Activity Guided Isolation of Nematicidal Constituents from the Roots of Berberis brevissima Jafri and Berberis parkeriana Schneid

Abstract

Biological screening of different parts of the selected Berberis species (B. brevissima Jafri and B. parkeriana Schneid) showed that methanolic root extract possessed significant efficacy against Meloidogyne javanica (a root knot nematode). From root methanolic extracts of selected Berberis species four isoquinoline alkaloids; jatrorrhizine, dehydrocheilnthifoline, berberine and berberrubine were isolated. Structures of the isolated compounds were determined by using EIMS, 1H and 13C NMR, and other 2D spectroscopic techniques. Percentage juveniles mortality of M. javanica was determined at various concentrations (100, 200 and 300 µg mL-1) using carbofuran as control. Berberine possessed the highest nematicidal activity (71.33%) followed by jatrorrhizine (59.50%). The in vitro results suggested that these compounds from Berberis species could be potential novel nematicides against M. javanica.

Keywords

• Nematicidal activity
• Berberis brevissima
• Berberis parkeriana
• Meloidogyne javanica
• isoquinoline alkaloids

References

1. Bai C Q, Liu Z L & Liu Q Z (2011). Nematicidal constituents from the essential oil of Chenopodium ambrosioides aerial parts. E-Journal of Chemistry 8: S143-S148 Baird A W, Taylor C T & Brayden D J (1997). Non antibiotic antidiarrhoeal drugs: factor affecting oral bioavailability of berberine and loperamide in intestinal tissue. Advanced Drug Delivery Review 23(1-3): 111-120
2. Bhandari N, Verma H C, Upadhyay C, Tripathi A & pathi R P (2000). Mossbauer Spectroscopy of K/T bound-ary clays: Characteristics of iron bearing minerals; In: Catastrophic events and mass extinctions: Impacts and beyond, Houston: Lunar and Planetary Institute, p. 12-13
3. Choi W Y, Giraldez A J & Schier A F (2007). Target Protectors Reveal Dampening and Balancing of Nodal Agonist and Antagonist by miR-430. Science 318(5848): 271-274
4. Das S, Das M K, Mazumder P M & Basu S P (2009). Cytotoxic Activity of Methanolic Extract of Berberis aristata DC. on Colon Cancer. Global Journal of Pharmacology 3(3): 137-140
5. Freiburghaus S, Kaminsky R, Nkunya M H H & Brun R (1996). Evaluation of African medicinal plants for their in-vitro trypanocidal activity Journal of Ethnopharmacology 55(1): 1-11
6. Ghoshal S, Krishna B N & Lakshmi V (1996). Antiamoebic activity of Piper longum fruits against Entamoeba histolytica in-vitro and in-vivo. Journal of Ethnopharmacology 50(3): 167-170
7. Gomez K A & Gomez A A (1984). Two factor experiment. In Statistical procedures for agriculture research, John Wiley and Sons: New York, USA, pp. 89-109.
8. Hong L J, Li G H, Zhou W, Wang W, & Zhang K Q (2007). Screening and isolation of a nematocidal sesquiterpene from Magnolia grandiflora L. Pest Management Sciences 63(3): 301-305

