Bioactive aristolactams from Piper umbellatum

Phytochemistry

Volumn 69, Issue 8, 2008, Pages 1726-1731

  Tabopda, Turibio Kuiate ^a,b   Ngoupayo, Joseph ^b   Liu, Jiawei ^a   Mitaine Offer, Anne Claire ^d   Tanoli, Sheraz A Khan ^c   Khan, Shamsun Nahar ^c   Ali, Muhammad Shaiq ^c   Ngadjui, Bonaventure Tchaleu ^b   Tsamo, Etienne ^b   Lacaille Dubois, Marie Aleth ^d   Luu, Bang ^a  

^a UNIVERSITÉ LOUIS PASTEUR   (France)

^b UNIVERSITY OF YAOUNDÉ I   (Cameroon)

^c UNIVERSITY OF KARACHI   (Pakistan)

^d UNIVERSITÉ DE BOURGOGNE   (France)

Author keywords

Glucosidase; Alkaloids; Antifungal; Antioxidant; Aristolactams; DPPH; Piper umbellatum

Indexed keywords

ALKALOID; ANTIFUNGAL AGENT; FUSED HETEROCYCLIC RINGS; LACTAM; PLANT EXTRACT; SCAVENGER;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ISOLATION AND PURIFICATION; PIPERACEAE; PLANT;

ALKALOIDS; ANTIFUNGAL AGENTS; FREE RADICAL SCAVENGERS; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; LACTAMS; MOLECULAR STRUCTURE; PIPER; PLANT COMPONENTS, AERIAL; PLANT EXTRACTS;

PIPER UMBELLATUM; PIPERACEAE;

EID: 43049113472     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2008.02.018     Document Type: Article

References (47)

