Extraction of Bioactive Sesquiterpene Lactones from Magnolia grandiflora Using Supercritical Carbon Dioxide and Near-Critical Propane

Journal of Agricultural and Food Chemistry

Volumn 43, Issue 1, 1995, Pages 63-68

  Castaneda Acosta, José ^a   Cain, Andrew W ^a   Fischer, Nikolaus H ^a   Knopf, F Carl ^a  

^a LOUISIANA STATE UNIVERSITY   (United States)

Author keywords

bioactive; Magnolia grandiflora; natural products; Supercritical fluid

Indexed keywords

EID: 0000934702     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf00049a013     Document Type: Article

References (45)

1. 1H-NMR Spectroscopy. J. Nat. Prod. 1991, 54, 1516-1521.
2. Belousova, N. I.; Dmitruk, S. E.; Khan, V. A. Essential Oils in Ledum L.: Antifungal Properties. Khim. Farm. Zh. 1989, 23, 317-319.
3. Bovill, M. J.; Cox, P. J.; Cradwick, P. D.; Guy, M. H. P.; Sim, G. A.; White, D. N. J. Sesquiterpenoids. XXV. X-ray Crystal Structure Analysis of Costunolide. Acta Crystallogr. 1976, B32, 3203-3209.
4. Bovill, M. J.; Cox, P. J.; Cradwick, P. D.; Guy, M. H. P.; Sim, G. A.; White, D. N. J. Sesquiterpenoids. XXV. X-ray Crystal Structure Analysis of Costunolide: Corrigendum. Acta Crystallogr. 1978, B34 (1), 349.
5. Chimowitz, E. H.; Pennisi, K. J. Process Synthesis Concepts for Supercritical Gas Extraction in the Crossover Region. AIChE J. 1986, 32, 1665-1676.
6. Coorens, H. G. A.; Peters, C. J.; De Swaan Arons, J. Phase Equilibria in Binary Mixtures of Propane and Tripalmitin. Fluid Phase Equilib. 1988, 40, 135-151.
7. Cygnarowicz-Provost, M.; O’Brien, D. J.; Maxwell, R. J.; Hampson, J. W. Supercritical-fluid Extraction of Fungal Lipids Using Mixed Solvents: Experiment and Modeling. J. Supercrit. Fluids 1992, 5, 24-30.
8. El-Feraly, F. S.; Chan, Y.-M. Isolation and Characterization of the Sesquiterpene Lactones Costunolide, Parthenolide, Costunolide Diepoxide, Santamarine, and Reynosin from Magnolia grandiflora L. J. Pharm. Sci. 1978, 67, 347-350.
9. El-Feraly, F. S.; Chan, Y.-M.; Capiton, G. A.; Doskotch, R. W.; Fairchild, E. H. Isolation and Characterization of Peroxycostunolide (Verlotorin) and Peroxyparthenolide from Magnolia grandiflora. Carbon-13 Nuclear Magnetic Resonance Spectroscopy of Costunolide and Related Compounds. J. Org. Chem. 1979, 44, 3952-3955.
10. Favati, F.; King, J. W.; Mazzanti, M. Extraction Dynamics and Optimization for the Supercritical Fluid Extraction of Evening Primrose Oil. Presented at the Second International Symposium on Supercritical Fluids, Boston, MA, May 20-22, 1991.
11. Fischer, N. H. Sesquiterpene Lactones: Biogenesis and Biomimetic Transformations. In Biochemistry of the Mevalonic Acid Pathway to Terpenoids; Towers, G. H. N., Stafford, H. A., Eds.; Plenum Press: New York, 1990; Vol. 24, Chapter 4, pp 161-201.
12. Fischer, N. H. Sesquiterpenoid Lactones. In Methods in Plant Biochemistry, Charlwood, B. V., Banthorpe, D. V., Eds.; Academic Press: London, 1991; Vol. 7, Chapter 5, pp 187-211.
