Skip to content
Licensed Unlicensed Requires Authentication Published by De Gruyter February 7, 2020

Comparative studies of the biological activities of selected herbal extracts and phenolic compounds isolated from Rosa gallica

Atsumi Shimada, Hiroshi Ueno, Masanori Inagaki and Hitoshi Yoshimitsu

Abstract

This study aimed to compare the biological activities of 35 herbal hydroethanolic extracts and select high potential extract, which showed antioxidative activity and inhibitory activities of α-glucosidase, lipase, and hyaluronidase, and to investigate the isolation, structural elucidation, and biological activities of five phenolic compounds from the selected extracts of Rosa gallica. On the basis of one-dimensional nuclear magnetic resonance together with the comparison with the literature values, the phenolic compounds were identified as methyl gallate (1), kaempferol-3-O-arabinofuranoside (2), multinoside A acetate (3), kaempferol (4), and quercetin (5), respectively. The results suggest that the extracts from R. gallica show the strongest biological activities in 35 herbal extracts and that 1, 4, and 5 among the five isolated compounds from rose extracts are effective in promoting antioxidative and enzymatic inhibitory activities.

  1. Funding sources: This research did not receive any specific grant from funding agencies in the public, commercial, or not-for-profit sectors.

  2. Conflicts of interest: The authors state no conflict of interest.

References

1. Comfort Keepers. Herbal gardening and its benefits. 2014. https://www.comfortkeepers.com/home/info-center/senior-independent-living/benefits-of-herbal-gardening. Accessed: 27 February 2019.Search in Google Scholar

2. Ruiz-Cruz S, Chaparro-Hernandez S, Hernandez-Ruiz KL, Cira-Chavez LA, Estrada-Alvarado MI, Gassos Ortega LE, et al. Flavonoids: important biocompounds in food. In: Justino GC, editor. Flavonoids: from biosynthesis to human health. London: IntechOpen, 2017:353–70.Search in Google Scholar

3. Bohn T. Carotenoids, chronic disease prevention and dietary recommendations. Int J Vitam Nutr Res 2017;87:121–30.10.1024/0300-9831/a000525Search in Google Scholar PubMed

4. Cor D, Knez Z, Hrncic MK. Antitumour, antimicrobial, antioxidant and antiacetylcholinesterase effect of Ganoderma lucidum terpenoids and polysaccharides: a review. Molecules 2018;23:1–21.10.3390/molecules23030649Search in Google Scholar PubMed PubMed Central

5. Mariyappan S, Pichaiyan V, Ramalingam S, Saravanan R. A review on the role of phytoconstituents in cancer cells. J Glob Pharm Technol 2018;10:16–24.Search in Google Scholar

6. Johnson RL, Foster S, Dog TL, Kiefer D. The world of medicinal herbs. In: Grogan BB, editor. Guide to medicinal herbs. Washington, DC: National Geographic Society, 2010:8–10.Search in Google Scholar

7. Spínola V, Castilho PC. Evaluation of Asteraceae herbal extracts in the management of diabetes and obesity. Contribution of caffeoylquinic acids on the inhibition of digestive enzymes activity and formation of advanced glycation end-products (in vitro). Phytochemistry 2017;143:29–35.10.1016/j.phytochem.2017.07.006Search in Google Scholar PubMed

8. Tang KS, Konczak I, Zhao J. Phenolic compounds of the Australian native herb Prostanthera rotundifolia and their biological activities. Food Chem 2017;233:530–9.10.1016/j.foodchem.2017.04.137Search in Google Scholar PubMed

9. Masuda H, Hironaka S, Matsui Y, Hirooka S, Hirai M, Hirata Y, et al. Comparative study of the antioxidative activity of culinary herbs and spices, and hepatoprotective effects of three selected Lamiaceae plants on carbon tetrachloride-induced oxidative stress in rats. Food Sci Technol Res 2015;21:407–18.10.3136/fstr.21.407Search in Google Scholar

10. Yamaguchi S, Sugahara T, Nakashima Y, Okada A, Akiyama K, Kishida T, et al. Radical and superoxide scavenging activities of matairesinol and oxidized matairesinol. Biosci Biotechnol Biochem 2006;70:1934–40.10.1271/bbb.60096Search in Google Scholar PubMed

