Analysis of Flavonoid Composition of Korean Herbs in the Family of Compositae and their Utilization for Health

Agung Nugroho; Jae Sue Choi; Hee-Juhn Park

doi:10.20307/nps.2016.22.1.1

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Nugroho, Choi, and Park: Analysis of Flavonoid Composition of Korean Herbs in the Family of Compositae and their Utilization for Health

Original Article

Natural Product Sciences 2016;22(1):1-12.

Published online: 17 December 2016

DOI: https://doi.org/10.20307/nps.2016.22.1.1

Analysis of Flavonoid Composition of Korean Herbs in the Family of Compositae and their Utilization for Health

Agung Nugroho¹, Jae Sue Choi², Hee-Juhn Park^3,^∗

¹Department of Agro-industrial Technology, Faculty of Agriculture, Lambung Mangkurat University, Banjarbaru 70712, Indonesia

²Department of Food Science and Nutrition, Pukyong National University, Busan 608-737, Korea

³Department of Pharmaceutical Engineering, Sangji University, Wonju 220-702, Korea

^∗Author for correspondence Dr. Hee-Juhn Park, Department of Pharmaceutical Engineering, Sangi University, Woosan-Dong, Wonju 220-702, Korea. Tel: +82-33-730-0564; E-mail: hjpark@sangji.ac.kr

Received 19 September 2015 Revised 19 October 2015 Accepted 19 October 2015

This is an Open Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License (http://creativecommons.org/licenses/by-nc/3.0) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

Compositional differences in flavonoids are varied in the big family of Compositae. By summarizing our previous analytical studies and other scientific evidences, new strategy will be possible to further analyze flavonoids and utilize them for human health. The HPLC analytical method has been established in terms of linearity, sensitivity, accuracy, and precision. Herbs of the family of Compositae have considerable amounts of peroxynitrite (ONOO⁻)-scavenging effects and their phenolic substances. These effects may contribute to the prevention of disease associated with excess production of ONOO⁻, depending on the high content of flavonoid substances.

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Keywords: Compositae, Flavonoids, Phenolic substance, HPLC analysis, Peroxynitrite

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Fig. 1.

Characteristics of Compositae.

The head with ray florets arranged around the perimeter, disc florets in the center, and an involucre with bracts (phyllaries) surrounding the outermost florets. B. The pollen is released via the style pushing out through the anthers, which are fused at the margins; sometimes the style branches are recurved and come in contact with the style shaft. C. Some of the achene (cypsela) and pappus types found in Compositae (Funk et al., 2009).

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Fig. 2.

Traditional use of Hemitepta lyrata as one of Compositae herbs.

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Fig. 3.

Chemical structures of several flavonols and flavones.

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Fig. 4.

Structure of luteolin, acacetin, Lut-7-Glc, Lut-7-GlcU and acacetin identified from Y. japonica and their presumed pathway. A dotted arrow represents a less favored pathway.

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Fig. 5.

HPLC chromatograms of MeOH extracts of the four Compositae herbs (Compound names are abbreviated).

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Fig. 6.

Composition of flavonoids and caffeoylquinic acids in the five Compositae herbs.

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Fig. 7.

Peroxynitrite-scavenging activities (IC₅₀ s) of the flavonoids and caffeoylquinic acids identified in the five Compositae herbs.

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Table 1.

Recapitulation of the phenolics identified in the five Compositae herbs

Type	Compounds	C. setidens	S. grandifolia	S. brachyotus	C. boreale	H. lyrata
	Caffeic acid					●
	CAME	●
Caffeoyl type	Chlorogenic acid	●	●	●	●	●
	3,4-DQ	●
	3,5-DQ				●	●
	Quercetin		●
	Isoquercitrin		●
Flavonol type	Saxifragin		●
Flavonol type	Hyperoside	●
	Rutin		●			●
	Kp 3-rut					●
	Luteolin			●
	Luteolin 7-glc			●
	Luteolin 7-glcU			●
	Luteolin 7-rut			●
	Acacetin				●	●
	Linarin	●			●	●
Flavone type	Acacetintrisaccharide				●
	Pectolinarigenin					●
	Pectolinarin	●				●
	Apigenin					●
	Isorhoifolin					●
	Diosmetin					●
	Diosmin					●

Table 2.