13. Fischer, N. H.; Weidenhamer, J. D.; Riopel, J. L.; Quijano, L.; Menalaou, M. Stimulation of Witchweed Germination by Sesquiterpene Lactones: A Structure Activity Study. Phytochemistry 1990, 29, 2479-2483.
14. Fischer, N. H.; Vargas, D.; Menelaou, M. Modem NMR Methods in Phytochemical Studies; In Modern Phytochemical Methods; Fischer, N. H., Isman, M. B., Stafford, H. A., Eds.; Plenum Press: New York, 1991; Vol. 25, Chapter 8, pp 271-317.
15. Garcia, M.; da Silva, A. J. R.; Baker, P. M.; Gilbert, B.; Rabi, J. A. Absolute Stereochemistry of Eremanthine, A Schistosomicidal Sesquiterpene Lactone from Eremanthus elaegnus. Phytochemistry 1976, 15, 331-332.
16. Govindachari, T. R.; Joshi, B. S.; Kamat, V. N. Structure of Parthenolide. Tetrahedron 1965, 21, 1509-1519.
17. Groenewegen, W. A.; Heptinstall, S. A Comparison of the Effects of an Extract of Feverfew and Parthenolide, a Component of Feverfew, on Human Platelet Activity in vitro. J. Pharm. Pharmacol. 1990, 42, 553-557.
18. Hellyer, R. O.; Lassak, E. V. Cyclocolorenone in Boronia ledifolia. Aust. J. Chem. 1967, 20, 2297-2298.
19. Heptinstall, S.; Williamson, L.; White, A.; Mitchell, J. R. A. Extracts of Feverfew Inhibit Granule Secretion in Blood Platelets and Polymorphonuclear Leucocytes. Lancet 1985, 1071-1074.
20. Hostettmann, K.; Marston, A. Plant Molluscicide Research-An Update. In Plant Molluscicides; Mott, K. E., Ed.; Wiley: New York, 1987; Chapter 12, pp 299-320.
21. Jacyno, J. M.; Montemurro, N.; Bates, A. D.; Cutler, H. G. Phytotoxic and Antimicrobial Properties of Cyclocolorenone from Magnolia grandiflora L. J. Agric. Food Chem. 1991, 39, 1166-1168.
22. Johnson, E. S.; Kadam, N. P.; Hylands, D. M.; Hylands, P. J. Efficacy of Feverfew as Prophylactic Treatment of Migraine. Br. Med. J. 1985, 291, 569.
23. Larson, K. A.; King, M. L. Evaluation of supercritical fluid extraction in the pharmaceutical industry. Biotechnol. Prog. 1986, 2, 73-82.
24. Lee, H.; Hong, W.; Yoon, J.; Song, K; Kwak, S.; Liu, J. Extraction of indole alkaloids from Catharanthus roseus by using supercritical carbon dioxide. Biotechnol. Tech. 1992, 6 (March/April), 127-130.
25. 2. Presented at the Second International Symposium on Supercritical Fluids, Boston, MA, May 20-22, 1991.
26. Linek, A.; Novak, C. Refinement of the Structure of the Costunolide-Silver Nitrate Complex. Acta Crystallogr. 1978, B34, 3369-3372.
27. Maries, R. J.; Kaminski, J.; Amason, J. T.; Pazos-Sanou, L.; Heptinstall, S.; Fischer, N. H.; Crompton C. W.; Kindack, D. G.; Awang, D. V. C. A Bioassay for Inhibition of Serotonin Release from Bovine Platelets: Screening for Potential Migraine Prophylactics. J. Nat. Prod. 1992, 55, 1044-1056.
28. Marston, A.; Hostettmann, K. Plant Molluscicides. Phytochemistry 1985, 24, 639-652.
