Cytotoxic tirucallane triterpenoids from Melia azedarach fruits

Molecules

Volumn 15, Issue 9, 2010, Pages 5866-5877

  Ntalli, Nikoletta G ^a   Cottiglia, Filippo ^b   Bueno, Carlos A ^c   Alché, Laura E ^c   Leonti, Marco ^b   Vargiu, Simona ^b   Bifulco, Ersilia ^b   Menkissoglu Spiroudi, Urania ^a   Caboni, Pierluigi ^b  

^a ARISTOTLE UNIVERSITY OF THESSALONIKI   (Greece)

^b UNIVERSITY OF CAGLIARI   (Italy)

^c UNIVERSIDAD DE BUENOS AIRES   (Argentina)

Author keywords

21 Acetoxy melianone; 3 Tigloylmelianol; Cytotoxicity; Melianone; Methyl kulonate

Indexed keywords

CYTOTOXIN; PLANT EXTRACT; TIRUCALLANE; TRITERPENE;

ADENOCARCINOMA; ANIMAL; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; EPITHELIUM CELL; FRUIT; HUMAN; ISOLATION AND PURIFICATION; LUNG TUMOR; MELIA AZEDARACH; NEMATODE; PATHOLOGY; TUMOR CELL LINE;

ADENOCARCINOMA; ANIMALS; CELL LINE, TUMOR; CYTOTOXINS; EPITHELIAL CELLS; FRUIT; HUMANS; LUNG NEOPLASMS; MELIA AZEDARACH; MOLECULAR STRUCTURE; PLANT EXTRACTS; TRITERPENES; TYLENCHOIDEA;

EID: 77957314681     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules15095866     Document Type: Article

References (40)

