Journal of Applied Biological Chemistry

The Korean Society for Applied Biological Chemistry (한국응용생명화학회)
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Phytochemical constituents of Lactuca serriola leaves and their content analysis by HPLC-UV

  • Kim, Juree (Department of Plant Science and Technology, Chung-Ang University) ;
  • Lee, Hak-Dong (Department of Plant Science and Technology, Chung-Ang University) ;
  • Choi, Jungwon (Department of Plant Science and Technology, Chung-Ang University) ;
  • Lee, Sanghyun (Department of Plant Science and Technology, Chung-Ang University)
  • Received : 2022.06.17
  • Accepted : 2022.07.19
  • Published : 2022.09.30
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Abstract

This study aimed to identify the phytochemical constituents of Lactuca serriola leaves and perform quantitative analysis of the methanol (MeOH) extract of L. serriola, L. indica, L. raddeana, L. sativa, and L. triangulata. Six compounds were isolated from the MeOH extracts of L. serriola using open column chromatography and identified as protocatechuic acid (1), caffeic acid (2), cynaroside (3), apigenin 7-glucuronide (4), luteolin (5), and apigenin (6) using 1H-, 13C-nuclear magnetic resonance, and mass spectrometry. Quantitative analysis of the six compounds was performed on the MeOH extract of Lactuca species using high-performance liquid chromatography (HPLC) and an ultraviolet (UV). A reverse-phased column was used, and the UV absorbance was set to 280 nm. The contents of compounds 2 and 3 were the highest (1.58 and 2.64 mg/g ext., respectively) in L. serriola extracts. However, compounds 4 and 6 were higher (1.46 and 0.40 mg/g ext., respectively) in L. triangulata. These results provide quantitative data for the application of Lactuca species in the pharmaceutical and functional food industries.

Keywords

Acknowledgement

This research was supported by a grant from Natural Product Institute of Science and Technology, Anseong 17546, Republic of Korea. We gratefully acknowledge Mr. Dong-gun Woo for the collection of the plant material and fundamental side experiments.

