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DOI: 10.1055/s-2006-931556
© Georg Thieme Verlag KG Stuttgart · New York
Antiproliferative Activity of Pteleopsis suberosa Leaf Extract and its Flavonoid Components in Human Prostate Carcinoma Cells
Publikationsverlauf
Received: July 27, 2005
Accepted: January 15, 2006
Publikationsdatum:
24. April 2006 (online)
Abstract
In this work we describe the chemical composition of Pteleopsis suberosa (Combretaceae) leaf extract and its biological activity against androgen-insensitive human prostate cancer cells (DU-145). The methanol extract of the plant leaves exhibited activity against tumor cell growth. Fractionation of this active extract led to the isolation and identification of sixteen flavonoids, including gallocatechin and flavonols having kaempferol, quercetin, and myricetin as aglycones. Among the myricetin derivatives, myricetin 3-O-(3′′-acetyl)-α-L-arabinopyranoside (1) and myricetin 3-O-(4′′-acetyl)-α-L-arabinopyranoside (2) are now reported for the first time. Six compounds, myricetin 3-O-α-L-rhamnopyranoside (4), myricetin 3-O-β-D-galactopyranoside (7), myricetin 3-O-(6′′-galloyl)-β-D-galactopyranoside (9), myricetin 3-O-β-D-xylopyranoside (10), myricetin 3-O-α-L-arabinofuranoside (12), and gallocatechin (14), exhibited significant activity, reducing cell vitality and inducing apoptosis via the caspase-dependent pathway in DU-145 cells that can be, in part, correlated to modulation of redox-sensitive mechanisms.
Key words
Pteleopsis suberosa - Combretaceae - flavonoids - antiproliferative activity
References
- 1 Gapter L, Wang Z, Glinski J, Ng K Y. Induction of apoptosis in prostate cancer cells by pachymic acid from Poria cocos . Biochem Biophys Res Commun. 2005; 332 1153-61
- 2 Kanadaswami C, Lee L T, Lee P P, Hwang J J, Ke F C, Huang Y T. et al . The antitumor activities of flavonoids. In Vito. 2005; 19 895-909
- 3 Adjanhoun E J, Ahyi M RA, Akè Assi L, Chibon P, Eyme J, Garba M. et al .Contribution aux études ethnobotaniques et floristiques du Togo. Paris; ACCT 1986: p 133
- 4 Germanò M P, Sanogo R, Guglielmo N, De Pasquale R, Crisafi G, Bisiognano G. Effects of Pteleopsis suberosa extracts on experimental ulcers and Helicobacter pylori growth. J Ethnopharmacol. 1998; 59 167-72
- 5 De Pasquale R, Germanò M P, Keitha A, Sanogo R, Iauk L. Antiulcer activity of Pteleopsis suberosa . J Ethnopharmacol. 1995; 47 55-8
- 6 Russo A, Cardile V, Sanchez F, Troncoso N, Vanella A, Garbarino J A. Chilean propolis: antioxidant activity and antiproliferative action in human tumor cell lines. Life Sci. 2004; 76 545-58
- 7 Russo A, Borrelli F, Campisi A, Acquaviva R, Raciti G, Vanella A. Nitric oxide-related toxicity in cultured astrocytes: effect of Bacopa monniera . Life Sci. 2003; 73 1517-26
- 8 Braca A, De Tommasi N, Morelli I, Pizza C. New metabolites from Onopordon illyricum . J Nat Prod. 1999; 62 1371-5
- 9 Timbola A K, Szpoganicz B, Branco A, Delle Monache F, Pizzolatti M G. A new flavonol from the leaves of Eugenia jambolana . Fitoterapia. 2002; 73 174-6
- 10 Fossen T, Larsen A, Kiremire B T, Andersen O M. Flavonoids from blue flowers of Nymphea caerulea . Phytochemistry. 1999; 51 1133-7
- 11 Slacanin I, Marston A, Hostettmann K, Delabays N, Darbellay C. Isolation and determination of flavonol glycoside from Epilobium species. J Chromatogr A. 1991; 557 391-8
- 12 Bohm B A. Chemotaxonomic studies in the Saxfrigaceae. Part 11. Flavonoids of Tolmiea menziesii . Phytochemistry. 1979; 18 1079-80
- 13 Foo L Y, Lu Y, Molan A L, Woodfiled D R, McNabb W C. The phenols and prodelphinidins of white clover flowers. Phytochemistry. 2000; 54 539-48
- 14 Zhang Z, El-Sohly H N, Li X C, Khan S I, Broedel S E, Raulli R E. et al . Phenolic compounds from Nymphaea odorata . J Nat Prod. 2003; 66 548-50
- 15 Kadota S, Takamori Y, Khin N N, Kikuchi T, Tanaka K, Ekimoto H. Constituents of the leaves of Woodfordia fruticosa Kurz. I. Isolation, structure, and proton and carbon-13 nuclear magnetic resonance signal assignments of woodfruticosin (woodfordin C), an inhibitor of deoxyribonucleic acid topoisomerase II. Chem Pharm Bull. 1990; 38 2687-97
- 16 Vvedenskaya I O, Rosen R T, Guido J E, Russell D J, Mills K A, Vorsa N. Characterization of flavonols in cranberry (Vaccinium macrocarpon) powder. J Agric Food Chem. 2004; 52 188-95
- 17 Yan X, Murphy B T, Hammond G B, Vinson J A, Neto C C. Antioxidant activities and antitumor screening of extracts from cranberry fruit (Vaccinium microcarpon). J Agric Food Chem. 2002; 50 5844-9
- 18 Ismail N, Alam M. A novel cytotoxic flavonoid glycoside from Physalis angulata . Fitoterapia. 2001; 72 676-9
- 19 Davis A L, Cai Y, Davies A P, Lewis J R. 1H and 13C assignments of some green tea polyphenols. Magn Reson Chem. 1996; 34 887-90
- 20 Collins F W, Bohm B A, Wilkins C K. Flavonol glycosides gallates from Tellina grandiflora . Phytochemistry. 1975; 14 1099
- 21 Fuchino H, Konishi S, Satoh T, Yagi A, Saitsu K, Tatsumi T. et al . Chemical evaluation of Betula species in Japan. II. Constituents of Betula platyphylla var. japonica . Chem Pharm Bull. 1996; 44 1033-8
- 22 Agrawal P K. Carbon-13 NMR of flavonoids. Amsterdam; Elsevier 1989: p 336-9
- 23 Kuntz S, Wenzel U, Daniel H. Comparative analysis of the effects of flavonoids on proliferation, cytotoxicity, and apoptosis in human colon cancer cell lines. Eur J Nutr. 1999; 38 133-42
- 24 Singh R P, Agrawal P, Yin D, Agarwal C, Agarwal R. Acacetin inhibits cell growth and cell cycle progression, and induces apoptosis in human prostate cancer cells: structure-activity relationship with linarin and linarin acetate. Carcinogenesis. 2005; 26 845-54
- 25 Loo G. Redox-sensitive mechanisms of phytochemical-mediated inhibition of cancer cell proliferation. J Nutr Biochem. 2003; 14 64-73
Prof. Nunziatina DeTommasi
Dipartimento di Scienze Farmaceutiche
Università di Salerno
Via Ponte Don Melillo
84084 Fisciano (SA)
Italy
Fax: +39-089-962-647
eMail: detommasi@unisa.it