1. Isman, M. B. Botanical insecticides, deterrents, and repellents in modern agriculture and an increasingly regulated world. Annu. Rev. Entomol. 2006, 51, 45-66.
2. Akhtar, Y.; Yeoung, Y. R.; Isman, M. B. Comparative bioactivity of selected extracts from Meliaceae and some commercial botanical insecticides against two noctuid caterpillars, Trichoplusia ni and Pseudaletia unipuncta. Phytochem. Rev. 2008, 7, 77-88.
3. Carpinella, C.; Ferrayoli, C.; Valladares, G.; Defago, M.; Palacios, S. Potent limonoid insect antifeedant from Melia azedarach. Biosci. Biotechnol. Biochem. 2002, 66, 1731-1736.
4. Coria, C.; Almiron, W.; Valladares, G.; Carpinella, C.; Ludueña, F.; Defago, M.; Palacios. S. Larvicide and oviposition deterrent effects of fruit and leaf extracts from Melia azedarach L. on Aedes aegypti (L.) (Diptera: Culicidae). Bioresource Technol. 2008, 99, 3066-3070.
5. Kamaraj, C.; Rahuman, A. A.; Bagavan, A.; Mohamed, M. J.; Elango, G.; Rajakumar, G.; Zahir, A. A.; Santhoshkumar, T.; Marimuthu, S. Unit Ovicidal and larvicidal activity of crude extracts of Melia azedarach against Haemonchus contortus (Strongylida). Parasitol. Res. 2010, 106, 1071-1077.
6. Carpinella, M. C.; Giorda, L. M.; Ferrayoli, C. G.; Palacios, S. M. Antifungal effects of different organic extracts from Melia azedarach L. on phytopathogenic fungi and their isolated active components. J. Agric. Food Chem. 2003, 51, 2506-2511.
7. Carpinella, M. C.; Ferrayoli, C. G.; Palacios, S. M. Antifungal synergistic effect of scopoletin, a hydroxycoumarin isolated from Melia azedarach L. fruits. J. Agric. Food Chem. 2005, 53, 2922-2927.
8. Ntalli, N. G.; Menkisoglu-Spiroudi, U.; Giannakou, I. Nematicidal activity of powder and extracts of Melia azedarach fruits against Meloidogyne incognita. Ann. Appl. Biol. 2010, 156, 309-317.
9. Vishnukanta, A. C. R. Melia azedarach: A phytopharmacological review. Pharmacogn. Rev. 2008, 2, 173-179.
10. Bueno, C. A.; Alché, L. A.; Barquero, A. A. 1-Cinnamoyl-3, 11-dihydroxymeliacarpinin delays glycoprotein transport restraining virus multiplication without cytotoxicity. Biochem. Biophys. Res. Commun. 2010, 393, 32-37.
11. Wu, S. B.; Ji, Y. P.; Zhu, J. J.; Zhao, Y.; Xia, G.; Hu, Y. H.; Hu, J. F. Steroids from the leaves of Chinese Melia azedarach and their cytotoxic effects on human cancer cell lines. Steroids 2009, 74, 761-765.
12. Mazumder, M. E. H.; Rahman, S. Pharmacological evaluation of Bangladeshi medicinal plants for antioxidant activity. Pharm. Biol. 2008, 46, 704-709.
13. Roy, A.; Saraf, S. Limonoids: Overview of significant bioactive triterpenes distributed in plants kingdom. Biol. Pharm. Bull. 2006, 29, 191-201.
14. Morgan, E. D. Azadirachtin, a scientific gold mine. Bioorg. Med. Chem. 2009, 17, 4096-4105.
15. Patil, B. S.; Jayaprakasha, G. K.; Murthy, K. N. C.; Vikram, A. Bioactive compounds: Historical perspectives, opportunities, and challenges. J. Agric. Food Chem. 2009, 57, 8142-8160.
16. Zhang, B.; Wang, Z. F.; Tang, M. Z.; Shi, Y. L. Growth inhibition and apoptosis-induced effect on human cancer cells of toosendanin, a triterpenoid derivative from Chinese traditional medicine. Invest. New Drug. 2005, 23, 547-553.
17. Muregi, F. W.; Chhabra, S. C.; Njagi, E. N. M.; Lang'at-Thoruwa, C. C.; Njue, W. M.; Orago, A. S. S.; Omar, S. A.; Ndiege, I. O. Anti-plasmodial activity of some Kenyan medicinal plant extracts singly and in combination with chloroquine. Phytother. Res. 2004, 18, 379-384.
18. Madibela, O. R.; Kelemogile, K. M. Exposure of Melia azedarach fruits to Eimeria lowers oocyst output in yearling Tswana goats. Small Ruminant Res. 2008, 76, 207-210.
19. Khanavi, M.; Safavi, M.; Siavoshi, F.; Fallah Tafti, A.; Haji Mahmoodi, M.; Haji Akhoondi, A.; Rezazadeh Sh, R.; Foroumadi, A. Evaluation of anti Helicobacter pylori activity of methanol extracts of some species of Stachys and Melia. J. Med. Plants 2008, 7, 74-80.
20. Peveling, R.; Ely, S. O. Side-effects of botanical insecticides derived from Meliaceae on coccinellid predators of the date palm scale. Crop Prot. 2006, 25, 1253-1258.
