	ND	ND	ND	ND
Aril	0.8	ND	ND	2.9 ± 0.0	0.02	ND	ND	ND	ND	0.01 ± 0.0	0.08 (μg/g)	ND	ND	2.9	0.002	ND	1	ND	ND	ND	ND
Stalk	13.7	ND	ND	2.9 ± 0.1	0.4	ND	ND	ND	ND	0.01 ± 0.0	1.37 (μg/g)	ND	ND	2.9	0.4	ND	1	ND	ND	ND	ND
Leaves	1.8	ND	ND	2.9 ± 0.0	0.05	ND	ND	1.4 ± 0.0	0.03	0.04 ± 0.0	0.72 (μg/g)	ND	ND	4.3	0.08	ND	1	ND	0.4	0.02	ND
Bark	3.8	ND	ND	5.3 ± 0.2	0.2	ND	ND	0.01 ± 0.0	0.38 (μg/g)	0.2 ± 0.0	7.6 (μg/g)	1.7 ± 0.1	0.06	7.3	0.3	ND	1	ND	ND	0.04	0.3
Stem	1.9	ND	ND	3.2 ± 0.1	0.1	ND	ND	0.03 ± 0.0	0.57 (μg/g)	0.2 ± 0.1	3.8 (μg/g)	0.9 ± 0.1	0.02	4.8	0.009	ND	1	ND	0.01	0.05	0.3

ND: Not determined because the level was below quantification limit. Numbers label: (1) mangostanol; (2) 3-isomangostin; (3) garcinone C; (4) γ-mangostin; (5) 8-deoxygartanin; (6) α-mangostin.

^a‘Extract’ means the content of the compounds in the extract, e.g., 8.6 mg of mangostanol is present in each g of methanol extract of pericarp.

^b'RW’ means the content of the compounds in the dry powdered raw material, e.g., 3.1 mg of mangostanol is present in each g of dry powdered pericarp raw material.

^cThe relative distribution indicates the ratio of the compounds relative to 3-isomangostin. The idea of relative distribution is to indicate the magnitude of the ratio between two compounds, e.g., in methanol extract of pericarp, there is 38.6 times more α-mangostin, 5.4 times more γ-mangostin and 1.1 times more 8-deoxygartanin than 3-isomangostin.

Table 3. Cholinesterase inhibitory activities of the methanol and aqueous extracts of different parts of Garcinia mangostana.

Sample	% of inhibition at 100 µg/mL		IC50 (µg/mL)		Selectivity
	AChE	BCHE	AChE	BChE	AChE	BChE
Methanol extract
Pericarp	82.19 ± 2.89	74.63 ± 1.03	0.90 ± 0.10	1.94 ± 0.14	2.15	0.46
Calyx	92.92 ± 3.86	94.10 ± 4.12	9.71 ± 1.20	0.37 ± 0.04	0.04	26.24
Aril	22.00 ± 0.48	5.26 ± 0.37	ND	ND	ND	ND
Stalk	65.54 ± 3.51	80.11 ± 0.74	22.81 ± 0.72	20.84 ± 0.02	0.91	1.09
Leaves	32.76 ± 2.09	76.46 ± 1.67	ND	25.83 ± 0.77	ND	ND
Bark	83.90 ± 1.35	76.46 ± 0.18	7.88 ± 0.82	19.89 ± 2.68	2.52	0.39
Stem	94.0 3 ± 1.75	89.95 ± 0.78	22.64 ± 0.77	1.82 ± 0.16	0.08	12.44
Aqueous extract
Pericarp	55.37 ± 1.53	82.59 ± 0.09	52.74 ± 8.98	11.14 ± 0.61	0.21	4.73
Calyx	17.90 ± 3.13	NI	ND	ND	ND	ND
Aril	NI	NI	ND	ND	ND	ND
Stalk	59.20 ± 3.60	2.36 ± 0.37	72.22 ± 2.58	ND	ND	ND
Leaves	15.70 ± 0.93	65.19 ± 0.56	ND	38.81 ± 1.84	ND	ND
Bark	NI	15.09 ± 8.56	ND	ND	ND	ND
Stem	11.60 ± 1.16	11.23 ± 0.93	ND	ND	ND	ND
Galantamine			0.27 ± 0.07	5.55 ± 0.24	20.55	0.04

Each value represents mean ± SD of triplicates. NI: No inhibition at 100 µg/mL. ND: Not determined.

Selectivity against AChE: IC₅₀BChE/IC5₀AChE.

Selectivity against BChE: IC₅₀AChE/IC5₀BChE.

Figure 3. Scatter plot of IC₅₀ of AChE and BChE versus total xanthone content.

Figure 4. Nonmetric Multidimensional Scaling Ordination of the xanthones. The loading of the variables was projected on the ordination plot. The sample was labelled based on (A) solvent, (B) plant parts. (C) Bubble plot based on the concentration of α-mangostin and γ-mangostin superimposed on the NMDS.

Figure 5. Box plot for comparison of IC₅₀ between “Pericarp”, “Bark + Calyx” and “Others”. (A) AChE, (B) BChE.