1. Asano N., Nishida M., Kizu H., and Matsui K. Homonojirimycin isomers and glycosides from Aglaonema treubii. J. Nat. Prod. 60 (1997) 98-101
2. Brass C., Shainhouse J.Z., and Stevens D.A. Antimicrob. Agents Chemother. 15 (1979) 763
3. Bylka W., and Matławska I. Flavonoids from Aquilegia vulgaris. Isocytisoside and its glycosides. Acta Polon. Pharm. 54 (1997) 331-333
4. Chang F.R., Chen C.Y., Hsieh T.J., Cho C.P., and Wu Y.C. Chemical Constituents from Annona glabra III. J. Chin. Chem. Soc. 47 (2000) 913-920
5. 13C NMR spectroscopy of polymethoxyxanthones. Tetrahedron 34 (1978) 1837-1843
6. Christov R., Trusheva B., Popova M., Bankova V., and Bertrand M. Chemical composition of propolis from Canada, its antiradical activity and plant origin. Nat. Prod. Res. 19 7 (2005) 673-678
7. Clark T.A., and Hajjeh R.A. Recent trends in the epidemiology of invasive mycoses. Curr. Opin. Infect. Dis. 15 (2002) 569-574
8. Cornwell D.G., Jones K.H., Jiang Z., Lantry L.E., Southwell Keely P., Kohar I., and Thornton D.E. Cytotoxicity of tocopherols and their quinones in drug-sensitive and multidrug-resistant leukemia cells. Lipids 33 (1998) 295-301
9. Desai S.J., Prabhu B.R., and Mulchandani N.B. Aristolactams and 4,5-dioxoaporphines from Piper longum. Phytochemistry 27 (1988) 1511-1515
10. Desai S.J., Chaturvedi R.N., and Mulchandani N.B. Piperolactam D, a new aristolactam from Indian Piper species. J. Nat. Prod. 53 (1990) 496-497
11. Diplock A.T., Charleux J.L., Crozier-Willi G., Kok F.J., Rice-Evans C., Roberfroid M., Stahl W., and Vina-Ribes J. Functional food science and defence against reactive oxidative species. Br. J. Nutr. 80 Suppl. 1 (1998) S77-S112
12. Domínguez X.A., and Alcorn J.B. Screening of medicinal plants used by huastec mayans of northeastern Mexico. J. Ethnopharmacol. 13 (1985) 139-156
13. Duh C.Y., Wu Y.C., and Wang S.K. Cytotoxic pyridone alkaloids from the leaves of Piper aborescens. J. Nat. Prod. 53 (1990) 1575-1577
14. Faure M., Lissi E., Torres R., and Videla R. Antioxidant activities of lignans and flavanoids. Phytochemistry 29 (1990) 3773-3775
15. Feher J., and Pronai L. The role of free radical scavengers in gastrointestinal diseases. Orvosi. Hetilap. 134 (1993) 693-696
16. Hage C.A., Goldman M., and Wheat L. Mucosal and invasive fungal infections in HIV/AIDS. J. Eur. J. Med. Res. 7 (2002) 236
17. Helmerhorst E.J., Reijnders I.M., Van't Hof W., Simoons-Smit I., Veerman E.C.J., and Amerongen A.V.N. Amphotericin B- and Muconazole-resistant Candida spp., Aspergillus fumigatus, and other newly emerging pathogenic fungi are susceptible to basic antifungal peptides. Antimicrob. Agents Chemother. 43 (1999) 702-704
18. Inouye S., Tsuruoka T., Ito T., and Niida T. Structure and synthesis of nojirimycin. Tetrahedron 23 (1968) 2125-2144
19. Kijjoa A., Giesbrecht A.M., Akisue M.K., Gottlieb O.R., and Gottlieb H.E. 4-Nerolidylcatechol from Potomorphe umbellata. Planta Med. 39 (1980) 85
20. Kumar V., Poonam, Prasad A.K., and Parmar V.S. Naturally occurring aristolactams, aristolochic acids and dioxoaporphines and their biological activities. Nat. Prod. Rep. 20 (2003) 565-583
21. Kusumi T. Determination of the absolute configuration of organic compounds by means of NMR Spectroscopy-Modified Mosher's Method. Synth. Org. Chem. 51 (1993) 462-470
22. Lajide L., Escoubas P., and Mizutani J. Termite antifeedant activity in Xylopia aethiopica. Phytochemistry 40 (1995) 1105-1112
23. Lin L.C., Shen C.C., Shen Y.C., and Tsai T.H. Anti-inflammatory neolignans from Piper kadsura. J. Nat. Prod. 69 (2006) 842-844
24. Mabry T.J., Markham K.R., and Thomas M.B. The Systematic Identification of Flavonoids (1970), Springer-Verlag, Berlin/New York pp. 77-121
25. Matsu T.I., Yashimoto C., Osajimo K., Ok T.I., and Psajima Y. In vitro survey of α-glucosidase inhibitory food components. Biosci. Biotech. Biochem. 60 (1996) 2019-2022