11. Kim SH, Kwon C, Lee JS, Son KH, Lim JK, Kim J. Inhibition of carbohydrate-digesting enzymes and amelioration of glucose tolerance by Korean medicinal herbs. J Food Sci Nutr 2002;7: 62–6.10.3746/jfn.2002.7.1.062Search in Google Scholar

12. Kwon YI, Vattem DA, Shetty K. Evaluation of clonal herbs of Lamiaceae species for management of diabetes and hypertension. Asia Pac J Clin Nutr 2006;15:107–18.Search in Google Scholar

13. Itoh N, Kurokawa J, Isogai Y, Ogasawara M, Matsunaga T, Okubo T, et al. Functional characterization of epitheaflagallin 3-O–gallate generated in laccase-treated green tea extracts in the presence of gallic acid. J Agric Food Chem 2017;65:10473–81.10.1021/acs.jafc.7b04208Search in Google Scholar PubMed

14. Kawaguchi K, Mizuno T, Aida K, Uchino K. Hesperidin as an inhibitor of lipases from porcine pancreas and Pseudomonas. Biosci Biotechnol Biochem 1997;61:102–4.10.1271/bbb.61.102Search in Google Scholar PubMed

15. Kim M, Kim Y, Chung S. Identification and in vitro biological activities of flavonols in garlic leaf and shoot: inhibition of soybean lipoxygenase and hyaluronidase activities and scavenging of free radicals. J Agric Food Chem 2005;85:633–40.10.1002/jsfa.1899Search in Google Scholar

16. Kim KH, Park SJ, Lee JE, Lee YJ, Song CH, Choi SH, et al. Anti–skin-aging benefits of exopolymers from Aureobasidium pullulans SM2001. J Cosmet Sci 2014;65:285–98.Search in Google Scholar

17. Kuppusamy UR, Khoo HE, Das NP. Structure-activity studies of flavonoids as inhibitors of hyaluronidase. Biochem Pharm 1990;40:397–401.10.1016/0006-2952(90)90709-TSearch in Google Scholar

18. Camacho-Cristobal JJ, Anzellotti D, Gonzalez-Fontes A. Changes in phenolic metabolism of tobacco plants during short-term boron deficiency. Plant Physiol Biochem 2002;40:997–1002.10.1016/S0981-9428(02)01463-8Search in Google Scholar

19. McCord JM, Fridovich I. Superoxide dismutase an enzymic function for erythrocuprein (hemocuprein). J Biol Chem 1969;244:6049–55.10.1016/S0021-9258(18)63504-5Search in Google Scholar

20. Sanbongi C, Takano H, Osakabe N, Sasa N, Natsume M, Yanagisawa R, et al. Rosmarinic acid inhibits lung injury induced by diesel exhaust particles. Free Rad Biol Med 2003;34:1060–106.10.1016/S0891-5849(03)00040-6Search in Google Scholar

21. Yamaki K, Mori Y. Evaluation of α-glucosidase inhibitory activity in colored foods: a trial using slope factors of regression curves (in Japanese). Nippon Shokuhin Kagaku Kogaku Kaishi 2006;53:229–31.10.3136/nskkk.53.229Search in Google Scholar

22. Bilal A, Usman AA, Muhammad M. Medicinal plant phytochemicals and their inhibitory activities against pancreatic lipase: molecular docking combined with molecular dynamics simulation approach. Nat Prod Res 2018;32:1123–9.10.1080/14786419.2017.1320786Search in Google Scholar PubMed

23. Murata T, Watahiki M, Tanaka Y, Miyase T, Yoshizaki F. Hyaluronidase inhibitors from Takuran, Lycopus lucidus. Chem Pharm Bull 2010;58:394–7.10.1248/cpb.58.394Search in Google Scholar PubMed

