Polyisoprenylated benzophenones and an unusual polyisoprenylated tetracyclic xanthone from the fruits of Garcinia cambogia

Journal of Agricultural and Food Chemistry

Volumn 56, Issue 13, 2008, Pages 5205-5210

  Masullo, Milena ^a   Bassarello, Carla ^a   Suzuki, Hisanori ^b   Pizza, Cosimo ^a   Piacente, Sonia ^a  

^a UNIVERSITY OF SALERNO   (Italy)

^b UNIVERSITY OF VERONA   (Italy)

Author keywords

Garcinia cambogia fruits; Guttiferae; Oxy guttiferone K; Polyisoprenylated benzophenones; Polyisoprenylated tetracyclic xanthone

Indexed keywords

BENZOPHENONE DERIVATIVE; GARCINOL; GUTTIFERONE K; PLANT EXTRACT; POLYISOPRENYL BENZOPHENONE; TERPENE;

ARTICLE; CHEMISTRY; FRUIT; GARCINIA CAMBOGIA; ISOLATION AND PURIFICATION; METABOLISM; OXIDATION REDUCTION REACTION;

BENZOPHENONES; FRUIT; GARCINIA CAMBOGIA; OXIDATION-REDUCTION; PLANT EXTRACTS; TERPENES;

CLUSIACEAE; GARCINIA CAMBOGIA;

EID: 47849120898     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf800416j     Document Type: Article

References (18)

1. The Wealth of India (Raw Materials); CSIR: New Delhi, India, 1956; Vol. IV, pp 99-108.
2. Jena, B. S.; Jayaprakasha, G. K.; Singh, R. P.; Sakariah, K. K. Chemistry and biochemistry of (-)-hydroxycitric acid from Garcinia. J. Agric. Food Chem. 2002, 50, 10-22.
3. Duke, J. A.; Bogenschutz-Godwin, M. J.; duCellier, J.; Duke, P.-A. K. In Handbook of Medicinal Herbs, 2nd ed.; CRC Press, Boca Raton, FL, 2002; p 481.
4. Bennet, G. J.; Lee, H. H. Xanthones from Guttiferae. Phytochemistry 1989, 28, 967-998.
5. Williams, R. B.; Hoch, J.; Glass, T. E.; Evans, R.; Miller, J. S.; Wisse, J. H.; Kingston, D. G. I. A novel cytotoxic guttiferone analogue from Garcinia macrophylla from the Surinam rainforest. Planta Med. 2003, 69, 864-866.
6. Tandon, R. N.; Srivastava, O. P.; Baslas, R. K.; Kumar, P. Preliminary investigation on the antimicrobial activity of a phytochemical, xanthochymol from the fruits of Garcinia xanthochymus Hook. f. Curr. Sci. 1980, 49, 472-3.
7. McKee, C. T.; Covington, C. D.; Fuller, R. W.; Bokesch, H. R.; Young, S.; Cardellina, J. H.; Kadushin, M. R.; Soejarto, D. D.; Stevens, P. F.; Cragg, G. M.; Boyd, M. R. Pyranocoumarins from tropical species of the genus Calophyllum: a chemotaxonomic study of extracts in the National Cancer Institute collection. J. Nat. Prod. 1998, 61, 1252-1256.
8. Yamaguchi, F.; Saito, M.; Ariga, T.; Yoshimura, Y.; Nakazawa, H. Free radical scavenging activity and antiulcer activity of garcinol from Garcinia indica fruit Rind. J. Agric. Food Chem. 2000, 48, 2320-2325.
9. Ciochina, R.; Grossman, R. B. Polycyclic Polyprenylated acylphloroglucinols. Chem. Rev. 2006, 106, 3963-3986.
10. Pan, M. H.; Chang, W. L.; Lin-Shiau, S. Y.; Ho, C. T.; Lin, J. K. Induction of apoptosis by garcinol and curcumin through cytochrome c release and activation of caspases in human leukemia HL-60 cells. J. Agric. Food Chem. 2001, 49, 1464-1474.
11. Sang, S.; Pan, M. H.; Cheng, X.; Bai, N.; Stark, R. E.; Rosen, R. T.; Lin-Shiau, S. Y.; Lin, J. K.; Ho, C. T. Chemical studies on antioxidant mechanism of garcinol: analysis of radical reaction products of garcinol and their antitumor activities. Tetrahedron 2001, 57, 9931-9938.
12. Sang, S.; Liao, C. H.; Pan, M. H.; Rosen, R. T.; Lin-Shiau, S. Y.; Lin, J. K.; Ho, C. T. Chemical studies on antioxidant mechanism of garcinol: analysis of radical reaction products of garcinol with peroxyl radicals and their antitumor activities. Tetrahedron 2002, 58, 10095-10102.
13. Hong, J.; Sang, S.; Park, H. J.; Kwon, S. J.; Suh, N.; Huang, M. T.; Ho, C. T.; Yang, C. S. Modulation of arachidonic acid metabolism and nitric oxide synthesis by garcinol and its derivatives. Carcinogenesis 2006, 27, 278-286.
14. Iinuma, M.; Ito, T.; Miyake, R.; Tosa, H.; Tanaka, T.; Chelladurai, V. A xanthone from Garcinia cambogia. Phytochemistry 1998, 47, 1169-1170.
15. Nilar; Nguyen, L.-H. D.; Venkatraman, G.; Sim, K.-Y.; Harrison, L. J. Xanthones and benzophenones from Garcinia griffithii and Garcinia mangostana. Phytochemistry 2005, 66, 1718-1723.
16. Merza, J.; Mallet, S.; Litaudon, M.; Dumontet, V.; Sèraphin, D.; Richomme, P. New cytotoxic guttiferone analogues from G. virgata from New Caledonia. Planta Med. 2006, 72, 87-89.
17. Cao, S.; Brodie, P. J.; Miller, J. S.; Ratovoson, F.; Birkinshaw, C.; Randrianasolo, S.; Rakotobe, E.; Rasamison, V. E.; Kingston, D. G. I. Guttiferones K and L, antiproliferative compounds of Rheedia calcicola from the Madagascar rain forest. J. Nat. Prod. 2007, 70, 686-688.
18. Krishnamurthy, N.; Lewis, Y. S.; Ravindranath, B. On the structure of garcinol, isogarcinol, and camboginol. Tetrahedron Lett. 1981, 22, 793-796.