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

Atsumi Shimada 1 , Hiroshi Ueno 2 , Masanori Inagaki 3 ,  and Hitoshi Yoshimitsu 4
  • 1 Division of Food and Nutrition, Nakamura Gakuen University Junior College, 5-7-1 Befu, Jonan-ku, Fukuoka 814-0198, Japan
  • 2 Department of Medical Technology, Kawasaki University of Medical Welfare, 701-0193, Okayama, Japan
  • 3 Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Yasuda Women’s University, 731-0153, Hiroshima, Japan
  • 4 Department of Pharmaceutical Sciences, Faculty of Pharmacy, Sojo University, 860-0082, Kumamoto, Japan
Atsumi Shimada
  • Corresponding author
  • Division of Food and Nutrition, Nakamura Gakuen University Junior College, 5-7-1 Befu, Jonan-ku, Fukuoka 814-0198, Japan
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, Hiroshi Ueno
  • Department of Medical Technology, Kawasaki University of Medical Welfare, Okayama, 701-0193, Japan
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, Masanori Inagaki
  • Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Yasuda Women’s University, Hiroshima, 731-0153, Japan
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and Hitoshi Yoshimitsu
  • Department of Pharmaceutical Sciences, Faculty of Pharmacy, Sojo University, Kumamoto, 860-0082, Japan
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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.

    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.

  • 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.

  • 3.

    Bohn T. Carotenoids, chronic disease prevention and dietary recommendations. Int J Vitam Nutr Res 2017;87:121–30.

    • Crossref
    • PubMed
    • Export Citation
  • 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.

  • 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.

  • 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.

  • 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.

    • Crossref
    • PubMed
    • Export Citation
  • 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.

    • Crossref
    • PubMed
    • Export Citation
  • 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.

    • Crossref
    • Export Citation
  • 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.

    • Crossref
    • PubMed
    • Export Citation
  • 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.

  • 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.

    • PubMed
    • Export Citation
  • 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.

    • Crossref
    • PubMed
    • Export Citation
  • 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.

    • Crossref
    • PubMed
    • Export Citation
  • 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.

    • Crossref
    • Export Citation
  • 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.

    • PubMed
    • Export Citation
  • 17.

    Kuppusamy UR, Khoo HE, Das NP. Structure-activity studies of flavonoids as inhibitors of hyaluronidase. Biochem Pharm 1990;40:397–401.

    • Crossref
    • Export Citation
  • 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.

    • Crossref
    • Export Citation
  • 19.

    McCord JM, Fridovich I. Superoxide dismutase an enzymic function for erythrocuprein (hemocuprein). J Biol Chem 1969;244:6049–55.

    • PubMed
    • Export Citation
  • 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.

    • Crossref
    • Export Citation
  • 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.

    • Crossref
    • Export Citation
  • 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.

    • Crossref
    • PubMed
    • Export Citation
  • 23.

    Murata T, Watahiki M, Tanaka Y, Miyase T, Yoshizaki F. Hyaluronidase inhibitors from Takuran, Lycopus lucidus. Chem Pharm Bull 2010;58:394–7.

    • Crossref
    • PubMed
    • Export Citation
  • 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.

    • Crossref
    • Export Citation
  • 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.

    • Crossref
    • Export Citation
  • 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.

    • Crossref
    • PubMed
    • Export Citation
  • 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.

  • 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.

    • Crossref
    • Export Citation
  • 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.

  • 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.

  • 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.

    • Crossref
    • Export Citation
  • 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.

    • Crossref
    • Export Citation
  • 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.

    • Crossref
    • Export Citation
  • 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.

    • Crossref
    • Export Citation
  • 35.

    Huguet AI, Manez S, Alcaraz MJ. Superoxide scavenging properties of flavonoids in a non-enzymic system. Z Naturforsch 1990;45c:19–24.

  • 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.

    • Crossref
    • PubMed
    • Export Citation
  • 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.

    • Crossref
    • Export Citation
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A Journal of Biosciences: Zeitschrift für Naturforschung C (ZNC) is an international scientific journal for the emerging field of natural and natural-like products. ZNC publishes original research on the isolation, bio-chemical synthesis and bioactivities of natural products, their biochemistry, pharmacology, biotechnology, and biological activity and innovative developed computational methods for predicting their structure and/or function.

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