Abstract
Phytochemical investigation of the semi-parasitic plant, Plicosepalus curviflorus (Loranthaceae) growing in Saudi Arabia resulted in the isolation of a new catechin–gallic acid derivative of inositol, plicosepalin A (1) [(+) catechin-4′-O-(1″-O-galloyl-5″-O-methyl)-myo-inositol], along with seven known compounds: methyl gallate (2), catechin (3), quercetin (4), gallic acid (5), lupeol (6), β-sitosterol (7), and ursolic acid (8). Their structures were elucidated on the basis of spectroscopic analyses, including HRESIMS, ESIMS, 1H and 13C NMR, HSQC, and HMBC, as well as comparison with reported data. The antioxidant and antimicrobial activities of 1 were evaluated using 2,2-diphenyl-1-picrylhydrazyl (DPPH) and the disc diffusion assay, respectively. Compound 1 exhibited potent free radical scavenging activity with an IC50 value of 9.0 ± 0.27 μM. Moreover, significant activities against Staphylococcus aureus and Bacillus subtilis were recorded.
References
1. Moghadamtousi SZ, Hajrezaei M, Abdul Kadir H, Zandi K. Loranthus micranthus Linn.: Biological activities and phytochemistry. Evid Based Complement Altern Med 2013;2013:1–9.10.1155/2013/273712Search in Google Scholar
2. Deeni YY, Sadiq NM. Antimicrobial properties and phytochemical constituents of the leaves of African mistletoe (Tapinanthus dodoneifolius (DC) Danser) (Loranthaceae): an ethnomedicinal plant of Hausaland, Northern Nigeria. J Ethnopharmacol 2002;83:235–40.10.1016/S0378-8741(02)00244-1Search in Google Scholar
3. Costa RM, Vaz AF, Oliva ML, Coelho LC, Correia MT, Carneiro-da-Cunha MG. A new mistletoe Phthirusa pyrifolia leaf lectin with antimicrobial properties. Process Biochem 2010;45:526–33.10.1016/j.procbio.2009.11.013Search in Google Scholar
4. Obatomi DK, Bikomo EO, Temple VJ. Anti-diabetic properties of the African mistletoe in streptozotocin-induced diabetic rats. J Ethnopharmacol 1994;43:13–7.10.1016/0378-8741(94)90111-2Search in Google Scholar
5. Osadebe PO, Okide GB, Akabogu IC. Study on anti-diabetic activities of crude methanolic extracts of Loranthus micranthus (Linn.) sourced from five different host trees. J Ethnopharmacol 2004;95:133–8.10.1016/j.jep.2004.06.029Search in Google Scholar PubMed
6. Moreno-Salazara SF, Robles-Zepedab RE, Johnsona DE. Plant folk medicines for gastrointestinal disorders among the main tribes of Sonora, Mexico. Fitoterapia 2008;79:132–41.10.1016/j.fitote.2007.07.009Search in Google Scholar PubMed
7. Al-Taweel AM, Perveen S, Fawzy GA, Alqasoumi SI, El Tahir KE. New flavane gallates isolated from the leaves of Plicosepalus curviflorus and their hypoglycemic activity. Fitoterapia 2012;83:1610–15.10.1016/j.fitote.2012.09.010Search in Google Scholar PubMed
8. Waly NM, Ali A EE, Jrais RN. Botanical and biological studies of six parasitic species of family Loranthaceae growing in Kingdom of Saudi Arabia. Int J Enviro Sci 2012;4:196–205.Search in Google Scholar
9. Fawzy GA, Al-Taweel AM, Perveen S. Anticancer activity of flavane gallates isolated from Plicosepalus curviflorus, Pharmacogn Mag 2014;10:S519–S23.10.4103/0973-1296.139787Search in Google Scholar PubMed PubMed Central
10. Mohamed GA, Ibrahim SR, Shaaban MI, Ross SA. Mangostanaxanthones I and II, new xanthones from the pericarp of Garcinia mangostana. Fitoterapia 2014;98:215–21.10.1016/j.fitote.2014.08.014Search in Google Scholar PubMed
11. Zhang M, Swarts SG, Yin L, Liu C, Tian Y, Cao Y. Antioxidant properties of quercetin. Adv Exp Med Biol 2011;701:283–9.10.1007/978-1-4419-7756-4_38Search in Google Scholar PubMed
12. Acar JF, Goldstein FW. Disk susceptibility test. In: Lorian V, editor. Antibiotics in laboratory medicine, 4th ed. Baltimore, MD: Williams and Wilkins, 1996:1–51.Search in Google Scholar
13. Harborne JB, Mabry H. The Flavonoids. New York, NY: Chapman & Hall, 1975.10.1007/978-1-4899-2909-9Search in Google Scholar
14. Markham K. Techniques of flavonoid identification. New York, NY: Academic Press, 1982.Search in Google Scholar