29. McHugh, M. A.; Krukonis, V. J. Processing Pharmaceuticals, Natural Products, and Specialty Chemicals, and Waste Streams: Coffee Decaffeination. In Supercritical Fluid Extraction: Principles and Practice; Butterworth: Boston, MA, 1986; pp 182-188.
30. Mikhailova, N. S.; Konovalova, O. A.; Zakharov, P. I.; Rybalko, K. S. Isolation of Cyclocolorenone from Ledum palustre Essential Oil. Khim. Prir. Soedin. 1978, 2, 212-215.
31. Murphy, J. J.; Heptinstall, S.; Mitchell, J. R. A. Randomized Double-Blind Placebo-Controlled Trial of Feverfew in Migraine Prevention. Lancet 1988, 2, 189.
32. Ogura, M.; Cordell, G. A.; Farnsworth, N. R. Anticancer Sesquiterpene Lactones of Michellia compressa (Magnoliaceae). Phytochemistry 1978, 17, 957-961.
33. Pang, T.-H.; McLaughlin, E. Supercritical Extraction of Aromatic Hydrocarbon Solids and Tar Sand Bitumens. Ing. Eng. Chem. Process Des. Dev. 1985, 24, 1027-1032.
34. Pattrick, M.; Heptinstall, S.; Doherty, M. Feverfew in Rheumatoid Arthritis: A Double Blind, Placebo Controlled Study. Ann. Rheum. Dis. 1989, 48, 547-549.
35. Picman, A. K. Biological Activities of Sesquiterpene Lactones. Biochem. Syst. Ecol. 1986, 14, 155-281.
36. Quick, A.; Rogers, D. Crystal and Molecular Structure of Parthenolide[4, 5-Epoxigermacra-1(10), 11(13)-dien-12, 6-olactone]. J. Chem. Soc., Perkin Trans. 2 1976, 5, 465-469.
37. Ramaiah, K. V. In Striga: Biology and Control; Ayensu, E. S., Doggett, H., Keynes, R. D., Marton-Lefevre, J., Musselman, L. J., Parker, C., Pickering, A., Eds.; ICSU Press: Paris, 1983; pp 71-92.
38. Rao, K. V.; Davis, T. L. Constituents of Magnolia grandiflor a, Cyclocolorenone. Planta Med. 1982, 44, 249-253.
39. Richardson, D. P.; Messer, A. C.; Breenberg, S.; Hagedorn, H. H.; Meinwald, J. Defensive Sesquiterpenoids from a Dipterocarp (Dipterocarpus kerrii). J. Chem. Ecol. 1989, 15 (2), 731-747.
40. Rodrigues, A. A.; Garcia, M.; Rabi, J. A. Facile Biomimetic Synthesis of Costunolide-1, 10-epoxide, Santamarin and Reynosin. Phytochemistry 1978, 17, 953-954.
41. Seki, K.; Hashimoto, A.; Kobayashi, H.; Kawahara, Y.; Yamahara, J. Motility Inhibitory Effect on Anchusan and Jintan and Its Active Components in Anisakis Type I Larvae. Yakuri to Chiryo 1991, 19, 3657-3666.
42. Vichnewski, W.; Sarti, S. J.; Gilbert, B.; Herz, W. Goyazensolide, A Schistosomicidal Heliangolide from Eremanthus goyzensis. Phytochemistry 1976, 15, 191-193.
43. Wigfield, Y. Y.; Lanouette, M. Supercritical fluid Extraction of the Fortified Residues of Fluazifop-P-butyl (Fusilade II) and Its Major Metabolite, Fluazifop-P, in Onions. J. Agric. Food Chem. 1993, 41, 84-88.
44. Wong, J. M.; Johnston, K. P. Solubilization of Biomolecules in Carbon Dioxide Based Supercritical Fluids. Biotechnol. Prog. 1986, 2, 29.
45. Yamahara, J.; Kobayashi, M.; Miki, K.; Kozuka, M.; Sawada, T.; Fujimura, H. Cholagogic and Antiulcer Effect of Saussureae radix and Its Active Components. Chem. Pharm. Bull. 1985, 33, 1285-1288.