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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 Park3, ∗

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

Copyright © 2016 The Korean Society of Pharmacognosy

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.

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

REFERENCES

(1). Fraisse D., Felgines C., Texier O., Lamaison J. L.Food Nutr. Sci. 2011; 2:181–192.
(2). Nugroho A., Kim K. H., Lee K. R., Alam M. B., Choi J. S., Kim W. B., Park H. J.Arch. Pharm. Res. 2009; 32:1361–1367.
(3). Nugroho A., Lee K. R., Alam M. B., Choi J. S., Park H. J.Arch. Pharm. Res. 2010; 33:703–708.
(4). Pacher P., Beckman J. S., Liaudet L.Physiol. Rev. 2007; 87:315–424.
(5). Nugroho A., Kim M. H., Lim S. C., Choi J. W., Choi J. S., Park H. J.Nat. Prod. Sci. 2011; 17:342–349.
(6). Nugroho A., Lim S. C., Lee C. M., Choi J. S., Park H. J. J.Pharm. Biomed. Anal. 2012; 61:247–251.
(7). Nugroho A., Kim M. H., Lee C. M., Choi J. S., Lee S. H., Park H. J.Nat. Prod. Sci. 2012; 18:39–46.
(8). Nugroho A., Lim S. C., Choi J. W., Park H. J.Arch. Pharm. Res. 2013; 36:51–60.
(9). Nugroho A., Lim S. C., Byeon J. S., Choi J. S., Park H. J. J.Pharm. Biomed. Anal. 2013; 76:139–144.
(10). Schmidt R. J.Clin. Dermatol. 1986; 4:46–61.
(11). Funk V. A., Susanna A., Stuessy T. F., Robinson H.Classifi-cation of Compositae. Systematics, evolution, and biogeography of the Compositae. Funk V.A., Susanna A., Bayer R. J., editorsInternational Association for Plant Taxonomy;Vienna: 2009. p. 174–189.
(12). Konarev A. V., Anisimova I. N., Gavrilova V. A., Vachrusheva T. E., Konechnaya G. Y., Lewis M., Shewry P. R.Phytochemistry. 2002; 59:279–291.
(13). Wegiera M., Smolarz H. D., Jedruch M., Korczak M., Kopro ní K.Acta Pol. Pharm. 2012; 69:263–268.
(14). Jan G., Khan M. A., Jan F.Ethnobot. Leaflets. 2009; 13:1205–1215.
(15). Ha T. J., Hwang S. W., Jung H. J., Park K. H., Yang M. S.Agric. Chem. Biotechnol. 2002; 45:170–172.
(16). Hitmi A., Barthomeuf C., Coudret A. J.Plant Phys. 1998; 153:233–236.
(17). Nicholson R. L., Hammerschmidt R.Annu. Rev. Phytopathol. 1992; 30:369–389.
crossref
(18). Ksouri R., Megdiche W., Falleh H., Trabelsi N., Boulaaba M., Smaoui A., Abdelly C. C. R.Biol. 2008; 331:865–873.
(19). Han H., Baik B. K.Int. J. Food Sci. Tech. 2008; 43:1971–1978.
crossref
(20). Youdim K. A., Shukitt-Hale B., Joseph J. A.Free Radic. Biol. Med. 2004; 37:1683–1693.
(21). Haenen G. R., Paquay J. B., Korthouwer R. E., Bast A.Biochem. Biophys. Res. Commun. 1997; 236:591–593.
(22). Korda M., Kubant R., Patton S., Malinski T.Am. J. Physiol. Heart Circ. Physiol. 2008; 295:1514–1521.
(23). Rayalam S., Della-Fera M. A., Baile C. A. J.Nutr. Biochem. 2008; 19:717–726.
(24). Tórtora V., Quijano C., Freeman B., Radi R., Castro L.Free Radic. Biol. Med. 2007; 42:1075–1088.
(25). Zhu S., Haddad I. Y., Matalon S.Arch. Biochem. Biophys. 1996; 333:282–290.
(26). Radi R., Beckman J. S., Bush K. M., Freeman B.A.J. Biol. Chem. 1991; 266:4244–4250.
(27). Tamura Y., Nakajima K., Nagayasu K., Takabayashi C.Phytochemistry. 2002; 59:275–278.
(28). Velíšek J., Davídek J., Cejpek K.Czech J. Food Sci. 2008; 26:73–98.
(29). Bowles D., Isayenkova J., Lim E. K., Poppenberger B.Curr. Opin. Plant Biol. 2005; 8:254–263.
(30). Agati G., Biricolti S., Guidi L., Ferrini F., Fini A., Tattini M. J.Plant Physiol. 2011; 168:204–212.
(31). Karki S., Park H. J., Nugroho A., Kim E. J., Jung H. A., Choi J. S. J.Med. Food. 2015; 18:83–94.
(32). Nugroho A., Choi J. S., An H. J., Park H. J.Nat. Prod. Sci. 2015; 21:42–48.
(33). Shimoi K., Okada H., Furugori M., Goda T., Takase S., Suzuki M., Hara Y., Yamamoto H., Kinae N.FEBS Lett. 1998; 438:220–224.
(34). Schneider H., Blaut M.Arch. Microbiol. 2000; 173:71–75.
(35). Lu J., Feng X., Sun Q., Lu H., Manabe M., Sugahara K., Ma D., Sagara Y., Kodama H.Clin. Chim. Acta. 2002; 316:95–99.
(36). Hu C., Kitts D. D.Mol. Cell. Biochem. 2004; 265:107–113.
