Antioxidant and cytotoxic isoprenylated coumarins from Mammea americana

Planta Medica

Volumn 71, Issue 9, 2005, Pages 852-860

  Yang, Hui ^a   Protiva, Petr ^b   Gil, Roberto R ^c   Jiang, Bei ^b   Baggett, Scott ^a   Basile, Margaret J ^d   Reynertson, Kurt A ^a   Weinstein, I Bernard ^b   Kennelly, Edward J ^a  

^a CITY UNIVERSITY OF NEW YORK   (United States)

^b NewYork Presbyterian Hospital   (United States)

^c CARNEGIE MELLON UNIVERSITY   (United States)

^d UNIVERSITY OF MIAMI MILLER SCHOOL OF MEDICINE   (United States)

Author keywords

Antioxidant activity; Clusiaceae; Cytotoxicity; Isoprenylated coumarin; Mamey; Mammea americana; SAR studies

Indexed keywords

[2,3 DIHYDRO 3,4 DIHYDROXY 2 (1 HYDROXY 1 METHYLETHYL) 5 (3 METHYL 1 OXOBUTYL) 9 PROPYL 7H FURO[2,3 F] 1 BENZOPYRAN 2 ONE]; [5,7 DIHYDROXY 4 [1 (ACETOXY)PROPYL] 6 (3 METHYL 2 BUTENYL) 8 (1 OXOBUTYL) 2H 1 BENZOPYRAN 2 ONE]; [5,7 DIHYDROXY 4[1 (ACETOXY)PROPYL] 6 (3 METHYL 2 BUTENYL) 8 (2 METHYL 1 OXOPROPYL) 2H 1 BENZOPYRAN 2 ONE]; CATECHIN; COUMARIN DERIVATIVE; EPICATECHIN; FLUOROURACIL; MAMMEA AMERICANA EXTRACT; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; APOPTOSIS; ARTICLE; CANCER CELL CULTURE; CELL STRAIN HCT116; CELL STRAIN HT29; COLON CANCER; CONTROLLED STUDY; CYTOTOXICITY; DRUG IDENTIFICATION; DRUG SCREENING; FLOW CYTOMETRY; FRACTIONATION; HUMAN; HUMAN CELL; ISOPRENYLATION; MAMMEA; PLANT SEED; STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; ANTIOXIDANTS; CELL LINE, TUMOR; COUMARINS; FLOW CYTOMETRY; FRUIT; HUMANS; INHIBITORY CONCENTRATION 50; MAMMEA; PHYTOTHERAPY; PICRATES; PLANT EXTRACTS; PROTEIN ISOPRENYLATION; STRUCTURE-ACTIVITY RELATIONSHIP;

CLUSIACEAE; MAMMEA; MAMMEA AMERICANA;

EID: 27144457781     PISSN: 00320943     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-871257     Document Type: Article

References (23)