21. Matter, M. M.; Gesraha, M. A.; Ahmed, A. A. I.; Farag, N. A. Impact of neem and chinaberry fruit extracts on the pest/parasitoid (Pieris rapae/Hyposoter ebeninus) interactions. Anzeiger für Schädlingskunde 2002, 75, 13-18.
22. Caboni, P.; Sarais, G.; Angioni, A.; Garcia, A. J.; Lai, F.; Dedola, F.; Cabras, P. Residues and persistence of neem formulations on strawberry after field treatment. J. Agric. Food Chem. 2006, 54, 10026-10032.
23. Sarais, G.; Angioni, A.; Lai, F.; Cabras, P.; Caboni, P. Persistence of two neem formulations on peach leaves and fruit: effect of the distribution. J. Agric. Food Chem. 2009, 57, 2457-2461.
24. Phua, D. H.; Tsai, W. J.; Ger, J.; Deng, J. F.; Yang, C. C. Human Melia azedarach poisoning. Clin. Toxicol. 2008, 46, 1067-1070.
25. Nakanishi, T.; Inada, A.; Lavie, D. A new tirucallane-type triterpenoid derivative, lipomelianol from fruits of Melia toosendan SIEB. Et ZUCC. Chem. Pharm. Bull. 1986, 34, 100-104.
26. Joseph-Nathan, P.; Wesener, J. R.; Günther, H. A two-dimensional NMR study of angelic and tiglic acid. Magn. Res. Chem. 1984, 23, 190-191.
27. Su, R.; Kim, M.; Kawaguchi, H.; Yamamoto, T.; Goto, K.; Taga, T.; Miwa, Y.; Kozuka, M.; Takahashi, S. triterpenoids from the fruits of Phellodendron chinense SCHNEID.: the stereostructure of niloticin. Chem. Pharm. Bull. 1990, 38, 1616-1619.
28. Chiang, C.; Chang, F. C. Tetracyclic triterpenoids from Melia azedarach, L.-III. Tetrahedron 1973, 29, 1911-1929.
29. Itokawa, H.; Kishi, E.; Morita, H.; Takeya, K. Cytotoxic quassinoids and tirucallane-type triterpenes from woods of Eurycoma longifolia. Chem Pharm. Bull. 1992, 40, 1053-1055.
30. Zhou, H.; Hamazaki, A.; Fontana, J. D.; Takahashi, H.; Wandscheer, C. B.; Fukuyama, Y. Cytotoxic limonoids from Brazilian Melia azedarach. Chem. Pharm. Bull. 2005, 53, 1362-1365.
31. Zhou, H.; Hamazaki, A.; Fontana, J. D.; Takahashi, H.; Esumi, T.; Wandscheer, C. B.; Tsujimoto, H.; Fukuyama, Y. New ring C-seco limonoids from Brazilian Melia azedarach and their cytotoxic activity. J. Nat. Prod. 2004, 67, 1544-1547.
32. Tada, K.; Takido, M.; Kitanaka, S. Limonoids from fruit of Melia toosendan and their cytotoxic activity. Phytochemistry 1999, 51, 787-791.
33. Pettit, G. R.; Numata, A.; Iwamoto, C.; Morito, H.; Yamada, T.; Goswami, A.; Clewlow, P. J.; Cragg, G. M.; Schmidt, J. M. Antineoplastic agents. 489. Isolation and structures of meliastatins 1-5 and related euphane triterpenes from the tree Melia dubia. J. Nat. Prod. 2002, 65, 1886-1891.
34. Priyadarsini, R. V.; Murugan, R. S.; Sripriya, P.; Karunagaran, D.; Nagini, S. The neem limonoids azadirachtin and nimbolide induce cell cycle arrest and mitochondria-mediated apoptosis in human cervical cancer (HeLa) cells. Free Radical Res. 2010, 44, 624-634
35. Biavatti, M. W.; Vieira, P. C.; da Silva, M. F. G.; Fernandes, J. B.; Albuquerque, S.; Magalhaes, C. M. I.; Pagnocca, F. C. Chemistry and bioactivity of Raulinoa echinata Cowan, an endemis Brazilian Rutaceae species. Phytomedicine 2001, 8, 121-124.
36. Kim, B.; Kim, H.; Choi, J. W.; Lee, C. K. The effects of meliae toosendan fructus on liver function. III. Effects of melianone and 28-deacetyl sendanin on drug metabolism and bile juice secretion. Korean J. Pharmacogn. 1996, 27, 47-52.
37. Ntalli, N. G.; Menkissoglu-Spiroudi, U.; Giannakou, I. O.; Prophetou-Athanasiadou, D. A. Efficacy evaluation of a neem (Azadirachta indica A. Juss) formulation against root-knot nematodes Meloidogyne incognita. Crop Prot. 2009, 28, 489-494.
38. Denizot, F.; Lang, R. Rapid colorimetric assay for cell growth and survival. Modifications to the tetrazolium dye procedure giving improved sensitivity and reliability. J. Immunol. Methods 1986, 89, 271-277.
39. Hussey, R. S.; Barker, K. R. A comparison of methods of collecting inocula of Meloidogyne spp. including a new technique. Plant Dis. Rep. 1973, 57, 1025-1028.
40. Puntener, W. Manual for Field Trials in Plant Protection, 2nd ed.; Ciba Geigy Limited: Basel, Switzerland, 1981; p. 205.