Cell-cycle specific cytotoxicity mediated by rearranged ent-kaurene diterpenoids isolated from Parinari curatellifolia

Chemico-Biological Interactions

Volumn 99, Issue 1-3, 1996, Pages 193-204

  Lee, Ik Soo ^a,d   Shamon, Lisa A ^a   Chai, Hee Byung ^a   Chagwedera, Tangai E ^b   Besterman, Jeffrey M ^c   Farnsworth, Norman R ^a   Cordell, Geoffrey A ^a   Pezzuto, John M ^a   Kinghorn, A Douglas ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^b UNIVERSITY OF ZIMBABWE   (Zimbabwe)

^c GLAXOSMITHKLINE   (United States)

^d Chonnam National University   (South Korea)

Author keywords

Antitumor activity; Cultured human cancer cells; Cytotoxic potential; Ent Kaurene diterpenoids; Michael type addition; Mode of action; Structure elucidation; , Unsaturated carbonyl

Indexed keywords

13 HYDROXY 15 OXOZOAPATLIN; 13 METHOXY 15 OXOZOAPATLIN; 15 OXOZOAPATLIN; DITERPENOID; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; ASTROCYTOMA CELL; BREAST CANCER; CANCER; CANCER CELL; CELL CULTURE; CELL CYCLE; CONTROLLED STUDY; CYTOTOXICITY; DNA SYNTHESIS; DRUG STRUCTURE; HUMAN; HUMAN CELL; INTRAPERITONEAL DRUG ADMINISTRATION; MOUSE; MUTAGENICITY; NONHUMAN; PROTEIN SYNTHESIS; RAT; RNA SYNTHESIS; STRUCTURE ACTIVITY RELATION;

EID: 0030026773     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/0009-2797(95)03669-5     Document Type: Article

References (25)