1. Morton JF. Fruits of Warm Climates. Julia F. Morton (self published) Miami, Florida: 1987. p. 304-7.
2. Kennard WC, Winters HF. Some fruits and nuts for the tropics. Miscellaneous Publication 801 U.S. Department of Agriculture, Agricultural Research Service, Washington, D.C.: 1960. p. 85-6.
3. Crombie L, Games DE. Extractives of Mammea americana L. Part I. The 4-n-alkylcoumarins. Isolation and structure of mammea B/BA, B/BB, B/BC and C/BB. J Chem Soc (C) 1967: 2545-52
4. Crombie L, Games DE. Extractives of Mammea americana L. Part II. The 4-phenylcoumarins. Isolation and structure of mammea B/AA, A/A cyclo D, A/BA, A/AB and A/BB. J Chem Soc (C) 1967: 2553-9
5. Crombie L, Games DE, Haskins NJ, Reed GF, Finnegan RA, Merkel KE. Identification of new Mammea coumarins: Four 7,8-annulated relative of the mammea coumarins B/AA, B/AA, and two of the 6-acyl family, B/AA (isomammein) and B/AB. Tetrahedron Lett 1970; 46: 3979-82
6. Crombie L, Games DE, Haskins NJ, Reed GF. Extractives of Mammea americana L. Part III. Identification of new coumarin relatives of Mammea B/BA, B/BB, and B/BC having 5,6-annulation and higher oxidation records. J Chem Soc [Perkin I] 1972: 2241-8
7. Crombie L, Games DE, Haskins NJ, Reed GF. Extractives of Mammea americana L. Part IV. Identification of new 7,8-annulated relates of the coumarins Mammea B/AA, A/AB, B/AA, and B/AB and new members of the 6-acyl family B/AA, B/AB, and B/AC. J Chem Soc [Perkin I] 1972: 2248-54
8. Crombie L, Games DE, Haskins NJ, Reed GF. Extractives of Mammea americana L. Part V. The insecticidal compounds. J Chem Soc [Perkin I] 1972: 2255-60
9. Crombie L, Jones RC, Palmer CJ. Synthesis of the Mammea coumarins. Part 1. The coumarins of the Mammea A, B, and C series. J Chem Soc [Perkin I] 1987: 317-31
10. Yang H, Protiva P, Cui BL, Ma CY, Baggett S, Hequet V et al. New bioactive polyphenols from Theobroma grandiflorum ("Cupuaçu"). J Nat Prod 2003; 66: 1501-4
11. Ma J, Luo XD, Protiva P, Yang H, Ma CY, Basile MJ et al. Bioactive novel polyphenols from the fruit of Manilkara zapota (sapodilla). J Nat Prod 2003; 66: 983-6
12. Smith RC, Reeves JC, Dage RC, Schnettler RA. Antioxidant properties of 2-imidazolones and 2-imidazolthiones. Biochem Pharmacol 1987; 36: 1457-60
13. Darzynkiewicz Z, Bruno S, Del Bino G, Gorczyca W, Hotz MA, Lassota P et al. Features of apoptotic cells measured by flow cytometry. Cytometry 1992; 13: 795-808
14. Morel C, Guilet D, Oger J, Seraphin D, Sevenet T, Wiart C et al. 6-Acylcoumarins from Mesua racemosa. Phytochemistry 1999; 50: 1243-47
15. Mahidol C, Kaweetripob W, Prawat H, Ruchirawat S. Mammea coumarins from the flowers of Mammea siamensis. J Nat Prod 2002; 65: 757-60
16. Bala K, Seshadri T. Isolation and synthesis of some coumarin components of Mesua ferrea seed oil. Phytochemistry 1971; 10: 1131-4
17. Guilet D, Helesbeux JJ, Seraphin D, Sevenet T, Richomme P, Bruneton J. Novel cytotoxic 4-phenylfruanocoumarins from Calophyllum dispar. J Nat Prod 2001; 64: 563-8
18. Thebtaranonth C, Imraporn S, Padungkul N. Phenylcoumarins from Ochrocarpus siamensis. Phytochemistry 1981; 20: 2305-6
19. Kashman Y, Gustafson KR, Fuller RW, Cardellian JHC II, McMahon JB, Currens MJ et al. The calanolides. A novel HIV-Inhibitory class of coumarin derivatives from the tropical rainforest tree, Calophyllum lanigerum. J Med Chem 1992; 35: 2735-43
20. Patil AD, Freyer AJ, Eggleston DS, Haltiwanger RC, Bean MF, Taylor PB et al. The inophyllums, novel inhibitors of HIV-1 reverse transcriptase isolated from the Malaysian tree, Calophyllum inophyllum Linn. J Med Chem 1993; 36: 4131-8
21. Itoigawa M, Ito C, Tan HT-W, Kuchide M, Tokuda H, Nishino H et al. Cancer chemo-preventive agents, 4-phenylcoumarins from Calophyllum inophyllum. Cancer Lett 2001; 169: 15-9
22. Ito C, Itoigawa M, Mishina Y, Filho VC, Enjo F, Tokuda H et al. Chemical constituents of Calphyllum brasiliense. 2. Structure of three new coumarins and cancer chemopreventive activity of 4-substituted coumarins. J Nat Prod 2003; 66: 368-71
23. Cao G, Sofic E, Prior R. Antioxidant capacity of tea and common vegetables. J Agric Food Chem 1996; 44: 3426-31