(-)-Kunstleramide, a new antioxidant and cytotoxic dienamide from the bark of Beilschmiedia kunstleri gamble

Molecules

Volumn 17, Issue 4, 2012, Pages 4197-4208

  Mollataghi, Abbas ^a   Hadi, A Hamid A ^a   Cheah, Shiau Chuen ^a,b  

^a UNIVERSITY OF MALAYA   (Malaysia)

^b UCSI UNIVERSITY   (Malaysia)

Author keywords

Alkaloid; Antioxidant; Beilschmiedia kunstleri; Cytotoxicity; Dienamide; Lauraceae

Indexed keywords

AMIDE; ANTIOXIDANT; KUNSTLERAMIDE; PLANT EXTRACT;

ARTICLE; BARK; CELL LINE; CELL SURVIVAL; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECT; HUMAN; LAURACEAE; NUCLEAR MAGNETIC RESONANCE;

AMIDES; ANTIOXIDANTS; CELL LINE; CELL SURVIVAL; DOSE-RESPONSE RELATIONSHIP, DRUG; HUMANS; LAURACEAE; MODELS, MOLECULAR; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PLANT BARK; PLANT EXTRACTS;

EID: 84860246405     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules17044197     Document Type: Article

References (27)

1. Kochummen, K.M. Tree Flora of Malaya: A Manual For Foresters; Ng, F.S.P., Ed.; Longman: Selangor, Malaysia, 1989; Volume 4, p. 98.
2. Pudjiastuti, P.; Mukhtar, M.R.; Hadi, A.H.A.; Saidi, N.; Morita, H.; Litaudon, M.; Awang, K. (6, 7-Dimethoxy-4-methylisoquinolinyl)-(4'- methoxyphenyl)-methanone, a new benzylisoquinoline alkaloid from Beilschmiedia brevipes. Molecules 2010, 15, 2339-2346.
3. Funasaki, M.; Lordello, A.L.; Viana, A.M.; Santa-Catarina, C.; Floh, E.I.S.; Yoshida, M.; Kato, M.J. Neolignans and sesquiterpenes from leaves and embryogenic cultures of Ocotea catharinensis (Lauraceae). J. Braz. Chem. Soc. 2009, 20, 853-859.
4. Cava, M.P.; Rao, K.V.; Douglas, B.; Weisbach, J.A. Alkaloids of Cassytha Americana. J. Org. Chem. 1968, 33, 2443-2446.
5. Chung-hsiung, C.; Shoei-shen, L.; Chung-fang, L.; Jinn, W.; Jack, L.B. A caryachnine N-methosalt from Cryptocarya chinensis and PMR spectral characteristics of some quaternary pavine alkaloids. J. Nat. Prod. 1979, 42, 163-167.
6. Pinheiro, M.L.B.; Xavier, C.M.; Souza, A.D.L.D.; Rabelo, D.D.M.; Batista, C.L.; Batista, R.L.; Costa, E.V.; Campos, F.R.; Barison, A.; Valdez, R.H.; et al. Acanthoic acid and other constituents from the stem of Annona amazonica (Annonaceae). J. Braz. Chem. Soc. 2009, 20, 1095-1102.
7. Babkock, P.A.; Segelman, A.B. Alkaloids of Lindera benzoin (L.) Blume (lauraceae), I: Isolation and identification of laurotetanine. J. Pharm. Sci. 1974, 63, 1495-1496.
8. Cave, A.; Leboeuf, M.; Moskowitz, H.; Ranaivo, A.; Bick, I.; Sinchai, W.; Nieto, M.; Sevenet, T.; Cabalion, P. Alkaloids of Cryptocarya phyllostemon. Aust. J. Chem. 1989, 42, 2243-2263.
9. Ramana, M.M.V.; Prashant, V.P. Tandem acylation-cycloalkylation with cyclohexene-1-acetic acid: A new entry to phenanthrene alkaloids. Nat. Prod. Res.1996, 8, 317-324.
10. Mollataghi, A.; Hamid, A.H.A.; Awang, K.; Jamaludin, M.; Litaudon, M.; Mukhtar, M.R. (+)-Kunstlerone, a new antioxidant neolignan from the leaves of Beilschmiedia kunstleri Gamble. Molecules 2011, 16, 6582-6590.
11. Ahmad, F.; Jamil, S.; Ibrahim, A.Z.; Read, R.W. Alkenylalamides from Piper maingayi Hk. F. Pertanika. J. Sci. Technol.1996, 4, 167-171.
12. Marques, J.V.; Oliveira, A.D.; Raggi, L.; Young, M.C.M.; Kato, M.J. Antifungal activity of natural and synthetic amides from piper species. J. Braz. Chem. Soc. 2010, 21, 1807-1813.