(37). Jin M., Yang J. H., Lee E. K., Lu Y., Kwon S., Son K. H., Son J. K., Chang H. W.Biol. Pharm. Bull. 2009; 32:1500–1503.
(38). Qiusheng Z., Xiling S., Xubo X. S., Meng S., Changhai W.Pharmazie. 2004; 59:286–289.
(39). Vilela F. C., Soncini R., Giusti-Paiva A. J.Ethnopharmacol. 2009; 124:325–327.
(40). Freitas C. S., Baggio C. H., Finau J., Anginoni M., Pizzolatti M. G., Santos A. R., Marques M. C. J.Pharm. Pharmacol. 2008; 60:1105–1110.
(41). Kim J. S., Kwon C. S., Son K. H.Biosci. Biotechnol. Biochem. 2000; 64:2458–2461.
(42). Han X. H., Hong S. S., Hwang J. S., Lee M. K., Hwang B. Y., Ro J. S.Arch. Pharm. Res. 2007; 30:13–17.
(43). Brown J. E., Rice-Evans C. A.Free Radic. Res. 1998; 29:247–255.
(44). Min Y. S., Bai K. L., Yim S. H., Lee Y. J., Song H. J., Kim J. H., Ham I. H., Whang W. K., Sohn U. D.Arch. Pharm. Res. 2006; 29:484–489.
(45). Nagy M., Krizková L., Mucaji P., Kontseková Z., Sersen F., Krajcovic J.Molecules. 2009; 14:509–518.
(46). Vilela F. C., Padilha-Mde M., Alves-da-Silva G., Soncini R., Giusti-Paiva A. J.Med. Food. 2010; 13:219–222.
(47). Choi S. M., Kim B. C., Cho Y. H., Choi K. H., Chang J., Park M. S., Kim M. K., Cho K. H., Kim J. K.Chonnam Med. J. 2014; 50:45–51.
(48). Salqueiro J. B., Ardenghi P., Dias M., Ferreira M. B. C., Izquierdo I., Medina J. H.Pharmacol. Biochem. Behav. 1997; 58:887–891.
(49). Patil S. P., Jain P. D., Sancheti J. S., Ghumatkar P. J., Tambe R., Sathaye S.Neuropharmacolgy. 2014; 86:192–202.
(50). Ha S. K., Moon E., Lee P., Ryu J. H., Oh M. S., Kim S. Y.Neurochem. Res. 2012; 37:1560–1567.
(51). Watanabe K., Kanno S., Tomizawa A., Yomogida S., Ishikawa M.Oncol. Rep. 2012; 27:204–209.
(52). Fan S. Y., Zeng H. W., Pei Y. H., Li L., Ye J., Pan Y. X., Zhang J. G., Yuan X., Zhang W. D. J.Ethnopharmacol. 2012; 141:647–652.
(53). Calderone V., Chericoni S., Martinelli C., Testai L., Nardi A., Morelli I., Breschi M. C., Martinotti E.Naunyn Schmiedebergs Arch. Pharmacol. 2004; 370:290–298.
(54). Kim H. R., Park C. G., Jung J. Y.Int. J. Mol. Med. 2014; 33:317–324.
(55). Lim H., Son K. H., Chang H. W., Bae K., Kang S. S., Kim H. P.Biol. Pharm. Bull. 2008; 31:2063–2067.
(56). Yoo Y. M., Nam J. H., Kim M. Y., Choi J., Park H. J.Biol Pharm Bull. 2008; 31:760–764.
(57). Juckmeta T., Thongdeeying P., Itharat A.Evid. Based Complement. Alternat. Med. 2014; 2014:828760.
(58). Bors W., Heller W., Michael C., Saran M.Adv. Exp. Med. Biol. 1990; 264:165–170.
(59). Quiñones M., Miguel M., Aleixandre A.Pharmacol. Res. 2013; 68:125–131.
(60). Iwai K., Kishimoto N., Kakino Y., Mochida K., Fujita T. J.Agric. Food Chem. 2004; 52:4893–4898.

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).
nps-22-1f1.tif
Fig. 2.
Traditional use of Hemitepta lyrata as one of Compositae herbs.
nps-22-1f2.tif
Fig. 3.
Chemical structures of several flavonols and flavones.
nps-22-1f3.tif
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.
nps-22-1f4.tif
Fig. 5.
HPLC chromatograms of MeOH extracts of the four Compositae herbs (Compound names are abbreviated).
nps-22-1f5.tif
Fig. 6.
Composition of flavonoids and caffeoylquinic acids in the five Compositae herbs.
nps-22-1f6.tif
Fig. 7.
Peroxynitrite-scavenging activities (IC50 s) of the flavonoids and caffeoylquinic acids identified in the five Compositae herbs.
nps-22-1f7.tif
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   ●      
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 tR (min) Linear regressiona R2b LODc (µg/ml) LOQd (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
Leaf Flower
  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        
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
Leaf Flower
  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        
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
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
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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