References

  1. Baquar SR (1989) Medicinal and poisonous plants of Pakistan. Karachi, Pakistan
  2. Mucina L (1978) Ruderal communities with dominant species Lactuca serriola. Biologia (Bratislava) 33: 809-819
  3. Hussein N, Amen Y, Abdel Bar F, Halim A, Saad H-E (2020) Antioxidants and α-glucosidase inhibitors from Lactuca serriola L. Rec Nat Prod 14: 410-415 https://doi.org/10.25135/rnp.189.2005.1647
  4. Bouimeja B, Yetongnon K, Touloun O, Berrougui H, Laaradia M, Ouanaimi F, Chait A, Boumezzough A (2019) Studies on antivenom activity of Lactuca serriola methanolic extract against Buthus atlantis scorpion venom by in vivo methods. S Afr J Bot 125: 270-279. doi:10.1016/j.sajb.2019.07.044
  5. Dymock W, Warden CJH, Hooper D (1983) Pharmacographia Indica: A history of the principal drugs of vegetable origin, met with in British India. K. Paul, Trench, Trubner & Company
  6. Usmanghani K, Saeed A, Alam MT (1997) Indusyunic medicine : traditional medicine of herbal animal and mineral origin in Pakistan. Karachi: Dept. of Pharmacognosy, Faculty of Pharmacy, University of Karachi
  7. Marco JA, Sanz JF, Albiach R (1992) A sesquiterpene ester from Lactuca-serriola. Phytochemistry 31: 2539-2540. doi: 10.1016/0031-9422(92)83321-O
  8. Kim DK (2001) Antioxidative components from the aerial parts of Lactuca scariola L. Arch Pharm Res 24: 427-430. doi: 10.1007/BF02975189
  9. Ryu T-B, Lim J-C, Lee C-H, Kim E-J, Choi B-K (2017) Distribution of invasive species in metropolitan Busan, South Korea. J Life Sci 27: 408-416. doi: 10.5352/JLS.2017.27.4.408
  10. Kim G (2020) Alien species, american bullfrog (Lithobatus catesbeianus) and making invasive species in Korea. Dissertation, Seoul National University
  11. Lee I-Y, Kim S-H, Hong S-H (2021) Occurrence characteristics and management of invasive weeds, Ambrosia artemisiifolia, Ambrosia trifida and Humulus japonicus. Weed Turf Sci 10: 227-242
  12. Lim DO, Hwang IC, Chekar E, Choi DH (2016) A management of invasive alien species and naturalized plant at Jeonju city. Proceeding of the Korean J Environ Ecol Conference 2016: 93
  13. Awan AF, Akhtar MS, Anjum I, Mushtaq MN, Fatima A, Mannan A, Ali I (2020) Anti-oxidant and hepatoprotective effects of Lactuca serriola and its phytochemical screening by HPLC and FTIR analysis. Pak J Pharm Sci 33: 2823-2830
  14. Moon S-I, Kim S-W, Huh W, Kim S-Y, Kim J-S, Lee K-J (2009) Isolation and characterization of bio-active materials from prickly lettuce (Lactuca serriola). J Life Sci 19: 206-212. doi: 10.5352/JLS.2009.19.2.206
  15. Werk KS, Ehleringer J (1985) Photosynthetic characteristics of Lactuca serriola L. Plant Cell Environ 8: 345-350. doi: 10.1111/j.1365-3040.1985.tb01409.x
  16. Guo S, Fang F, Ni L, Chen W, Shi L (2006) Photosynthetic characteristics and coenological survey of Lactuca serriola in its invaded area. Chin J Appl Ecol 17: 2316-2320
  17. Alexander JM (2010) Genetic differences in the elevational limits of native and introduced Lactuca serriola populations. J Biogeogr 37: 1951-1961. doi: 10.1111/j.1365-2699.2010.02335.x
  18. El-Esawi MA, Elkelish A, Elansary HO, Ali HM, Elshikh M, Witczak J, Ahmad M (2017) Genetic transformation and hairy root induction enhance the antioxidant potential of Lactuca serriola L. Oxid Med Cell 2017: 5604746. doi: 10.1155/2017/5604746
  19. Novotna A, Dolezalova I, Lebeda A, Krskova M, Berka T (2011) Morphological variability of achenes of some European populations of Lactuca serriola L. Flora 206: 473-483. doi: 10.1016/j.flora.2010.09.012
  20. An L, Guan S, Shi G, Bao Y, Duan Y, Jiang B (2006) Protocatechuic acid from Alpinia oxyphylla against MPP+-induced neurotoxicity in PC12 cells. Food Chem Toxicol 44: 436-443. doi: 10.1016/j.fct.2005.08.017
  21. Jeong C-H, Jeong HR, Choi GN, Kim D-O, Lee U, Heo HJ (2011) Neuroprotective and anti-oxidant effects of caffeic acid isolated from Erigeron annuus leaf. Chin Med 6: 1-9. doi: 10.1186/1749-8546-6-25
  22. Kim MJ, Wang HS, Lee MW (2020) Anti-inflammatory effects of fermented bark of Acanthopanax sessiliflorus and its isolated compounds on lipopolysaccharide-treated RAW 264.7 macrophage cells. Evid-based Complement Altern 2020. doi: 10.1155/2020/6749425
  23. Liu W, Nisar MF, Wan C (2020) Characterization of phenolic constituents from Prunus cerasifera Ldb leaves. J Chem 2020. doi: 10.1155/2020/5976090
  24. Eshbakova K, Toshmatov Z, Yili A, Aisa H, Abdullaev N (2013) Flavonoid galacturonides and glucuronide from the aerial part of Scutellaria schachristanica. Chem Nat Compd 49: 103-105. doi:10.1007/s10600-013-0519-y
  25. Fajriah S, Megawati M, Darmawan A (2016) Apigenin, an anticancer isolated from Macaranga gigantifolia leaves. J Trop Life Sci 6: 7-9 https://doi.org/10.11594/jtls.06.01.02
  26. Hu W, Wang X, Wu L, Shen T, Ji L, Zhao X, Si C-L, Jiang Y, Wang G (2016) Apigenin-7-O-β-D-glucuronide inhibits LPS-induced inflammation through the inactivation of AP-1 and MAPK signaling pathways in RAW 264.7 macrophages and protects mice against endotoxin shock. Food Funct 7: 1002-1013. doi: 10.1039/c5fo01212k
  27. Lin L-C, Pai Y-F, Tsai T-H (2015) Isolation of luteolin and luteolin-7-O-glucoside from Dendranthema morifolium Ramat Tzvel and their pharmacokinetics in rats. J Agric Food Chem 63: 7700-7706. doi:10.1021/jf505848z
  28. Park C-H, Hur J-M, Song K-S, Park J-C (2007) Phenolic compounds from the leaves of Nelumbo nucifera showing DPPH radical scavenging effect. Korean J Pharmacogn 38: 263-269
  29. Van Loo P, De Bruyn A, Budesinsky M (1986) Reinvestigation of the structural assignment of signals in the 1H and 13C NMR spectra of the flavone apigenin. Magn Reson Chem 24: 879-882. doi: 10.1002/mrc.1260241007
  30. Delage B (2015) Flavonoids. Linus Pauling Institute, Oregon State University, Corvallis, Oregon
  31. Sedlarova M, Lebeda A (2001) Histochemical detection and role of phenolic compounds in the defense response of Lactuca spp. to lettuce downy mildew (Bremia lactucae). J Phytopathol 149: 693-697. doi:10.1046/j.1439-0434.2001.00698.x
  32. Wang SY, Chang HN, Lin KT, Lo CP, Yang NS, Shyur LF (2003) Antioxidant properties and phytochemical characteristics of extracts from Lactuca indica. J Agric Food Chem 51: 1506-1512. doi: 10.1021/jf0259415
  33. Nugroho A, Choi JS, An H-J, Park H-J (2015) Phytochemical analysis of the phenolic fat-suppressing substances in the leaves of Lactuca raddeana in 3T3-L1 adipocytes. Nat Prod Sci 21: 42-48
  34. Kim MJ, Moon Y, Tou JC, Mou B, Waterland NL (2016) Nutritional value, bioactive compounds and health benefits of lettuce (Lactuca sativa L.). J Food Compos Anal 49: 19-34. doi: 10.1016/j.jfca.2016.03.004
  35. Degl'Innoocenti E, Pardossi A, Tattini M, Guidi L (2008) Phenolic compounds and antioxidant power in minimally processed salad. J Food Biochem 32: 642-653. doi: 10.1111/j.1745-4514.2008.00188.x
  36. Kim M-H, Nugroho A, Lim S-C, Moon H-E, Choi J-S, Park H-J (2011) Phytochemical analysis of phenolic compounds in 30% ethanolic extracts from the Compositae plants and peroxynitrite-scavenging effect. Korean J Pharmacogn 42: 149-15