1. R.B. Bhat, E.O. Eterjere and V.T. Oladipo, Ethnobotanical studies from Central Nigeria, Econ. Bot., 44 (1990) 382-390.
2. M.E. Mathias, Some medicinal plants of the Hehe (Southern Highlands Province, Tanzania), Taxon, 31 (1982) 488-494.
3. J.M. Watt and M.G. Breyer-Brandwijk, Medicinal and Poisonous Plants of Eastern Africa, E & S Livingston Ltd., London, UK, 2nd Ed., 1962.
4. H.J. Arnold and M. Gulumian, Pharmacopoeia of traditional medicine in Venda, J. Ethnopharmacol., 12 (1984) 35-74.
5. S.A. Malcolm and E.A. Sofowora, Antimicrobial activity of selected Nigerian folk remedies and their constituent plants, Lloydia, 32 (1969) 512-517.
6. H. Weenen, M.H.H. Nkunya, D.H. Bray, L.B. Mwasumbi, L.S. Kinabo and V.A.E.B. Kilimali, Antimalarial activity of Tanzanian medicinal plants, Planta Med., 56 (1990) 368-370.
7. V. Spitzer, F. Marx, J.G.S. Maia and K. Pfeilsticker, Occurrence of α-eleostearic acid in the seed oil of Parinari montana (Chrysobalanaceae), Fett. Wiss. Technol., 94 (1992) 58-60.
8. L.A. Sklar, B.S. Hudson and R.D. Simoni, Parinaric acid from Parinarium glaberrimum, Methods Enzymol., 72 (1981) 479-482.
9. M.J. Chisholm and C.Y. Hopkins, Kamloenic acid and other conjugated fatty acids in certain seed oils, J. Am. Oil Chem. Soc., 43 (1966) 390-392.
10. L. Coradin, D.E. Giannasi and G.T. Prance, Chemosystematic studies in the Chrysobalanaceae. I. Flavonoids in Parinari, Brittonia, 37 (1985) 169-178.
11. G. Delgado, L. Alvarez and A. Romo de Vivar, 15-Oxozoapatlin, a diterpene lactone from Viguiera maculata, Phytochemistry, 23 (1984) 2674-2675.
12. T.C. McMorris, M.J. Keiner, W. Wang, S. Moon and R. Taetle, On the mechanism of toxicity of illudins: the role of glutathione, Chem. Res. Toxicol., 3 (1990) 574-579.
13. H. Weenen, M.H. Nkunya, D.H. Bray, L.B. Mwasumbi, L.S. Kinabo, V.A. Kilimali and J.B. Wijnberg, Antimalarial compounds containing an α,β-unsaturated carbonyl moiety from Tanzanian medicinal plants, Planta Med., 56 (1990) 371-373.
14. M. Fukushima, T. Kato, S. Narumiya, Y. Mizushima, H. Sasaki, Y. Terashima, Y. Nishiyama and M.G. Santoro, Prostaglandin A and J: antitumor and antiviral prostaglandins, Adv. Prostaglandin Thromboxane Leukot. Res., 19 (1989) 415-418.
15. M. Novelo, J.G. Cruz, L. Hernandez, R. Pereda-Miranda, H. Chai, W. Mar and J.M. Pezzuto, Cytotoxic constituents from Hyptis verticillata, J. Nat. Prod., 56 (1993) 1728-1736.
16. A.D. Deitch, H. Law and W.R. Devere, A stable propidium iodide staining procedure for flow cytometry, J. Histochem. Cytochem., 30 (1982) 967-972.
17. J.M. Pezzuto, C.T. Che, D.D. McPherson, J.P. Zhu, G. Topcu, C.A.J. Erdelmeier and G.A. Cordell, DNA as an affinity probe useful in the detection and isolation of biologically active natural products, J. Nat. Prod., 54 (1991) 1522-1530.
18. N.I. Back, M.S. Chung, L. Shamon, L.B. Kardono, S. Tsauri, K. Padmawinata, J.M. Pezzuto, D.D. Soejarto and A.D. Kinghorn, Selligueain A, a novel highly sweet proanthocyanidin from the rhizomes of Selliguea feei, J. Nat. Prod., 56 (1993) 1532-1538.
19. D.B. Wickramaratne, T. Pengsuparp, W. Mar, H.-B. Chai, T.E. Chagwedera, C.W.W. Beecher, N.R. Farnsworth, A.D. Kinghorn, J.M. Pezzuto and G.A. Cordell, Novel antimitotic dibenzocyclo-octadiene lignan constituents of the stem bark of Steganotaenia araliacea, J. Nat. Prod., 56 (1993) 2083-2090.
20. W. Herz, S.V. Govindan and J.F. Blount, Tetracyclic analogues of rosane lactones from Eupatorium album, J. Org. Chem., 44 (1979) 2999-3003.
21. N. Ohno, T.J. Mabry, V. Zabel and W.H. Watson, Tetrachyrin, a new rearranged kaurenoid lactone, and diterpene acids from Tetrachyron orizabaensis and Helianthus debilis, Phytochemistry, 18 (1979) 1687-1689.
22. G. Delgado and A. Romo de Vivar, ent-Kaurenoid methyl esters from Viguiera stenoloba, structural revision of stenolobin and its biomimetic conversion to zoapatlin, Chem. Lett. ,7 (1984) 1237-1240.
23. G.A. Cordell and A.D. Kinghorn, One dimensional proton-carbon correlations for the structure determination of natural products, Tetrahedron, 47 (1991) 3521-3534.
24. C.Y. Duh, A.D. Kinghorn and J.M. Pezzuto, Cell-cycle specific cytotoxicity mediated by stizophyllin (2α,3β,12β-trihydroxypregna-4,7,16-trien-20-one), a novel electrophilic pregnane isolated from Stizophyltum riparium, Chem.-Biol. Interact., 80 (1991) 43-56.
25. J.R. Lillehang, K. Kleppe, C.W. Sigel and S.M. Kupchan, Reaction of biological thiols with the tumor inhibitor jatrophone. Inhibition of RNA polymerase, Biochim. Biophys. Acta, 327 (1973) 92-100.