13. Cheng, M.J.; Tsai, I.L. Chen, I.S. Chemical constituents from the root bark of Formosan Zanthoxylum ailanthoides. J. Chin. Chem. Soc. 2003, 50, 1241-1246.
14. Chaaib, F.; Queiroz, E.F.; Ndjoko, K.; Diallo, D.; Hostettmann, K. Antifungal and antioxidant compounds from the root bark of Fagara zanthoxyloides. Planta Med. 2003, 69, 316-320.
15. Zhao, J.; Muhammad, I.; Dunbar, D.C.; Mustafa, J.; Khan, I.A. New alkamides from maca (Lepidium meyenii). J. Agric. Food Chem. 2005, 53, 690-693.
16. Caturla, F.; Najera, C. Lithiated (E)-N-isopropyl-5-tosyl-4-pentenamide: Synthetic applications as new δ-acyldienyl anion equivalent. Tetrahedron 1998, 54, 11255-11270.
17. Harada, N.; Nakanishi, K. Exciton chirality method and its application to configurational and conformational studies of natural products. Acc. Chem. Res. 1972, 5, 257-263.
18. Smith, H.E. Chiroptical properties of the benzene chromophore. A method for the determination of the absolute configurations of benzene compounds by application of the benzene sector and benzene chirality rules. Chem. Rev. 1998, 98, 1709-1740.
19. Blot, W.J.; Li, J.Y.; Taylor, P.R.; Guo, W.; Dawsey, S.; Wang, G.Q.; Yang, C.S.; Zheng, S.F.; Gail, M.; Li, G.Y.; et al. Nutrition intervention trials in Linxian, China: Supplementation with specific vitamin/mineral combinations, cancer incidence, and disease-specific mortality in the general population. J. Natl. Cancer Inst. 1993, 85, 1483-1492.
20. Uddin, N.; Rahman, A.; Uddin, N.A.; Rana, S.; Akter, R.; Chowdhury, M.A. Antioxidant, cytotoxic and antimicrobial properties of Eclipta alba ethanol extract. Int. J. Biol. Med. Res. 2010, 1, 341-346.
21. Price, J.A.; Sanny, C.G.; Sherlin, D. Application of manual assessment of oxygen radical absorbent capacity (ORAC) for use in high throughput assay of "total" antioxidant activity of drugs and natural products. J. Pharmacol. Toxicol. Methods 2006, 54, 56-61.
22. Orhan, M.K.; Naz, Q.; Ejaz, A.; Yilmaz, G.; Kan, Y.; Konuklugil, B.; Sener B.; Choudhary, M.I. Antioxidant and anticholinesterase evaluation of selected Turkish Salvia species. Food Chem. 2007, 103, 1247-1254.
23. Brem, B.; Seger, C.; Pacher, T.; Harti, M.; Hadacek, F.; Hofer, O.; Vajrodaya, S.; Greger, H. Antioxidant dehydrotocopherols as a new chemical character of Stemona species. Phytochemistry 2004, 65, 2719-2729.
24. Enayat, S.; Banerjee, S. Comparative antioxidant activities of extracts from leaves, bark and catkins of Salixa egyptiaca species. Food Chem. 2009, 116, 23-28.
25. Cheah, S.C.; Appleton, D.R.; Lee, S.T.; Lam, M.L.; Hadi, A.H.A.; Mustafa, M.R. Panduratin a inhibits the growth of A549 cells through induction of apoptosis and inhibition of NF-Kappa B translocation. Molecules 2011, 16, 2583-2598.
26. Mosmann, T. Rapid colorimetric assay for the cellular growth and survival: Application to proliferation and cytotoxicity assays. J. Immunol. Methods 1983, 65, 55-63.
27. Braga, P.A.; Dos Santos, D.A.; Da Silva, M.F.; Vieira, P.C.; Fernandes, J.B.; Houghton, P.J.; Fang, R. In vitro cytotoxicity activity on several cancer cell lines of acridone alkaloids and N-phenylethyl-dienamide derivatives from Swinglea glutinosa (Bl.) Merr. Nat. Prod. Res. 2007, 21, 47-55.