9. Hsieh T J, Chia Y C, Wu Y C & Chen C Y (2004). Chemical constituents from the stems of Mahonia japonica. Journal of Chinese Chemical Society 51(2): 443-446
10. Hussey R S & Barker K R (1973). A comparison of methods of collecting inocula of Meloidogyne spp., including a new technique. Plant Disease Report 57: 1025–1028
11. Isman M B (2006) Botanical insecticides, deterrents, and repellents in modern agriculture and an increasingly regulated world. Annual Review of Entomology 51: 45-66
12. Ju H S, Li X J, Zhao B L, Han Z W & Xin W J (1990). The scavenging effect of berbarmineon active oxygen radicals in phorbol ester stimulated human polymorphonuclear leukocytes. Biochemical Pharmacology 39(11): 1673-1678
13. Kondo Y, Imai Y, Hojo H, Hashimoto Y & Nozoe S (1992). Selective inhibition of T cell dependent immune responses by bisbenzylisoquinoline alkaloids in vivo. International Journal of Immunopharmacology 14(7): 1181-1186
14. Kupeli E, Kos M, Yesilada E, Husnu K & Baser C (2002). A comparative study on the antiinflammatory, antinociceptive and antipyretic effects of isoquinoline alkaloids from the roots of Turkish Berberis species. Life Sciences 72(6): 645-657
15. Li S Y, Ling L H, Teh B S, Seow W K & Thong Y H (1989). Antiinflammatory and immunosuppressive properties of the bisbenzylisoquinolines: In vitro comparisions of tetrandine and berberine. International Journal of Immunopharmacology 11(4): 395-401
16. Liu J H, Wang L, Qiu J Y, Jiang L I, Yan J Y, Liu T, Liu W C & Duan Y X (2011). Nematocidal activity of Gymnoascus reesii against Meloidogyne incognita. African Journal of Microbiology Research 5(18): 2715-2719
17. Liu Y T, Hao H P, Xie H G, Lai L, Wang Q, Liu C X & Wang G J (2010). Extensive intestinal first pass elimination and predominant hepatic distribution of berberine explain its low plasma levels in rats. Drug Metabolism and Disposition 38(10); 1779-1784
18. Naz I, Rius J E, Saifullah, Blok V, Khan S R, Ali S & Ali S (2012). In vitro and in planta nematicidal activity of Fumaria parviflora (Fumariacea) againt Southern Root knot nematode Meloidogyne incognita. Plant Pathology 62: 943-952
19. Ntalli N G, Ferrari F, Giannakou I & Spiroudi M (20100. Phytochemistry and nematocidal activity of the essential oils from 8 greek lamiaceae aromatic plants and 13 terpene components. Journal of Agriculture and food Chemistry 58(13): 7856-7863
20. Omulokoli E, Khan B & Chhabra S C (1997). Antiplasmodial activity of four Kenyan medicinal plants. Journal of Ethnopharmacology 56(2): 133 – 137
21. Phillipson O T, Kilpatrick I C & Jones M W (1987). Dopaminergic innervation of the primary visual cortex in the rat, and some correlations with human cortex. Brain Research Bulletin 18: 621-33
22. Quevedo R, Valderrama K, Murillo M B, Laverde M & Fajardo V (2008). A new bisbenzyltetrahydroisoquinoline alkaloid from Berberis tabiensis (Berberidaceae). Biochemical Systematics and Ecology 36(10): 812–814
23. Rattan R S (2010). Mechanism of action of insecticidal secondary metabolites of plant origin. Crop Protection 29(9): 913-920
24. Reynolds A M, Dutta T K, Curtis R S C, Power S J, Gaur H S & Kerry B R (2011). Chemotaxis can take plant parasitic nematodes to the source of a chemo attractant via the shortest possible routes. Journal of the Royal Society Interface 8: 568-577
25. Saied S & Begum S (2004). Phytochemical studies of Berberis vulgaris. Chemistry of Natural Compounds 40(2): 137-140
26. Santavy F (1979). Berbine (dibenzo[a,g]quinolizidine) (protoberberine, pseudoprotoberberine, corydaline and corytenchirine types) group. In The Alkaloids, Manske R H F Eds.; Academic Press: New York, USA, 17, pp. 439–461.
27. Seow W K, Ferrante A, Summors A & Thong Y H (1992). Comparative effects of tetrandrine and berbamine on production of the inflammatory cytokines interleukin-1 and tumour necrosis factor. Life Sciences 50(8): PL53-PL58
28. Shahid M, Rahim T, Shahzad A, Tajuddin, Latif A, Fatma T, Rashid M, Raza A & Mustafa S (2009). Ethnobotanical studies on Berberis aristata DC. root extracts. African Journal of Biotechnology 8(4): 556-563
29. Shamma M & Rahimizadech M (1986). The identity of chileninone with berberrubine. The problem of true natural products vs. artifacts of isolation. Journal of Natural Products 49(3): 398–405
30. Singh M, Srivastava S & Rawat A K S (2007). Antimicrobial activities of Indian Berberis species. Fitoterapia 78(7): 574–576
31. Suau R, Rico R, Romero J M L, Najera F & Cuevas A (1998). Isoquinoline alkaloids from Berberis vulgaris Subsp. australis. Phytochemistry 49(8): 2545-2549
32. Teh B S, Seow W K, Li S Y & Thong Y H (1990). Inhibition of prostaglandin and leukotriene generation by the plant alkaloids tetrandrine and berbamine. International Journal of Immunopharmacology 12(3): 321-326
33. Thoden T C, Boppre M & Hallmann J (2009). Effects of pyrrolizidine alkaloids on the presence of plant parasitic and free living nematodes. Pest Management Sciences 65(7): 823-830
34. Tian B, Yang J & Zhang K Q (2007). Bacteria used in the biological control of plant parasitic nematodes: Populations, mechanisms of action, and future prospects. FEMS Microbiology Ecology 61(2): 197-213.
35. Villinski J, Dumas E, Chai H B, Pezzuto J, Angerhofer C & Gafner S (2003). Antibacterial Activity and Alkaloid Content of Berberis thunbergii, Berberis vulgaris and Hydrastis Canadensis. Pharmaceutical Biology 41(8): 551-557
36. Wright C W, Marshall S J, Russell P F, Anderson M M, Phillipson J D, Kirby G C, Warharst D C & Schiff J P L (2000). In vitro antiplasmodial, antiamoebic and cytotoxic activities of some monomeric isoquinoline alkaloids. Journal of Natural Products 63(12): 1638-1640
37. Zuckerman B M & Esnard J (1994). Biological control of plant nematodes current status and hypothesis. Japanese Journal of Nematology 24: 1-13