24. Ippoushi K, Yamaguchi Y, Itou H, Azuma K, Higashio H. Evaluation of inhibitory effects of vegetables and herbs on hyaluronidase and identification of rosmarinic acid as a hyaluronidase inhibitor in lemon balm (Melissa officinalis L.). Food Sci Technol Res 2000;6:74–7.10.3136/fstr.6.74Search in Google Scholar

25. Kang W, Song Y, Zhang L. Glucosidase inhibitory and antioxidant properties and antidiabetic activity of Hypericum ascyron L. Med Chem Res 2011;20:809–16.10.1007/s00044-010-9391-5Search in Google Scholar

26. Lee M, Nam TG, Lee I, Shin EJ, Han A, Lee P, et al. Skin anti-inflammatory activity of rose petal extract (Rosa gallica) through reduction of MAPK signaling pathway. Food Sci Nutr 2018;6:2560–7.10.1002/fsn3.870Search in Google Scholar PubMed PubMed Central

27. Ochir S, Nishizawa M, Park BJ, Ishii K, Kanazawa T, Funaki M, et al. Inhibitory effects of Rosa gallica on the digestive enzymes. J Nat Med 2010;6:275–80.10.1007/s11418-010-0402-0Search in Google Scholar PubMed

28. Ochir S, Yuki T, Kanazawa T, Nishizawa M, Yamagishi T. Two galloylated flavonoids as antioxidants in Rosa gallica petals. Chem Nat Comp 2013;49:940–2.10.1007/s10600-013-0787-6Search in Google Scholar

29. Abd EI-Azim MH, Abdelgawad AA, EI-Gerby M, Ali S, EI-Mesallamy AM. Phenolic compounds and cytotoxic activities of methanol extract of basil (Ocimum basilicum L.). J Microb Biochem Technol 2015;7:182–5.10.4172/1948-5948.1000202Search in Google Scholar

30. Orabi MA, Orabi EA. Antiviral and antioxidant activities of flavonoids of Ficus virens: experimental and theoretical investigations. J Pharm Phytochem 2016;5:120–8.Search in Google Scholar

31. Nabavi SF, Habtemariam S, Lorenzo AD, Sureda A, Khanjani S, Nabavi SM, et al. Post-stroke depression modulation and in vivo antioxidant activity of gallic acid and its synthetic derivatives in a murine model system. Nutrients 2016;8:248–60.10.3390/nu8050248Search in Google Scholar PubMed PubMed Central

32. Seto T, Yasuda I, Akiyama K. Purgative activity and principals of the fruits of Rosa multiflora and R. wichuraiana. Chem Pharm Bull 1992;40:2080–2.10.1248/cpb.40.2080Search in Google Scholar PubMed

33. Correia S, David JM, David JP, Lopes LM, Guedes ML. Flavonóides, norisoprenóides e outros terpenos das folhas de Tapirira guianensis. Química Nova 2008;31:2056–9.10.1590/S0100-40422008000800027Search in Google Scholar

34. Reber JD, Eggett DL, Parker TL. Antioxidant capacity interactions and a chemical/structural model of phenolic compounds found in strawberries. Int J Food Sci Nutr 2011;62:445–52.10.3109/09637486.2010.549115Search in Google Scholar PubMed

35. Huguet AI, Manez S, Alcaraz MJ. Superoxide scavenging properties of flavonoids in a non-enzymic system. Z Naturforsch 1990;45c:19–24.10.1515/znc-1990-1-205Search in Google Scholar PubMed

36. Tadera K, Minami Y, Takamatsu K, Matsuoka T. Inhibition of α-glucosidase and α-amylase by flavonoids. J Nutr Sci Vitaminol 2006;52:149–53.10.3177/jnsv.52.149Search in Google Scholar PubMed

37. Lee J, Kim G. Evaluation of antioxidant and inhibitory activities for different subclasses flavonoids on enzymes for rheumatoid arthritis. J Food Sci 2010;75:212–7.10.1111/j.1750-3841.2010.01755.xSearch in Google Scholar PubMed

Received: 2019-06-18
Revised: 2019-07-31
Accepted: 2019-09-18
Published Online: 2020-02-07
Published in Print: 2020-01-28

©2020 Walter de Gruyter GmbH, Berlin/Boston

Scroll Up Arrow