26. 2-dependent lipid peroxidation. Biochem. Educ. 15 (1987) 58-62
27. 2 from Bothrops snake venoms: isolation of 4-nerolidylcatechol as active principle. Phytochemistry 66 (2005) 1017-1025
28. Ohtani I., Kusumi T., Kashman Y., and Kkisawa H. High-field FT NMR application of Mosher's method. The absolute configuration of marine terpenoids. J. Am. Chem. Soc. 113 (1991) 4092-4096
29. Olsen C.E., Tyagi O.D., Boll P.M., Hussaini F.A., Parmar V.S., Sharma N.K., Taneja P., and Jain S.C. An aristolactam from Piper acutisleginum and revision of the structures of piperolactam B and D. Phytochemistry 33 (1993) 518-520
30. Parmar V.S., Jain S.C., Bisht K.S., Jain R., Taneja P., Jha A., Tyagi O.D., Prasad A.K., Wengel J., Olsen C.E., and Boll P.M. Phytochemistry of the genus Piper. Phytochemistry 46 (1997) 597-673
31. Ramarathnam N., Osawa H., Ochi T., and Kawakishi S. The contribution of plant food antioxidants to human health. Trend Food Sci. Technol. 6 (1995) 75
32. Rayyan S., Fossen T., Nateland H.S., and Andersen Ø.M. Isolation and identification of flavonoids, including flavone rotamers, from the herbal drug 'Crataegi Folium Cum Flore' (Hawthorn). Phytochem. Anal. 16 (2005) 334-341
33. Reese E.T., and Parrish F.W. Nojirimycin and d-glucono-l,5-lactone as inhibitors of carbohydrases. Carbohydr. Res. 18 (1968) 381-388
34. Romani L. Immunity to fungal infections. Nat. Rev. Immunol. 4 (2004) 1-23
35. Ruangrungsi N., Prathanturarug S., Lange H.L., and Organ M.G. An N-methyl aristolactam and an oxygenated cyclohexane derivative from Piper ribesioides. Phytochemistry 31 (1992) 2397-2400
36. Shahidi F., and Wandasundara P.K. Phenolic antioxidants. Crit. Rev. Food Sci. Nutr. 32 (1992) 67-103
37. Shen T.Y., and Hussaini I.M. Kadsurenone and other related lignans as antagonists of platelet-activating factor receptor. Method Enzymol. 187 (1990) 446-454
38. Singh S.K., Ashok P.K., Olsen C.E., Jha A., Jain S.C., Parmar V.S., and Wenge J. Neolignans and alkaloids from Piper argyrophylum. Phytochemistry 43 (1996) 1355-1360
39. Sonei S., Satoshi M., Hiroyasu T., Ryu Y., Shizuo K., Mikiko S.M., and Yuichi H. Novel α-glucosidase inhibitors with a tetrachlorophthalimide skeleton. Bioorg. Med. Chem. Lett. 10 (2000) 1081-1084
40. Sun N.J., Antoun M., Chang C.J., and Cassady J.M. New cytotoxic aristolactams from Pararistolochia flos-avis. J. Nat. Prod. 50 (1987) 843-846
41. Takao T., Kiatani F., Watanabe N., Yagi A., and Sakata K. A simple screening method for antioxidants and isolation of several antioxidants produced by marine bacteria from fish and shellfish. Biosci. Biotechnol. Biochem. 58 (1994) 1780-1783
42. Truscheit E., Frommer W., Junge B., Muller L., Schmidt D.D., and Wingender W. Chemistry and biochemistry of microbial α-glucosidase inhibitors. Angew. Chem. Int. 20 (1981) 744-761
43. Wakabayashi H., Abe S., Teraguchi S., Hayasawa H., and Yamaguchi H. Inhibition of hyphal growth of azole-resistant strains of Candida albicans by triazole antifungal agents in the presence of lactoferrin-related compounds. Antimicrob. Agent Chemother. 42 (1998) 1587-1591
44. Wan C., Luo H.B., Zheng Y., Cheng Y.K., and Cai Z. Investigation of the metabolism and reductive activation of carcinogenic aristolochic acids in rats. Drug Metab. Dis. 35 (2007) 866
45. Woldemichael G.M., Franzblau S.G., Zhang F., Wang Y., and Timmermann B.N. Inhibitory effect of sterols from Ruprechtia triflora and diterpenes from Calceolaria pinnifolia on the growth of Mycobacterium tuberculosis. Planta Med. 69 (2003) 628-631
46. Wu Q.-L., Wang S.-P., Tu G.-Z., Feng Y.-X., and Yang J.-S. Alkaloids from Piper puberullum. Phytochemistry 44 (1997) 727-730
47. Yamaguchi L.F., Lago J.H.G., Tanizaki T.M., Mascio P.D., and Kato M.J. Antioxidant activity of prenylated hydroquinone and benzoic acid derivatives from Piper crassinervium Kunth. Phytochemistry 67 (2006) 1838-1843