Linearities and detection/quantification limits of the standard compounds

Standard compound	t_R (min)	Linear regression^a	R²^b	LOD^c (µg/ml)	LOQ^d (µg/ml)
Chlorogenic acid	8.32	y = 166.80 x + 58.46	0.9998	0.30	1.01
Caffeic acid	10.36	y = 253.42 x + 50.84	0.9999	0.22	0.72
Saxifragin	14.78	y = 414.62 x + 65.93	0.9998	0.12	0.40
Luteolin 7-rutinoside	15.63	y = 175.25 x + 34.55	0.9999	0.38	1.26
Rutin	16.13	y = 143.53 x + 15.18	0.9999	0.42	1.39
Luteolin 7-glucoside	16.29	y = 200.82 x + 40.73	0.9999	0.34	1.13
Hyperoside	16.37	y = 217.04 x + 46.33	0.9999	0.14	0.46
Luteolin 7-glucuronide	16.63	y = 48.813 x + 95.76	0.9997	0.85	2.83
Isoquercitrin	16.76	y = 472.75 x + 75.62	0.9999	0.11	0.36
3,5-dicaffeoylquinic acid	16.95	y = 157.87 x + 75.02	0.9999	0.27	0.90
Isorhoifolin	18.09	y = 232.85 x + 65.10	0.9999	0.17	0.57
Acacetintrisaccharide	18.42	y = 104.76 x + 81.54	0.9999	0.30	1.01
Kaempferol 3-rutinoside	18.71	y = 236.19 x + 54.25	0.9998	0.22	0.72
3,4-dicaffeoylquinic acid	18.95	y = 133.62 x + 45.50	0.9999	0.23	0.76
Diosmin	19.10	y = 244.78 x + 53.54	0.9999	0.21	0.71
Caffeic acid methyl ester	19.68	y = 172.39 x + 44.58	0.9999	0.12	0.40
Quercetin	24.79	y = 659.28 x + 87.33	0.9999	0.09	0.23
Linarin	24.85	y = 309.18 x + 30.86	0.9999	0.23	0.76
Luteolin	25.26	y = 399.22 x + 164.9	0.9997	0.25	0.83
Pectolinarin	25.58	y = 103.76 x + 60.10	0.9997	0.43	1.44
Apigenin	28.67	y = 529.46 x + 49.28	0.9999	0.11	0.35
Diosmetin	29.53	y = 741.76 x + 96.14	0.9999	0.01	0.04
Acacetin	36.88	y = 369.27 x + 45.71	0.9999	0.15	0.50
Pectolinarigenin	37.73	y = 199.06 x + 33.37	0.9999	0.20	0.67

^a y, peak area at 254 nm; x, concentration of the standard (µg/ml);

^b R

² correlation coefficient for 6 data points in the calibration curves (n = 4);

^c LOD, limit of detection (S/N = 3);

^d LOQ, limit of quantification (S/N = 10).

Table 3.

Contents of the flavonoids and caffeoylquinic acids in MeOH extracts of the five Compositae herbs (mg/g)

Type	Compounds	C. setidens	S. grandifolia	S. brachyotus	C. boreale		H. lyrata
Type	Compounds	C. setidens	S. grandifolia	S. brachyotus	Leaf	Flower	H. lyrata
	Caffeic acid						0.69
	CAME	0.51
Caffeic acid-type	Chlorogenic acid	8.41	89.87	2.53	20.86	13.02	4.22
	3,4-DQ	5.74
	3,5-DQ				60.43	47.28	4.32
	Quercetin		0.99
	Isoquercitrin		24.46
Flavonol-type	Saxifragin		30.76
Flavonol-type	Hyperoside	4.33
	Rutin		33.74				8.81
	Kp 3-rut						7.03
	Luteolin			1.05
	Luteolin 7-glc			1.64
	Luteolin 7-glcU			143.01
	Luteolin 7-rut			26.7
	Acacetin				0.86	0.46	0.74
	Linarin	18.99			63.80	43.59	23.2
Flavone-type	Acacetintrisaccharide				2.99	6.97
	Pectolinarigenin						0.24
	Pectolinarin	156.48					1.10
	Apigenin						1.59
	Isorhoifolin						0.49
	Diosmetin						0.16
	Diosmin						5.40
	Total amount	194.46	179.82	174.93	148.94	111.32	57.99

Table 4.