15. Silverstein RM, Webster FX. Spectrometric identification of organic compounds, 6th ed. New York, NY: John Wiley, & Sons, Inc., 1998.Search in Google Scholar
16. Abraham RJ, Byrne JJ, Griffiths L, Koniotou R. 1H chemical shifts in NMR: Part 22+-Prediction of the 1H chemical shifts of alcohols, diols and inositols in solution, a conformational and salvation investigation. Magn Reson Chem 2005;43:611–24.10.1002/mrc.1611Search in Google Scholar
17. Salazar-Pereda V, Martinez-Martinez FJ, Contreras R, Flores-Parra A. NMR and X-ray diffraction study of some inositol derivatives. J Carb Chem 1997;16:1479–507.10.1080/07328309708005762Search in Google Scholar
18. Rebecca OP, Boyce AN, Somasundram C. Isolation and identification of myo-inositol crystals from dragon fruit (Hylocereus polyrhizus). Molecules 2012;17:4583–94.10.3390/molecules17044583Search in Google Scholar
19. Khalid SA, Yagi SM, Khristova P, DuddecK H. (+)-Catechin-5-galloyl ester as a new natural polyphenol from the bark of Acacia nilotica of Sudanese origin. Planta Med 1989;55:556–8.10.1055/s-2006-962094Search in Google Scholar
20. Ivanov SA, Nomura K, Malfanov IL, Sklyar IV, Ptitsyn LR. Isolation of a new catechin from Bergenia rhizomes that has pronounced lipase-inhibiting and antioxidative properties. Fitoterapia 2011;82:212–8.10.1016/j.fitote.2010.09.013Search in Google Scholar
21. Davis AL, Cai Y, Davies AP, Lewie JR. 1H and 13C NMR assignments of some green tea polyphenols. Magn Reson Chem 1996;34:887–90.10.1002/(SICI)1097-458X(199611)34:11<887::AID-OMR995>3.0.CO;2-USearch in Google Scholar
22. Mohamed GA, Ibrahim SR, Abdelkader MS, Al-Musayeib NM, Ghoneim M, Ross SA. Zeaoxazolinone, a new antifungal agent from Zea mays roots. Med Chem Res 2014;23:4627–30.10.1007/s00044-014-1026-9Search in Google Scholar
23. Sang S, Lapsley K, Rosen RT, Ho C. New prenylated benzoic acid and other constituents from almond hulls (Prunus amygdalus Batsch). J Agric Food Chem 2002;50;607–9.10.1021/jf0110194Search in Google Scholar
24. Al-Musayeib NM, Mohamed GA, Ibrahim SR, Ross SA. New thiophene and flavonoid from Tagetes minuta leaves growing in Saudi Arabia. Molecules 2014;19:2819–28.10.3390/molecules19032819Search in Google Scholar
25. Gerothanassis IP, Exarchou V, Lagouri V, Troganis A, Tsimidou M, Boskou D. Methodology for identification of phenolic acids in complex phenolic mixtures by high-resolution twodimensional nuclear magnetic resonance: application to methanolic extracts of two Oregano species. J Agric Food Chem 1998;46:4185–92.10.1021/jf9804591Search in Google Scholar
26. Al-Musayeib NM, Mohamed GA, Ibrahim SR, Ross SA. Lupeol-3-O-decanoate, a new triterpene ester from Cadaba farinosa Forssk. growing in Saudi Arabia. Med Chem Res 2013;22:5 297–302.10.1007/s00044-013-0536-1Search in Google Scholar
27. Mohamed GA, Abdel-Lateff A, Fouad MA, Ibrahim SR, Elkhayat ES, Okino T. Chemical composition and hepatoprotective activity of Imperata cylindrica Beauv. Pharmacogn Mag 2009; 4:28–36.Search in Google Scholar
28. Mohamed GA, Ibrahim SR. Eucalyptone G. A new phloroglucinol derivative and other constituents from Eucalyptus globulus Labill. ARKIVOC 2007;xv:281–91.10.3998/ark.5550190.0008.f27Search in Google Scholar
29. Maiese K, Chong ZZ, Shang YC. Mechanistic insights into diabetes mellitus and oxidative stress. Curr Med Chem 2007;14:1729–38.10.2174/092986707781058968Search in Google Scholar PubMed PubMed Central
30. Naziro M, Butterworth P. Protective effects of moderate exercise with dietary vitamin C and E on blood antioxidant defense mechanism in rats with streptozotocin-induced diabetes. Can J Appl Physiol 2005;30:172–85.10.1139/h05-113Search in Google Scholar PubMed
31. Tachakittirungrod S, Okonogi S, Chowwanapoonpohn S. Study on antioxidant activity of certain plants in Thailand: Mechanism of antioxidant action of guava leave extract. J Food Chem 2007;103:381–8.10.1016/j.foodchem.2006.07.034Search in Google Scholar
32. Bansal P, Paul P, Mudgal J, Nayak PG, Pannakal ST, Priyadarsini KI, et al. Antidiabetic, antihyperlipidemic and antioxidant effects of the flavonoid rich fraction of Pilea microphylla (L.) in high fat diet/streptozotocin-induced diabetes in mice. Exp Toxicol Pathol 2012;64:651–8.10.1016/j.etp.2010.12.009Search in Google Scholar PubMed