Contents of the flavonoids and caffeoylquinic acids in the dry plant material (DM) of the five Compositae herbs (mg/g of dry weight)

Type	Compounds	C. setidens	S. grandifolia	S. brachyotus	C. boreale		H. lyrata
Type	Compounds	C. setidens	S. grandifolia	S. brachyotus	Leaf	Flower	H. lyrata
	Caffeic acid						0.13
Caffeic acid-type	CAME	0.08
	Chlorogenic acid	1.35	12.35	0.32	3.90	2.54	0.78
	3,4-DQ	0.92
	3,5-DQ				11.30	9.22	0.80
	Quercetin		0.14
	Isoquercitrin		3.37
Flavonol-type	Saxifragin		4.24
Flavonol-type	Hyperoside	0.69
	Rutin		4.65				1.62
	Kp 3-rut						1.29
	Luteolin			0.13
	Luteolin 7-glc			0.21
	Luteolin 7-glcU			18.30
	Luteolin 7-rut			3.40
	Acacetin				0.16	0.09	0.14
	Linarin	3.06			11.93	8.50	4.26
Flavone-type	Acacetintrisaccharide				0.56	1.36
	Pectolinarigenin						0.05
	Pectolinarin	25.19					0.20
	Apigenin						0.29
	Isorhoifolin						0.09
	Diosmetin						0.03
	Diosmin						0.99
	Total amount	31.29	24.75	22.36	27.85	21.71	10.67

Table 5.

Peroxynitrite-scavenging activities (IC₅₀ s) of the flavonoids and caffeoylquinic acids identified in the five Compositae herbs

Type	Compound	Concentration (µ g/ml)					IC₅₀
Type	Compound	50.00	10.00	2.00	0.40	0.08	(µ g/ml)	µ M
	Caffeic acid	−	97.34±0.23	73.95±0.84	30.65±3.21	−	0.89	4.94
Caffeic acid-type	CAME	−	93.32±0.30	67.33±1.02	18.67±1.90	−	1.31	6.76
	Chlorogenic ac.	−	94.34±0.58	78.70±1.85	56.56±4.38	12.67±8.55	0.47	1.34
	3,4-DQ	−	93.05±0.68	75.31±1.18	47.92±0.65	15.32±4.65	0.55	1.06
	3,5-DQ	−	94.26±1.11	86.03±2.31	50.53±3.18	17.72±4.90	0.43	0.83
	Quercetin	−	94.82±1.49	82.68±3.19	47.44±3.93	6.88±4.22	0.58	1.93
	Isoquercitrin	−	94.58±1.69	76.71±3.35	25.17±3.11	3.97±2.57	0.88	1.90
	Saxifragin	−	95.45±1.84	86.40±0.56	61.29±1.51	19.59±8.79	0.33	0.71
Flavonol-type	Hyperoside	−	95.70±0.27	75.62±4.21	26.94±3.22	9.97±4.58	0.80	1.73
Flavonol-type	Rutin	−	97.30±0.21	81.06±1.02	48.89±1.10	6.34±3.43	0.57	0.94
	Kaempferol	−	94.41±0.11	92.50±1.45	28.95±4.18	3.58±3.88	0.71	2.48
	Astragalin	−	74.38±1.18	42.50±2.02	36.66±4.64	13.77±4.29	1.60	4.02
	Kp 3-rut	−	71.34±1.71	38.97±2.34	25.93±3.41	19.32±5.64	2.47	4.15
	Luteolin	−	97.56±5.71	96.15±0.27	85.85±3.70	10.80±9.65	0.23	0.81
	Luteolin 7-glc	−	97.16±0.71	88.80±1.27	54.34±3.41	17.01±3.50	0.39	0.86
	Luteolin 7-glcU	−	96.19±2.17	83.36±0.31	48.39±1.57	11.48±4.33	0.52	1.12
	Acacetin	82.33±0.45	59.54±1.22	21.66±1.34	−	−	7.87	27.72
Flavone-type	Linarin	97.45±0.24	66.89±0.98	32.56±1.21	−	−	4.60	7.77
	Acacetintrisaccharide	97.57±0.31	81.44±1.39	45.14±1.24	−	−	2.19	2.91
	Pectolinarigenin	88.69±0.39	66.00±1.46	30.46±1.13	−	−	5.23	16.99
	Pectolinarin	90.65±0.59	69.94±0.68	35.86±1.36	−	−	4.03	6.47
	Apigenin	54.49±1.85	36.73±1.45	18.22±2.21	−	−	33.19	122.9
Control	L-penicillamine	−	91.76±1.05	83.55±1.51	47.28±2.89	8.75±5.87	0.57	3.86

Data represent mean±SD (n = 2).

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