33. Prasad V, Anjana T, Banerji A, Gopalakrishnapilla A. Gallic acid induces GLUT4 translocation and glucose uptake activity in 3T3-L1 cells. FEBS Lett 2010;584:531–6.10.1016/j.febslet.2009.11.092Search in Google Scholar PubMed
34. Abdelmoaty MA, Ibrahim MA, Ahmed NS, Abdelaziz MA. Confirmatory studies on the antioxidant and antidiabetic effect of quercetin in rats. Indian J Clin Biochem 2010;25:188–92.10.1007/s12291-010-0034-xSearch in Google Scholar PubMed PubMed Central
35. Firdous SM. Phytochemicals for treatment of diabetes. EXCLI J 2014;13:451–3.Search in Google Scholar
36. Lakshmi V, Mahdi AA, Ahmad MK, Agarwal SK, Srivastava AK. Antidiabetic activity of lupeol and lupeol esters in streptozotocin-induced diabetic rats. Bangladesh Pharm J 2014;17:138–46.10.3329/bpj.v17i2.22330Search in Google Scholar
37. Aldawsari HM, Hanafy A, Labib GS, Badr JM. Antihyperglycemic activities of extracts of the mistletoes Plicosepalus acaciae and P. curviflorus in comparison to their solid lipid nanoparticle suspension formulations. Z Naturforsch 2014;69c:391–8.10.5560/znc.2014-0047Search in Google Scholar PubMed
©2016 Walter de Gruyter GmbH, Berlin/Boston
Articles in the same Issue
- Frontmatter
- Research Articles
- Seasonal variation of gastroprotective terpenoids in Maytenus robusta (Celastraceae) quantified by gas chromatography-flame ionization detection (GC-FID)
- Plicosepalin A, a new antioxidant catechin–gallic acid derivative of inositol from the mistletoe Plicosepalus curviflorus
- New lupan-type triterpenoids
- Penicilloitins A and B, new antimicrobial fatty acid esters from a marine endophytic Penicillium species
- Anti-acetylcholinesterase activity of essential oils and their major constituents from four Ocimum species
- The chemical composition, antimicrobial, and antioxidant activities of Pycnocycla spinosa and Pycnocyla flabellifolia essential oils
- Biological evaluation and docking studies of some benzoxazole derivatives as inhibitors of acetylcholinesterase and butyrylcholinesterase
- LC/ESI-MS/MS profiling of Ulmus parvifolia extracts and evaluation of its anti-inflammatory, cytotoxic, and antioxidant activities
- Antiproliferative effect of synthetic cyclic imides (methylphtalimides, carboxylic acid phtalimides and itaconimides) against human cancer cell lines
- Anti-inflammatory activity of highly oxygenated terpenoids from Achillea biebersteinii Afan
- Annual Reviewer Acknowledgement
- Reviewer acknowledgement Biosciences – Zeitschrift für Naturforschung C, volume 71 (2016)
Articles in the same Issue
- Frontmatter
- Research Articles
- Seasonal variation of gastroprotective terpenoids in Maytenus robusta (Celastraceae) quantified by gas chromatography-flame ionization detection (GC-FID)
- Plicosepalin A, a new antioxidant catechin–gallic acid derivative of inositol from the mistletoe Plicosepalus curviflorus
- New lupan-type triterpenoids
- Penicilloitins A and B, new antimicrobial fatty acid esters from a marine endophytic Penicillium species
- Anti-acetylcholinesterase activity of essential oils and their major constituents from four Ocimum species
- The chemical composition, antimicrobial, and antioxidant activities of Pycnocycla spinosa and Pycnocyla flabellifolia essential oils
- Biological evaluation and docking studies of some benzoxazole derivatives as inhibitors of acetylcholinesterase and butyrylcholinesterase
- LC/ESI-MS/MS profiling of Ulmus parvifolia extracts and evaluation of its anti-inflammatory, cytotoxic, and antioxidant activities
- Antiproliferative effect of synthetic cyclic imides (methylphtalimides, carboxylic acid phtalimides and itaconimides) against human cancer cell lines
- Anti-inflammatory activity of highly oxygenated terpenoids from Achillea biebersteinii Afan
- Annual Reviewer Acknowledgement
- Reviewer acknowledgement Biosciences – Zeitschrift für Naturforschung C, volume 71 (2016)